(2R)-2-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-phenylpropanoic acid

• ChemBase ID: 175755
• Molecular Formular: C20H19NO6
• Molecular Mass: 369.36796
• Monoisotopic Mass: 369.12123733
• SMILES: [C@@H]1(OC(=O)c2c(C1)ccc(c2O)C(=O)N[C@H](Cc1ccccc1)C(=O)O)C
• Canonical SMILES: C[C@H]1OC(=O)c2c(C1)ccc(c2O)C(=O)N[C@@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C20H19NO6/c1-11-9-13-7-8-14(17(22)16(13)20(26)27-11)18(23)21-15(19(24)25)10-12-5-3-2-4-6-12/h2-8,11,15,22H,9-10H2,1H3,(H,21,23)(H,24,25)/t11-,15-/m1/s1
• InChIKey: DAEYIVCTQUFNTM-IAQYHMDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl]formamido}-3-phenylpropanoic acid
• IUPAC Traditional name: (2R)-2-{[(3R)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl]formamido}-3-phenylpropanoic acid
• Synonyms: N-[[(3R)-3,4-Dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-L-phenylalanine; N-[(8-Hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-3-phenyl-L-alanine; (R)-N-[(3,4-Dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl)carbonyl]-L-phenylalanine; Ochratoxin B

Database IDs

• CAS Number: 4825-86-9
• PubChem SID: 164231665
• PubChem CID: 71751271

CALCULATED PROPERTIES

• Acid pKa: 3.1589692
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6907457
• LogD (pH = 7.4): 0.51493925
• Log P: 4.0070114
• Molar Refractivity: 96.9652 cm^3
• Polarizability: 36.834732 Å^3
• Polar Surface Area: 112.93 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O148500

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)