(3S)-3-[(2S)-2-[(2S)-2-(3-{[(tert-butoxy)carbonyl]amino}propanamido)-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoylpropyl]carbamoyl}propanoic acid

• ChemBase ID: 72764
• Molecular Formular: C32H47N7O9S
• Molecular Mass: 705.82208
• Monoisotopic Mass: 705.31559712
• SMILES: c1c2c(ccc1)[nH]cc2C[C@@H](C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC)C(=O)N)NC(=O)CCNC(=O)OC(C)(C)C
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CC)CC(=O)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)CCNC(=O)OC(C)(C)C
• InChI: InChI=1S/C32H47N7O9S/c1-6-20(27(33)43)37-30(46)24(16-26(41)42)39-28(44)22(12-14-49-5)38-29(45)23(15-18-17-35-21-10-8-7-9-19(18)21)36-25(40)11-13-34-31(47)48-32(2,3)4/h7-10,17,20,22-24,35H,6,11-16H2,1-5H3,(H2,33,43)(H,34,47)(H,36,40)(H,37,46)(H,38,45)(H,39,44)(H,41,42)/t20-,22-,23-,24-/m0/s1
• InChIKey: WNCIKJQZZFAOGE-BIHRQFPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-(3-{[(tert-butoxy)carbonyl]amino}propanamido)-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoylpropyl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-{3-[(tert-butoxycarbonyl)amino]propanamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoylpropyl]carbamoyl}propanoic acid
• Synonyms: Peptavlon; Pentagastrin

Database IDs

• CAS Number: 5534-95-2
• PubChem SID: 162037685
• PubChem CID: 49867932

CALCULATED PROPERTIES

• Acid pKa: 4.0305977
• H Acceptors: 8
• H Donor: 8
• LogD (pH = 5.5): -1.5642855
• LogD (pH = 7.4): -3.2254295
• Log P: -0.08415681
• Molar Refractivity: 179.9412 cm^3
• Polarizability: 71.375305 Å^3
• Polar Surface Area: 250.91 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1612

Research Area: Endocrinology
Biological Activity:
Pentagastrin is a synthetic polypeptide that has effects like gastrin when given parenterally. [1] It stimulates the secretion of gastric acid, pepsin, and intrinsic factor and has been used as a diagnostic aid as the pentagastrin-stimulated calcitonin test. Pentagastrin binds to the cholecystokinin-B receptor, which is expressed widely in the brain. Activation of these receptors activates the phospholipase C second messenger system. When given intravenously it causes panic attacks. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Citalopram