(2H14)hexacyclo[10.10.2.02,7.09,23.014,19.020,24]tetracosa-1(22),2,4,6,8,10,12,14,16,18,20,23-dodecaene

• ChemBase ID: 166873
• Molecular Formular: C24H14
• Molecular Mass: 302.36796
• Monoisotopic Mass: 302.10955045
• SMILES: c1c2c(ccc1)cc1c3c2ccc2c3c(cc1)cc1c2cccc1
• Canonical SMILES: c1ccc2c(c1)c1ccc3c4c1c(c2)ccc4cc1c3cccc1
• InChI: InChI=1S/C24H14/c1-3-7-19-15(5-1)13-17-9-10-18-14-16-6-2-4-8-20(16)22-12-11-21(19)23(17)24(18)22/h1-14H
• InChIKey: TUGYIJVAYAHHHM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (^2H₁₄)hexacyclo[10.10.2.0^2,^7.0^9,^2^3.0^1^4,^1^9.0^2^0,^2^4]tetracosa-1(22),2,4,6,8,10,12,14,16,18,20,23-dodecaene
• IUPAC Traditional name: (^2H₁₄)hexacyclo[10.10.2.0^2,^7.0^9,^2^3.0^1^4,^1^9.0^2^0,^2^4]tetracosa-1(22),2,4,6,8,10,12,14,16,18,20,23-dodecaene
• Synonyms: Benzo[rst]pentaphene-d14; Benzo[rst]pentacene-d14; 1,2:7,8-Dibenzpyrene-d14; 3,4:9,10-Dibenzopyrene-d14; Dibenzo[b,h]pyrene-d14; NSC 87521-d14; Dibenzo[a,i]pyrene-d14

Database IDs

• PubChem SID: 162261006
• PubChem CID: 56845951

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.262881
• LogD (pH = 7.4): 6.262881
• Log P: 6.262881
• Molar Refractivity: 99.623 cm^3
• Polarizability: 45.514893 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D416987

Labelled analogue of Dibenzo[a,i]pyrene, a polycyclic aromatic hydrocarbon (PAH) with potent carcinogenic activity. Dibenzo[a,i]pyrene was shown to induce DNA adduction, tumorigenicity as well as Ki-ras oncogene mutations in strain A/J mouse lung. Dibenzo

REFERENCES

• Prahalad, A.K. et al.: Carcinogenesis, 18, 1955 (1997)
• Wynder, E.L. et al.: Nature, 192, 1092 (1997)
• Homburger, F. et al.: J. Nat. Cancer Inst., 44, 357 (1997)