(4R)-4-[(2R)-2-amino-3-(2H11)cyclohexylpropanamido]-4-[(carboxymethyl)carbamoyl]butanoic acid

• ChemBase ID: 165202
• Molecular Formular: C16H27N3O6
• Molecular Mass: 357.40208
• Monoisotopic Mass: 357.1899856
• SMILES: C1(C[C@H](C(=O)N[C@H](CCC(=O)O)C(=O)NCC(=O)O)N)CCCCC1
• Canonical SMILES: OC(=O)CC[C@H](C(=O)NCC(=O)O)NC(=O)[C@@H](CC1CCCCC1)N
• InChI: InChI=1S/C16H27N3O6/c17-11(8-10-4-2-1-3-5-10)15(24)19-12(6-7-13(20)21)16(25)18-9-14(22)23/h10-12H,1-9,17H2,(H,18,25)(H,19,24)(H,20,21)(H,22,23)/t11-,12-/m1/s1
• InChIKey: CNDMSQXUUIBFPE-VXGBXAGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(2R)-2-amino-3-(^2H₁₁)cyclohexylpropanamido]-4-[(carboxymethyl)carbamoyl]butanoic acid
• IUPAC Traditional name: (4R)-4-[(2R)-2-amino-3-(^2H₁₁)cyclohexylpropanamido]-4-(carboxymethylcarbamoyl)butanoic acid
• Synonyms: D-(Cyclohexyl-d11)alanine-D-glutamateglycine; 3-Cyclohexyl-D-alanyl-D-α-glutamylglycine-d11

Database IDs

• PubChem SID: 162259335
• PubChem CID: 71315076

CALCULATED PROPERTIES

• Acid pKa: 3.1633089
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -4.2854247
• LogD (pH = 7.4): -5.9773264
• Log P: -3.064438
• Molar Refractivity: 87.063 cm^3
• Polarizability: 34.606937 Å^3
• Polar Surface Area: 158.82 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C988007

Labelled 3-Cyclohexyl-D-alanyl-D-α-glutamylglycine (C988005). Antiinflammatory peptides used for the treatment of neuropathic pain.

REFERENCES

• Llinas-Brunet., et al.: J. Med. Chem., 42, 722 (1999)
• Yu, Y., et al.: Peptides, 25, 2257 (1999)