Bovine Metabolome Database: Showing metabocard for 5-alpha-Dihydrotestosterone glucuronide (BMDB0006203)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:20:20 UTC

Update Date

2020-05-11 20:24:36 UTC

BMDB ID

BMDB0006203

Secondary Accession Numbers

BMDB06203

Metabolite Identification

Common Name

5-alpha-Dihydrotestosterone glucuronide

Description

5-alpha-Dihydrotestosterone glucuronide, also known as stanolone glucuronate or 17b-hydroxy-5a-androstan-3-one glucuronide, belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. Thus, 5-alpha-dihydrotestosterone glucuronide is considered to be a steroid conjugate. Based on a literature review a significant number of articles have been published on 5-alpha-Dihydrotestosterone glucuronide.

Structure

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

Synonyms

Value	Source
(5alpha,17beta)-3-Oxoandrostan-17-yl beta-D-glucopyranosiduronic acid	ChEBI
17beta-Hydroxy-5alpha-androstan-3-one glucuronide	ChEBI
5alpha-Dihydrotestosterone 17-(beta-D-glucuronide)	ChEBI
5alpha-Dihydrotestosterone 17-beta-glucuronide	ChEBI
5alpha-Dihydrotestosterone 17-O-(beta-D-glucuronic acid)	ChEBI
5alpha-Dihydrotestosterone glucuronide	ChEBI
5alpha-Dihydrotestosterone-17g	ChEBI
Dihydrotestosterone 17-glucuronide	ChEBI
Dihydrotestosterone glucuronide	ChEBI
Stanolone 17-glucuronide	ChEBI
Stanolone glucuronate	ChEBI
(5a,17b)-3-Oxoandrostan-17-yl b-D-glucopyranosiduronate	Generator
(5a,17b)-3-Oxoandrostan-17-yl b-D-glucopyranosiduronic acid	Generator
(5alpha,17beta)-3-Oxoandrostan-17-yl beta-D-glucopyranosiduronate	Generator
(5Α,17β)-3-oxoandrostan-17-yl β-D-glucopyranosiduronate	Generator
(5Α,17β)-3-oxoandrostan-17-yl β-D-glucopyranosiduronic acid	Generator
17b-Hydroxy-5a-androstan-3-one glucuronide	Generator
17Β-hydroxy-5α-androstan-3-one glucuronide	Generator
5a-Dihydrotestosterone 17-(b-D-glucuronide)	Generator
5Α-dihydrotestosterone 17-(β-D-glucuronide)	Generator
5a-Dihydrotestosterone 17-b-glucuronide	Generator
5Α-dihydrotestosterone 17-β-glucuronide	Generator
5a-Dihydrotestosterone 17-O-(b-D-glucuronate)	Generator
5a-Dihydrotestosterone 17-O-(b-D-glucuronic acid)	Generator
5alpha-Dihydrotestosterone 17-O-(beta-D-glucuronate)	Generator
5Α-dihydrotestosterone 17-O-(β-D-glucuronate)	Generator
5Α-dihydrotestosterone 17-O-(β-D-glucuronic acid)	Generator
5a-Dihydrotestosterone glucuronide	Generator
5Α-dihydrotestosterone glucuronide	Generator
5a-Dihydrotestosterone-17g	Generator
5Α-dihydrotestosterone-17g	Generator
Stanolone glucuronic acid	Generator
5-a-Dihydrotestosterone glucuronide	Generator
5-Α-dihydrotestosterone glucuronide	Generator
Dihydrotestosterone glucuronide, (5beta,17beta)-isomer	MeSH
Dihydrotestosterone diglucuronide	MeSH

Chemical Formula

C₂₅H₃₈O₈

Average Molecular Weight

466.5644

Monoisotopic Molecular Weight

466.256668192

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(1S,2S,7S,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(1S,2S,7S,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

42037-24-1

SMILES

[H][C@@]12CC[C@H](O[C@]3([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C25H38O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h12,14-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1

InChI Key

CLQMBSSRTBUNDV-CPKOJWPQSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroid glucuronide conjugates

Alternative Parents

Substituents

Steroid-glucuronide-skeleton
Androgen-skeleton
Androstane-skeleton
3-oxosteroid
3-oxo-5-alpha-steroid
Oxosteroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Hydroxy acid
Oxane
Monosaccharide
Pyran
Cyclic ketone
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Glucuronides (LMST05010041 )

Ontology

Status

Expected but not 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	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	2.1	ALOGPS
logP	1.96	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	115.88 m³·mol⁻¹	ChemAxon
Polarizability	50.03 Å³	ChemAxon
Number of Rings	5	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	splash10-007a-6264900000-caa236f8fcb97291d23b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-014i-1261029000-94f9c3d5903740431670	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, Positive	splash10-00r7-0190600000-74d7352cda2362ddb906	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-0290000000-8dcf4c902df6743a8f9e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-0490000000-278db46d2af73936b3be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01bi-1260900000-3c796e68ff231c8976b1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1290200000-f56012a4058dcff174ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-4190000000-14bb869866e58062e6fc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-8ccc8d81a1705cd514f7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ara-9421500000-426185885a7fcd23f188	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9103100000-942b47d6aa0fb6b5c1ac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ba-0150900000-8a78977927165645dce7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01vk-0954600000-159af7866ca65a3c8336	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ap0-1911000000-5865b00a94ace6eedd9f	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Endoplasmic reticulum
Membrane

Biospecimen Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details