(2S,3S,4R,5R,6S)-6-methyl-5-{[(1R,4R,5S,6R)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxane-2,3,4-triol

• ChemBase ID: 1970
• Molecular Formular: C13H23NO8
• Molecular Mass: 321.32362
• Monoisotopic Mass: 321.1423667
• SMILES: C[C@@H]1O[C@H](O)[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)O[C@@H]([C@H]([C@@H]2O)O)O)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H23NO8/c1-4-7(10(18)12(20)13(21)22-4)14-6-2-5(3-15)8(16)11(19)9(6)17/h2,4,6-21H,3H2,1H3/t4-,6+,7-,8+,9+,10+,11-,12-,13-/m0/s1
• InChIKey: RBZIIHWPZWOIDU-IJZUXERNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R,6S)-6-methyl-5-{[(1R,4R,5S,6R)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxane-2,3,4-triol
• IUPAC Traditional name: (2S,3S,4R,5R,6S)-6-methyl-5-{[(1R,4R,5S,6R)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}oxane-2,3,4-triol
• Synonyms: 4-Deoxy-4-((5-Hydroxymethyl-2,3,4-Trihydroxycyclohex-5,6-Enyl)Amino)Fructose; N-[4-Hydroxymethyl-Cyclohexan-6-Yl-1,2,3-Triol]-4,6-Dideoxy-4-Aminoglucopyranoside

Database IDs

• PubChem SID: 160965425; 46507169; 46506058
• PubChem CID: 46936324

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.306119
• H Acceptors: 9
• H Donor: 8
• LogD (pH = 5.5): -5.32506
• LogD (pH = 7.4): -4.1573253
• Log P: -4.0728874
• Molar Refractivity: 72.7758 cm^3
• Polarizability: 29.78394 Å^3
• Polar Surface Area: 162.87 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.22
• LOG S: -0.28
• Solubility (Water): 1.68e+02 g/l

DETAILS

DrugBank - DB03269

Drug information: experimental

DrugBank - DB02218

Drug information: experimental