Livestock Metabolome Database: Showing metabocard for 17a-Hydroxypregnenolone (LMDB00146)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:22 UTC

Update Date

2016-07-19 23:06:30 UTC

Lmdb

LMDB00146

Secondary Accession Numbers

None

Metabolite Identification

Common Name

17a-Hydroxypregnenolone

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. (PMID: 12573809 ).

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 Weight

332.477

Monoisotopic Molecular Weight

332.23514489

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

CAS Registry Number

387-79-1

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected and Quantified	0.00022 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.00171 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.00204 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.00383 uM	Not Available	Bovine	21172370	details