pentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(18),2,4,6,8,10,12,14,16,19-decaen-4-ol

• ChemBase ID: 170267
• Molecular Formular: C20H12O
• Molecular Mass: 268.30868
• Monoisotopic Mass: 268.088815
• SMILES: c1(ccc2c(c1)c1c3c(c2)ccc2c3c(cc1)ccc2)O
• Canonical SMILES: Oc1ccc2c(c1)c1ccc3c4c1c(c2)ccc4ccc3
• InChI: InChI=1S/C20H12O/c21-16-8-6-14-10-15-5-4-12-2-1-3-13-7-9-17(18(14)11-16)20(15)19(12)13/h1-11,21H
• InChIKey: OBBBXCAFTKLFGZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pentacyclo[10.6.2.0^2,^7.0^9,^1^9.0^1^6,^2^0]icosa-1(18),2,4,6,8,10,12,14,16,19-decaen-4-ol
• IUPAC Traditional name: 9-hydroxybenzo(a)pyrene
• Synonyms: Benzo[a]pyren-9-ol; 9-Hydroxybenzo[a]pyrene; 9-Hydroxy Benzopyrene

Database IDs

• CAS Number: 17573-21-6
• PubChem SID: 164226177
• PubChem CID: 28598

CALCULATED PROPERTIES

• Acid pKa: 9.746607
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.9698143
• LogD (pH = 7.4): 4.9679
• Log P: 4.969839
• Molar Refractivity: 85.1537 cm^3
• Polarizability: 38.127537 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H829410

A metabolite of Benzopyrene (BaP), a carcinogenic component of tobacco smoke implicated in lung cancer.

REFERENCES

• DiBiasio, K., et al.: Drug Metab. Dispos.,19, 227 (1991)
• Beach, J., et al.: J. Anal. Toxicol., 24, 670 (1991)
• Borman, S., et al.: Toxicol. Appl. Pharmacol., 167, 191 (1991)
• Tsai-Turton, M., et al.: Biol. Reprod., 77, 442 (1991)