Structure Database (LMSD)

Common Name
2-hydroxyestradiol
Systematic Name
estra-1,3,5(10)-triene-2,3,17β-triol
Synonyms
LM ID
LMST02010027
Formula
C18H24O3
Exact Mass
Calculate m/z
288.172545
Sum Composition
ST 18:3;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-Hydroxyestradiol (2-HE2) is a cytochrome P450 metabolite of estradiol with low affinity for estrogen receptors. 2-HE is rapidly metabolized by catechol-O-methyltransferase (COMT) to form 2-methoxy estradiol (2-ME2) with a half-life of approximately ten minutes in rat.1 2-ME2 has achieved considerable attention as an anti-cancer agent acting as an angiogenesis inhibitor via the HIF-1a pathway.2,3,4 Due to the rapid metabolism of 2-HE2, the effects attributed to 2-HE2, may actually be those of 2-ME2.1

This information has been provided by Cayman Chemical

References

1. Mooberry, S.L. New insights into 2-methoxyestradiol, a promising antiangiogenic and antitumor agent. Curr. Opin. Oncol. 15(6), 425-430 (2003).
2. Mooberry, S.L. Mechanism of action of 2-methoxyestradiol: New developments. Drug Resist. Updat. 6(6), 355-361 (2003).
3. Zacharia, L.C., Piché, C.A., Fielding, R.M., et al. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol. J. Pharmacol. Exp. Ther. 309(3), 1093-1097 (2004).
4. Becker, C.M., Rohwer, N., Funakoshi, T., et al. 2-methoxyestradiol inhibits hypoxia-inducible factor-1α and suppressess growth of lesions in a mouse model of endometriosis. Am. J. Pathol. 172(2), 534-544 (2008).

Reactions

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String Representations

InChiKey (Click to copy)
DILDHNKDVHLEQB-XSSYPUMDSA-N
InChi (Click to copy)
InChI=1S/C18H24O3/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/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1
SMILES (Click to copy)
C1(O)=CC2[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CCC=2C=C1O

Other Databases

KEGG ID
C05301
HMDB ID
HMDB0000338
CHEBI ID
28744
PubChem CID
247304
SwissLipids ID
SLM:000485705
Cayman ID
13019
PDB ID
ECS

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 4
Aromatic Rings 1
Rotatable Bonds 0
Van der Waals Molecular Volume 278.07
Topological Polar Surface Area 60.69
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 3.60
Molar Refractivity 80.91

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Updated at
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