CHEBI:379896 - 17β-hydroxy-17-methylestra-4,9,11-trien-3-one

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ChEBI Name 17β-hydroxy-17-methylestra-4,9,11-trien-3-one
ChEBI ID CHEBI:379896
ChEBI ASCII Name 17beta-hydroxy-17-methylestra-4,9,11-trien-3-one
Definition A synthetic non-aromatisable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Secondary ChEBI IDs CHEBI:59645, CHEBI:45313
Supplier Information
Download Molfile XML SDF
Formula C19H24O2
Net Charge 0
Average Mass 284.39270
Monoisotopic Mass 284.17763
InChI InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1
InChIKey CCCIJQPRIXGQOE-XWSJACJDSA-N
SMILES [H][C@@]12CCC3=CC(=O)CCC3=C1C=C[C@@]1(C)[C@@]2([H])CC[C@]1(C)O
Roles Classification
Biological Role(s): androgen
A sex hormone that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors.
(via anabolic androgenic steroid )
anabolic agent
A compound which stimulates anabolism and inhibits catabolism. Anabolic agents stimulate the development of muscle mass, strength, and power.
(via anabolic androgenic steroid )
hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
(via steroid hormone )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 17β-hydroxy-17-methylestra-4,9,11-trien-3-one (CHEBI:379896) has parent hydride estrane (CHEBI:23966)
17β-hydroxy-17-methylestra-4,9,11-trien-3-one (CHEBI:379896) has role androgen (CHEBI:50113)
17β-hydroxy-17-methylestra-4,9,11-trien-3-one (CHEBI:379896) is a 17β-hydroxy steroid (CHEBI:35343)
17β-hydroxy-17-methylestra-4,9,11-trien-3-one (CHEBI:379896) is a 3-oxo steroid (CHEBI:47788)
17β-hydroxy-17-methylestra-4,9,11-trien-3-one (CHEBI:379896) is a anabolic androgenic steroid (CHEBI:50786)
IUPAC Name
17β-hydroxy-17-methylestra-4,9,11-trien-3-one
INNs Sources
metribolona ChemIDplus
metribolone ChemIDplus
metribolonum ChemIDplus
Synonyms Sources
17-beta-Hydroxy-17-methylestra-4,9,11-trien-3-one KEGG COMPOUND
17-methyloestra-4,9,11-trien-3-one,17β-ol ChEBI
17alpha-Methyltrienolone ChemIDplus
Methyltrienolone ChemIDplus
Metribolone KEGG COMPOUND
R1881 ChEBI
R1881 (synthetic androgen) ChEBI
Manual Xrefs Databases
C14257 KEGG COMPOUND
DB02998 DrugBank
NL6401555 Patent
R18 PDBeChem
View more database links
Registry Numbers Types Sources
2626053 Beilstein Registry Number Beilstein
965-93-5 CAS Registry Number KEGG COMPOUND
965-93-5 CAS Registry Number ChemIDplus
Citation Waiting for Citations Type Source
17077481 PubMed citation Europe PMC
Last Modified
28 July 2014