2-hydroxyestrone

2-Hydroxyestrone

Names
IUPAC name (8R,9S,13S,14S)-2,3-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
Other names 2-OHE1; 2,3-Dihydroxyestra-1,3,5(10)-trien-17-one; Estra-1,3,5(10)-trien-2,3-diol-17-one
Identifiers
CAS Number	362-06-1
3D model (Jmol)	Interactive image
ChEBI	CHEBI:1156
ChEMBL	ChEMBL1627343
ChemSpider	389514
KEGG	C05298
PubChem	440623
UNII	UQS3A06ILY
InChI InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1 Key: SWINWPBPEKHUOD-JPVZDGGYSA-N
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC(=C(C=C34)O)O
Properties
Chemical formula	C18H22O3
Molar mass	286.371 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Hydroxyestrone (2-OHE1), also known as estra-1,3,5(10)-trien-2,3-diol-17-one, is an endogenous, naturally occurring catechol estrogen and a major metabolite of estrone and estradiol. It is formed irreversibly from estrone in the liver and to a lesser extent in other tissues via 2-hydroxylation mediated by enzymes, mainly the CYP3A and CYP1A subfamilies. 2-OHE1 is the most abundant catechol estrogen in the body. It is not significantly uterotrophic in bioassays, whereas other hydroxylated estrogen metabolites including 2-hydroxyestradiol, 16α-hydroxyestrone, estriol (16α-hydroxyestradiol), 4-hydroxyestradiol, and 4-hydroxyestrone all are.