(2S)-2-[(2R)-2-benzyl-3-(hydroxycarbamoyl)propanamido]propanoic acid

• ChemBase ID: 5668
• Molecular Formular: C14H18N2O5
• Molecular Mass: 294.30312
• Monoisotopic Mass: 294.12157169
• SMILES: O=C(NO)C[C@H](C(=O)N[C@@H](C)C(=O)O)Cc1ccccc1
• Canonical SMILES: ONC(=O)C[C@H](C(=O)N[C@H](C(=O)O)C)Cc1ccccc1
• InChI: InChI=1S/C14H18N2O5/c1-9(14(19)20)15-13(18)11(8-12(17)16-21)7-10-5-3-2-4-6-10/h2-6,9,11,21H,7-8H2,1H3,(H,15,18)(H,16,17)(H,19,20)/t9-,11+/m0/s1
• InChIKey: OJCFZTVYDSKXNM-GXSJLCMTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2R)-2-benzyl-3-(hydroxycarbamoyl)propanamido]propanoic acid
• IUPAC Traditional name: kelatorphan
• Synonyms: N-[(2R)-2-benzyl-4-(hydroxyamino)-4-oxobutanoyl]-L-alanine; Kelatorphan

Database IDs

• CAS Number: 92175-57-0
• PubChem SID: 160969095; 99444511
• PubChem CID: 123982
• Chemspider ID: 110501
• DrugBank ID: DB08040
• Wikipedia Title: Kelatorphan

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8009434
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -1.325223
• LogD (pH = 7.4): -2.8991933
• Log P: 0.37623262
• Molar Refractivity: 73.6917 cm^3
• Polarizability: 28.707697 Å^3
• Polar Surface Area: 115.73 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.3
• LOG S: -2.83
• Solubility (Water): 4.33e-01 g/l

PROPERTIES

Pharmacology Properties

• Legal Status: Non-regulated

DETAILS

DrugBank - DB08040

Drug information: experimental