Bovine Metabolome Database: Showing metabocard for 5b-Dihydrotestosterone (BMDB0006770)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:25:51 UTC

Update Date

2020-04-22 15:18:32 UTC

BMDB ID

BMDB0006770

Secondary Accession Numbers

BMDB06770

Metabolite Identification

Common Name

5b-Dihydrotestosterone

Description

5b-Dihydrotestosterone, also known as 5-beta-DHT or 5-β-DHT, 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, 5b-dihydrotestosterone is considered to be a steroid lipid molecule. 5b-Dihydrotestosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5b-Dihydrotestosterone can be converted into testosterone through its interaction with the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In cattle, 5b-dihydrotestosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(5beta,17beta)-17-Hydroxyandrostan-3-one	ChEBI
(5beta,8alpha,17beta)-17-Hydroxyandrostan-3-one	ChEBI
17beta-Hydroxyetiocholan-3-one	ChEBI
5-beta-DHT	ChEBI
5beta,17beta-Hydroxyandrostan-3-one	ChEBI
5beta-Androstan-17beta-ol-3-one	ChEBI
Etiocholan-17-beta-ol-3-one	ChEBI
(5b,17b)-17-Hydroxyandrostan-3-one	Generator
(5Β,17β)-17-hydroxyandrostan-3-one	Generator
(5b,8a,17b)-17-Hydroxyandrostan-3-one	Generator
(5Β,8α,17β)-17-hydroxyandrostan-3-one	Generator
17b-Hydroxyetiocholan-3-one	Generator
17Β-hydroxyetiocholan-3-one	Generator
5-b-DHT	Generator
5-Β-DHT	Generator
5b,17b-Hydroxyandrostan-3-one	Generator
5Β,17β-hydroxyandrostan-3-one	Generator
5b-Androstan-17b-ol-3-one	Generator
5Β-androstan-17β-ol-3-one	Generator
Etiocholan-17-b-ol-3-one	Generator
Etiocholan-17-β-ol-3-one	Generator
5beta-Dihydrotestosterone	HMDB
17beta-Hydroxy-5beta-androstan-3-one	HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

IUPAC Name

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

Traditional Name

5β-dihydrotestosterone

CAS Registry Number

571-22-2

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=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/h12,14-17,21H,3-11H2,1-2H3/t12-,14+,15+,16+,17+,18+,19+/m1/s1

InChI Key

NVKAWKQGWWIWPM-MISPCMORSA-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
3-oxosteroid
3-oxo-5-beta-steroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:2150 )
17beta-hydroxyandrostan-3-one (CHEBI:2150 )
C19 steroids (androgens) and derivatives (C05293 )
C19 steroids (androgens) and derivatives (LMST02020069 )

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	3.37	ALOGPS
logP	3.41	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	19.38	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.6 m³·mol⁻¹	ChemAxon
Polarizability	34.46 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gj-0390000000-9eeab8ff981af1be878c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-007k-2249000000-51ef016e7481976493bd	View in MoNA
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, Negative	splash10-000i-0090000000-62e8fc46490b14aee68a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0090000000-d712d8c85325f4935c06	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fu-2190000000-d8e9f38bc70955a04aea	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-c8c452fd99c6bb4f3631	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0090000000-20b22a4e3152e3639e64	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0190000000-32b12edcbd16045a4a2e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-0390000000-a2704bedea3c7bf92d65	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016r-2790000000-d1a3cc2c786b582339b3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-48f400d66433b81d9a66	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aba-1950000000-acfc6238e1a13c48e859	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066s-2900000000-1bc41566c7dc5d14c903	View in MoNA