2-{2-[2-(2-{2-[2-(2-amino-4-methylpentanamido)-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido}-3-(1H-indol-3-yl)propanamido)-3-hydroxypropanamido]-4-methylpentanamido}acetic acid

• ChemBase ID: 105276
• Molecular Formular: C40H66N14O9
• Molecular Mass: 887.04044
• Monoisotopic Mass: 886.51371976
• SMILES: CC(C)CC(N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)NCC(=O)O
• Canonical SMILES: OCC(C(=O)NC(C(=O)NCC(=O)O)CC(C)C)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C(NC(=O)C(CC(C)C)N)CCCNC(=N)N)CCCNC(=N)N
• InChI: InChI=1S/C40H66N14O9/c1-21(2)15-25(41)33(58)50-27(11-7-13-46-39(42)43)35(60)51-28(12-8-14-47-40(44)45)36(61)53-30(17-23-18-48-26-10-6-5-9-24(23)26)37(62)54-31(20-55)38(63)52-29(16-22(3)4)34(59)49-19-32(56)57/h5-6,9-10,18,21-22,25,27-31,48,55H,7-8,11-17,19-20,41H2,1-4H3,(H,49,59)(H,50,58)(H,51,60)(H,52,63)(H,53,61)(H,54,62)(H,56,57)(H4,42,43,46)(H4,44,45,47)
• InChIKey: MSFGAYLGJZPYIQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[2-(2-{2-[2-(2-amino-4-methylpentanamido)-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido}-3-(1H-indol-3-yl)propanamido)-3-hydroxypropanamido]-4-methylpentanamido}acetic acid
• IUPAC Traditional name: {2-[2-(2-{2-[2-(2-amino-4-methylpentanamido)-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido}-3-(1H-indol-3-yl)propanamido)-3-hydroxypropanamido]-4-methylpentanamido}acetic acid
• Synonyms: [Trp^4]-KEMPTIDE

Database IDs

• CAS Number: 80224-16-4
• PubChem SID: 162093334
• PubChem CID: 4599357

CALCULATED PROPERTIES

• Acid pKa: 3.458663
• H Acceptors: 16
• H Donor: 16
• LogD (pH = 5.5): -9.502305
• LogD (pH = 7.4): -7.8049994
• Log P: -5.1227984
• Molar Refractivity: 251.2358 cm^3
• Polarizability: 90.53046 Å^3
• Polar Surface Area: 397.74 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 02159614

Leu-Arg-Arg-Trp-Ser-Leu-Gly
Substrate for cAMP-dependent protein kinase.

REFERENCES

• Wright, D.E., et al., Proc. Nat. Acad. Sci. USA, 78: 6048 (1981).