Showing Compound 21-Hydroxypregnenolone (FDB023281)

Record Information

Version

1.0

Creation date

2011-09-21 00:27:25 UTC

Update date

2015-07-21 06:57:37 UTC

Primary ID

FDB023281

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

21-Hydroxypregnenolone

Description

21-hydroxypregnenolone is an essential intermediate in corticosterone synthesis. The hydrolysis of 21-hydroxypregnenolone of fetal origin by steryl-sulfatase (SOS, EC 3.1.6.2), may be important in the biosynthesis of deoxycorticosterone, which is present in the plasma of pregnant women in high concentration. 21-hydroxypregnenolone has been identified in follicular fluid from follicles of women. Pregnenolone is transformed to 21-hydroxypregnenolone by human adrenal microsomal preparations, suggesting the involvement of alternative paths via 17a,21-dihydroxypregnenolone in human. (PMID 974176, 3347051, 3495701, 7382480, 6247575) [HMDB]

CAS Number

1164-98-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(3b)-3,21-Dihydroxy-pregn-5-en-20-one	HMDB
(3b)-3,21-dihydroxy-Pregn-5-en-20-one	hmdb
(3b)-3,21-Dihydroxypregn-5-en-20-one	Generator
(3beta)-3,21-Dihydroxypregn-5-en-20-one	ChEBI
(3Β)-3,21-dihydroxypregn-5-en-20-one	Generator
(3β)-3,21-dihydroxypregn-5-en-20-one	Generator
21-hydroxypregnenolone	hmdb
3b,21-Dihydroxy-5-pregnen-20-one	HMDB
3b,21-Dihydroxy-pregn-5-en-20-one	HMDB
3b,21-dihydroxy-Pregn-5-en-20-one	hmdb

Showing 1 to 10 of 15 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	3.22	ALOGPS
logP	2.76	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.86	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	2	ChemAxon
Refractivity	95.46 m³·mol⁻¹	ChemAxon
Polarizability	38.84 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H32O3

IUPAC name

2-hydroxy-1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one

InChI Identifier

InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h3,14-18,22-23H,4-12H2,1-2H3/t14-,15-,16-,17-,18+,20-,21-/m0/s1

InChI Key

MOIQRAOBRXUWGN-WPWXJNKXSA-N

Isomeric SMILES

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

Average Molecular Weight

332.477

Monoisotopic Molecular Weight

332.23514489

Classification

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:28043 )
21-hydroxy steroid (CHEBI:28043 )
hydroxypregnenolone (CHEBI:28043 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030167 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	21-Hydroxypregnenolone, 1 MEOX; 2 TMS, GC-MS Spectrum	splash10-004u-4910000000-a498e59adb4a11849d3e	Spectrum
GC-MS	21-Hydroxypregnenolone, non-derivatized, GC-MS Spectrum	splash10-004u-4910000000-a498e59adb4a11849d3e	Spectrum
Predicted GC-MS	21-Hydroxypregnenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-0196000000-9576ba4a3e3fe81eccd0	Spectrum
Predicted GC-MS	21-Hydroxypregnenolone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dj-1014900000-72c174690c4421659ce6	Spectrum
Predicted GC-MS	21-Hydroxypregnenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	21-Hydroxypregnenolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0039000000-34e73b29188e789dcd9c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015a-0196000000-bd55e2f11df2c7f294d3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-2391000000-3937d95bf8b6f55a8382	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-9d13365707b48184b4b3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06si-2069000000-284db8a88c06364a507e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3091000000-fbd05f20ca5983385f71	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0019000000-5c433edd4be0c3ead061	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015a-0795000000-5a50473d4855707105c5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-2940000000-422ddbc116e22dfcd136	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-c4eb2a470a7bc24bb787	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0049000000-c8287b111bc120527734	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001j-0092000000-cfcf5197be411a0f0d7e	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28043

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04026

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Showing 1 to 2 of 2 entries

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 21-Hydroxypregnenolone (FDB023281)

Structure for FDB023281 (21-Hydroxypregnenolone)