pentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(18),2,4,6,8,10,12,14,16,19-decaen-13-ol

• ChemBase ID: 170265
• Molecular Formular: C20H12O
• Molecular Mass: 268.30868
• Monoisotopic Mass: 268.088815
• SMILES: c1ccc2c(c1)c1c3c(c2)ccc2c3c(cc1)ccc2O
• Canonical SMILES: Oc1ccc2c3c1ccc1c3c(cc2)c2c(c1)cccc2
• InChI: InChI=1S/C20H12O/c21-18-10-7-12-5-8-16-15-4-2-1-3-13(15)11-14-6-9-17(18)19(12)20(14)16/h1-11,21H
• InChIKey: SPUUWWRWIAEPDB-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-13-ol
• IUPAC Traditional name: 3-hydroxybenzo(a)pyrene
• Synonyms: Benzo[a]pyren-3-ol; 3-Hydroxy-3,4-benzo[a]pyrene; 3-Hydroxybenzo[a]pyrene; 3-Hydroxy Benzopyrene

Database IDs

• CAS Number: 13345-21-6
• PubChem SID: 164226175
• PubChem CID: 25890

CALCULATED PROPERTIES

• Acid pKa: 9.495978
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.969795
• LogD (pH = 7.4): 4.966393
• Log P: 4.969839
• Molar Refractivity: 85.1537 cm^3
• Polarizability: 38.130318 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Dark Yellow to Green Solid
• Melting Point: 186-188°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H829400

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)