版本
5.0
创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-09-14 15:41:24 UTC
登录号
HMDB0000053
地位
quantified
二级访问
HMDB00053

名称
Androstenedione
描述
Androstenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while the production of gonadal androstenedione is under control by gonadotropins.
同义词
1:4-Androstene-3,17-dione

2:4-ANDROSTENE-3-17-dione

3:delta(4)-Androsten-3,17-dione

4:delta(4)-Androstene-3,17-dione

5:Δ(4)-Androsten-3,17-dione

6:Δ(4)-Androstene-3,17-dione

7:(4)-Androsten-3,17-dione

8:17-Ketotestosterone

9:3,17-Dioxoandrost-4-ene

10:4-Androsten-3,17-dione

11:4-Androstenedione

12:Androst-4-ene-3,17-dione

13:Androstendione

14:D4-Androstene-3,17-dione

15:delta4-Androstenedione

16:Fecundin

17:delta 4 Androstenedione

18:delta-4-Androstenedione

19:4 Androstene 3,17 dione

20:Androstenedione

21:delta4-Androstene-3,17-dione

22:Δ4-Androstene-3,17-dione

化学式
C19H26O2
平均分子量
286.4085
等位分子量
286.193280076
化学名称
(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
传统名称
(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
CAS 登记号
63-05-8
代谢物结构字符串
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
inchi标识符
InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
印记键
AEMFNILZOJDQLW-QAGGRKNESA-N
分类学
description: belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

description:Androgens and derivatives

kingdom:Organic compounds

super_class:Lipids and lipid-like molecules

class:Steroids and steroid derivatives

sub_class:Androstane steroids

molecular_framework:Aliphatic homopolycyclic compounds

1:17-oxosteroids

2:3-oxo delta-4-steroids

3:Cyclohexenones

4:Delta-4-steroids

5:Hydrocarbon derivatives

6:Organic oxides

7:17-oxosteroid

8:3-oxo-delta-4-steroid

9:3-oxosteroid

10:Aliphatic homopolycyclic compound

11:Androgen-skeleton

12:Carbonyl group

13:Cyclic ketone

14:Cyclohexenone

15:Delta-4-steroid

16:Hydrocarbon derivative

17:Ketone

18:Organic oxide

19:Organic oxygen compound

20:Organooxygen compound

21:Oxosteroid

22:17-oxo steroid

23:3-oxo Delta(4)-steroid

24:Androgens

25:Androstane and derivatives

26:C19 steroids (androgens) and derivatives

27:C19 steroids (androgens) and derivatives

28:androstane

29:androstanoid

本体论
term:Physiological effect

definition:The effect on an organism physiology, resulting from its exposure to a chemical.

parent_id:

level:1

type:parent

term:Health effect

definition:A health condition or observation associated with a stimuli or with a biological activity of a chemical.

parent_id:7693

*level:2

type:parent

term:Health condition

definition:A health effect that consists on short or long-term disease, condition, disorder, syndrome or constant abnormality.

parent_id:7694

**level:3

type:parent

term:Cushing's syndrome

definition:

parent_id:7695

***level:4

type:child

synonym:Hypercorticism

synonym:Hyperadrenocorticism

synonym:Cushing's

term:Schizophrenia

definition:A psychotic disorder that is characterized by a disintegration of thought processes and of emotional responsiveness. (do).

parent_id:7695

***level:4

type:child

term:Polycystic ovary syndrome

definition:A syndrome characterized by hyperandrogenism, polycystic ovaries, hirsutism, oligomenorrhea or amenorrhea, anovulation and excessive body weight. (do).

parent_id:7695

***level:4

type:child

synonym:Pcos

synonym:Polycystic ovary disease

synonym:Polycystic ovaries

term:Congenital adrenal hyperplasia

definition:A steroid inherited metabolic disorder that is characterized by adrenal insufficiency and variable degrees of hyper or hypo androgeny manifestations resulting from steroidogenic enzyme deficiency. (do).

parent_id:7695

***level:4

type:child

term:Cardiac disorders

definition:Any disorder that affects the heart.

parent_id:7695

***level:4

type:parent

term:Psychiatric disorders

definition:A group of disorders characterized by behavioral and/or psychological abnormalities, often accompanied by physical symptoms. the symptoms may cause clinically significant distress or impairment in social and occupational areas of functioning. representative examples include anxiety disorders, cognitive disorders, mood disorders and schizophrenia. (nci).

parent_id:7695

***level:4

type:parent

term:Cancer

definition:A group of disorders characterized by the presense of malignant neoplasm.

parent_id:7695

***level:4

type:parent

term:Disposition

definition:A concept that describes the origin of a chemical, its location within an organism, or its route of exposure.

parent_id:

level:1

type:parent

term:Route of exposure

definition:A mean by which a chemical agent comes in contact with an organism, either under intended or unintended circumstances.

parent_id:7724

*level:2

type:parent

term:Enteral

definition:Chemical exposure via the alimentary canal (mouth to anus).

parent_id:7743

**level:3

type:parent

term:Ingestion

definition:Chemical exposure facilitated by entry through the mouth.

parent_id:7744

***level:4

type:child

synonym:Digestion

term:Source

definition:Natural or synthetic origin of a chemical.

parent_id:7724

*level:2

type:parent

term:Endogenous

definition:

parent_id:7735

**level:3

type:child

term:Food

definition:

parent_id:7735

**level:3

type:child

term:Biological location

definition:The physiological origin within an organism, including anatomical compnents, biofluids and excreta.

parent_id:7724

*level:2

type:parent

term:Tissue and substructures

definition:An anatomical organizational level including multiple cells yet not comprising a complete organ .

parent_id:7725

**level:3

type:parent

term:Placenta

definition:An organ present in some vertebrates during embryonic gestation that surrounds the fetus and provides it with nutrients and oxygen, facilitates gas and waste exchange between the fetus and mother, and provides parasitic cloaking from the mother's immune system by excretion of neurokinin b. (nci).

parent_id:7729

***level:4

type:child

term:Adipose tissue

definition:A specialized form of connective tissue consisting primarily of adipocytes (fat cells), surrounded by a meshwork of collagen fibers. (NCI)

parent_id:7729

***level:4

type:child

synonym:Fat tissue

synonym:Body fat

synonym:Adipose

term:Muscle

definition:A fibrous soft tissue with the ability to contract to produce force and motion. (nci).

parent_id:7729

***level:4

type:child

term:Hepatic tissue

definition:The tissue of the liver. It includes the hepatic lobules, hepatic sinusoids, perisinusoidal spaces, and portal triad. The hepatic lobules are composed of hepatocytes. (NCI Thesaurus).

parent_id:7729

***level:4

type:child

synonym:Liver tissue

term:Cell and elements

definition:An anatomical organizational level comprising of a single cell (or a fragment in some exceptions). a cell is defined by its type or function. it is the smallest unit of living structure capable of independent existence, composed of a membrane-enclosed mass of protoplasm and containing a nucleus or nucleoid.

parent_id:7725

**level:3

type:parent

term:Extracellular

definition:The space external to the outermost structure of a cell.

parent_id:7732

***level:4

type:child

synonym:Extracellular region

term:Cell

definition:

parent_id:7732

***level:4

type:parent

term:Organ and components

definition:An anatomical organizational level including multiple tissues or substructures, which enables a common biological function.

parent_id:7725

**level:3

type:parent

term:Gonad

definition:A reproductive system organ that produces and releases either sperm (testis) or eggs (ovary). (nci).

parent_id:7727

***level:4

type:child

term:Testicle

definition:Either of the paired male reproductive glands that produce the male germ cells and the male hormones. (nci).

parent_id:7727

***level:4

type:child

synonym:Testes

synonym:Testis

term:Liver

definition:An abdominal organ that has variable lobation which are composed mainly of hepatic lobules. (nci).

parent_id:7727

***level:4

type:child

term:Skin

definition:An organ that constitutes the external surface of the body. it consists of the epidermis, dermis, and skin appendages. (nci).

parent_id:7727

***level:4

type:child

term:Prostate

definition:The male reproductive accessory gland that produces prostatic fluid and is located adjacent to or around the urethra distal to the urinary bladder in mammals. (nci).

parent_id:7727

***level:4

type:child

synonym:Prostate gland

term:Kidney

definition:The organs of the urinary tract located in the retroperitoneal cavity adjacent to the spine and composed of the renal cortex and the renal medulla. (nci).

parent_id:7727

***level:4

type:child

synonym:Kidneys

term:Endocrine gland

definition:

parent_id:7727

***level:4

type:parent

term:Subcellular

definition:An anatomical organizational level including a component within a biological cell .

parent_id:7725

**level:3

type:parent

term:Cytoplasm

definition:The portion of the cell contained within the plasma membrane but excluding the nucleus.

parent_id:7730

***level:4

type:child

synonym:Cytoplasma

term:Membrane

definition:

parent_id:7730

***level:4

type:child

term:Endoplasmic reticulum

definition:A network of tubular membranes within the cytoplasm of the cell, occurring either with a smooth surface (smooth endoplasmic reticulum) or studded with ribosomes (rough endoplasmic reticulum), involved in the transport of materials. (Infoplease Dictionary via NCI)

parent_id:7730

***level:4

type:child

synonym:Er

term:Cell membrane

definition:A cellular compartment that separates a cellВ interiorВ from its exterior.

parent_id:7730

***level:4

type:child

synonym:Cellular membrane

term:Mitochondria

definition:

parent_id:7730

***level:4

type:child

term:Biofluid and excreta

definition:A liquid, semi-solid or solid material originating in the body.

parent_id:7725

**level:3

type:parent

term:Urine

definition:Excretion in liquid state processed by the kidney.

parent_id:7731

***level:4

type:child

term:Blood

definition:A liquid tissue with the primary function of transporting oxygen and carbon dioxide (nci). it supplies the tissues with nutrients, removes waste products, and contains various components of the immune system defending the body against infection.

parent_id:7731

***level:4

type:child

term:Cerebrospinal fluid

definition:The fluid that is contained within the brain ventricles, the subarachnoid space and the central canal of the spinal cord. (nci).

parent_id:7731

***level:4

type:child

synonym:Csf

term:Process

definition:Biological or chemical events, or a series thereof, leading to a known function or end-product.

parent_id:

level:1

type:parent

term:Naturally occurring process

definition:Naturally-occurring molecular events or a series thereof, leading to a known function or end-product.

parent_id:7659

*level:2

type:parent

term:Biological process

definition:Biological or chemical events or a series thereof, leading to a known function or end-product within an organism.

parent_id:7660

**level:3

type:parent

term:Biochemical process

definition:A biological process occurring at the subcellular level, involving biochemical reactions.

parent_id:7661

***level:4

type:parent

term:Chemical reaction

definition:A defined chemical event that occurs within or between organism cells.

parent_id:7661

***level:4

type:parent

term:System process

definition:A biological process occurring in an organ, a system or at the organism level.

parent_id:7661

***level:4

type:parent

term:Cellular process

definition:A biological process occurring within a cell or its surroundings.

parent_id:7661

***level:4

type:parent

term:Biochemical pathway

definition:A linked series of chemical reactions that occur in a defined order within or between organism cells, and lead to a known function or end product.

parent_id:7661

***level:4

type:parent

term:Role

definition:The purpose or function assumed by a chemical, either naturally or as intended by humans .

parent_id:

level:1

type:parent

term:Biological role

definition:The biological function of a chemical. the biological role answers the question how a chemical is involved in molecular processes in an organism. this can include biochemical effects of non-endogenous chemicals, which are also assigned an industrial application such as pharmaceuticals. the biological role is limited to cellular levls, and will not include role at system process level, such as a chemical which has a role in a disease.

parent_id:7671

*level:2

type:parent

term:Membrane stabilizer

definition:A chemical substance that supports the formation and maintenance of a structurally-sound and functioning cell or organelle membrane. Phospholipids form a bilayer and maintain the stability of the membrane structure together with proteins, and other lipids (i.e. cholesterol) which further strengthen it and decrease its permeability.

parent_id:7672

**level:3

type:child

synonym:Membrane stability agent

synonym:Membrane integrity agent

term:Energy source

definition:

parent_id:7672

**level:3

type:child

term:Energy storage

definition:A chemical substance which can be utilized for production of energy in the organism.

parent_id:7672

**level:3

type:child

term:Molecular messenger

definition: a chemical substance that is involved in transmission of biochemical signals.

parent_id:7672

**level:3

type:parent

term:Hormone

definition:Substances produces in animals or plant that regulate the activity of certain organs or control processes in other parts of the plant.

parent_id:7677

***level:4

type:child

term:Signaling molecule

definition:A chemical substance that particpiates in signal transduction processes in a living cell.

parent_id:7677

***level:4

type:child

synonym:Signalling molecule

synonym:Signaling agent

synonym:Cell signaling agent

term:Industrial application

definition:The assumed function of a chemical utilized by human.

parent_id:7671

*level:2

type:parent

term:Surfactant

definition:A chemical substance that has the ability to lower the surface tension of water or to reduce the interfacial tension between two immiscible substances. in the cspa consumer product ingredients dictionary, surfactants are classified on the basis of their ionic characteristics, as amphoteric, anionic, cationic, or nonionic; and functions, which are subdivided into the following major groups: surfactant - cleaning agent, surfactant - conditioning agent, surfactant - emulsifying agent, surfactant - foam booster , surfactant hydrotrop , surfactant - solubility agent, surfactant - suspending agent.

parent_id:7678

**level:3

type:child

synonym:Surface-active agent

term:Emulsifier

definition:Substances that promote the formation and stability of a suspension of fine particles of a liquid in another liquid.

parent_id:7678

**level:3

type:child

term:Pharmaceutical industry

definition:A pharmacologic activity for which a chemical substance is utilized owing to its biological role.

parent_id:7678

**level:3

type:parent

term:Pharmaceutical

definition:

parent_id:7679

***level:4

type:child

状态
Solid
实验性质
1:

kind:water_solubility

value:0.0578 mg/mL

source:

2:

kind:logp

value:2.75

source:HANSCH,C ET AL. (1995)

3:

kind:melting_point

value:170 - 173 °C

source:

预测性质
1:

kind:logp

value:2.93

source:ALOGPS

2:

kind:logs

value:-4.03

source:ALOGPS

3:

kind:solubility

value:0.027 g/L

source:ALOGPS

4:

kind:logp

value:3.93

source:ChemAxon

5:

kind:pka_strongest_acidic

value:19.03

source:ChemAxon

6:

kind:pka_strongest_basic

value:-4.8

source:ChemAxon

7:

kind:iupac

value:(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione

source:ChemAxon

8:

kind:average_mass

value:286.4085

source:ChemAxon

9:

kind:mono_mass

value:286.193280076

source:ChemAxon

10:

kind:smiles

value:[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

source:ChemAxon

11:

kind:formula

value:C19H26O2

source:ChemAxon

12:

kind:inchi

value:InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

source:ChemAxon

13:

kind:inchikey

value:AEMFNILZOJDQLW-QAGGRKNESA-N

source:ChemAxon

14:

kind:polar_surface_area

value:34.14

source:ChemAxon

15:

kind:refractivity

value:83.61

source:ChemAxon

16:

kind:polarizability

value:33.21

source:ChemAxon

17:

kind:rotatable_bond_count

value:0

source:ChemAxon

18:

kind:acceptor_count

value:2

source:ChemAxon

19:

kind:donor_count

value:0

source:ChemAxon

20:

kind:physiological_charge

value:0

source:ChemAxon

21:

kind:formal_charge

value:0

source:ChemAxon

22:

kind:number_of_rings

value:4

source:ChemAxon

23:

kind:bioavailability

value:Yes

source:ChemAxon

24:

kind:rule_of_five

value:Yes

source:ChemAxon

25:

kind:ghose_filter

value:Yes

source:ChemAxon

26:

kind:veber_rule

value:Yes

source:ChemAxon

27:

kind:mddr_like_rule

value:No

source:ChemAxon

光谱
生物学性质
1:

cellular:(1):Cytoplasm

cellular:(2):Endoplasmic reticulum

cellular:(3):Extracellular

cellular:(4):Membrane

2:

biospecimen:(1):Blood

biospecimen:(2):Cerebrospinal Fluid (CSF)

biospecimen:(3):Urine

3:

tissue:(1):Adipose Tissue

tissue:(2):Adrenal Cortex

tissue:(3):Adrenal Gland

tissue:(4):Epidermis

tissue:(5):Fibroblasts

tissue:(6):Kidney

tissue:(7):Liver

tissue:(8):Ovary

tissue:(9):Placenta

tissue:(10):Prostate

tissue:(11):Skeletal Muscle

tissue:(12):Testis

4:

[1]:

name:17-Beta Hydroxysteroid Dehydrogenase III Deficiency

smpdb_id:SMP00356

kegg_map_id:

[2]:

name:Androgen and Estrogen Metabolism

smpdb_id:SMP00068

kegg_map_id:map00150

[3]:

name:Androstenedione Metabolism

smpdb_id:SMP30406

kegg_map_id:

[4]:

name:Aromatase deficiency

smpdb_id:SMP00565

kegg_map_id:

正常浓度
1:

biospecimen:Blood

concentration_value:0.000698

concentration_units:uM

subject_age:Newborn (0-30 days old)

subject_sex:Female

subject_condition:Normal

2:

biospecimen:Blood

concentration_value:0.00244-0.00768

concentration_units:uM

subject_age:Not Specified

subject_sex:Not Specified

subject_condition:Normal

3:

biospecimen:Blood

concentration_value:<0.0140

concentration_units:uM

subject_age:Infant (0-1 year old)

subject_sex:Not Specified

subject_condition:Normal

4:

biospecimen:Blood

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

5:

biospecimen:Blood

concentration_value:0.00489 +/- 0.00196

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

6:

biospecimen:Blood

concentration_value:0.0059 (0.0023-0.0094)

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

7:

biospecimen:Blood

concentration_value:0.00315 (0.00000-0.00630)

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

8:

biospecimen:Blood

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

9:

biospecimen:Blood

concentration_value:0.00524 +/- 0.00140

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

10:

biospecimen:Blood

concentration_value:0.000978-0.00803

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

11:

biospecimen:Blood

concentration_value:0.00061 +/- 0.00022

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

12:

biospecimen:Blood

concentration_value:<0.00100

concentration_units:uM

subject_age:Not Specified

subject_sex:Both

subject_condition:Normal

13:

biospecimen:Blood

concentration_value:0.0022 (0.0010-0.0034)

concentration_units:uM

subject_age:Children (1-13 years old)

subject_sex:Both

subject_condition:Normal

14:

biospecimen:Blood

concentration_value:0.005 (0.0024-0.0070)

concentration_units:uM

subject_age:Adolescent (13-18 years old)

subject_sex:Female

subject_condition:Normal

15:

biospecimen:Blood

concentration_value:0.0040 (0.0013-0.0066)

concentration_units:uM

subject_age:Children (1-13 years old)

subject_sex:Female

subject_condition:Normal

16:

biospecimen:Blood

concentration_value:0.001 (0.00034-0.00170)

concentration_units:uM

subject_age:Children (1-13 years old)

subject_sex:Female

subject_condition:Normal

17:

biospecimen:Blood

concentration_value:0.0057 (0.00069-0.01)

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

18:

biospecimen:Cerebrospinal Fluid (CSF)

concentration_value:0.00101 (0.00002-0.002)

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Not Specified

subject_condition:Normal

19:

biospecimen:Urine

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

20:

biospecimen:Urine

concentration_value:0.00009 (0.00003-0.00077)

concentration_units:umol/mmol creatinine

subject_age:Newborn (0-30 days old)

subject_sex:Both

subject_condition:Normal

21:

biospecimen:Urine

concentration_value:0.0007 (0-0.0052)

concentration_units:umol/mmol creatinine

subject_age:Newborn (0-30 days old)

subject_sex:Both

subject_condition:Normal

22:

biospecimen:Urine

concentration_value:0.090 +/- 0.058

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

23:

biospecimen:Urine

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

24:

biospecimen:Urine

concentration_value:0.0068 +/- 0.0013

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

异常浓度
1:

biospecimen:Blood

concentration_value:0.000698-0.0583

concentration_units:uM

patient_age:Newborn (0-30 days old)

patient_sex:Male

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

2:

biospecimen:Blood

concentration_value:0.0066 +/- 0.0038

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:Polycystic ovary syndrome (PCOS)

3:

biospecimen:Blood

concentration_value:0.00663

concentration_units:uM

patient_age:Adolescent (13-18 years old)

patient_sex:Female

patient_information:21-hydroxylase deficiency

4:

biospecimen:Blood

concentration_value:0-0.00244

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:21-hydroxylase deficiency

5:

biospecimen:Blood

concentration_value:0.517

concentration_units:uM

patient_age:Infant (0-1 year old)

patient_sex:Both

patient_information:Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency (CAH)

6:

biospecimen:Blood

concentration_value:0.00154-0.0174

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:21-hydroxylase deficiency

7:

biospecimen:Blood

concentration_value:0.00137 +/- 0.000800

concentration_units:uM

patient_age:Newborn (0-30 days old)

patient_sex:Not Specified

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

8:

biospecimen:Blood

concentration_value:0.000810 +/- 0.00140

concentration_units:uM

patient_age:Children (1-13 years old)

patient_sex:Not Specified

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

9:

biospecimen:Blood

concentration_value:0.000900-0.00420

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Male

patient_information:X-linked ichthyosis

10:

biospecimen:Blood

concentration_value:0.0017

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Male

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

11:

biospecimen:Blood

concentration_value:0.0041

concentration_units:uM

patient_age:Adolescent (13-18 years old)

patient_sex:Male

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

12:

biospecimen:Blood

concentration_value:0.00175-0.0770

concentration_units:uM

patient_age:Newborn (0-30 days old)

patient_sex:Both

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

13:

biospecimen:Blood

concentration_value:0.000270-0.0480

concentration_units:uM

patient_age:Children (1-13 years old)

patient_sex:Both

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

14:

biospecimen:Blood

concentration_value:0.000570 +/- 0.000200

concentration_units:uM

patient_age:Children (1-13 years old)

patient_sex:Both

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

15:

biospecimen:Blood

concentration_value:0.00103 +/- 0.00100

concentration_units:uM

patient_age:Infant (0-1 year old)

patient_sex:Not Specified

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

16:

biospecimen:Blood

concentration_value:0.00380 +/- 0.00100

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Male

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

17:

biospecimen:Blood

concentration_value:0.00430 +/- 0.00180

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

18:

biospecimen:Blood

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Male

patient_information:Schizophrenia

19:

biospecimen:Blood

concentration_value:<0.00003

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:Lipoid Adrenal Hyperplasia

20:

biospecimen:Blood

concentration_value:<0.00003

concentration_units:uM

patient_age:Adolescent (13-18 years old)

patient_sex:Female

patient_information:Lipoid Adrenal Hyperplasia

21:

biospecimen:Blood

concentration_value:0.00279-0.00454

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

22:

biospecimen:Blood

concentration_value:0.12

concentration_units:uM

patient_age:Newborn (0-30 days old)

patient_sex:Female

patient_information:11-beta-hydroxylase deficiency

23:

biospecimen:Blood

concentration_value:0.00360-0.0227

concentration_units:uM

patient_age:Children (1-13 years old)

patient_sex:Both

patient_information:11-beta-hydroxylase deficiency

24:

biospecimen:Blood

concentration_value:0.0090 +/- 0.0046

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:Polycystic ovary syndrome (PCOS)

25:

biospecimen:Blood

concentration_value:0.0090 +/- 0.0065

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Cushing's syndrome

26:

biospecimen:Blood

concentration_value:0.0031 +/- 0.0030

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Cushing's syndrome

27:

biospecimen:Blood

concentration_value:0.000873

concentration_units:uM

patient_age:Newborn (0-30 days old)

patient_sex:Female

patient_information:Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete

28:

biospecimen:Urine

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:Ovarian cancer

29:

biospecimen:Urine

concentration_value:0.090 +/- 0.073

concentration_units:umol/mmol creatinine

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:Thyroid cancer

30:

biospecimen:Urine

concentration_value:0.0017 +/- 0.00034

concentration_units:umol/mmol creatinine

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Rheumatoid arthritis

31:

biospecimen:Urine

concentration_value:0.0025 +/- 0.00071

concentration_units:umol/mmol creatinine

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Rheumatoid arthritis

32:

biospecimen:Urine

concentration_value:0.0025 +/- 0.00042

concentration_units:umol/mmol creatinine

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Systemic lupus erythematosus (SLE)

33:

biospecimen:Urine

concentration_value:0.0047 +/- 0.0005

concentration_units:umol/mmol creatinine

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Systemic lupus erythematosus (SLE)

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1:

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4:

name:Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency

omim_id:201810

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name:11-beta-Hydroxylase deficiency

omim_id:202010

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6:

name:21-Hydroxylase deficiency

omim_id:201910

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reference_text:Gmyrek GA, New MI, Sosa RE, Poppas DP: Bilateral laparoscopic adrenalectomy as a treatment for classic congenital adrenal hyperplasia attributable to 21-hydroxylase deficiency. Pediatrics. 2002 Feb;109(2):E28.

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reference_text:MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)

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7:

name:Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete

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reference_text:Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8.

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8:

name:Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency

omim_id:201910

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reference_text:Janzen N, Peter M, Sander S, Steuerwald U, Terhardt M, Holtkamp U, Sander J: Newborn screening for congenital adrenal hyperplasia: additional steroid profile using liquid chromatography-tandem mass spectrometry. J Clin Endocrinol Metab. 2007 Jul;92(7):2581-9. Epub 2007 Apr 24.

pubmed_id:17456574

[2]:

reference_text:Homoki J, Teller WM: Increased urinary excretion of total 16 alpha-hydroxypregnenolone in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Klin Wochenschr. 1982 Apr 15;60(8):407-10.

pubmed_id:6980322

[3]:

reference_text:Schwarz E, Liu A, Randall H, Haslip C, Keune F, Murray M, Longo N, Pasquali M: Use of steroid profiling by UPLC-MS/MS as a second tier test in newborn screening for congenital adrenal hyperplasia: the Utah experience. Pediatr Res. 2009 Aug;66(2):230-5. doi: 10.1203/PDR.0b013e3181aa3777.

pubmed_id:19390483

9:

name:X-linked ichthyosis

omim_id:308100

[1]:

reference_text:Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93.

pubmed_id:3864567

10:

name:Lipoid Congenital Adrenal Hyperplasia

omim_id:201710

[1]:

reference_text:Fujieda K, Tajima T, Nakae J, Sageshima S, Tachibana K, Suwa S, Sugawara T, Strauss JF 3rd: Spontaneous puberty in 46,XX subjects with congenital lipoid adrenal hyperplasia. Ovarian steroidogenesis is spared to some extent despite inactivating mutations in the steroidogenic acute regulatory protein (StAR) gene. J Clin Invest. 1997 Mar 15;99(6):1265-71. doi: 10.1172/JCI119284.

pubmed_id:9077535

[2]:

reference_text:Hauffa BP, Miller WL, Grumbach MM, Conte FA, Kaplan SL: Congenital adrenal hyperplasia due to deficient cholesterol side-chain cleavage activity (20, 22-desmolase) in a patient treated for 18 years. Clin Endocrinol (Oxf). 1985 Nov;23(5):481-93.

pubmed_id:3841304

11:

name:Rheumatoid arthritis

omim_id:180300

[1]:

reference_text:Laitinen O, Seppala E, Nissila M, Vapaatalo H: Plasma levels and urinary excretion of prostaglandins in patients with rheumatoid arthritis. Clin Rheumatol. 1983 Dec;2(4):401-6.

pubmed_id:6589104

[2]:

reference_text:Chiang EP, Smith DE, Selhub J, Dallal G, Wang YC, Roubenoff R: Inflammation causes tissue-specific depletion of vitamin B6. Arthritis Res Ther. 2005;7(6):R1254-62. Epub 2005 Sep 13.

pubmed_id:16277678

[3]:

reference_text:Jensen T, Klarlund M, Hansen M, Jensen KE, Skjodt H, Hyldstrup L: Connective tissue metabolism in patients with unclassified polyarthritis and early rheumatoid arthritis. Relationship to disease activity, bone mineral density, and radiographic outcome. J Rheumatol. 2004 Sep;31(9):1698-708.

pubmed_id:15338487

[4]:

reference_text:Chavis C, Fraissinet L, Chanez P, Thomas E, Bousquet J: A method for the measurement of plasma hydroxyeicosatetraenoic acid levels. Anal Biochem. 1999 Jun 15;271(1):105-8.

pubmed_id:10361015

[5]:

reference_text:Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8.

pubmed_id:15249323

[6]:

reference_text:Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70: https://link.springer.com/article/10.1007/s11306-016-1000-2

12:

name:Thyroid cancer

omim_id:

[1]:

reference_text:Sakai T, Yamamoto K, Yokota H, Hakozaki-Usui K, Hino F, Kato I: Rapid, simple enzymatic assay of free L-fucose in serum and urine, and its use as a marker for cancer, cirrhosis, and gastric ulcers. Clin Chem. 1990 Mar;36(3):474-6.

pubmed_id:2311216

[2]:

reference_text:Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9.

pubmed_id:14643447

[3]:

reference_text:Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamine concentrations in pancreatic tissue, serum, and urine of patients with pancreatic cancer. Pancreas. 1990 Mar;5(2):119-27.

pubmed_id:2315288

13:

name:Ovarian cancer

omim_id:167000

[1]:

reference_text:Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8.

pubmed_id:7482520

[2]:

reference_text:Lakhani NJ, Lepper ER, Sparreboom A, Dahut WL, Venitz J, Figg WD: Determination of 2-methoxyestradiol in human plasma, using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(9):1176-82.

pubmed_id:15818726

[3]:

reference_text:Zhang T, Wu X, Yin M, Fan L, Zhang H, Zhao F, Zhang W, Ke C, Zhang G, Hou Y, Zhou X, Lou G, Li K: Discrimination between malignant and benign ovarian tumors by plasma metabolomic profiling using ultra performance liquid chromatography/mass spectrometry. Clin Chim Acta. 2012 May 18;413(9-10):861-8. doi: 10.1016/j.cca.2012.01.026. Epub 2012 Jan 30.

pubmed_id:22309680

[4]:

reference_text:Woo HM, Kim KM, Choi MH, Jung BH, Lee J, Kong G, Nam SJ, Kim S, Bai SW, Chung BC: Mass spectrometry based metabolomic approaches in urinary biomarker study of women's cancers. Clin Chim Acta. 2009 Feb;400(1-2):63-9. doi: 10.1016/j.cca.2008.10.014. Epub 2008 Oct 30.

pubmed_id:19010317

[5]:

reference_text:Gaul DA, Mezencev R, Long TQ, Jones CM, Benigno BB, Gray A, Fernandez FM, McDonald JF: Highly-accurate metabolomic detection of early-stage ovarian cancer. Sci Rep. 2015 Nov 17;5:16351. doi: 10.1038/srep16351.

pubmed_id:26573008

KEGG数据库编号
C00280
DrugBank数据库编号
DB01536
foodb数据库编号
FDB030678
ChemSpider数据库编号
5898
公共化学化合物编号
6128
PDB数据库编号
生物利益的化学实体数据库编号
16422
knapsack数据库编号
C00003644
维基百科编号
Androstenedione
代谢途径的数据库编号
ANDROST4ENE
苯酚资源管理器化合物数据库编号
比格数据库编号
2210012
梅林编号
2795
虚拟机身份证编号
ANDRSTNDN
fbonto数据库编号
综合参考
Egorova, Olga V.; Gulevskaya, Seraphima A.; Puntus, Irina F.; Filonov, Andrey E.; Donova, Marina V. Production of androstenedione using mutants of Mycobacterium sp. Journal of Chemical Technology and Biotechnology (2002), 77(2), 141-147.
一般参考
1:

protein_accession:HMDBP00360

name:Aldo-keto reductase family 1 member C3

uniprot_id:P42330

gene_name:AKR1C3

protein_type:Unknown

2:

protein_accession:HMDBP00445

name:Cytochrome P450 11B1, mitochondrial

uniprot_id:P15538

gene_name:CYP11B1

protein_type:Unknown

3:

protein_accession:HMDBP00447

name:Estradiol 17-beta-dehydrogenase 2

uniprot_id:P37059

gene_name:HSD17B2

protein_type:Unknown

4:

protein_accession:HMDBP00453

name:Estradiol 17-beta-dehydrogenase 8

uniprot_id:Q92506

gene_name:HSD17B8

protein_type:Unknown

5:

protein_accession:HMDBP00550

name:3-oxo-5-beta-steroid 4-dehydrogenase

uniprot_id:P51857

gene_name:AKR1D1

protein_type:Enzyme

6:

protein_accession:HMDBP00698

name:3-oxo-5-alpha-steroid 4-dehydrogenase 2

uniprot_id:P31213

gene_name:SRD5A2

protein_type:Enzyme

7:

protein_accession:HMDBP00699

name:3-oxo-5-alpha-steroid 4-dehydrogenase 1

uniprot_id:P18405

gene_name:SRD5A1

protein_type:Enzyme

8:

protein_accession:HMDBP00846

name:Testosterone 17-beta-dehydrogenase 3

uniprot_id:P37058

gene_name:HSD17B3

protein_type:Enzyme

9:

protein_accession:HMDBP01018

name:Cytochrome P450 3A4

uniprot_id:P08684

gene_name:CYP3A4

protein_type:Unknown

10:

protein_accession:HMDBP01036

name:Cytochrome P450 2C9

uniprot_id:P11712

gene_name:CYP2C9

protein_type:Unknown

11:

protein_accession:HMDBP01038

name:Cytochrome P450 2C19

uniprot_id:P33261

gene_name:CYP2C19

protein_type:Unknown

12:

protein_accession:HMDBP01043

name:Steroid 17-alpha-hydroxylase/17,20 lyase

uniprot_id:P05093

gene_name:CYP17A1

protein_type:Unknown

13:

protein_accession:HMDBP01544

name:Cytochrome P450 2E1

uniprot_id:P05181

gene_name:CYP2E1

protein_type:Unknown

14:

protein_accession:HMDBP01546

name:Cytochrome P450 3A43

uniprot_id:Q9HB55

gene_name:CYP3A43

protein_type:Unknown

15:

protein_accession:HMDBP01547

name:Cytochrome P450 1B1

uniprot_id:Q16678

gene_name:CYP1B1

protein_type:Unknown

16:

protein_accession:HMDBP01549

name:Cytochrome P450 2C18

uniprot_id:P33260

gene_name:CYP2C18

protein_type:Unknown

17:

protein_accession:HMDBP01551

name:Cytochrome P450 2F1

uniprot_id:P24903

gene_name:CYP2F1

protein_type:Unknown

18:

protein_accession:HMDBP01552

name:Cytochrome P450 4X1

uniprot_id:Q8N118

gene_name:CYP4X1

protein_type:Unknown

19:

protein_accession:HMDBP01553

name:Cytochrome P450 2B6

uniprot_id:P20813

gene_name:CYP2B6

protein_type:Unknown

20:

protein_accession:HMDBP01554

name:Cytochrome P450 3A5

uniprot_id:P20815

gene_name:CYP3A5

protein_type:Unknown

21:

protein_accession:HMDBP01556

name:Cytochrome P450 2A13

uniprot_id:Q16696

gene_name:CYP2A13

protein_type:Unknown

22:

protein_accession:HMDBP01557

name:Cytochrome P450 3A7

uniprot_id:P24462

gene_name:CYP3A7

protein_type:Unknown

23:

protein_accession:HMDBP01558

name:Cytochrome P450 4B1

uniprot_id:P13584

gene_name:CYP4B1

protein_type:Unknown

24:

protein_accession:HMDBP01559

name:Cytochrome P450 4Z1

uniprot_id:Q86W10

gene_name:CYP4Z1

protein_type:Unknown

25:

protein_accession:HMDBP01560

name:Cytochrome P450 1A2

uniprot_id:P05177

gene_name:CYP1A2

protein_type:Unknown

26:

protein_accession:HMDBP01561

name:Cytochrome P450 19A1

uniprot_id:P11511

gene_name:CYP19A1

protein_type:Unknown

27:

protein_accession:HMDBP01562

name:Cytochrome P450 2C8

uniprot_id:P10632

gene_name:CYP2C8

protein_type:Unknown

28:

protein_accession:HMDBP01563

name:Cytochrome P450 2S1

uniprot_id:Q96SQ9

gene_name:CYP2S1

protein_type:Unknown

29:

protein_accession:HMDBP01565

name:Cytochrome P450 2J2

uniprot_id:P51589

gene_name:CYP2J2

protein_type:Unknown

30:

protein_accession:HMDBP01566

name:Cytochrome P450 2A7

uniprot_id:P20853

gene_name:CYP2A7

protein_type:Unknown

31:

protein_accession:HMDBP01567

name:Cytochrome P450 2A6

uniprot_id:P11509

gene_name:CYP2A6

protein_type:Unknown

32:

protein_accession:HMDBP01624

name:Androgen receptor

uniprot_id:P10275

gene_name:AR

protein_type:Enzyme

33:

protein_accession:HMDBP02582

name:Leptin

uniprot_id:P41159

gene_name:LEP

protein_type:Enzyme

34:

protein_accession:HMDBP02862

name:17-beta-hydroxysteroid dehydrogenase type 6

uniprot_id:O14756

gene_name:HSD17B6

protein_type:Unknown

35:

protein_accession:HMDBP04403

name:3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

uniprot_id:P14060

gene_name:HSD3B1

protein_type:Unknown

36:

protein_accession:HMDBP04404

name:3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2

uniprot_id:P26439

gene_name:HSD3B2

protein_type:Unknown

37:

protein_accession:HMDBP05268

name:Cytochrome P450 11B2, mitochondrial

uniprot_id:P19099

gene_name:CYP11B2

protein_type:Unknown

38:

protein_accession:HMDBP07417

name:Cytochrome P450, family 1, subfamily A, polypeptide 1

uniprot_id:A0N0X8

gene_name:CYP1A1

protein_type:Enzyme

39:

protein_accession:HMDBP09115

name:HSD17B3 protein

uniprot_id:Q6FH62

gene_name:HSD17B3

protein_type:Enzyme

40:

protein_accession:HMDBP09117

name:Mutated cytochrome P-450c11 protein

uniprot_id:Q8TDD0

gene_name:

protein_type:Enzyme

41:

protein_accession:HMDBP09118

name:Cytochrome P450, family 17, subfamily A, polypeptide 1

uniprot_id:Q1HB44

gene_name:CYP17A1

protein_type:Enzyme

42:

protein_accession:HMDBP09188

name:Polyprenol reductase

uniprot_id:Q9H8P0

gene_name:SRD5A3

protein_type:Enzyme

43:

protein_accession:HMDBP09335

name:Cytochrome P450 2D6

uniprot_id:Q6NWU0

gene_name:CYP2D6

protein_type:Enzyme

蛋白质结合
1:

reference_text:Berkovitz GD, Guerami A, Brown TR, MacDonald PC, Migeon CJ: Familial gynecomastia with increased extraglandular aromatization of plasma carbon19-steroids. J Clin Invest. 1985 Jun;75(6):1763-9.

pubmed_id:3924954

2:

reference_text:Cutolo M, Sulli A, Capellino S, Villaggio B, Montagna P, Pizzorni C, Paolino S, Seriolo B, Felli L, Straub RH: Anti-TNF and sex hormones. Ann N Y Acad Sci. 2006 Jun;1069:391-400.

pubmed_id:16855166

3:

reference_text:Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82.

pubmed_id:1620285

4:

reference_text:van Vloten WA, van Haselen CW, van Zuuren EJ, Gerlinger C, Heithecker R: The effect of 2 combined oral Contraceptives containing either drospirenone or cyproterone acetate on acne and seborrhea. Cutis. 2002 Apr;69(4 Suppl):2-15.

pubmed_id:12096825

5:

reference_text:Jasuja R, Ramaraj P, Mac RP, Singh AB, Storer TW, Artaza J, Miller A, Singh R, Taylor WE, Lee ML, Davidson T, Sinha-Hikim I, Gonzalez-Cadavid N, Bhasin S: Delta-4-androstene-3,17-dione binds androgen receptor, promotes myogenesis in vitro, and increases serum testosterone levels, fat-free mass, and muscle strength in hypogonadal men. J Clin Endocrinol Metab. 2005 Feb;90(2):855-63. Epub 2004 Nov 2.

pubmed_id:15522925

6:

reference_text:Egloff M, Savoure N, Tardivel-Lacombe J, Massart C, Nicol M, Degrelle H: Influence of sex hormone binding globulin and serum albumin on the conversion of androstenedione to testosterone by human erythrocytes. Acta Endocrinol (Copenh). 1981 Jan;96(1):136-40.

pubmed_id:7192922

7:

reference_text:Zarrilli S, Lombardi G, Paesano L, Di Somma C, Colao A, Mirone V, De Rosa M: Hormonal and seminal evaluation of Leydig cell tumour patients before and after orchiectomy. Andrologia. 2000 May;32(3):147-54.

pubmed_id:10863969

8:

reference_text:Heikkila R, Aho K, Heliovaara M, Hakama M, Marniemi J, Reunanen A, Knekt P: Serum testosterone and sex hormone-binding globulin concentrations and the risk of prostate carcinoma: a longitudinal study. Cancer. 1999 Jul 15;86(2):312-5.

pubmed_id:10421267

9:

reference_text:Schlaghecke R, Kley HK, Kruskemper HL: The measurement of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) by radioimmunoassay in human plasma. Steroids. 1984 Jul;44(1):23-33.

pubmed_id:6100340

10:

reference_text:King DS, Sharp RL, Vukovich MD, Brown GA, Reifenrath TA, Uhl NL, Parsons KA: Effect of oral androstenedione on serum testosterone and adaptations to resistance training in young men: a randomized controlled trial. JAMA. 1999 Jun 2;281(21):2020-8.

pubmed_id:10359391

11:

reference_text:Johansson A, Henriksson A, Olofsson BO, Olsson T: Adrenal steroid dysregulation in dystrophia myotonica. J Intern Med. 1999 Apr;245(4):345-51.

pubmed_id:10356596

12:

reference_text:Atkinson G, Campbell DJ, Cawood ML, Oakey RE: Steroids in human intrauterine fluids of early pregnancy. Clin Endocrinol (Oxf). 1996 Apr;44(4):435-40.

pubmed_id:8706310

13:

reference_text:Zarrilli S, Paesano L, Mirone V, Finelli L, De Rosa M: [Evaluation of seminal and hormonal parameters in idiopathic varicocele before and after surgical intervention]. Chir Ital. 1998 Mar-Aug;50(2-4):21-8.

pubmed_id:11762080

14:

reference_text:Berria R, Gastaldelli A, Lucidi S, Belfort R, De Filippis E, Easton C, Brytzki R, Cusi K, Jovanovic L, DeFronzo R: Reduction in hematocrit level after pioglitazone treatment is correlated with decreased plasma free testosterone level, not hemodilution, in women with polycystic ovary syndrome. Clin Pharmacol Ther. 2006 Aug;80(2):105-14. Epub 2006 Jun 30.

pubmed_id:16890572

15:

reference_text:Thomson S, Wallace AM, Cook B: A 125I-radioimmunoassay for measuring androstenedione in serum and in blood-spot samples from neonates. Clin Chem. 1989 Aug;35(8):1706-12.

pubmed_id:2758640

16:

reference_text:Riikonen RS: How do cryptogenic and symptomatic infantile spasms differ? Review of biochemical studies in Finnish patients. J Child Neurol. 1996 Sep;11(5):383-8.

pubmed_id:8877606

17:

reference_text:Azurmendi A, Braza F, Sorozabal A, Garcia A, Braza P, Carreras MR, Munoz JM, Cardas J, Sanchez-Martin JR: Cognitive abilities, androgen levels, and body mass index in 5-year-old children. Horm Behav. 2005 Aug;48(2):187-95.

pubmed_id:15878571

18:

reference_text:Schairer C, Hill D, Sturgeon SR, Fears T, Mies C, Ziegler RG, Hoover RN, Sherman ME: Serum concentrations of estrogens, sex hormone binding globulin, and androgens and risk of breast hyperplasia in postmenopausal women. Cancer Epidemiol Biomarkers Prev. 2005 Jul;14(7):1660-5.

pubmed_id:16030098

19:

reference_text:Feldman PS, Kovacs K, Horvath E, Adelson GL: Malignant Leydig cell tumor: clinical, histologic and electron microscopic features. Cancer. 1982 Feb 15;49(4):714-21.

pubmed_id:7055782

20:

reference_text:Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.

pubmed_id:11413487

21:

reference_text:Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.

pubmed_id:16902246

22:

reference_text:Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.

pubmed_id:17374880

23:

reference_text:Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.

pubmed_id:20044567

24:

reference_text:The lipid handbook with CD-ROM

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