4-hydroxy-2,3,3',4',5-pentachlorobiphenyl

Synonyms: "2,3,3',4',5-pentachloro-4-hydroxybiphenyl", "2,3,3',4',5-pentachloro-4-biphenylol", "2,3,6-trichloro-4-(3,4-dichlorophenyl)phenol"

Source: 4-hydroxy-2,3,3',4',5-pentachlorobiphenyl is one of the major metabolites of PCBs detected in human blood.

Identifiers:

IUPAC Name: 2,3,6-trichloro-4-(3,4-dichlorophenyl)phenol
CAS Number: 152969-11-4
PubChem ID: 177947
InChiKey: WGNCTWHUJUDFCH-UHFFFAOYSA-N
Canonical SMILES: C1=CC(=C(C=C1C2=CC(=C(C(=C2Cl)Cl)O)Cl)Cl)Cl

Structural Properties:

Molecular Formula: C12H5Cl5O
Molecular Weight: 342,433

Pharmacophore Features:

Number of bond donors: 1
Number of bond acceptors: 1
Number of atoms different from hydrogen: 18

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Toxicological Information

ACToR (Aggregated Computational Toxicology Resource)

Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors


Kramer VJ, Giesy JP. 1999. Specific binding of hydroxylated polychlorinated biphenyl metabolites and other substances to bovine calf uterine estrogen receptor: structure-binding relationships. Sci Total Environ 233(1-3):141-161.
Moore M, Mustain M, Daniel K, Chen I, Safe S, Zacharewski T, Gillesby B, Joyeux A, Balaguer P. 1997. Antiestrogenic activity of hydroxylated polychlorinated biphenyl congeners identified in human serum. Toxicol Appl Pharmacol 142(1):160-168.
Schuur AG, Brouwer A, Bergman A, Coughtrie MWH, Visser TJ. 1998. Inhibition of thyroid hormone sulfation by hydroxylated metabolites of polychlorinated biphenyls. Chem Biol Interact 109(1-3):293-297.

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