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CHEBI:88730 - 5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)

ChEBI IDCHEBI:88730
ChEBI Name5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)
Stars
ASCII Name5alpha-androstane-3beta,17beta-diol 3-O-(beta-D-glucuronide)
DefinitionA steroid glucosiduronic acid that is 5α-androstane-3β,17β-diol having a single β-D-glucuronic acid residue attached at position 3. It is a biochemical marker of peripheral tissue androgen metabolism.
Last Modified14 September 2021
DownloadsMolfile
FormulaC25H40O8
Net Charge0
Average Mass468.587
Monoisotopic Mass468.27232
SMILES[H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@@H](O)CC[C@@]34[H])[C@@]1(C)CC[C@@H](O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)C2
InChIInChI=1S/C25H40O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-21,23,26-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1
InChIKeyGYNWSIBKBBWJJW-WWLGJQRMSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606)
urine (BTO:0001419) PubMed (22624806)
blood serum (BTO:0000133) PubMed (10438402)
Roles Classification
Biological Roles:
human urinary metabolite  Any metabolite (endogenous or exogenous) found in human urine samples.
human blood serum metabolite  Any metabolite (endogenous or exogenous) found in human blood serum samples.
ChEBI Ontology
Outgoing Relation(s)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide) (CHEBI:88730) has functional parent 5α-androstane-3α,17β-diol (CHEBI:36713)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide) (CHEBI:88730) has functional parent β-D-glucuronic acid (CHEBI:28860)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide) (CHEBI:88730) has role human blood serum metabolite (CHEBI:85234)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide) (CHEBI:88730) has role human urinary metabolite (CHEBI:84087)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide) (CHEBI:88730) is a 17β-hydroxy steroid (CHEBI:35343)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide) (CHEBI:88730) is a steroid glucosiduronic acid (CHEBI:26763)
5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide) (CHEBI:88730) is a β-D-glucosiduronic acid (CHEBI:15341)
IUPAC Name 
17β-hydroxy-5α-androstan-3α-yl β-D-glucopyranosiduronic acid
Synonyms  Source
(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1-hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl β-D-glucopyranosiduronic acidChEBI
(3α,5α,17β)-17-hydroxyandrostan-3-yl β-D-glucopyranosiduronic acidChEBI
17-hydroxyandrostane-3-glucuronosideChemIDplus
17β-hydroxy-5α-androstan-3α-yl glucosiduronic acidChEBI
5α-androstan-3α,17β-diol-O-3-β-glucuronic acidChEBI
Adiol 3-GChemIDplus
Manual XrefsDatabases
LMST05010004LIPID MAPS
HMDB0010359HMDB
FDB027511FooDB
Androstanediol_glucuronideWikipedia
20558912ChemSpider
Registry NumbersSources
CAS:65535-18-4ChemIDplus
Citations