(2R,4R,5S,6R)-4-carbamimidamido-5-acetamido-6-[(1R,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 3099
• Molecular Formular: C12H22N4O7
• Molecular Mass: 334.32568
• Monoisotopic Mass: 334.14884906
• SMILES: CC(=O)N[C@H]1[C@@H](C[C@@H](O[C@H]1[C@H](O)[C@@H](O)CO)C(=O)O)NC(=N)N
• Canonical SMILES: OC[C@@H]([C@H]([C@@H]1O[C@H](C[C@H]([C@@H]1NC(=O)C)NC(=N)N)C(=O)O)O)O
• InChI: InChI=1S/C12H22N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h5-10,17,19-20H,2-3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,7-,8+,9-,10-/m1/s1
• InChIKey: DAAUVSVERFXBSX-WHSUVHHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5S,6R)-4-carbamimidamido-5-acetamido-6-[(1R,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4R,5S,6R)-4-carbamimidamido-5-acetamido-6-[(1R,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: 2,4-Deoxy-4-Guanidino-5-N-Acetyl-Neuraminic Acid

Database IDs

• PubChem SID: 160966543; 46508350
• PubChem CID: 46936668

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6541796
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -5.827466
• LogD (pH = 7.4): -5.822438
• Log P: -5.822413
• Molar Refractivity: 85.0247 cm^3
• Polarizability: 29.744942 Å^3
• Polar Surface Area: 198.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.61
• LOG S: -2.08
• Solubility (Water): 2.78e+00 g/l

DETAILS

DrugBank - DB03420

Drug information: experimental