(2S)-2-amino-3-{[(2R,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid

• ChemBase ID: 2136
• Molecular Formular: C11H20N2O8
• Molecular Mass: 308.2851
• Monoisotopic Mass: 308.12196561
• SMILES: CC(=O)N[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1OC[C@H](N)C(=O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](OC[C@@H](C(=O)O)N)[C@H]([C@@H]([C@H]1O)O)NC(=O)C
• InChI: InChI=1S/C11H20N2O8/c1-4(15)13-7-9(17)8(16)6(2-14)21-11(7)20-3-5(12)10(18)19/h5-9,11,14,16-17H,2-3,12H2,1H3,(H,13,15)(H,18,19)/t5-,6-,7-,8-,9-,11+/m0/s1
• InChIKey: REDMNGDGDYFZRE-ABBMGWFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{[(2R,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-{[(2R,3S,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid
• Synonyms: O-(2-Acetamido-2-Deoxy-Alpha-D-Galactopyranosyl)-L-Serine

Database IDs

• PubChem SID: 46508292; 160965590
• PubChem CID: 70789218; 46936373

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8044195
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -5.9466543
• LogD (pH = 7.4): -5.961738
• Log P: -5.946677
• Molar Refractivity: 65.5556 cm^3
• Polarizability: 27.125751 Å^3
• Polar Surface Area: 171.57 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -3.19
• LOG S: -0.58
• Solubility (Water): 8.20e+01 g/l

DETAILS

DrugBank - DB02397

Drug information: experimental