(2R,3E)-4-(2-aminoethoxy)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]but-3-enoic acid

• ChemBase ID: 2979
• Molecular Formular: C14H22N3O8P
• Molecular Mass: 391.313541
• Monoisotopic Mass: 391.11445131
• SMILES: Cc1ncc(COP(=O)(O)O)c(CN[C@H](/C=C/OCCN)C(=O)O)c1O
• Canonical SMILES: NCCO/C=C/[C@H](C(=O)O)NCc1c(cnc(c1O)C)COP(=O)(O)O
• InChI: InChI=1S/C14H22N3O8P/c1-9-13(18)11(10(6-16-9)8-25-26(21,22)23)7-17-12(14(19)20)2-4-24-5-3-15/h2,4,6,12,17-18H,3,5,7-8,15H2,1H3,(H,19,20)(H2,21,22,23)/b4-2+/t12-/m1/s1
• InChIKey: ZYLUFTNLRAGXLR-FXMSTWTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3E)-4-(2-aminoethoxy)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]but-3-enoic acid
• IUPAC Traditional name: (2R,3E)-4-(2-aminoethoxy)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]but-3-enoic acid
• Synonyms: 4-(2-Amino-Ethoxy)-2-[(3-Hydroxy-2-Methyl-5-Phosphonooxymethyl-Pyridin-4-Ylmethyl)-Amino]-but-3-Enoic Acid

Database IDs

• PubChem SID: 46504501; 160966426
• PubChem CID: 46936632

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.0788691
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -8.066612
• LogD (pH = 7.4): -8.331089
• Log P: -8.074544
• Molar Refractivity: 91.0816 cm^3
• Polarizability: 35.685677 Å^3
• Polar Surface Area: 184.46 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.03
• LOG S: -2.95
• Solubility (Water): 4.36e-01 g/l

DETAILS

DrugBank - DB03287

Drug information: experimental