(3S,7R,14S)-14-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione

• ChemBase ID: 159594
• Molecular Formular: C17H12O7
• Molecular Mass: 328.27298
• Monoisotopic Mass: 328.05830272
• SMILES: c12c(cc(c3c1oc(=O)c1c3[C@H](CC1=O)O)OC)O[C@@H]1[C@H]2C=CO1
• Canonical SMILES: COc1cc2O[C@@H]3[C@H](c2c2c1c1[C@@H](O)CC(=O)c1c(=O)o2)C=CO3
• InChI: InChI=1S/C17H12O7/c1-21-9-5-10-11(6-2-3-22-17(6)23-10)15-14(9)12-7(18)4-8(19)13(12)16(20)24-15/h2-3,5-7,17-18H,4H2,1H3/t6-,7-,17+/m0/s1
• InChIKey: GYNOTJLCULOEIM-XKRJZGAWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7R,14S)-14-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^2,^9.0^3,^7.0^1^3,^1^7]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione
• IUPAC Traditional name: (3S,7R,14S)-14-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.0^2,^9.0^3,^7.0^1^3,^1^7]nonadeca-1,4,9,11,13(17)-pentaene-16,18-dione
• Synonyms: (3S,6aR,9aS)-2,3,6a,9a-Tetrahydro-3-hydroxy-4-methoxycyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione; [3S-(3α,6aα,9aα)]-2,3,6a,9a-Tetrahydro-3-hydroxy-4-methoxycyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-1,11-dione; Aflatoxin Q1

Database IDs

• CAS Number: 52819-96-2
• PubChem SID: 162253729
• PubChem CID: 104757

CALCULATED PROPERTIES

• Acid pKa: 13.9715805
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.5094773
• LogD (pH = 7.4): 0.5094772
• Log P: 0.5094773
• Molar Refractivity: 79.9466 cm^3
• Polarizability: 30.868114 Å^3
• Polar Surface Area: 91.29 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A357530

A metabolite of Aflatoxin B1; a hepatocarcinogen in many animal models and probably a human carcinogen. It is produced by the predominant forms of cytochrome P 450 enzymes responsible for the biotransformation of AFB1. It shows potential predictive value

REFERENCES

• Mykkaenen, H. et al.: Int. J. Cancer, 115, 879 (2005)
• Van Vleet, T.R. et al.: J. Toxicol. Environ. Health, 65, 853 (2005)