(2R)-2-[(4-{2-[(6S)-2-amino-4-oxo-1H,4H,5H,6H,7H,8H-pyrido[2,3-d]pyrimidin-6-yl]ethyl}phenyl)formamido]pentanedioic acid

• ChemBase ID: 3283
• Molecular Formular: C21H25N5O6
• Molecular Mass: 443.4531
• Monoisotopic Mass: 443.18048355
• SMILES: Nc1nc(=O)c2c(NC[C@@H](CCc3ccc(cc3)C(=O)N[C@H](CCC(=O)O)C(=O)O)C2)[nH]1
• Canonical SMILES: OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)CC[C@@H]1CNc2c(C1)c(=O)nc([nH]2)N
• InChI: InChI=1S/C21H25N5O6/c22-21-25-17-14(19(30)26-21)9-12(10-23-17)2-1-11-3-5-13(6-4-11)18(29)24-15(20(31)32)7-8-16(27)28/h3-6,12,15H,1-2,7-10H2,(H,24,29)(H,27,28)(H,31,32)(H4,22,23,25,26,30)/t12-,15+/m0/s1
• InChIKey: ZUQBAQVRAURMCL-SWLSCSKDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(4-{2-[(6S)-2-amino-4-oxo-1H,4H,5H,6H,7H,8H-pyrido[2,3-d]pyrimidin-6-yl]ethyl}phenyl)formamido]pentanedioic acid
• IUPAC Traditional name: (2R)-2-[(4-{2-[(6S)-2-amino-4-oxo-1H,5H,6H,7H,8H-pyrido[2,3-d]pyrimidin-6-yl]ethyl}phenyl)formamido]pentanedioic acid
• Synonyms: 5,10-Dideazatetrahydrofolic Acid

Database IDs

• PubChem SID: 160966725; 46506505
• PubChem CID: 46936736

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.0330744
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.7401922
• LogD (pH = 7.4): -6.4106164
• Log P: -1.4129827
• Molar Refractivity: 121.9982 cm^3
• Polarizability: 42.577194 Å^3
• Polar Surface Area: 183.21 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.75
• LOG S: -3.69
• Solubility (Water): 9.11e-02 g/l

DETAILS

DrugBank - DB03625

Drug information: experimental