Bovine Metabolome Database: Showing metabocard for Androst-5-ene-3b,17b-diol (BMDB0003818)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:06:09 UTC

Update Date

2020-05-11 20:56:18 UTC

BMDB ID

BMDB0003818

Secondary Accession Numbers

BMDB03818

Metabolite Identification

Common Name

Androst-5-ene-3b,17b-diol

Description

Androstenediol, also known as hermaphrodiol or tetrabol, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androstenediol is considered to be a steroid. Based on a literature review a small amount of articles have been published on Androstenediol.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta,17beta)-Androst-5-ene-3,17-diol	ChEBI
3beta,17beta-Dihydroxy-5-androstene	ChEBI
3beta,17beta-Dihydroxyandrost-5-ene	ChEBI
5-Androstenediol	ChEBI
Androst-5-en-3beta,17beta-diol	ChEBI
Androst-5-enediol	ChEBI
Hermaphrodiol	ChEBI
Androst-5-ene-3beta,17beta-diol	Kegg
Tetrabol	Kegg
(3b,17b)-Androst-5-ene-3,17-diol	Generator
(3Β,17β)-androst-5-ene-3,17-diol	Generator
3b,17b-Dihydroxy-5-androstene	Generator
3Β,17β-dihydroxy-5-androstene	Generator
3b,17b-Dihydroxyandrost-5-ene	Generator
3Β,17β-dihydroxyandrost-5-ene	Generator
Androst-5-en-3b,17b-diol	Generator
Androst-5-en-3β,17β-diol	Generator
Androst-5-ene-3b,17b-diol	Generator
Androst-5-ene-3β,17β-diol	Generator
Androstenediol	ChEBI
Androst-5-ene-3,17-diol	HMDB
b,17b-Diol	HMDB
delta-5-Androstenediol	HMDB
Delta5-Androstenediol	HMDB
5 Androstene 3,17 diol	MeSH, HMDB
Delta 5-Androstenediol	MeSH, HMDB
Parke davis brand OF androstenediol	MeSH, HMDB
delta 5-Androstene-3 beta,17 beta-diol	MeSH, HMDB
5 Androstene 3beta 17beta diol	MeSH, HMDB
Androst 5 ene 3 beta,17 beta diol	MeSH, HMDB
Androst-5-ene-3 beta,17 beta-diol	MeSH, HMDB
5-Androstene-3beta-17beta-diol	MeSH, HMDB
Bisexovister	MeSH, HMDB
Delta 5 Androstenediol	MeSH, HMDB
5-Androstene-3,17-diol	MeSH, HMDB
Androst 5 ene 3,17 diol	MeSH, HMDB
delta 5 Androstene 3 beta,17 beta diol	MeSH, HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

IUPAC Name

(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol

Traditional Name

5-androstenediol

CAS Registry Number

521-17-5

SMILES

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

InChI Identifier

InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-17,20-21H,4-11H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

InChI Key

QADHLRWLCPCEKT-LOVVWNRFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
17-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-5-steroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:2710 )
17beta-hydroxy steroid (CHEBI:2710 )
C19 steroids (androgens) and derivatives (C04295 )
Androstane and derivatives (C04295 )
C19 steroids (androgens) and derivatives (LMST02020005 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

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	3.42	ALOGPS
logP	2.8	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-0.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.48 m³·mol⁻¹	ChemAxon
Polarizability	34.68 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 (2 TMS)	splash10-004l-3920000000-6d05021a14366bfd40ba	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-004l-3920000000-6d05021a14366bfd40ba	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ea-0190000000-3ceb1bf6f3d53ee5d7e5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-014i-2126900000-1bc7293586fc53c1c457	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0090000000-551d3445a2c6cdfa61ee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-0390000000-5cfc4d0f79fea1c885b8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02bf-3890000000-e55a0a62bc36fe9049ec	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-d1deb080063b126f79ce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-0090000000-4d0bb4d4f197bc1e6846	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-1190000000-3f4cb9035ceae26a4876	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-9de0edc3a8b815dd7071	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abd-1940000000-90cd37c3652265920678	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aos-1900000000-76460d7bb552466d1504	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-c8c452fd99c6bb4f3631	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-1ce9bb01eb35f26908c4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0090000000-aeda10893d01c46acf8c	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Prostate Tissue
Skeletal Muscle
Testis

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Cortex	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0003818

DrugBank ID

DB01524

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023228

KNApSAcK ID

Not Available

Chemspider ID

10188

KEGG Compound ID

C04295

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Androstenediol

METLIN ID

Not Available

PubChem Compound

10634

PDB ID

Not Available

ChEBI ID

2710

References

Synthesis Reference

Ristovic, Lj.; Cobanovic, M.; Jovanovic, Z.; Orlic, M. Synthesis of androstenediol and determination of its physicochemical constants. Kemija u Industriji (1975), 24(7), 389-92.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Androst-5-ene-3b,17b-diol (BMDB0003818)

Structure for BMDB0003818 (Androst-5-ene-3b,17b-diol)