15α-Hydroxyestradiol

15α-Hydroxyestradiol
Names
	IUPAC name (8R,9S,13S,14S,15S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,17-triol
	Other names 15α-OH-E2; 15α-Hydroxy-17β-estradiol; Estra-1,3,5(10)-triene-3,15α,17β-triol; 3,15α,17β-Trihydroxyestra-1,3,5(10)-triene
Identifiers
CAS Number	570-30-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:87593;
ChemSpider	59792;
PubChem CID	66418;
CompTox Dashboard (EPA)	DTXSID00972490 ;
	InChI InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)17(18)15(20)9-16(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16+,17-,18-/m1/s1 Key: QVQMPLATUBCZMQ-GVLSGGHMSA-N;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1[C@H](C[C@@H]2O)O)CCC4=C3C=CC(=C4)O;
Properties
Chemical formula	C18H24O3
Molar mass	288.387 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

15α-Hydroxyestradiol (15α-OH-E2) is an endogenous estrogen which occurs during pregnancy.[1][2][3] It is structurally related to estriol (16α-hydroxyestradiol) and estetrol (15α-hydroxyestriol or 15α,16α-dihydroxyestradiol).

References

Lisboa BP, Goebelsmann U, Diczfalusy E (March 1967). "Isolation of 15-alpha-hydroxyoestradiol from human pregnancy urine". Acta Endocrinol. 54 (3): 467–72. doi:10.1530/acta.0.0540467. PMID 6071364.
Jirku H, Kadner S, Levitz M (October 1972). "Metabolism of 15alpha-hydroxyestradiol in human pregnancy". J. Clin. Endocrinol. Metab. 35 (4): 522–34. doi:10.1210/jcem-35-4-522. PMID 4559652.
Lee AJ, Kosh JW, Conney AH, Zhu BT (August 2001). "Characterization of the NADPH-dependent metabolism of 17beta-estradiol to multiple metabolites by human liver microsomes and selectively expressed human cytochrome P450 3A4 and 3A5". J. Pharmacol. Exp. Ther. 298 (2): 420–32. PMID 11454902.

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[pmid6071364-1] Lisboa BP, Goebelsmann U, Diczfalusy E (March 1967). "Isolation of 15-alpha-hydroxyoestradiol from human pregnancy urine". Acta Endocrinol. 54 (3): 467–72. doi:10.1530/acta.0.0540467. PMID 6071364.

[pmid4559652-2] Jirku H, Kadner S, Levitz M (October 1972). "Metabolism of 15alpha-hydroxyestradiol in human pregnancy". J. Clin. Endocrinol. Metab. 35 (4): 522–34. doi:10.1210/jcem-35-4-522. PMID 4559652.

[pmid11454902-3] Lee AJ, Kosh JW, Conney AH, Zhu BT (August 2001). "Characterization of the NADPH-dependent metabolism of 17beta-estradiol to multiple metabolites by human liver microsomes and selectively expressed human cytochrome P450 3A4 and 3A5". J. Pharmacol. Exp. Ther. 298 (2): 420–32. PMID 11454902.