Showing Compound Androst-5-ene-3beta,17beta-diol (FDB023228)

Record Information

Version

1.0

Creation date

2011-09-21 00:26:36 UTC

Update date

2015-07-21 06:57:35 UTC

Primary ID

FDB023228

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

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

Description

Androstenediol is a term used to refer to two different steroids with molecular weights of 290.44: '4-androstenediol' (4-androstene-3beta,17beta-diol) and '5-androstenediol' (5-androstene-3beta,17beta-diol). 4-Androstenediol is closer to testosterone structurally, and has androgenic effects. 5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Coffey, 1988). Because it induces production of white blood cells and platelets, 5-androstenediol is being developed as a radiation countermeasure as Neumune(HE2100). An intermediate in testosterone biosynthesis, found in the testis or the adrenal. Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-fydroxysteroid dehydrogenaseS), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-fydroxysteroid dehydrogenase). [HMDB]

CAS Number

521-17-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
(3β,17β)-androst-5-ene-3,17-diol	Generator
3β,17β-dihydroxy-5-androstene	Generator
3β,17β-dihydroxyandrost-5-ene	Generator
androst-5-ene-3,17-diol	hmdb
b,17b-diol	hmdb
delta(sup 5)-Androstenediol	hmdb
delta5-Androstenediol	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.055 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C19H30O2

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

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

Isomeric 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

Average Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

Classification

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Organ and components:

Endocrine gland:

Adrenal cortex

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

System process:

Reproduction

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Androst-5-ene-3beta,17beta-diol, 2 TMS, GC-MS Spectrum	splash10-004l-3920000000-6d05021a14366bfd40ba	Spectrum
GC-MS	Androst-5-ene-3beta,17beta-diol, non-derivatized, GC-MS Spectrum	splash10-004l-3920000000-6d05021a14366bfd40ba	Spectrum
Predicted GC-MS	Androst-5-ene-3beta,17beta-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03ea-0190000000-3ceb1bf6f3d53ee5d7e5	Spectrum
Predicted GC-MS	Androst-5-ene-3beta,17beta-diol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-2126900000-1bc7293586fc53c1c457	Spectrum
Predicted GC-MS	Androst-5-ene-3beta,17beta-diol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Androst-5-ene-3beta,17beta-diol, 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	splash10-00dl-0090000000-551d3445a2c6cdfa61ee	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-0390000000-5cfc4d0f79fea1c885b8	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02bf-3890000000-e55a0a62bc36fe9049ec	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-d1deb080063b126f79ce	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-0090000000-4d0bb4d4f197bc1e6846	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-1190000000-3f4cb9035ceae26a4876	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-9de0edc3a8b815dd7071	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abd-1940000000-90cd37c3652265920678	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aos-1900000000-76460d7bb552466d1504	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-c8c452fd99c6bb4f3631	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-1ce9bb01eb35f26908c4	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0090000000-aeda10893d01c46acf8c	2021-09-25	View Spectrum