1-hydroxybenzo(a)pyrene

Synonyms: "benzo[a]pyren-1-ol", "benzo(a)pyren-1-ol", "1-hydroxybenzo[a]pyrene", "hydroxybenzo[a]pyrene".

Source: 1-hydroxybenzo(a)pyrene is a metabolite of benzo(a)pyrene.

Identifiers:

IUPAC Name: benzo[a]pyren-1-ol
CAS Number: 13345-23-8
PubChem ID: 25891
InChiKey: GPIRWWPRDKGKPS-UHFFFAOYSA-N
Canonical SMILES: C1=CC=C2C3=C4C(=CC2=C1)C=CC5=C4C(=C(C=C5)O)C=C3

Structural Properties:

Molecular Formula: C₂₀H₁₂O
Molecular Weight: 268.315

Pharmacophore Features:

Number of bond donors: 1
Number of bond acceptors: 1
Number of atoms different from hydrogen: 21

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3D structure (.sdf)
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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Fertuck KC, Matthews JB, Zacharewski TR. 2001. Hydroxylated benzo[a]pyrene metabolites are responsible for in vitro estrogen receptor-mediated gene expression induced by benzo[a]pyrene, but do not elicit uterotrophic effects in vivo. Toxicol Sci 59(2):231-240. DOI: 10.1093/toxsci/59.2.231. URL: https://academic.oup.com/toxsci/article/59/2/231/1667180.
van Lipzig MM, Vermeulen NP, Gusinu R, Legler J, Frank H, Seidel A, Meerman JH. 2005. Formation of estrogenic metabolites of benzo[a]pyrene and chrysene by cytochrome P450 activity and their combined and supra-maximal estrogenic activity. Environ Toxicol Pharmacol 19(1):41-55. DOI: 10.1016/j.etap.2004.03.010. URL: https://www.sciencedirect.com/science/article/pii/S1382668904001279.