(2S,3S,4R,5R,6R)-3-{[(2S,4aR,6S,7S,8R,8aS)-2-carboxy-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-4,5,6-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 4161
• Molecular Formular: C15H22O14
• Molecular Mass: 426.32678
• Monoisotopic Mass: 426.10095538
• SMILES: C[C@@]1(OC[C@H]2O[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)O[C@@H]3C(=O)O)[C@@H](O)[C@@H](O)[C@@H]2O1)C(=O)O
• Canonical SMILES: O[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H]1O)O[C@@](OC2)(C)C(=O)O)O[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)O)C(=O)O
• InChI: InChI=1S/C15H22O14/c1-15(14(23)24)25-2-3-8(29-15)5(17)7(19)13(26-3)28-9-4(16)6(18)12(22)27-10(9)11(20)21/h3-10,12-13,16-19,22H,2H2,1H3,(H,20,21)(H,23,24)/t3-,4-,5-,6-,7+,8-,9+,10+,12-,13+,15+/m1/s1
• InChIKey: GZJXZKGVHLWBOW-RJABHKQUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R,6R)-3-{[(2S,4aR,6S,7S,8R,8aS)-2-carboxy-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-4,5,6-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4R,5R,6R)-3-{[(2S,4aR,6S,7S,8R,8aS)-2-carboxy-7,8-dihydroxy-2-methyl-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}-4,5,6-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4,6-O-(1-CARBOXYETHYLIDENE)-BETA-D-MANNOSE-(1->4)-BETA-D-GLUCURONIC ACID

Database IDs

• PubChem SID: 160967593; 46509174
• PubChem CID: 6602345

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.6273286
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -7.892624
• LogD (pH = 7.4): -9.861414
• Log P: -2.9120698
• Molar Refractivity: 81.7317 cm^3
• Polarizability: 34.59972 Å^3
• Polar Surface Area: 221.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.82
• LOG S: -0.66
• Solubility (Water): 9.41e+01 g/l

DETAILS

DrugBank - DB04596

Drug information: experimental