(2S,3R)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]-3-methylpentanoic acid

• ChemBase ID: 2361
• Molecular Formular: C14H23N2O7P
• Molecular Mass: 362.315381
• Monoisotopic Mass: 362.12428772
• SMILES: CC[C@@H](C)[C@H](NCc1c(O)c(C)ncc1COP(=O)(O)O)C(=O)O
• Canonical SMILES: CC[C@H]([C@@H](C(=O)O)NCc1c(cnc(c1O)C)COP(=O)(O)O)C
• InChI: InChI=1S/C14H23N2O7P/c1-4-8(2)12(14(18)19)16-6-11-10(7-23-24(20,21)22)5-15-9(3)13(11)17/h5,8,12,16-17H,4,6-7H2,1-3H3,(H,18,19)(H2,20,21,22)/t8-,12+/m1/s1
• InChIKey: GZZDWFDWHXPWJK-PELKAZGASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]-3-methylpentanoic acid
• IUPAC Traditional name: (2S,3R)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]-3-methylpentanoic acid
• Synonyms: N-[O-Phosphono-Pyridoxyl]-Isoleucine

Database IDs

• PubChem SID: 46508097; 160965812
• PubChem CID: 46936443

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.1889315
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -4.0877576
• LogD (pH = 7.4): -4.885322
• Log P: -2.7665927
• Molar Refractivity: 85.5854 cm^3
• Polarizability: 33.65195 Å^3
• Polar Surface Area: 149.21 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.15
• LOG S: -2.72
• Solubility (Water): 6.91e-01 g/l

DETAILS

DrugBank - DB02635

Drug information: experimental