(1R,2S,3R,6R)-6-{[(2R,3R,4S,5S)-4,5-dihydroxy-2-methyloxan-3-yl]amino}-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol

• ChemBase ID: 3783
• Molecular Formular: C13H23NO7
• Molecular Mass: 305.32422
• Monoisotopic Mass: 305.14745208
• SMILES: C[C@H]1OC[C@H](O)[C@@H](O)[C@H]1N[C@@H]1C=C(CO)[C@@H](O)[C@H](O)[C@@H]1O
• Canonical SMILES: OCC1=C[C@@H](N[C@H]2[C@@H](C)OC[C@@H]([C@H]2O)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H23NO7/c1-5-9(12(19)8(16)4-21-5)14-7-2-6(3-15)10(17)13(20)11(7)18/h2,5,7-20H,3-4H2,1H3/t5-,7-,8+,9+,10-,11-,12-,13+/m1/s1
• InChIKey: LTAGIBUDYBSPEG-HCDBHUNCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3R,6R)-6-{[(2R,3R,4S,5S)-4,5-dihydroxy-2-methyloxan-3-yl]amino}-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
• IUPAC Traditional name: (1R,2S,3R,6R)-6-{[(2R,3R,4S,5S)-4,5-dihydroxy-2-methyloxan-3-yl]amino}-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
• Synonyms: 1,4-Deoxy-4-((5-Hydroxymethyl-2,3,4-Trihydroxycyclohex-5-Enyl)Amino)Fructose

Database IDs

• PubChem SID: 160967220; 46504993
• PubChem CID: 46936908

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.649952
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -5.2537756
• LogD (pH = 7.4): -3.8662884
• Log P: -3.7086637
• Molar Refractivity: 71.7459 cm^3
• Polarizability: 29.092789 Å^3
• Polar Surface Area: 142.64 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.1
• LOG S: -0.27
• Solubility (Water): 1.64e+02 g/l

DETAILS

DrugBank - DB04164

Drug information: experimental