(2S)-2-amino-3-{2-[(3S)-3-carbamoyl-3-(trimethylazaniumyl)propyl]-1H-imidazol-4-yl}propanoate

• ChemBase ID: 2920
• Molecular Formular: C13H23N5O3
• Molecular Mass: 297.35342
• Monoisotopic Mass: 297.18008962
• SMILES: C[N+](C)(C)[C@@H](CCc1[nH]cc(C[C@H](N)C(=O)[O-])n1)C(=O)N
• Canonical SMILES: N[C@H](C(=O)[O-])Cc1c[nH]c(n1)CC[C@H]([N+](C)(C)C)C(=O)N
• InChI: InChI=1S/C13H23N5O3/c1-18(2,3)10(12(15)19)4-5-11-16-7-8(17-11)6-9(14)13(20)21/h7,9-10H,4-6,14H2,1-3H3,(H3-,15,16,17,19,20,21)/t9-,10-/m0/s1
• InChIKey: FOOBQHKMWYGHCE-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{2-[(3S)-3-carbamoyl-3-(trimethylazaniumyl)propyl]-1H-imidazol-4-yl}propanoate
• IUPAC Traditional name: (2S)-2-amino-3-{2-[(3S)-3-carbamoyl-3-(trimethylaminio)propyl]-1H-imidazol-4-yl}propanoate
• Synonyms: 2-(3-Carboxyamido-3-(Trimethylammonio)Propyl)Histidine; Diphthamide

Database IDs

• CAS Number: 75645-22-6
• PubChem SID: 160966367; 46508643
• PubChem CID: 46936613; 70789228

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.4995813
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -8.338723
• LogD (pH = 7.4): -6.8155336
• Log P: -7.1857805
• Molar Refractivity: 99.2202 cm^3
• Polarizability: 30.217922 Å^3
• Polar Surface Area: 137.92 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.61
• LOG S: -3.44
• Solubility (Water): 1.20e-01 g/l

DETAILS

DrugBank - DB03223

Drug information: experimental