Structure Database (LMSD)

Common Name
2-Hydroxyestrone
Systematic Name
2,3-dihydroxy-estra-1,3,5(10)-trien-17-one
Synonyms
LM ID
LMST02010032
Formula
C18H22O3
Exact Mass
Calculate m/z
286.156895
Sum Composition
ST 18:4;O3
Status
Curated
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Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C18 steroids (estrogens) and derivatives [ST0201]

Biological Context

2-hydroxy Estrone is an active metabolite of the endogenous estrogen estrone .1 It is formed from estrone primarily by the cytochrome P450 (CYP) isoforms CYP1A2, CYP1A1, and CYP1B1 and metabolized to 2-methoxy estrone by catechol-O-methyltransferase (COMT). 2-hydroxy Estrone (10 µM) inhibits the proliferation of estrogen receptor-positive MCF-7, but not estrogen receptor-negative MDA-MB-231, breast cancer cells cultured with the COMT inhibitor quinalizarin.2 It inhibits iron-ADP-adriamycin complex-induced lipid peroxidation of liposomes prepared from rat liver microsomes (IC50 = 2.7 µM).3

This information has been provided by Cayman Chemical

References

1. Nakano, M., Sugioka, K., Naito, I., et al. Novel and potent biological antioxidants on membrane phospholipid peroxidation: 2-Hydroxy estrone and 2-hydroxy estradiol. Biochem. Biophys. Res. Commun. 142(3), 919-924 (1987).
2. Schneider, J., Huh, M.M., Bradlow, H.L., et al. Antiestrogen action of 2-hydroxyestrone on MCF-7 human breast cancer cells. J. Biol. Chem. 259(8), 4840-4845 (1984).
3. Cribb, A.E., Knight, M.J., Dryer, D., et al. Role of polymorphic human cytochrome P450 enzymes in estrone oxidation. Cancer Epidemiol. Biomarkers Prev. 15(3), 551-558 (2006).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
SWINWPBPEKHUOD-JPVZDGGYSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@]12([H])CC[C@]3(C)C(CC[C@@]3([H])[C@]1([H])CCC1C=C(C(O)=CC2=1)O)=O

Other Databases

KEGG ID
C05298
HMDB ID
HMDB0000343
CHEBI ID
1156
PubChem CID
440623
SwissLipids ID
SLM:000485704
Cayman ID
34154

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 4
Aromatic Rings 1
Rotatable Bonds 0
Van der Waals Molecular Volume 275.43
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 3.52
Molar Refractivity 79.40

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Created at
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Updated at
9th Jun 2022