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

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ChEBI Name 5α-androstane-3β,17β-diol 3-O-(β-D-glucuronide)
ChEBI ID CHEBI:88730
ChEBI ASCII Name 5alpha-androstane-3beta,17beta-diol 3-O-(beta-D-glucuronide)
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB9258118, ZINC000003875484
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Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, breast cancer in women, and anemia. It is taken by mouth. Side effects of fluoxymesterone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage and cardiovascular side effects like high blood pressure. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization. Fluoxymesterone was first described in 1956 and was introduced for medical use in 1957. In addition to its medical use, fluoxymesterone is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit.
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Formula C25H40O8
Net Charge 0
Average Mass 468.587
Monoisotopic Mass 468.27232
InChI InChI=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
InChIKey GYNWSIBKBBWJJW-WWLGJQRMSA-N
SMILES [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: PubMed
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 functional parent 5α-androstane-3α,17β-diol (CHEBI:36713)
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 β-D-glucosiduronic acid (CHEBI:15341)
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)
IUPAC Name
17β-hydroxy-5α-androstan-3α-yl β-D-glucopyranosiduronic acid
Synonyms Sources
(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1-hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl β-D-glucopyranosiduronic acid ChEBI
(3α,5α,17β)-17-hydroxyandrostan-3-yl β-D-glucopyranosiduronic acid ChEBI
17-hydroxyandrostane-3-glucuronoside ChemIDplus
17β-hydroxy-5α-androstan-3α-yl glucosiduronic acid ChEBI
3α-androstanediol glucuronide ChEBI
3α-diolG ChEBI
5α-androstan-3α,17β-diol-O-3-β-glucuronic acid ChEBI
Adiol 3-G ChemIDplus
androstanediol glucuronide ChEBI
Manual Xrefs Databases
20558912 ChemSpider
Androstanediol_glucuronide Wikipedia
FDB027511 FooDB
HMDB0010359 HMDB
LMST05010004 LIPID MAPS
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Registry Number Type Source
65535-18-4 CAS Registry Number ChemIDplus
Citations Types Sources
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Last Modified
14 September 2021