7-hydroxybenzo(a)pyrene

Synonyms: "benzo[a]pyren-7-ol", "benzo(a)pyren-7-ol", "7-hydroxybenzo[a]pyrene", "7-hydroxy benzo[a]pyrene".

Source: 7-hydroxybenzo(a)pyrene is a metabolite of benzo(a)pyrene.

Identifiers:

IUPAC Name: benzo[a]pyren-7-ol
CAS Number: 37994-82-4
PubChem ID: 37880
InChiKey: CNQAYISXCZTDQX-UHFFFAOYSA-N
Canonical SMILES: C1=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4C=CC=C5O)C=C2

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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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.