CHEBI:6784 - mestranol

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ChEBI Name mestranol
ChEBI ID CHEBI:6784
Definition A terminal acetylenic compound that is (17α)-17-ethynylestra-1(10),2,4-triene substituted by a methoxy group at position 3 and a hydroxy group at position 17.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H26O2
Net Charge 0
Average Mass 310.42994
Monoisotopic Mass 310.193
InChI InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1
InChIKey IMSSROKUHAOUJS-MJCUULBUSA-N
SMILES [H][C@]12CC[C@@]3(C)[C@@]([H])(CC[C@@]3(O)C#C)[C@]1([H])CCc1cc(OC)ccc21
Roles Classification
Biological Role(s): xenoestrogen
A synthetic or semi-synthetic compound that has oestrogenic activity.
Application(s): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
xenoestrogen
A synthetic or semi-synthetic compound that has oestrogenic activity.
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ChEBI Ontology
Outgoing mestranol (CHEBI:6784) has functional parent 17β-estradiol (CHEBI:16469)
mestranol (CHEBI:6784) has role prodrug (CHEBI:50266)
mestranol (CHEBI:6784) has role xenoestrogen (CHEBI:76988)
mestranol (CHEBI:6784) is a 17β-hydroxy steroid (CHEBI:35343)
mestranol (CHEBI:6784) is a aromatic ether (CHEBI:35618)
mestranol (CHEBI:6784) is a terminal acetylenic compound (CHEBI:73477)
IUPAC Name
17-ethynyl-3-methoxyestra-1(10),2,4-trien-17β-ol
INNs Sources
mestranol KEGG DRUG
mestranolum ChemIDplus
Synonyms Sources
(+)-17α-Ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratriene NIST Chemistry WebBook
(+)-17α-Ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-oestratriene NIST Chemistry WebBook
17-ethynyl-3-methoxyoestra-1(10),2,4-trien-17β-ol ChEBI
3-Methoxy-17α-ethynylestradiol NIST Chemistry WebBook
3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-ol NIST Chemistry WebBook
Ethynylestradiol 3-methyl ether NIST Chemistry WebBook
Mestranol KEGG COMPOUND
Database Links Databases
1714 DrugCentral
C07618 KEGG COMPOUND
D00575 KEGG DRUG
DB01357 DrugBank
HMDB0015446 HMDB
LSM-2693 LINCS
Mestranol Wikipedia
US2666769 Patent
View more database links
Registry Numbers Types Sources
2625905 Reaxys Registry Number Reaxys
2625905 Beilstein Registry Number Beilstein
72-33-3 CAS Registry Number KEGG COMPOUND
72-33-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
12139060 PubMed citation Europe PMC
16414683 PubMed citation Europe PMC
Last Modified
22 February 2017