(2S,3S)-2-[(2S,3R)-2-[(3S)-4-ethoxy-3-hydroxy-4-oxobutanamido]-3-hydroxybutanamido]-3-methylpentanoic acid

• ChemBase ID: 4146
• Molecular Formular: C16H28N2O8
• Molecular Mass: 376.40212
• Monoisotopic Mass: 376.18456587
• SMILES: CCOC(=O)[C@@H](O)CC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)O
• Canonical SMILES: CCOC(=O)[C@H](CC(=O)N[C@H](C(=O)N[C@@H]([C@H](CC)C)C(=O)O)[C@H](O)C)O
• InChI: InChI=1S/C16H28N2O8/c1-5-8(3)12(15(23)24)18-14(22)13(9(4)19)17-11(21)7-10(20)16(25)26-6-2/h8-10,12-13,19-20H,5-7H2,1-4H3,(H,17,21)(H,18,22)(H,23,24)/t8-,9+,10-,12-,13-/m0/s1
• InChIKey: TUAMLRIDHTYTCM-WKLONVCASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2-[(2S,3R)-2-[(3S)-4-ethoxy-3-hydroxy-4-oxobutanamido]-3-hydroxybutanamido]-3-methylpentanoic acid
• IUPAC Traditional name: (2S,3S)-2-[(2S,3R)-2-[(3S)-4-ethoxy-3-hydroxy-4-oxobutanamido]-3-hydroxybutanamido]-3-methylpentanoic acid
• Synonyms: N-{[(2S,3S)-3-(ETHOXYCARBONYL)OXIRAN-2-YL]CARBONYL}-

Database IDs

• PubChem SID: 160967578; 46504475
• PubChem CID: 5494386

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8055353
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.6790984
• LogD (pH = 7.4): -4.2420907
• Log P: -0.9822485
• Molar Refractivity: 88.5468 cm^3
• Polarizability: 35.39129 Å^3
• Polar Surface Area: 162.26 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.34
• LOG S: -1.51
• Solubility (Water): 1.17e+01 g/l

DETAILS

DrugBank - DB04579

Drug information: experimental