(2R)-2-({4-[(6aS)-3-amino-1-oxo-1H,4H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid

• ChemBase ID: 2047
• Molecular Formular: C20H21N7O6
• Molecular Mass: 455.42404
• Monoisotopic Mass: 455.15533143
• SMILES: Nc1nc(=O)c2c([nH]1)N=C[C@@H]1CN(CN21)c1ccc(cc1)C(=O)N[C@H](CCC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)N1C[C@@H]2N(C1)c1c(N=C2)[nH]c(nc1=O)N
• InChI: InChI=1S/C20H21N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,7,12-13H,5-6,8-9H2,(H,23,30)(H,28,29)(H,32,33)(H3,21,24,25,31)/t12-,13-/m1/s1
• InChIKey: BHJAPJNOACHPNI-CHWSQXEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-({4-[(6aS)-3-amino-1-oxo-1H,4H,6aH,7H,8H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
• IUPAC Traditional name: (2R)-2-({4-[(6aS)-3-amino-1-oxo-4H,6aH,7H,9H-imidazolidino[1,5-f]pteridin-8-yl]phenyl}formamido)pentanedioic acid
• Synonyms: 5,10-Methylene-6-Hydrofolic Acid

Database IDs

• PubChem SID: 160965502; 46505084
• PubChem CID: 6323520

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.2399886
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): -4.433215
• LogD (pH = 7.4): -7.305063
• Log P: -2.8540776
• Molar Refractivity: 123.2203 cm^3
• Polarizability: 42.04603 Å^3
• Polar Surface Area: 190.02 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.78
• LOG S: -3.13
• Solubility (Water): 3.35e-01 g/l

DETAILS

DrugBank - DB02301

Drug information: experimental