3-{2-[2-amino-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido}-3-[(1-carbamoyl-2-phenylethyl)carbamoyl]propanoic acid

• ChemBase ID: 103795
• Molecular Formular: C29H36N6O6S
• Molecular Mass: 596.69774
• Monoisotopic Mass: 596.2417039
• SMILES: CSCCC(NC(=O)C(N)Cc1c[nH]c2c1cccc2)C(=O)NC(CC(=O)O)C(=O)NC(Cc1ccccc1)C(=O)N
• Canonical SMILES: CSCCC(C(=O)NC(C(=O)NC(C(=O)N)Cc1ccccc1)CC(=O)O)NC(=O)C(Cc1c[nH]c2c1cccc2)N
• InChI: InChI=1S/C29H36N6O6S/c1-42-12-11-22(33-27(39)20(30)14-18-16-32-21-10-6-5-9-19(18)21)28(40)35-24(15-25(36)37)29(41)34-23(26(31)38)13-17-7-3-2-4-8-17/h2-10,16,20,22-24,32H,11-15,30H2,1H3,(H2,31,38)(H,33,39)(H,34,41)(H,35,40)(H,36,37)
• InChIKey: RGYLYUZOGHTBRF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{2-[2-amino-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido}-3-[(1-carbamoyl-2-phenylethyl)carbamoyl]propanoic acid
• IUPAC Traditional name: 3-{2-[2-amino-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido}-3-[(1-carbamoyl-2-phenylethyl)carbamoyl]propanoic acid
• Synonyms: CCK 30-33; Trp-Met-Asp-Phe-NH₂; CHOLECYSTOKININ, Fragment 30-33

Database IDs

• CAS Number: 35144-91-3
• PubChem SID: 162103280
• PubChem CID: 4329839

CALCULATED PROPERTIES

• Acid pKa: 3.6962147
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): -1.8366581
• LogD (pH = 7.4): -2.006547
• Log P: -1.8388988
• Molar Refractivity: 157.6603 cm^3
• Polarizability: 62.703262 Å^3
• Polar Surface Area: 209.5 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

DETAILS

MP Biomedicals - 02152862

A gastrin related tetrapeptide. Potent as a releaser of insulin and other islet hormones.

REFERENCES

• Rehfeld, R., et al., Nature, 284: 33 (1980).