4-hydroxy(4-13C)-2H,4H,6H-furo[3,2-c]pyran-2-one

• ChemBase ID: 176170
• Molecular Formular: C7H6O4
• Molecular Mass: 155.11279484
• Monoisotopic Mass: 155.02996351
• SMILES: O1CC=C2C(=CC(=O)O2)[13CH]1O
• Canonical SMILES: O=C1OC2=CCO[13CH](C2=C1)O
• InChI: InChI=1S/C7H6O4/c8-6-3-4-5(11-6)1-2-10-7(4)9/h1,3,7,9H,2H2/i7+1
• InChIKey: ZRWPUFFVAOMMNM-CDYZYAPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy(4-^1^3C)-2H,4H,6H-furo[3,2-c]pyran-2-one
• IUPAC Traditional name: 4-hydroxy(4-^1^3C)-4H,6H-furo[3,2-c]pyran-2-one
• Synonyms: 4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one-13C3; Clairformin-13C3; Clavacin-13C3; Clavatin-13C3; Claviformin-13C3; DL-Patulin-13C3; Expansin-13C3; Expansine-13C3; Mycoin-13C3; Mycoin C-13C3; NSC 8120-13C3; Patuline-13C3; Penicidin-13C3; Terinin-13C3; Patulin-13C3

Database IDs

• CAS Number: 748133-69-9
• PubChem SID: 164232080
• PubChem CID: 46782686

CALCULATED PROPERTIES

• Acid pKa: 11.653255
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.3772453
• LogD (pH = 7.4): -0.3772692
• Log P: -0.377245
• Molar Refractivity: 37.0348 cm^3
• Polarizability: 13.874448 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P206502

Labelled Patulin (PAT), a mycotoxin produced by certain species of Penicillium, Aspergillus, and Byssochlamys, is mainly found in ripe apple and apple products. Patulin-induced genotoxicity and modulation of glutathione in Hep G2 cells. Antibiotic.

REFERENCES

• Scott, P., et al.: J. Agric. Food Chem., 20, 450 (1972)
• Aden, D., et al.: Nature, 282, 615 (1972)
• Surralles, J., et al.: Mutat. Res., 341, 169 (1972)
• Alves, I., et al.: Mutagenesis, 15, 229 (1972)
• Liu, B., et al.: Toxicol. Appl. Pharmacol., 191, 255 (