(2R,3R,4R)-2-{[(2S,3R,4S,5S,6S)-4,6-dihydroxy-5-(sulfonatoamino)-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-4-hydroxy-3-(sulfonatooxy)-3,4-dihydro-2H-pyran-6-carboxylate

• ChemBase ID: 2067
• Molecular Formular: C12H15NO19S3----
• Molecular Mass: 573.4378
• Monoisotopic Mass: 572.94004027
• SMILES: O[C@H]1O[C@@H](COS(=O)(=O)[O-])[C@H](O[C@@H]2OC(=C[C@@H](O)[C@H]2OS(=O)(=O)[O-])C(=O)[O-])[C@@H](O)[C@@H]1NS(=O)(=O)[O-]
• Canonical SMILES: O[C@@H]1C=C(O[C@H]([C@@H]1OS(=O)(=O)[O-])O[C@H]1[C@H](COS(=O)(=O)[O-])O[C@@H]([C@H]([C@@H]1O)NS(=O)(=O)[O-])O)C(=O)[O-]
• InChI: InChI=1S/C12H19NO19S3/c14-3-1-4(10(16)17)30-12(8(3)32-35(25,26)27)31-9-5(2-28-34(22,23)24)29-11(18)6(7(9)15)13-33(19,20)21/h1,3,5-9,11-15,18H,2H2,(H,16,17)(H,19,20,21)(H,22,23,24)(H,25,26,27)/p-4/t3-,5+,6+,7+,8-,9+,11+,12+/m1/s1
• InChIKey: LRPGJWKAYQRIAQ-XKUCOZAXSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R)-2-{[(2S,3R,4S,5S,6S)-4,6-dihydroxy-5-(sulfonatoamino)-2-[(sulfonatooxy)methyl]oxan-3-yl]oxy}-4-hydroxy-3-(sulfonatooxy)-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: heparin disaccharide I-S
• Synonyms: Heparin Disaccharide I-S

Database IDs

• PubChem SID: 160965521; 46507297
• PubChem CID: 46936350

CALCULATED PROPERTIES

JChem

• Acid pKa: -2.5497794
• H Acceptors: 17
• H Donor: 4
• LogD (pH = 5.5): -14.071751
• LogD (pH = 7.4): -14.854316
• Log P: -9.685865
• Molar Refractivity: 107.9623 cm^3
• Polarizability: 43.020924 Å^3
• Polar Surface Area: 330.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.17
• LOG S: -1.73
• Solubility (Water): 1.20e+01 g/l

DETAILS

DrugBank - DB02322

Drug information: experimental