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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-12-07 02:44:43 UTC
Secondary Accession Numbers
  • HMDB14329
Metabolite Identification
Common NamePentagastrin
DescriptionPentagastrin is only found in individuals that have used or taken this drug. It is 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]The exact mechanism by which pentagastrin stimulates gastric acid, pepsin, and intrinsic factor secretion is unknown; however, since pentagastrin is an analogue of natural gastrin, it is believed that it excites the oxyntic cells of the stomach to secrete to their maximum capacity. Pentagastrin stimulates pancreatic secretion, especially when administered in large intramuscular doses. Pentagastrin also increases gastrointestinal motility by a direct effect on the intestinal smooth muscle. However, it delays gastric emptying time probably by stimulation of terminal antral contractions, which enhance retropulsion.
Chemical FormulaC37H49N7O9S
Average Molecular Weight767.891
Monoisotopic Molecular Weight767.331246891
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
Traditional Namepeptavlon
CAS Registry Number5534-95-2
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
  • Hybrid peptide
  • Phenylalanine or derivatives
  • Aspartic acid or derivatives
  • Methionine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Beta amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole or derivatives
  • Indole
  • Monocyclic benzene moiety
  • N-acyl-amine
  • Substituted pyrrole
  • Benzenoid
  • Fatty amide
  • Fatty acyl
  • Carbamic acid ester
  • Heteroaromatic compound
  • Pyrrole
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Carbonic acid derivative
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Biological location:


  Biofluid and excreta:


Industrial application:

Physical Properties
Experimental Properties
Melting Point229 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0031 g/LNot Available
LogP1.6Not Available
Predicted Properties
Water Solubility0.0031 g/LALOGPS
pKa (Strongest Acidic)4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area250.91 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity199.97 m³·mol⁻¹ChemAxon
Polarizability80.96 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9201202100-03c7742e24e5d199231fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-6313234900-1123e718f80b46bdfaadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9733121100-934fa32be6315d7ee109View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9854300000-12e21b9b9aa7ab4a9fd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ke-9210018500-b6b5e04da0538e923517View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-9200012000-c048ac77ac2d9b40660bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9300010000-19ca23c27c66ac77463cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00183 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00183 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID392037
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentagastrin
METLIN IDNot Available
PubChem Compound444007
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Weintraub HS, Rudolph A: Combination therapy for managing difficult-to-treat patients with stage 2 hypertension: focus on valsartan-based combinations. Am J Ther. 2011 Nov;18(6):e227-43. doi: 10.1097/MJT.0b013e3181da0437. [PubMed:20535014 ]


General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Chernysheva SV, Iaremko EE: [Cholinergic and hormonal correlations in the regulation of the secretory function of the small intestine]. Fiziol Zh SSSR Im I M Sechenova. 1983 Jun;69(6):827-31. [PubMed:6873393 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Isoform 2 is constitutively activated and may regulate cancer cell proliferation via a gastrin-independent mechanism
Gene Name:
Uniprot ID:
Molecular weight:
  1. Radu D, Ahlin A, Svanborg P, Lindefors N: Anxiogenic effects of the CCK(B) agonist pentagastrin in humans and dose-dependent increase in plasma C-peptide levels. Psychopharmacology (Berl). 2002 Jun;161(4):396-403. Epub 2002 Apr 17. [PubMed:12073167 ]
  2. Khan S, Liberzon I, Abelson JL: Effect of repeat exposure on neuroendocrine and symptom responses to pentagastrin. Psychiatry Res. 2004 May 30;126(3):189-95. [PubMed:15157745 ]
  3. Makovec F, Peris W, Revel L, Giovanetti R, Mennuni L, Rovati LC: Structure-antigastrin activity relationships of new (R)-4-benzamido-5-oxopentanoic acid derivatives. J Med Chem. 1992 Jan;35(1):28-38. [PubMed:1732532 ]
  4. Singh P, Walker JP, Townsend CM Jr, Thompson JC: Role of gastrin and gastrin receptors on the growth of a transplantable mouse colon carcinoma (MC-26) in BALB/c mice. Cancer Res. 1986 Apr;46(4 Pt 1):1612-6. [PubMed:3004700 ]
  5. Nishida A, Kobayashi-Uchida A, Akuzawa S, Takinami Y, Shishido T, Kamato T, Ito H, Yamano M, Yuki H, Nagakura Y, et al.: Gastrin receptor antagonist YM022 prevents hypersecretion after long-term acid suppression. Am J Physiol. 1995 Nov;269(5 Pt 1):G699-705. [PubMed:7491961 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]