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
HMDB0000031
地位
quantified
二级访问
HMDB00031

名称
Androsterone
描述
Androsterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone can also be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone, or androstenedione, and is considered an inactive end product. However, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role of uridine-diphospho-glucuronosyltransferase enzymes (EC 2.4.1.17, UGT) for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and it is widely recognized that the liver is a major site of glucuronidation. However, it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid, and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanolone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution (PMID: 9188497, 17017935, 14643063, 12943709, 9699884, 17260133).
同义词
1:(3alpha,5alpha)-3-Hydroxyandrostan-17-one

2:3-Epihydroxyetioallocholan-17-one

3:3alpha-Hydroxy-5alpha-androstan-17-one

4:3alpha-Hydroxyetioallocholan-17-one

5:5alpha-Androstane-3alpha-ol-17-one

6:5alpha-Androsterone

7:Androkinine

8:Androtine

9:cis-Androsterone

10:(3a,5a)-3-Hydroxyandrostan-17-one

11:(3Α,5α)-3-hydroxyandrostan-17-one

12:3a-Hydroxy-5a-androstan-17-one

13:3Α-hydroxy-5α-androstan-17-one

14:3a-Hydroxyetioallocholan-17-one

15:3Α-hydroxyetioallocholan-17-one

16:5a-Androstane-3a-ol-17-one

17:5Α-androstane-3α-ol-17-one

18:5a-Androsterone

19:5Α-androsterone

20:3-alpha-Hydroxy-5-alpha-androstan-17-one

21:3 alpha Hydroxy 5 alpha androstan 17 one

22:5 alpha Androstan 3 alpha ol 17 one

23:5 alpha-Androstan-3 alpha-ol-17-one

24:Epiandrosterone

25:3-alpha-Hydroxy-17-androstanone

26:3-alpha-Hydroxy-5-alpha-androstane-17-one

27:3-alpha-Hydroxy-5alpha-androstan-17-one

28:3-alpha-Hydroxyetioallocholan-17-one

29:3-Hydroxy-(3-alpha,5-alpha)-androstan-17-one

30:3-Hydroxyandrostan-17-one

31:3alpha-Hydroxy-17-androstanone

32:5-alpha-Androstan-3-alpha-ol-17-one

33:5-alpha-Androstane-3alpha-ol-17-one

34:5-alpha-Androsterone

35:Androstanon-3-alpha-ol-17-one

36:Atromide ici

37:3Α-hydroxy-17-androstanone

38:3Α-hydroxy-5α-androstane-17-one

39:5Α-androstan-17-one-3α-ol

40:5Α-androstan-3α-ol-17-one

41:3alpha-Hydroxy-5alpha-androstane-17-one

42:5alpha-Androstan-17-one-3alpha-ol

43:5alpha-Androstan-3alpha-ol-17-one

44:Androsterone

化学式
C19H30O2
平均分子量
290.4403
等位分子量
290.224580204
化学名称
(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
传统名称
(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
CAS 登记号
53-41-8
代谢物结构字符串
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
inchi标识符
InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1
印记键
QGXBDMJGAMFCBF-HLUDHZFRSA-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-alpha-hydroxysteroids

3:Cyclic alcohols and derivatives

4:Hydrocarbon derivatives

5:Ketones

6:Organic oxides

7:Secondary alcohols

8:17-oxosteroid

9:3-alpha-hydroxysteroid

10:3-hydroxysteroid

11:Alcohol

12:Aliphatic homopolycyclic compound

13:Androgen-skeleton

14:Carbonyl group

15:Cyclic alcohol

16:Hydrocarbon derivative

17:Hydroxysteroid

18:Ketone

19:Organic oxide

20:Organic oxygen compound

21:Organooxygen compound

22:Oxosteroid

23:Secondary alcohol

24:17-oxo steroid

25:3alpha-hydroxy steroid

26:Androstane and derivatives

27:C19 steroids (androgens) and derivatives

28:C19 steroids (androgens) and derivatives

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: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: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

definition:A living organism (species or a higher taxonomy rank), in which a chemical can be found.

parent_id:7735

**level:3

type:parent

term:Animal

definition:A living organism belonging to the kingdom animalia. it feeds on organic matter, typically having specialized sense organs and nervous system and able to respond rapidly to stimuli.

parent_id:7736

***level:4

type:child

synonym:Fauna

term:Biological location

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

parent_id:7724

*level:2

type:parent

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: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: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: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: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:Intestine

definition:The portion of the gastrointestinal tract that includes the small and large intestines.

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: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: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: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

状态
Solid
实验性质
1:

kind:water_solubility

value:0.012 mg/mL at 23 °C

source:

2:

kind:logp

value:3.69

source:HANSCH,C ET AL. (1995)

3:

kind:melting_point

value:185 °C

source:

预测性质
1:

kind:logp

value:3.71

source:ALOGPS

2:

kind:logs

value:-4.66

source:ALOGPS

3:

kind:solubility

value:0.0063 g/L

source:ALOGPS

4:

kind:logp

value:3.77

source:ChemAxon

5:

kind:pka_strongest_acidic

value:18.3

source:ChemAxon

6:

kind:pka_strongest_basic

value:-1.4

source:ChemAxon

7:

kind:iupac

value:(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one

source:ChemAxon

8:

kind:average_mass

value:290.4403

source:ChemAxon

9:

kind:mono_mass

value:290.224580204

source:ChemAxon

10:

kind:smiles

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

source:ChemAxon

11:

kind:formula

value:C19H30O2

source:ChemAxon

12:

kind:inchi

value:InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1

source:ChemAxon

13:

kind:inchikey

value:QGXBDMJGAMFCBF-HLUDHZFRSA-N

source:ChemAxon

14:

kind:polar_surface_area

value:37.3

source:ChemAxon

15:

kind:refractivity

value:83.81

source:ChemAxon

16:

kind:polarizability

value:34.56

source:ChemAxon

17:

kind:rotatable_bond_count

value:0

source:ChemAxon

18:

kind:acceptor_count

value:2

source:ChemAxon

19:

kind:donor_count

value:1

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):Intestine

tissue:(2):Prostate

tissue:(3):Testis

4:

[1]:

name:Androstenedione Metabolism

smpdb_id:SMP30406

kegg_map_id:

正常浓度
1:

biospecimen:Blood

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

2:

biospecimen:Blood

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

3:

biospecimen:Blood

concentration_value:0.00065 (0.00053-0.00088)

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

4:

biospecimen:Blood

concentration_value:0.12 +/- 0.014

concentration_units:uM

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

5:

biospecimen:Urine

concentration_value:0.69-96.48

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

6:

biospecimen:Urine

concentration_value:0.27 (0.23-0.33)

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Male

subject_condition:Normal

7:

biospecimen:Urine

concentration_value:0.16 (0.11-0.18)

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

8:

biospecimen:Urine

concentration_value:0.66

concentration_units:umol/mmol creatinine

subject_age:Children (1-13 years old)

subject_sex:Both

subject_condition:Normal

9:

biospecimen:Urine

concentration_value:6.69 +/- 1.65

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

10:

biospecimen:Urine

concentration_value:

concentration_units:

subject_age:Adult (>18 years old)

subject_sex:Both

subject_condition:Normal

11:

biospecimen:Urine

concentration_value:0.36 (0.11-0.67)

concentration_units:umol/mmol creatinine

subject_age:Adult (>18 years old)

subject_sex:Female

subject_condition:Normal

异常浓度
1:

biospecimen:Blood

concentration_value:

concentration_units:

patient_age:Adult (>18 years old)

patient_sex:Male

patient_information:Schizophrenia

2:

biospecimen:Cerebrospinal Fluid (CSF)

concentration_value:0.00007167 +/- 0.000119

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Not Specified

patient_information:Leuprolide acetate-induced hypogonadism

3:

biospecimen:Cerebrospinal Fluid (CSF)

concentration_value:0.000142 +/- 0.00009475

concentration_units:uM

patient_age:Adult (>18 years old)

patient_sex:Not Specified

patient_information:Leuprolide acetate-induced hypogonadism with testosterone replacment

4:

biospecimen:Urine

concentration_value:0.000092 +/- 0.000082

concentration_units:umol/mmol creatinine

patient_age:Adult (>18 years old)

patient_sex:Both

patient_information:Stress urinary incontinence

5:

biospecimen:Urine

concentration_value:0.77 +/- 0.08

concentration_units:umol/mmol creatinine

patient_age:Adult (>18 years old)

patient_sex:Female

patient_information:Hirsutism

疾病参考
1:

name:Schizophrenia

omim_id:181500

[1]:

reference_text:Harnryd C, Bjerkenstedt L, Grimm VE, Sedvall G: Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment. Psychopharmacology (Berl). 1979 Aug 8;64(2):131-4.

pubmed_id:115032

[2]:

reference_text:Kobayashi K, Koide Y, Yoshino K, Shohmori T: [P-hydroxyphenylacetic acid concentrations in cerebrospinal fluid]. No To Shinkei. 1982 Aug;34(8):769-74.

pubmed_id:7126379

[3]:

reference_text:Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7.

pubmed_id:2480613

[4]:

reference_text:Heresco-Levy U, Bar G, Levin R, Ermilov M, Ebstein RP, Javitt DC: High glycine levels are associated with prepulse inhibition deficits in chronic schizophrenia patients. Schizophr Res. 2007 Mar;91(1-3):14-21. Epub 2007 Feb 2.

pubmed_id:17276036

[5]:

reference_text:Walker EF, Bonsall R, Walder DJ: Plasma hormones and catecholamine metabolites in monozygotic twins discordant for psychosis. Neuropsychiatry Neuropsychol Behav Neurol. 2002 Mar;15(1):10-7.

pubmed_id:11877547

[6]:

reference_text:Hashimoto K, Fukushima T, Shimizu E, Komatsu N, Watanabe H, Shinoda N, Nakazato M, Kumakiri C, Okada S, Hasegawa H, Imai K, Iyo M: Decreased serum levels of D-serine in patients with schizophrenia: evidence in support of the N-methyl-D-aspartate receptor hypofunction hypothesis of schizophrenia. Arch Gen Psychiatry. 2003 Jun;60(6):572-6.

pubmed_id:12796220

[7]:

reference_text:Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62.

pubmed_id:7595563

[8]:

reference_text:Nikisch G, Baumann P, Wiedemann G, Kiessling B, Weisser H, Hertel A, Yoshitake T, Kehr J, Mathe AA: Quetiapine and norquetiapine in plasma and cerebrospinal fluid of schizophrenic patients treated with quetiapine: correlations to clinical outcome and HVA, 5-HIAA, and MHPG in CSF. J Clin Psychopharmacol. 2010 Oct;30(5):496-503. doi: 10.1097/JCP.0b013e3181f2288e.

pubmed_id:20814316

[9]:

reference_text:Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014.

pubmed_id:25004141

[10]:

reference_text:Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19.

pubmed_id:24713860

[11]:

reference_text:Ballesteros A, Summerfelt A, Du X, Jiang P, Chiappelli J, Tagamets M, O'Donnell P, Kochunov P, Hong LE: Electrophysiological intermediate biomarkers for oxidative stress in schizophrenia. Clin Neurophysiol. 2013 Nov;124(11):2209-15. doi: 10.1016/j.clinph.2013.05.021. Epub 2013 Jun 30.

pubmed_id:23823132

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reference_text:Bjerkenstedt L, Edman G, Hagenfeldt L, Sedvall G, Wiesel FA: Plasma amino acids in relation to cerebrospinal fluid monoamine metabolites in schizophrenic patients and healthy controls. Br J Psychiatry. 1985 Sep;147:276-82.

pubmed_id:2415198

[13]:

reference_text:Pickar D, Breier A, Hsiao JK, Doran AR, Wolkowitz OM, Pato CN, Konicki PE, Potter WZ: Cerebrospinal fluid and plasma monoamine metabolites and their relation to psychosis. Implications for regional brain dysfunction in schizophrenia. Arch Gen Psychiatry. 1990 Jul;47(7):641-8.

pubmed_id:1694425

[14]:

reference_text:Prell GD, Green JP, Kaufmann CA, Khandelwal JK, Morrishow AM, Kirch DG, Linnoila M, Wyatt RJ: Histamine metabolites in cerebrospinal fluid of patients with chronic schizophrenia: their relationships to levels of other aminergic transmitters and ratings of symptoms. Schizophr Res. 1995 Jan;14(2):93-104.

pubmed_id:7711000

[15]:

reference_text:Kim YK, Myint AM, Verkerk R, Scharpe S, Steinbusch H, Leonard B: Cytokine changes and tryptophan metabolites in medication-naive and medication-free schizophrenic patients. Neuropsychobiology. 2009;59(2):123-9. doi: 10.1159/000213565. Epub 2009 Apr 22.

pubmed_id:19390223

[16]:

reference_text:Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25.

pubmed_id:22024767

[17]:

reference_text:Xuan J, Pan G, Qiu Y, Yang L, Su M, Liu Y, Chen J, Feng G, Fang Y, Jia W, Xing Q, He L: Metabolomic profiling to identify potential serum biomarkers for schizophrenia and risperidone action. J Proteome Res. 2011 Dec 2;10(12):5433-43. doi: 10.1021/pr2006796. Epub 2011 Nov 8.

pubmed_id:22007635

[18]:

reference_text:Schwarz E, Guest PC, Rahmoune H, Harris LW, Wang L, Leweke FM, Rothermundt M, Bogerts B, Koethe D, Kranaster L, Ohrmann P, Suslow T, McAllister G, Spain M, Barnes A, van Beveren NJ, Baron-Cohen S, Steiner J, Torrey FE, Yolken RH, Bahn S: Identification of a biological signature for schizophrenia in serum. Mol Psychiatry. 2012 May;17(5):494-502. doi: 10.1038/mp.2011.42. Epub 2011 Apr 12.

pubmed_id:21483431

[19]:

reference_text:Mathe AA, Eberhard G, Saaf J, Wetterberg L: Plasma prostaglandin E2 metabolite--measured as 11-deoxy-15-keto-13,14-dihydro-11 beta,16 xi-cyclo-PGE2--in twins with schizophrenic disorder. Biol Psychiatry. 1986 Sep;21(11):1024-30.

pubmed_id:3741918

[20]:

reference_text:Kuloglu M, Ustundag B, Atmaca M, Canatan H, Tezcan AE, Cinkilinc N: Lipid peroxidation and antioxidant enzyme levels in patients with schizophrenia and bipolar disorder. Cell Biochem Funct. 2002 Jun;20(2):171-5.

pubmed_id:11979513

[21]:

reference_text:Zumarraga M, Davila R, Basterreche N, Arrue A, Goienetxea B, Zamalloa MI, Erkoreka L, Bustamante S, Inchausti L, Gonzalez-Torres MA, Guimon J: Catechol O-methyltransferase and monoamine oxidase A genotypes, and plasma catecholamine metabolites in bipolar and schizophrenic patients. Neurochem Int. 2010 May-Jun;56(6-7):774-9. doi: 10.1016/j.neuint.2010.02.015. Epub 2010 Mar 4.

pubmed_id:20206656

[22]:

reference_text:Peters JG: Dopamine, noradrenaline and serotonin spinal fluid metabolites in temporal lobe epileptic patients with schizophrenic symptomatology. Eur Neurol. 1979;18(1):15-8.

pubmed_id:436860

[23]:

reference_text:Yao JK, Dougherty GG Jr, Reddy RD, Keshavan MS, Montrose DM, Matson WR, Rozen S, Krishnan RR, McEvoy J, Kaddurah-Daouk R: Altered interactions of tryptophan metabolites in first-episode neuroleptic-naive patients with schizophrenia. Mol Psychiatry. 2010 Sep;15(9):938-53. doi: 10.1038/mp.2009.33. Epub 2009 Apr 28.

pubmed_id:19401681

[24]:

reference_text:Gattaz WF, Waldmeier P, Beckmann H: CSF monoamine metabolites in schizophrenic patients. Acta Psychiatr Scand. 1982 Nov;66(5):350-60.

pubmed_id:6184954

[25]:

reference_text:Nilsson-Todd LK, Nordin C, Jonsson EG, Skogh E, Erhardt S: Cerebrospinal fluid kynurenic acid in male patients with schizophrenia - correlation with monoamine metabolites. Acta Neuropsychiatr. 2007 Feb;19(1):45-52. doi: 10.1111/j.1601-5215.2006.00170.x.

pubmed_id:26952797

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reference_text:Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26.

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reference_text:Al Awam K, Haussleiter IS, Dudley E, Donev R, Brune M, Juckel G, Thome J: Multiplatform metabolome and proteome profiling identifies serum metabolite and protein signatures as prospective biomarkers for schizophrenia. J Neural Transm (Vienna). 2015 Aug;122 Suppl 1:S111-22. doi: 10.1007/s00702-014-1224-0. Epub 2014 May 1.

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reference_text:He Y, Yu Z, Giegling I, Xie L, Hartmann AM, Prehn C, Adamski J, Kahn R, Li Y, Illig T, Wang-Sattler R, Rujescu D: Schizophrenia shows a unique metabolomics signature in plasma. Transl Psychiatry. 2012 Aug 14;2:e149. doi: 10.1038/tp.2012.76.

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reference_text:Kaddurah-Daouk R, McEvoy J, Baillie RA, Lee D, Yao JK, Doraiswamy PM, Krishnan KR: Metabolomic mapping of atypical antipsychotic effects in schizophrenia. Mol Psychiatry. 2007 Oct;12(10):934-45. Epub 2007 Apr 17.

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reference_text:Fryar-Williams S, Strobel JE: Biomarkers of a five-domain translational substrate for schizophrenia and schizoaffective psychosis. Biomark Res. 2015 Feb 6;3:3. doi: 10.1186/s40364-015-0028-1. eCollection 2015.

pubmed_id:25729574

[32]:

reference_text:Oresic M, Seppanen-Laakso T, Sun D, Tang J, Therman S, Viehman R, Mustonen U, van Erp TG, Hyotylainen T, Thompson P, Toga AW, Huttunen MO, Suvisaari J, Kaprio J, Lonnqvist J, Cannon TD: Phospholipids and insulin resistance in psychosis: a lipidomics study of twin pairs discordant for schizophrenia. Genome Med. 2012 Jan 18;4(1):1. doi: 10.1186/gm300.

pubmed_id:22257447

2:

name:Hirsutism

omim_id:

[1]:

reference_text:Gilad S, Chayen R, Tordjman K, Kisch E, Stern N: Assessment of 5 alpha-reductase activity in hirsute women: comparison of serum androstanediol glucuronide with urinary androsterone and aetiocholanolone excretion. Clin Endocrinol (Oxf). 1994 Apr;40(4):459-64.

pubmed_id:8187312

KEGG数据库编号
C00523
DrugBank数据库编号
foodb数据库编号
FDB021881
ChemSpider数据库编号
5668
公共化学化合物编号
5879
PDB数据库编号
生物利益的化学实体数据库编号
16032
knapsack数据库编号
维基百科编号
Androsterone
代谢途径的数据库编号
苯酚资源管理器化合物数据库编号
比格数据库编号
35244
梅林编号
2797
虚拟机身份证编号
ANDRSTRN
fbonto数据库编号
综合参考
Marker, Russell E. Androsterone. Journal of the American Chemical Society (1935), 57 1755-6.
一般参考
1:

protein_accession:HMDBP00074

name:Aldo-keto reductase family 1 member C4

uniprot_id:P17516

gene_name:AKR1C4

protein_type:Unknown

2:

protein_accession:HMDBP00347

name:Bile salt sulfotransferase

uniprot_id:Q06520

gene_name:SULT2A1

protein_type:Enzyme

3:

protein_accession:HMDBP00360

name:Aldo-keto reductase family 1 member C3

uniprot_id:P42330

gene_name:AKR1C3

protein_type:Unknown

4:

protein_accession:HMDBP00386

name:Aldo-keto reductase family 1 member C1

uniprot_id:Q04828

gene_name:AKR1C1

protein_type:Unknown

5:

protein_accession:HMDBP00387

name:Aldo-keto reductase family 1 member C2

uniprot_id:P52895

gene_name:AKR1C2

protein_type:Unknown

6:

protein_accession:HMDBP00449

name:UDP-glucuronosyltransferase 2B28

uniprot_id:Q9BY64

gene_name:UGT2B28

protein_type:Enzyme

7:

protein_accession:HMDBP00458

name:UDP-glucuronosyltransferase 2B4

uniprot_id:P06133

gene_name:UGT2B4

protein_type:Enzyme

8:

protein_accession:HMDBP00478

name:UDP-glucuronosyltransferase 1-4

uniprot_id:P22310

gene_name:UGT1A4

protein_type:Enzyme

9:

protein_accession:HMDBP00479

name:UDP-glucuronosyltransferase 2B10

uniprot_id:P36537

gene_name:UGT2B10

protein_type:Enzyme

10:

protein_accession:HMDBP00480

name:UDP-glucuronosyltransferase 2B7

uniprot_id:P16662

gene_name:UGT2B7

protein_type:Enzyme

11:

protein_accession:HMDBP00481

name:UDP-glucuronosyltransferase 2B15

uniprot_id:P54855

gene_name:UGT2B15

protein_type:Enzyme

12:

protein_accession:HMDBP00482

name:UDP-glucuronosyltransferase 2A1

uniprot_id:Q9Y4X1

gene_name:UGT2A1

protein_type:Enzyme

13:

protein_accession:HMDBP00483

name:UDP-glucuronosyltransferase 1-1

uniprot_id:P22309

gene_name:UGT1A1

protein_type:Enzyme

14:

protein_accession:HMDBP00484

name:UDP-glucuronosyltransferase 1-9

uniprot_id:O60656

gene_name:UGT1A9

protein_type:Enzyme

15:

protein_accession:HMDBP00485

name:UDP-glucuronosyltransferase 1-8

uniprot_id:Q9HAW9

gene_name:UGT1A8

protein_type:Enzyme

16:

protein_accession:HMDBP00486

name:UDP-glucuronosyltransferase 1-3

uniprot_id:P35503

gene_name:UGT1A3

protein_type:Enzyme

17:

protein_accession:HMDBP00487

name:UDP-glucuronosyltransferase 1-10

uniprot_id:Q9HAW8

gene_name:UGT1A10

protein_type:Enzyme

18:

protein_accession:HMDBP00488

name:UDP-glucuronosyltransferase 2B17

uniprot_id:O75795

gene_name:UGT2B17

protein_type:Enzyme

19:

protein_accession:HMDBP00489

name:UDP-glucuronosyltransferase 1-6

uniprot_id:P19224

gene_name:UGT1A6

protein_type:Enzyme

20:

protein_accession:HMDBP00490

name:UDP-glucuronosyltransferase 1-5

uniprot_id:P35504

gene_name:UGT1A5

protein_type:Enzyme

21:

protein_accession:HMDBP00491

name:UDP-glucuronosyltransferase 2B11

uniprot_id:O75310

gene_name:UGT2B11

protein_type:Enzyme

22:

protein_accession:HMDBP00494

name:UDP-glucuronosyltransferase 1-7

uniprot_id:Q9HAW7

gene_name:UGT1A7

protein_type:Enzyme

23:

protein_accession:HMDBP01624

name:Androgen receptor

uniprot_id:P10275

gene_name:AR

protein_type:Enzyme

24:

protein_accession:HMDBP02607

name:Dehydrogenase/reductase SDR family member 9

uniprot_id:Q9BPW9

gene_name:DHRS9

protein_type:Enzyme

25:

protein_accession:HMDBP03004

name:Retinol dehydrogenase 16

uniprot_id:O75452

gene_name:RDH16

protein_type:Unknown

26:

protein_accession:HMDBP07348

name:UDP-glucuronosyltransferase 2A3

uniprot_id:Q6UWM9

gene_name:UGT2A3

protein_type:Enzyme

27:

protein_accession:HMDBP09238

name:HCG2039726, isoform CRA_f

uniprot_id:Q5DT02

gene_name:UGT1A10

protein_type:Enzyme

28:

protein_accession:HMDBP09239

name:HCG2039726, isoform CRA_e

uniprot_id:Q5DSZ6

gene_name:UGT1A8

protein_type:Enzyme

29:

protein_accession:HMDBP09240

name:UDP glycosyltransferase 1 family polypeptide A7

uniprot_id:Q5DSZ7

gene_name:UGT1A7

protein_type:Enzyme

蛋白质结合
1:

reference_text:Biswas MG, Russell DW: Expression cloning and characterization of oxidative 17beta- and 3alpha-hydroxysteroid dehydrogenases from rat and human prostate. J Biol Chem. 1997 Jun 20;272(25):15959-66.

pubmed_id:9188497

2:

reference_text:Muller L, Phillipou G: Quantification of 5 alpha- and 5 beta-androstanediols in urine by gas chromatography-mass spectrometry. Clin Chem. 1987 Feb;33(2 Pt 1):256-60.

pubmed_id:3802509

3:

reference_text:Schonberger W, Benes P, Morsches B, Zabel B, Scheidt E: [Improvement in the longitudinal growth in Ullrich-Turner syndrome with oxandrolone. Function of urinary excretion of steroid hormones]. Dtsch Med Wochenschr. 1982 Jul 2;107(26):1008-11.

pubmed_id:6211346

4:

reference_text:Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95.

pubmed_id:10625505

5:

reference_text:Labows JN, Preti G, Hoelzle E, Leyden J, Kligman A: Steroid analysis of human apocrine secretion. Steroids. 1979 Sep;34(3):249-58.

pubmed_id:158859

6:

reference_text:Raju U, Kadner S, Levitz M, Kaganowicz A, Blaustein A: Glucosiduronidation and esterification of androsterone by human breast tumors in vitro. Steroids. 1981 Apr;37(4):399-407.

pubmed_id:7245287

7:

reference_text:Kaminski RM, Marini H, Kim WJ, Rogawski MA: Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27.

pubmed_id:15946323

8:

reference_text:Grosse J, Anielski P, Hemmersbach P, Lund H, Mueller RK, Rautenberg C, Thieme D: Formation of 19-norsteroids by in situ demethylation of endogenous steroids in stored urine samples. Steroids. 2005 Jul;70(8):499-506. Epub 2005 Mar 29.

pubmed_id:15894033

9:

reference_text:Toth I, Faredin I: Steroids excreted by human skin. II. C19-steroid sulphates in human axillary sweat. Acta Med Hung. 1985;42(1-2):21-8.

pubmed_id:3162156

10:

reference_text:Teller WM, Homoki J, Wudy S, Schlickenrieder JH: Adrenarche is dissociated from gonadarche--studies in patients with Turner's syndrome. Acta Endocrinol Suppl (Copenh). 1986;279:232-40.

pubmed_id:2946134

11:

reference_text:Mitamura K, Setaka M, Shimada K, Honma S, Namiki M, Koh E, Mizokami A: Determination of sulfates of androsterone and epiandrosterone in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry. Biomed Chromatogr. 2005 Dec;19(10):796-801.

pubmed_id:15954157

12:

reference_text:Tchedam Ngatcha B, Luu-The V, Labrie F, Poirier D: Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship. J Med Chem. 2005 Aug 11;48(16):5257-68.

pubmed_id:16078844

13:

reference_text:Hammond GL: Endogenous steroid levels in the human prostate from birth to old age: a comparison of normal and diseased tissues. J Endocrinol. 1978 Jul;78(1):7-19.

pubmed_id:79632

14:

reference_text:Thevis M, Geyer H, Mareck U, Sigmund G, Henke J, Henke L, Schanzer W: Detection of manipulation in doping control urine sample collection: a multidisciplinary approach to determine identical urine samples. Anal Bioanal Chem. 2007 Aug;388(7):1539-43. Epub 2007 Jan 27.

pubmed_id:17260133

15:

reference_text:Matsuzaki Y, Honda A: Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents. Curr Pharm Des. 2006;12(26):3411-21.

pubmed_id:17017935

16:

reference_text:Belanger A, Pelletier G, Labrie F, Barbier O, Chouinard S: Inactivation of androgens by UDP-glucuronosyltransferase enzymes in humans. Trends Endocrinol Metab. 2003 Dec;14(10):473-9.

pubmed_id:14643063

17:

reference_text:Barbier O, Belanger A: The cynomolgus monkey (Macaca fascicularis) is the best animal model for the study of steroid glucuronidation. J Steroid Biochem Mol Biol. 2003 Jun;85(2-5):235-45.

pubmed_id:12943709

18:

reference_text:Belanger A, Hum DW, Beaulieu M, Levesque E, Guillemette C, Tchernof A, Belanger G, Turgeon D, Dubois S: Characterization and regulation of UDP-glucuronosyltransferases in steroid target tissues. J Steroid Biochem Mol Biol. 1998 Apr;65(1-6):301-10.

pubmed_id:9699884

19:

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

20:

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

21:

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

22:

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

23:

reference_text:The lipid handbook with CD-ROM

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