(3R,4S)-8-hydroxy-5-(2H2)methyl-3,4-dimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid

• ChemBase ID: 164813
• Molecular Formular: C13H14O5
• Molecular Mass: 251.23991484
• Monoisotopic Mass: 251.08747839
• SMILES: C12=C(C(=O)C(=C(C1=CO[C@@H]([C@H]2C)C)O)[13C](=O)O)C
• Canonical SMILES: C[C@H]1OC=C2C(=C(C)C(=O)C(=C2O)[13C](=O)O)[C@@H]1C
• InChI: InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1/i13+1
• InChIKey: CQIUKKVOEOPUDV-RLEFRNONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-8-hydroxy-5-(^2H₂)methyl-3,4-dimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid
• IUPAC Traditional name: (3R,4S)-8-hydroxy-5-(^2H₂)methyl-3,4-dimethyl-6-oxo-3,4-dihydro-2-benzopyran-7-carboxylic acid
• Synonyms: (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic Acid-13C,d2; (3R-trans)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic Acid-13C,d2; Citrinin-13C,d2; NSC 186-13C,d2; (-)-Citrinin-13C,d2

Database IDs

• PubChem SID: 162258947
• PubChem CID: 71314881

CALCULATED PROPERTIES

• Acid pKa: 3.9141996
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.78353536
• LogD (pH = 7.4): -2.4344025
• Log P: 0.8089524
• Molar Refractivity: 65.2535 cm^3
• Polarizability: 24.46187 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C523502

Labelled (-)-Citrinin (C523500). Antibiotic substance produced by a white spore aspergilus which has been placed under the species name Aspergillus niveus. Also produced in small quantities by Penicillium citrinum.

REFERENCES

• Ciegler, A., et al.: Appl. Microbiol., 26, 271 (1973)
• Creppy, E., et al.: Toxicol. Lett., 28, 29 (1973)
• DeGroene, E., et al.: Cancer Res., 56, 299 (1973)