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

• ChemBase ID: 68
• Molecular Formular: C37H49N7O9S
• Molecular Mass: 767.89146
• Monoisotopic Mass: 767.33124718
• SMILES: S(CC[C@H](NC(=O)[C@@H](NC(=O)CCNC(=O)OCC(C)C)Cc1c2c([nH]c1)cccc2)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N)C
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)CC(=O)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)CCNC(=O)OCC(C)C
• InChI: InChI=1S/C37H49N7O9S/c1-22(2)21-53-37(52)39-15-13-31(45)41-29(18-24-20-40-26-12-8-7-11-25(24)26)35(50)42-27(14-16-54-3)34(49)44-30(19-32(46)47)36(51)43-28(33(38)48)17-23-9-5-4-6-10-23/h4-12,20,22,27-30,40H,13-19,21H2,1-3H3,(H2,38,48)(H,39,52)(H,41,45)(H,42,50)(H,43,51)(H,44,49)(H,46,47)/t27-,28-,29-,30-/m0/s1
• InChIKey: ALXRNCVIQSDJAO-KRCBVYEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-3-(1H-indol-3-yl)-2-(3-{[(2-methylpropoxy)carbonyl]amino}propanamido)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid
• IUPAC Traditional name: peptavlon
• Brand Name: Peptavlon
• Synonyms: Pentagastrin

Database IDs

• CAS Number: 5534-95-2
• PubChem SID: 160963531; 46507747
• PubChem CID: 444007

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.996262
• H Acceptors: 8
• H Donor: 8
• LogD (pH = 5.5): -0.2730803
• LogD (pH = 7.4): -1.9212354
• Log P: 1.2399907
• Molar Refractivity: 199.9748 cm^3
• Polarizability: 79.07773 Å^3
• Polar Surface Area: 250.91 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.57
• LOG S: -5.4
• Solubility (Water): 3.09e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.6

DETAILS

DrugBank - DB00183

• Drug Groups: approved
• Description: A synthetic pentapeptide that has effects like gastrin when given parenterally. It stimulates the secretion of gastric acid, pepsin, and intrinsic factor, and has been used as a diagnostic aid. [PubChem]
• Indication: Used as a diagnostic aid for evaluation of gastric acid secretory function
• Pharmacology: Pentagastrin is indicated as a diagnostic aid for evaluation of gastric acid secretory function. It is effective in testing for anacidity (achlorhydria) in patients with suspected pernicious anemia, atrophic gastritis, or gastric carcinoma. It is also effective in determining the reduction in acid output after operations for peptic ulcer, such as vagotomy or gastric resection.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic
• Absorption: Rapidly absorbed after parenteral administration.
• Half Life: 10 minutes or less
• References: Weintraub HS, Rudolph A: Combination Therapy for Managing Difficult-to-Treat Patients With Stage 2 Hypertension: Focus on Valsartan-Based Combinations. Am J Ther. 2010 Jun 9. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Weintraub HS, Rudolph A: Combination Therapy for Managing Difficult-to-Treat Patients With Stage 2 Hypertension: Focus on Valsartan-Based Combinations. Am J Ther. 2010 Jun 9. Pubmed