(2R)-2-{[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid

• ChemBase ID: 2953
• Molecular Formular: C20H23N7O7
• Molecular Mass: 473.43932
• Monoisotopic Mass: 473.16589611
• SMILES: Nc1nc(=O)c2c(NC[C@H](CNc3ccc(cc3)C(=O)N[C@H](CCC(=O)O)C(=O)O)N2C=O)[nH]1
• Canonical SMILES: O=CN1[C@@H](CNc2ccc(cc2)C(=O)N[C@@H](C(=O)O)CCC(=O)O)CNc2c1c(=O)nc([nH]2)N
• InChI: InChI=1S/C20H23N7O7/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32)/t12-,13+/m0/s1
• InChIKey: VVIAGPKUTFNRDU-QWHCGFSZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[4-({[(6S)-2-amino-5-formyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• IUPAC Traditional name: (2R)-2-{[4-({[(6S)-2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}pentanedioic acid
• Synonyms: 5-Formyl-5,6,7,8-Tetrahydrofolate

Database IDs

• CAS Number: 58-05-9
• PubChem SID: 160966400; 46506235
• PubChem CID: 3033683

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.0870106
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -6.242469
• LogD (pH = 7.4): -8.894597
• Log P: -3.8975205
• Molar Refractivity: 126.462 cm^3
• Polarizability: 43.311886 Å^3
• Polar Surface Area: 215.55 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.06
• LOG S: -3.2
• Solubility (Water): 3.00e-01 g/l

DETAILS

DrugBank - DB03256

• Drug Groups: experimental
• Description: The active metabolite of FOLIC ACID. Leucovorin is used principally as its calcium salt as an antidote to folic acid antagonists which block the conversion of folic acid to folinic acid. [PubChem]