ethyl (2R)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-phenylpropanoate

• ChemBase ID: 175757
• Molecular Formular: C22H22ClNO6
• Molecular Mass: 431.86618
• Monoisotopic Mass: 431.11356511
• SMILES: [C@@H]1(OC(=O)c2c(C1)c(cc(c2O)C(=O)N[C@H](Cc1ccccc1)C(=O)OCC)Cl)C
• Canonical SMILES: CCOC(=O)[C@H](NC(=O)c1cc(Cl)c2c(c1O)C(=O)O[C@@H](C2)C)Cc1ccccc1
• InChI: InChI=1S/C22H22ClNO6/c1-3-29-21(27)17(10-13-7-5-4-6-8-13)24-20(26)15-11-16(23)14-9-12(2)30-22(28)18(14)19(15)25/h4-8,11-12,17,25H,3,9-10H2,1-2H3,(H,24,26)/t12-,17-/m1/s1
• InChIKey: BPZZWRPHVVDAPT-SJKOYZFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-phenylpropanoate
• IUPAC Traditional name: ethyl (2R)-2-{[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl]formamido}-3-phenylpropanoate
• Synonyms: N-[[(3R)-5-Chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-L-phenylalanine Ethyl Ester; N-[(5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-3-phenyl-L-alanine Ethyl Ester; Ochratoxin A Ethyl Ester; Ochratoxin C

Database IDs

• CAS Number: 4865-85-4
• PubChem SID: 164231667
• PubChem CID: 71751273

CALCULATED PROPERTIES

• Acid pKa: 7.9360104
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 5.112185
• LogD (pH = 7.4): 5.0040493
• Log P: 5.113758
• Molar Refractivity: 111.2877 cm^3
• Polarizability: 42.660633 Å^3
• Polar Surface Area: 101.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O148510

Ochratoxins are toxic metabolites from Aspergillus orchraceus.

REFERENCES

• Belli, N., et al.: Int. J. Food Microb., 96, 19 ( 2004), Pardo, E., et al.: Food Microb., 23, 35 (2006)