2-[(5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazol-4-yl)formamido]butanedioic acid

• ChemBase ID: 129359
• Molecular Formular: C13H19N4O12P
• Molecular Mass: 454.283321
• Monoisotopic Mass: 454.0737087
• SMILES: Nc1c(ncn1C1OC(COP(=O)(O)O)C(O)C1O)C(=O)NC(CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)CC(C(=O)O)NC(=O)c1ncn(c1N)C1OC(C(C1O)O)COP(=O)(O)O
• InChI: InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)
• InChIKey: NAQGHJTUZRHGAC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazol-4-yl)formamido]butanedioic acid
• IUPAC Systematic name: 2-[(5-Amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazol-4-yl)formamido]butanedioic acid
• IUPAC Traditional name: saicar
• Synonyms: 2-[(5-Amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazol-4-yl)formamido]butanedioic acid; SAICAR

Database IDs

• CAS Number: 3031-95-6
• PubChem SID: 162223653
• PubChem CID: 981
• CHEBI ID: 18319
• Chemspider ID: 956
• KEGG ID: C04823
• MeSH Name: SAICAR
• Wikipedia Title: SAICAR

CALCULATED PROPERTIES

• Acid pKa: 1.2173138
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -8.111787
• LogD (pH = 7.4): -12.394793
• Log P: -4.8253617
• Molar Refractivity: 90.6527 cm^3
• Polarizability: 35.7691 Å^3
• Polar Surface Area: 263.99 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false