ContaminantDB: 17a-Hydroxypregnenolone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:09:26 UTC

Update Date

2016-11-09 01:09:05 UTC

Accession Number

CHEM003221

Identification

Common Name

17a-Hydroxypregnenolone

Class

Small Molecule

Description

17a-Hydroxypregnenolone is a 21-carbon steroid that is converted from pregnenolone by cytochrome P450 17alpha hydroxylase/C17,20 lyase (CYP17, EC 1.14.99.9). 17a-Hydroxypregnenolone is an intermediate in the delta-5 pathway of biosynthesis of gonadal steroid hormones and the adrenal corticosteroids. The first, rate-limiting and hormonally regulated step in the biosynthesis of all steroid hormones is the conversion of cholesterol to pregnenolone. The conversion of cholesterol to pregnenolone is accomplished by the cleavage of the cholesterol side chain, catalyzed by a mitochondrial cytochrome P450 enzyme termed P450scc where scc designates Side Chain Cleavage. All steroid hormones are made from the pregnenolone produced by P450scc; thus, the presence or absence of each of the activities of CYP17 directs this pregnenolone towards its final metabolic pathway. While all cytochrome P450 enzymes can catalyze multiple reactions on a single active site, CYP17 is the only one described to date in which these multiple activities are differentially regulated by a physiologic process. 17a-Hydroxypregnenolone is converted to dehydroepiandrosterone by the 17,20 lyase activity of CYP17. The ratio of the 17,20 lyase to 17 alpha-hydroxylase activity of CYP17 determines the ratio of C21 to C19 steroids produced. This ratio is regulated post-translationally by at least three factors: the abundance of the electron-donating protein P450 oxidoreductase, the presence of cytochrome b5, and the serine phosphorylation of CYP17. (1).

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Animal Toxin
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(3beta)-3,17-Dihydroxypregn-5-en-20-one	ChEBI
17-Hydroxypregnenolone	ChEBI
5-Pregnen-3beta,17alpha-diol-20-one	ChEBI
(3b)-3,17-Dihydroxypregn-5-en-20-one	Generator
(3Β)-3,17-dihydroxypregn-5-en-20-one	Generator
5-Pregnen-3b,17a-diol-20-one	Generator
5-Pregnen-3β,17α-diol-20-one	Generator
17-Hydroxy-D5-pregnenolone	HMDB
17-OH-Pregnenolone	HMDB
17a-Hydroxypregnolone	HMDB
17alpha-Hydroxypregnanolone	HMDB
17alpha-Hydroxypregnenolone	HMDB
3b,17-Dihydroxy-5-pregnen-20-one	HMDB
3b,17-Dihydroxy-pregn-5-en-20-one	HMDB
3b,17a-Dihydroxypregn-5-en-20-one	HMDB
17alpha Hydroxypregnenolone	HMDB
Hydroxypregnenolone	HMDB
17 Hydroxypregnenolone	HMDB
17 alpha Hydroxypregnenolone	HMDB
17-Hydroxypregnenolone, (3alpha)-isomer	HMDB
17-Hydroxypregnenolone, (3beta,13alpha)-isomer	HMDB
17-alpha-Hydroxypregnenolone	HMDB
17 alpha-Hydroxypregnenolone	HMDB
17-Hydroxypregnenolone, (3beta,13alpha,17alpha)-isomer	HMDB
17-Hydroxypregnenolone, (3beta,17alpha)-isomer	HMDB

Chemical Formula

C₂₁H₃₂O₃

Average Molecular Mass

332.477 g/mol

Monoisotopic Mass

332.235 g/mol

CAS Registry Number

387-79-1

IUPAC Name

1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one

Traditional Name

1-[(1S,2R,5S,10R,11S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone

SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,15-18,23-24H,5-12H2,1-3H3/t15-,16+,17-,18-,19-,20-,21-/m0/s1

InChI Key

JERGUCIJOXJXHF-TVWVXWENSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
17-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
Hydroxysteroid
Delta-5-steroid
Alpha-hydroxy ketone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:28750 )
17alpha-hydroxy steroid (CHEBI:28750 )
hydroxypregnenolone (CHEBI:28750 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030089 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Adrenal Cortex
Testes

Pathways

Name	SMPDB Link	KEGG Link
Androgen and Estrogen Metabolism	SMP00068	map00150
Steroidogenesis	SMP00130	map00140
21-hydroxylase deficiency (CYP21)	SMP00576	Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency	SMP00373	Not Available

Applications

Not Available

Biological Roles

human metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	266 - 271°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.038 g/L	ALOGPS
logP	3.15	ALOGPS
logP	2.83	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.16 m³·mol⁻¹	ChemAxon
Polarizability	38.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-054x-4900000000-df86d10979d808f20e67	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-0a73-3910000000-7a0eea991ac4d2fac97e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f89-2891000000-3605ad7dd57f97382115	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ff0-3792000000-974e157d4c25e376b004	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-054x-4900000000-df86d10979d808f20e67	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a73-3910000000-7a0eea991ac4d2fac97e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-3295000000-48ed11374901b134a70d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-03di-0111900000-e55e71b4d8c63cde89c2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0039000000-28c103ca6cdf072557bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-0900000000-ae3004bb674d9632cd0c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-0900000000-a2f467560b451d5c9b0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0f89-2891000000-82e62584fff36943bcba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0029000000-131b75950fb7123106d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015i-0094000000-2a48017855d3965d5626	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g29-2690000000-3d1b2b0525a2f6da149c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-4c286aa6d88850e66ba9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-008i-0098000000-77ce542de402b225ac27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0avr-0092000000-e39f57cc01b46a017728	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-08a5ce4022cbdbf8bfa1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0029000000-8619dcbabe228085742a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0091000000-4088584830d78ccb6fb2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0029000000-275368791dddb24379f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014m-0910000000-b08f322c49579d81e79a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-1940000000-1f423724847a658c9f85	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000363

FooDB ID

FDB021982

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

45199

BioCyc ID

CPD66-23

METLIN ID

5352

PDB ID

Not Available

Wikipedia Link

17-Hydroxypregnenolone

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Kaspar, Emanuel; Hiersemann, Wolfgang; Schenck, Martin. Preparation from their esters of steroid alcohols that are sensitive to acids and alkali. (1958), DE 1028572 19580424 CAN 54:74845 AN 1960:74845 CAPLUS

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12213889

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20963882

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21787799

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23647561

5. Kaspar, Emanuel; Hiersemann, Wolfgang; Schenck, Martin. Preparation from their esters of steroid alcohols that are sensitive to acids and alkali. (1958), DE 1028572 19580424 CAN 54:74845 AN 1960:74845 CAPLUS

6. Shimozawa K, Saisho S, Yata J, Kambegawa A: Age-related changes in serum 17-hydroxypregnenolone and 17-hydroxypregnenolone sulfate concentrations in human infancy and childhood. Endocrinol Jpn. 1988 Apr;35(2):189-95.

7. Rodriguez-Rigau LJ, Weiss DB, Smith KD, Steinberger E: Suggestion of abnormal testicular steroidogenesis in some oligospermic men. Acta Endocrinol (Copenh). 1978 Feb;87(2):400-12.

8. Kaufman FR, Costin G, Goebelsmann U, Stanczyk FZ, Zachmann M: Male pseudohermaphroditism due to 17,20-desmolase deficiency. J Clin Endocrinol Metab. 1983 Jul;57(1):32-6.

9. Miller WL: Androgen biosynthesis from cholesterol to DHEA. Mol Cell Endocrinol. 2002 Dec 30;198(1-2):7-14.

17a-Hydroxypregnenolone (CHEM003221)

Structure for CHEM003221: 17a-Hydroxypregnenolone