Bovine Metabolome Database: Showing metabocard for 17a-Hydroxypregnenolone (BMDB0000363)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:29:20 UTC

Update Date

2020-06-04 20:39:42 UTC

BMDB ID

BMDB0000363

Secondary Accession Numbers

BMDB00363

Metabolite Identification

Common Name

17a-Hydroxypregnenolone

Description

17a-17a-17a-hydroxypregnenolone 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. Thus, 17a-17a-hydroxypregnenolone is considered to be a steroid lipid molecule. 17a-17a-17a-hydroxypregnenolone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 17a-17a-17a-hydroxypregnenolone participates in a number of enzymatic reactions, within cattle. In particular, 17a-17a-17a-hydroxypregnenolone can be converted into 17-hydroxyprogesterone; which is mediated by the enzyme 3-beta-HSD 1. In addition, 17a-17a-17a-hydroxypregnenolone can be biosynthesized from pregnenolone through the action of the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. In cattle, 17a-17a-hydroxypregnenolone is involved in the metabolic pathway called the steroidogenesis pathway. 17a-17a-17a-hydroxypregnenolone is a potentially toxic compound.

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

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	266 - 271 °C	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
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-054x-4900000000-df86d10979d808f20e67	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)	splash10-0a73-3910000000-7a0eea991ac4d2fac97e	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f89-2891000000-3605ad7dd57f97382115	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ff0-3792000000-974e157d4c25e376b004	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-054x-4900000000-df86d10979d808f20e67	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0a73-3910000000-7a0eea991ac4d2fac97e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-3295000000-48ed11374901b134a70d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-03di-0111900000-e55e71b4d8c63cde89c2	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-0039000000-28c103ca6cdf072557bf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-0900000000-ae3004bb674d9632cd0c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-0900000000-a2f467560b451d5c9b0e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	splash10-0f89-2891000000-82e62584fff36943bcba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0029000000-131b75950fb7123106d9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015i-0094000000-2a48017855d3965d5626	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g29-2690000000-3d1b2b0525a2f6da149c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-4c286aa6d88850e66ba9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-008i-0098000000-77ce542de402b225ac27	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0avr-0092000000-e39f57cc01b46a017728	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-08a5ce4022cbdbf8bfa1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0029000000-8619dcbabe228085742a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0091000000-4088584830d78ccb6fb2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0029000000-275368791dddb24379f9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014m-0910000000-b08f322c49579d81e79a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-1940000000-1f423724847a658c9f85	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Biospecimen Locations

Adrenal Cortex
Blood
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Steroidogenesis		Not Available
Androgen and Estrogen Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Cortex	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected and Quantified	0.00022 uM	Not Specified	Not Specified	Normal	PMID: 21172370	details
Blood	Detected and Quantified	0.00204 uM	Not Specified	Not Specified	Normal	PMID: 21172370	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00171 uM	Not Specified	Not Specified	Treated with estradiol benzoate and progesterone	PMID: 21172370	details
Blood	Detected and Quantified	0.00383 uM	Not Specified	Not Specified	Treated with estradiol benzoate	PMID: 21172370	details

External Links

HMDB ID

HMDB0000363

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021982

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

17-Hydroxypregnenolone

METLIN ID

5352

PubChem Compound

91451

PDB ID

Not Available

ChEBI ID

28750

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

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Steroid 17-alpha-hydroxylase/17,20 lyase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: A cytochrome P450 monooxygenase involved in corticoid and androgen biosynthesis. Catalyzes 17-alpha hydroxylation of C21 steroids, which is common for both pathways. A second oxidative step, required only for androgen synthesis, involves an acyl-carbon cleavage. The 17-alpha hydroxy intermediates, as part of adrenal glucocorticoids biosynthesis pathway, are precursors of cortisol. Hydroxylates steroid hormones, pregnenolone and progesterone to form 17-alpha hydroxy metabolites, followed by the cleavage of the C17-C20 bond to form C19 steroids, dehydroepiandrosterone (DHEA) and androstenedione. Has 16-alpha hydroxylase activity. Catalyzes 16-alpha hydroxylation of 17-alpha hydroxy pregnenolone, followed by the cleavage of the C17-C20 bond to form 16-alpha-hydroxy DHEA. Also 16-alpha hydroxylates androgens, relevant for estriol synthesis. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase).
Gene Name:: CYP17A1
Uniprot ID:: P05185
Molecular weight:: 57244.0

Reactions

17a-Hydroxypregnenolone → Dehydroepiandrosterone	details

Showing metabocard for 17a-Hydroxypregnenolone (BMDB0000363)

Structure for BMDB0000363 (17a-Hydroxypregnenolone)

Enzymes

Reactions