(2Z,3E)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)imino]-5-phosphonopent-3-enoic acid

• ChemBase ID: 2072
• Molecular Formular: C13H18N2O10P2
• Molecular Mass: 424.236942
• Monoisotopic Mass: 424.04366805
• SMILES: Cc1ncc(COP(=O)(O)O)c(C/N=C(/C=C/CP(=O)(O)O)\C(=O)O)c1O
• Canonical SMILES: OC(=O)/C(=N\Cc1c(cnc(c1O)C)COP(=O)(O)O)/C=C/CP(=O)(O)O
• InChI: InChI=1S/C13H18N2O10P2/c1-8-12(16)10(9(5-14-8)7-25-27(22,23)24)6-15-11(13(17)18)3-2-4-26(19,20)21/h2-3,5,16H,4,6-7H2,1H3,(H,17,18)(H2,19,20,21)(H2,22,23,24)/b3-2+,15-11-
• InChIKey: VKWJKURKEYQKKW-QDWZKYKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z,3E)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)imino]-5-phosphonopent-3-enoic acid
• IUPAC Traditional name: (2Z,3E)-2-[({3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)imino]-5-phosphonopent-3-enoic acid
• Synonyms: 2-[(3-Hydroxy-2-Methyl-5-Phosphonooxymethyl-Pyridin-4-Ylmethyl)-Imino]-5-Phosphono-Pent-3-Enoic Acid

Database IDs

• PubChem SID: 46505752; 160965526
• PubChem CID: 5288538

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6018313
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -7.2745266
• LogD (pH = 7.4): -9.390161
• Log P: -3.2567573
• Molar Refractivity: 92.7968 cm^3
• Polarizability: 35.313904 Å^3
• Polar Surface Area: 207.07 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.6
• LOG S: -2.45
• Solubility (Water): 1.52e+00 g/l

DETAILS

DrugBank - DB02328

Drug information: experimental