(3S,7R)-11-hydroxy-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: 159592
• Molecular Formular: C16H10O6
• Molecular Mass: 298.247
• Monoisotopic Mass: 298.04773804
• SMILES: c12c(cc(c3c1oc(=O)c1c3CCC1=O)O)O[C@@H]1[C@H]2C=CO1
• Canonical SMILES: O=C1CCc2c1c(=O)oc1c2c(O)cc2c1[C@@H]1C=CO[C@@H]1O2
• InChI: InChI=1S/C16H10O6/c17-8-2-1-6-11-9(18)5-10-13(7-3-4-20-16(7)21-10)14(11)22-15(19)12(6)8/h3-5,7,16,18H,1-2H2/t7-,16+/m0/s1
• InChIKey: NRCXNPKDOMYPPJ-HYORBCNSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7R)-11-hydroxy-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)-11-hydroxy-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: (6aR,9aS)-2,3,6a,9a-Tetrahydro-4-hydroxycyclopenta[c]furo[3’,2’:4,5]furo[2,3-h][1]benzopyran-1,11-dione; Aflatoxin P1

Database IDs

• CAS Number: 32215-02-4
• PubChem SID: 162253727
• PubChem CID: 5484726

CALCULATED PROPERTIES

• Acid pKa: 6.898373
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.4215943
• LogD (pH = 7.4): 0.8276717
• Log P: 1.4384868
• Molar Refractivity: 74.1028 cm^3
• Polarizability: 28.301748 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >240°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A357520

The oxidative metabolite of Aflatoxin B1; shows the highest risck of hepatocellular carcinoma.

REFERENCES

• Wong, Z., et al.: Toxicol. Appl. Pharmacol., 55, 115 (1980)
• Yu, M., et al.: Cancer Res., 51, 5621 (1980)
• Imaoka, S., et al.: Carcinogenesis, 14, 117 (1980)
• Aguilar, F., et al.: Science, 264, 1317 (1980)