(2S,4R,5S,6S)-2-{[(2S,3S,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2S,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 2987
• Molecular Formular: C23H39NO19
• Molecular Mass: 633.55106
• Monoisotopic Mass: 633.21162803
• SMILES: CC(=O)N[C@H]1[C@H](O)C[C@@](O[C@H]2[C@@H](O)[C@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)O[C@H]3CO)[C@H]2O)(O[C@@H]1[C@@H](O)[C@H](O)CO)C(=O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](O[C@@H]2[C@H](CO)O[C@H]([C@@H]([C@H]2O)O)O)[C@H]([C@H]([C@H]1O)O[C@@]1(C[C@@H](O)[C@@H]([C@H](O1)[C@H]([C@@H](CO)O)O)NC(=O)C)C(=O)O)O
• InChI: InChI=1S/C23H39NO19/c1-6(28)24-11-7(29)2-23(22(37)38,42-18(11)12(31)8(30)3-25)43-19-13(32)9(4-26)40-21(16(19)35)41-17-10(5-27)39-20(36)15(34)14(17)33/h7-21,25-27,29-36H,2-5H2,1H3,(H,24,28)(H,37,38)/t7-,8-,9+,10+,11+,12+,13+,14-,15-,16+,17-,18+,19+,20-,21+,23+/m1/s1
• InChIKey: CILYIEBUXJIHCO-ZPXYJZJDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R,5S,6S)-2-{[(2S,3S,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2S,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1S,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: α(2,3) sialyl lactose
• Synonyms: Alpha(2,3) Sialyl Lactose; Lactose Sialic Acid

Database IDs

• PubChem SID: 160966434; 46504931
• PubChem CID: 46936635

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.8378649
• H Acceptors: 19
• H Donor: 13
• LogD (pH = 5.5): -9.713415
• LogD (pH = 7.4): -10.596628
• Log P: -7.105609
• Molar Refractivity: 128.608 cm^3
• Polarizability: 53.884872 Å^3
• Polar Surface Area: 335.08 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.69
• LOG S: -0.73
• Solubility (Water): 1.17e+02 g/l

DETAILS

DrugBank - DB03296

Drug information: experimental