创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-09-14 15:40:12 UTC
描述
Pregnenolone is a derivative of cholesterol, the product of cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1. This reaction consists of three consecutive monooxygenations, a 22-hydroxylation, a 20-hydroxylation, and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum, and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted into pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell, angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and many steps in the transport to the inner membrane. Thus, it exerts a powerful control over the use of cholesterol for aldosterone production (PMID: 17222962, 15823613, 16632873, 15134809).
同义词
1:(3BETA)-3-HYDROXYPREGN-5-en-20-one
2:3beta-Hydroxypregn-5-en-20-one
3:5-Pregnen-3beta-ol-20-one
4:(3b)-3-HYDROXYPREGN-5-en-20-one
5:(3Β)-3-hydroxypregn-5-en-20-one
6:3b-Hydroxypregn-5-en-20-one
7:3Β-hydroxypregn-5-en-20-one
8:5-Pregnen-3b-ol-20-one
9:5-Pregnen-3β-ol-20-one
10:5-Pregnen-3-beta-ol-20-one
11:5 Pregnen 3 beta ol 20 one
化学名称
1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
传统名称
1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone
代谢物结构字符串
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
inchi标识符
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
印记键
ORNBQBCIOKFOEO-QGVNFLHTSA-N
分类学
description: belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
description:Gluco/mineralocorticoids, progestogins and derivatives
kingdom:Organic compounds
super_class:Lipids and lipid-like molecules
class:Steroids and steroid derivatives
sub_class:Pregnane steroids
molecular_framework:Aliphatic homopolycyclic compounds
1:20-oxosteroids
2:3-beta-hydroxy delta-5-steroids
3:3-beta-hydroxysteroids
4:Cyclic alcohols and derivatives
5:Delta-5-steroids
6:Hydrocarbon derivatives
7:Ketones
8:Organic oxides
9:Secondary alcohols
10:20-oxosteroid
11:3-beta-hydroxy-delta-5-steroid
12:3-beta-hydroxysteroid
13:3-hydroxy-delta-5-steroid
14:3-hydroxysteroid
15:Alcohol
16:Aliphatic homopolycyclic compound
17:Carbonyl group
18:Cyclic alcohol
19:Delta-5-steroid
20:Hydrocarbon derivative
21:Hydroxysteroid
22:Ketone
23:Organic oxide
24:Organic oxygen compound
25:Organooxygen compound
26:Oxosteroid
27:Progestogin-skeleton
28:Secondary alcohol
29:20-oxo steroid
30:3beta-hydroxy steroid
31:C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives
32:C21-steroid
33:Pregnane and derivatives [Fig]
34:Progestagens
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:Postpartum depression
definition:An endogenous depression that involves intense, sustained and sometimes disabling depression experienced by women after giving birth. (do).
parent_id:7695
***level:4
type:child
synonym:Postnatal depression
synonym:Ppd
term:Prepartum depression
definition:
parent_id:7695
***level:4
type:child
synonym:Antenatal depression
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:Premenstrual dysphoric disorder
definition:
parent_id:7695
***level:4
type:child
synonym:Pmdd
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:Plant
definition:A living organism belonging to the kingdom plantea. typically, it grows in a permanent site, absorbs water and inorganic substances through its roots, and synthesizes nutrients in its leaves by photosynthesis using the green pigment chlorophyll. examples incude trees, shrubs, herbs, grasses, ferns, and mosses.
parent_id:7736
***level:4
type:parent
synonym:Flora
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: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:Brain
definition:An organ composed of grey and white matter that is the center for intelligence and reasoning. it is protected by the bony cranium. (nci).
parent_id:7727
***level:4
type:child
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:Biofluid and excreta
definition:A liquid, semi-solid or solid material originating in the body.
parent_id:7725
**level:3
type:parent
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:Urine
definition:Excretion in liquid state processed by the kidney.
parent_id:7731
***level:4
type:child
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:Mitochondria
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:Myelin sheath
definition:A layer of phospholipids and protein found on neuronal axons. this structure acts as an electrical insulator that allows nerve impulses to travel faster by increasing the resistance and decreasing the capacitance over that found in unmyelinated nerve fibers. (nci).
parent_id:7730
***level:4
type:child
synonym:Myelin
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: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: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: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
实验性质
1:
kind:water_solubility
value:0.00706 mg/mL at 37 °C
source:
2:
kind:logp
value:4.22
source:HANSCH,C ET AL. (1995)
3:
kind:melting_point
value:192 °C
source:
预测性质
1:
kind:logp
value:4.06
source:ALOGPS
2:
kind:logs
value:-4.37
source:ALOGPS
3:
kind:solubility
value:0.014 g/L
source:ALOGPS
4:
kind:logp
value:3.58
source:ChemAxon
5:
kind:pka_strongest_acidic
value:18.2
source:ChemAxon
6:
kind:pka_strongest_basic
value:-1.4
source:ChemAxon
7:
kind:iupac
value:1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
source:ChemAxon
8:
kind:average_mass
value:316.4776
source:ChemAxon
9:
kind:mono_mass
value:316.240230268
source:ChemAxon
10:
kind:smiles
value:[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
source:ChemAxon
11:
kind:formula
value:C21H32O2
source:ChemAxon
12:
kind:inchi
value:InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
source:ChemAxon
13:
kind:inchikey
value:ORNBQBCIOKFOEO-QGVNFLHTSA-N
source:ChemAxon
14:
kind:polar_surface_area
value:37.3
source:ChemAxon
15:
kind:refractivity
value:93.76
source:ChemAxon
16:
kind:polarizability
value:38.09
source:ChemAxon
17:
kind:rotatable_bond_count
value:1
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
生物学性质
1:
cellular:(1):Cytoplasm
cellular:(2):Endoplasmic reticulum
cellular:(3):Extracellular
cellular:(4):Membrane
cellular:(5):Mitochondria
2:
biospecimen:(1):Blood
biospecimen:(2):Cerebrospinal Fluid (CSF)
biospecimen:(3):Urine
3:
tissue:(1):Adrenal Cortex
tissue:(2):Adrenal Gland
tissue:(3):Brain
tissue:(4):Kidney
tissue:(5):Neuron
tissue:(6):Ovary
tissue:(7):Placenta
tissue:(8):Testis
4:
[1]:
name:11-beta-hydroxylase deficiency (CYP11B1)
smpdb_id:SMP00575
kegg_map_id:
[2]:
name:17-alpha-hydroxylase deficiency (CYP17)
smpdb_id:SMP00566
kegg_map_id:
[3]:
name:21-hydroxylase deficiency (CYP21)
smpdb_id:SMP00576
kegg_map_id:
[4]:
name:3-Beta-Hydroxysteroid Dehydrogenase Deficiency
smpdb_id:SMP00718
kegg_map_id:
[5]:
name:Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency
smpdb_id:SMP00373
kegg_map_id:
[6]:
name:Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency
smpdb_id:SMP00372
kegg_map_id:
[7]:
name:Apparent mineralocorticoid excess syndrome
smpdb_id:SMP00717
kegg_map_id:
[8]:
name:Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH
smpdb_id:SMP00371
kegg_map_id:
[9]:
name:Corticosterone methyl oxidase I deficiency (CMO I)
smpdb_id:SMP00577
kegg_map_id:
[10]:
name:Corticosterone methyl oxidase II deficiency - CMO II
smpdb_id:SMP00578
kegg_map_id:
[11]:
name:Steroidogenesis
smpdb_id:SMP00130
kegg_map_id:map00140
正常浓度
1:
biospecimen:Blood
concentration_value:0.00474-0.0632
concentration_units:uM
subject_age:Newborn (0-30 days old)
subject_sex:Female
subject_condition:Normal
2:
biospecimen:Blood
concentration_value:0.00186 +/- 0.00090
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
3:
biospecimen:Blood
concentration_value:0.00083 +/- 0.00080
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Both
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:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Male
subject_condition:Normal
6:
biospecimen:Blood
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
7:
biospecimen:Blood
concentration_value:0.00424 +/- 0.00236
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
8:
biospecimen:Blood
concentration_value:0.0147 +/- 0.0084
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
9:
biospecimen:Blood
concentration_value:0.0429 +/- 0.0325
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
10:
biospecimen:Blood
concentration_value:0.0573 +/- 0.0133
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
11:
biospecimen:Blood
concentration_value:0.00985 +/- 0.00851
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
12:
biospecimen:Blood
concentration_value:0.00373 +/- 0.00214
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
13:
biospecimen:Blood
concentration_value:0.00168 +/- 0.00137
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
14:
biospecimen:Blood
concentration_value:0.00088 +/- 0.00062
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
15:
biospecimen:Blood
concentration_value:0.00054 +/- 0.00033
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Female
subject_condition:Normal
16:
biospecimen:Blood
concentration_value:0.013 +/- 0.0027
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
17:
biospecimen:Cerebrospinal Fluid (CSF)
concentration_value:0.00013 (0.000082-0.00019)
concentration_units:uM
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
18:
biospecimen:Urine
concentration_value:
concentration_units:
subject_age:Adult (>18 years old)
subject_sex:Both
subject_condition:Normal
异常浓度
1:
biospecimen:Blood
concentration_value:0.00401
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
2:
biospecimen:Blood
concentration_value:0.00082 +/- 0.00071
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Female
patient_information:Premenstrual dysphoric disorder (follicular stage of menstrual cycle)
3:
biospecimen:Blood
concentration_value:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Male
patient_information:Schizophrenia
4:
biospecimen:Blood
concentration_value:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Female
patient_information:Schizophrenia
5:
biospecimen:Blood
concentration_value:0.0423 +/- 0.0130
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Female
patient_information:Prepartum depression
6:
biospecimen:Blood
concentration_value:0.0684 +/- 0.0222
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Female
patient_information:Prepartum depression
7:
biospecimen:Blood
concentration_value:0.00974 +/- 0.00371
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Female
patient_information:Postpartum depression
8:
biospecimen:Blood
concentration_value:0.00209 +/- 0.00090
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Female
patient_information:Postpartum depression
9:
biospecimen:Blood
concentration_value:0.00179 +/- 0.00108
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Female
patient_information:Premenstrual dysphoric disorder (mid luteal stage of menstrual cycle)
10:
biospecimen:Blood
concentration_value:0.00169 +/- 0.00107
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Female
patient_information:Premenstrual dysphoric disorder (late luteal stage of menstrual cycle)
11:
biospecimen:Cerebrospinal Fluid (CSF)
concentration_value:0.00003510 +/- 0.00002656
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Not Specified
patient_information:Leuprolide acetate-induced hypogonadism
12:
biospecimen:Cerebrospinal Fluid (CSF)
concentration_value:0.00005312 +/- 0.00004775
concentration_units:uM
patient_age:Adult (>18 years old)
patient_sex:Not Specified
patient_information:Leuprolide acetate-induced hypogonadism with testosterone replacment
疾病参考
1:
name:Premenstrual dysphoric disorder
omim_id:
[1]:
reference_text:Epperson CN, Haga K, Mason GF, Sellers E, Gueorguieva R, Zhang W, Weiss E, Rothman DL, Krystal JH: Cortical gamma-aminobutyric acid levels across the menstrual cycle in healthy women and those with premenstrual dysphoric disorder: a proton magnetic resonance spectroscopy study. Arch Gen Psychiatry. 2002 Sep;59(9):851-8.
pubmed_id:12215085
2:
name:Prepartum depression
omim_id:
[1]:
reference_text:Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7.
pubmed_id:11739473
3:
name:Postpartum depression
omim_id:
[1]:
reference_text:Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7.
pubmed_id:11739473
4:
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.
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[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.
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[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.
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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.
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[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.
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[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
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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
[12]:
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
[26]:
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.
pubmed_id:22800120
[27]:
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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[28]:
reference_text:Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24.
pubmed_id:22944140
[29]:
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.
pubmed_id:22892715
[30]:
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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[31]:
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
5:
name:Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
omim_id:613743
[1]:
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.
pubmed_id:18182448
综合参考
Shingate, Bapurao B.; Hazra, Braja G.; Pore, Vandana S.; Gonnade, Rajesh G.; Bhadbhade, Mohan M. Stereoselective syntheses of 20-epi cholanic acid derivatives from 16-dehydropregnenolone acetate. Tetrahedron (2007), 63(25), 5622-5635.
一般参考
1:
protein_accession:HMDBP00355
name:Sulfotransferase family cytosolic 2B member 1
uniprot_id:O00204
gene_name:SULT2B1
protein_type:Enzyme
2:
protein_accession:HMDBP00493
name:Steryl-sulfatase
uniprot_id:P08842
gene_name:STS
protein_type:Unknown
3:
protein_accession:HMDBP00724
name:Cholesterol side-chain cleavage enzyme, mitochondrial
uniprot_id:P05108
gene_name:CYP11A1
protein_type:Unknown
4:
protein_accession:HMDBP01043
name:Steroid 17-alpha-hydroxylase/17,20 lyase
uniprot_id:P05093
gene_name:CYP17A1
protein_type:Unknown
5:
protein_accession:HMDBP01629
name:25-hydroxycholesterol 7-alpha-hydroxylase
uniprot_id:O75881
gene_name:CYP7B1
protein_type:Unknown
6:
protein_accession:HMDBP04403
name:3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
uniprot_id:P14060
gene_name:HSD3B1
protein_type:Unknown
7:
protein_accession:HMDBP04404
name:3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2
uniprot_id:P26439
gene_name:HSD3B2
protein_type:Unknown
8:
protein_accession:HMDBP07366
name:Cytochrome P450 21-hydroxylase
uniprot_id:Q16874
gene_name:P450-CYP21B
protein_type:Enzyme
9:
protein_accession:HMDBP09242
name:Cytochrome P450, family 21, subfamily A, polypeptide 2
uniprot_id:Q08AG9
gene_name:CYP21A2
protein_type:Enzyme
10:
protein_accession:HMDBP11648
name:Steroid 21-hydroxylase
uniprot_id:P08686
gene_name:CYP21A2
protein_type:Unknown
蛋白质结合
1:
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
2:
reference_text:Schoneshofer M, Weber B: Specific estimation of fifteen unconjugated, non-metabolized steroid hormones in human urine. J Steroid Biochem. 1983 Jan;18(1):65-73.
pubmed_id:6865405
3:
reference_text:Morfin R, Young J, Corpechot C, Egestad B, Sjovall J, Baulieu EE: Neurosteroids: pregnenolone in human sciatic nerves. Proc Natl Acad Sci U S A. 1992 Aug 1;89(15):6790-3.
pubmed_id:1386671
4:
reference_text:Eriksson CJ, Widenius TV, Leinonen P, Harkonen M, Ylikahri RH: Inhibition of testosterone biosynthesis by ethanol: relation to the pregnenolone-to-testosterone pathway. FEBS Lett. 1984 Jul 9;172(2):177-82.
pubmed_id:6540203
5:
reference_text:George MS, Guidotti A, Rubinow D, Pan B, Mikalauskas K, Post RM: CSF neuroactive steroids in affective disorders: pregnenolone, progesterone, and DBI. Biol Psychiatry. 1994 May 15;35(10):775-80.
pubmed_id:8043707
6:
reference_text:Hill M, Lukac D, Lapcik O, Sulcova J, Hampl R, Pouzar V, Starka L: Age relationships and sex differences in serum levels of pregnenolone and 17-hydroxypregnenolone in healthy subjects. Clin Chem Lab Med. 1999 Apr;37(4):439-47.
pubmed_id:10369116
7:
reference_text:Diallo S, Lecanu L, Greeson J, Papadopoulos V: A capillary gas chromatography/mass spectrometric method for the quantification of hydroxysteroids in human plasma. Anal Biochem. 2004 Jan 1;324(1):123-30.
pubmed_id:14654054
8:
reference_text:Saenger P, Klonari Z, Black SM, Compagnone N, Mellon SH, Fleischer A, Abrams CA, Shackelton CH, Miller WL: Prenatal diagnosis of congenital lipoid adrenal hyperplasia. J Clin Endocrinol Metab. 1995 Jan;80(1):200-5.
pubmed_id:7829612
9:
reference_text:Meloun M, Hill M, Militky J, Kupka K: Analysis of large and small samples of biochemical and clinical data. Clin Chem Lab Med. 2001 Jan;39(1):53-61.
pubmed_id:11256802
10:
reference_text:Lykkesfeldt G, Nielsen MD, Lykkesfeldt AE: Placental steroid sulfatase deficiency: biochemical diagnosis and clinical review. Obstet Gynecol. 1984 Jul;64(1):49-54.
pubmed_id:6234482
11:
reference_text:Hill M, Havlikova H, Vrbikova J, Kancheva R, Kancheva L, Pouzar V, Cerny I, Starka L: The identification and simultaneous quantification of 7-hydroxylated metabolites of pregnenolone, dehydroepiandrosterone, 3beta,17beta-androstenediol, and testosterone in human serum using gas chromatography-mass spectrometry. J Steroid Biochem Mol Biol. 2005 Jul;96(2):187-200.
pubmed_id:15908198
12:
reference_text:Weusten JJ, Smals AG, Hofman JA, Kloppenborg PW, Benraad TJ: Early time sequence in pregnenolone metabolism to testosterone in homogenates of human and rat testis. Endocrinology. 1987 May;120(5):1909-13.
pubmed_id:3569120
13:
reference_text:Doouss TW, Skinner SJ, Couch RA: Synthesis of dehydroepiandrosterone and dehydroepiandrosterone sulphate by the human adrenal. J Endocrinol. 1975 Jul;66(1):1-12.
pubmed_id:126268
14:
reference_text:Nishida S, Matsumura S, Horino M, Matsuki M, Oyama H, Tenku A, Kakita K, Tanaka H, Omukai Y: Dexamethasone suppressibility of plasma pregnenolone or dehydroepiandrosterone in gonadectomized patients. Steroids. 1979 Oct;34(4):471-6.
pubmed_id:229589
15:
reference_text:Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7.
pubmed_id:11739473
16:
reference_text:Ahboucha S, Pomier-Layrargues G, Mamer O, Butterworth RF: Increased levels of pregnenolone and its neuroactive metabolite allopregnanolone in autopsied brain tissue from cirrhotic patients who died in hepatic coma. Neurochem Int. 2006 Sep;49(4):372-8. Epub 2006 Mar 24.
pubmed_id:16563564
17:
reference_text:Tuckey RC: Progesterone synthesis by the human placenta. Placenta. 2005 Apr;26(4):273-81.
pubmed_id:15823613
18:
reference_text:Storbeck KH, Swart P, Swart AC: Cytochrome P450 side-chain cleavage: insights gained from homology modeling. Mol Cell Endocrinol. 2007 Feb;265-266:65-70. Epub 2007 Jan 12.
pubmed_id:17222962
19:
reference_text:Patte-Mensah C, Kibaly C, Boudard D, Schaeffer V, Begle A, Saredi S, Meyer L, Mensah-Nyagan AG: Neurogenic pain and steroid synthesis in the spinal cord. J Mol Neurosci. 2006;28(1):17-31.
pubmed_id:16632873
20:
reference_text:Capponi AM: The control by angiotensin II of cholesterol supply for aldosterone biosynthesis. Mol Cell Endocrinol. 2004 Mar 31;217(1-2):113-8.
pubmed_id:15134809