(2R)-2-({4-[(1R)-2-(2-amino-4-hydroxyquinazolin-6-yl)-1-carboxyethyl]phenyl}formamido)pentanedioic acid

• ChemBase ID: 3875
• Molecular Formular: C23H22N4O8
• Molecular Mass: 482.44278
• Monoisotopic Mass: 482.14376368
• SMILES: Nc1nc(O)c2cc(C[C@@H](C(=O)O)c3ccc(cc3)C(=O)N[C@H](CCC(=O)O)C(=O)O)ccc2n1
• Canonical SMILES: OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)[C@H](C(=O)O)Cc1ccc2c(c1)c(O)nc(n2)N
• InChI: InChI=1S/C23H22N4O8/c24-23-26-16-6-1-11(10-15(16)20(31)27-23)9-14(21(32)33)12-2-4-13(5-3-12)19(30)25-17(22(34)35)7-8-18(28)29/h1-6,10,14,17H,7-9H2,(H,25,30)(H,28,29)(H,32,33)(H,34,35)(H3,24,26,27,31)/t14-,17-/m1/s1
• InChIKey: DAOQLLQRJAXMGY-RHSMWYFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-({4-[(1R)-2-(2-amino-4-hydroxyquinazolin-6-yl)-1-carboxyethyl]phenyl}formamido)pentanedioic acid
• IUPAC Traditional name: (2R)-2-({4-[(1R)-2-(2-amino-4-hydroxyquinazolin-6-yl)-1-carboxyethyl]phenyl}formamido)pentanedioic acid
• Synonyms: (10r)-10-Formyl-5,8,10-Trideazafolic Acid

Database IDs

• PubChem SID: 162103348
• PubChem CID: 46936419

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.114191
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -3.4819775
• LogD (pH = 7.4): -7.8361173
• Log P: 1.7199887
• Molar Refractivity: 121.6634 cm^3
• Polarizability: 46.626152 Å^3
• Polar Surface Area: 213.03 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.08
• LOG S: -3.83
• Solubility (Water): 7.16e-02 g/l

DETAILS

DrugBank - DB04264

Drug information: experimental