You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:51 UTC
Secondary Accession Numbers
  • HMDB14547
Metabolite Identification
Common NameCeruletide
DescriptionCeruletide, also known as caerulein, is only found in individuals that have used or taken this drug. It is a specific decapeptide similar in action and composition to the natural gastrointestinal peptide hormone cholecystokinin. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle.Ceruletide acts according to its similarity to the natural gastrointestinal peptide hormone cholecystokinin. Cholecystokinin is a peptide hormone of the gastrointestinal system responsible for stimulating the digestion of fat and protein. Cholecystokinin is secreted by the duodenum, the first segment of the small intestine. There it binds to CCK receptors, activating them and causing downstream effects. Specifically, it results in the release of digestive enzymes and bile from the pancreas and gall bladder, respectively. It also acts as a hunger suppresant. Cholecystokinin is secreted by the duodenum when fat- or protein-rich chyme leaves the stomach and enters the duodenum. The hormone acts on the pancreas to stimulate the secretion of the enzymes lipase, amylase, trypsin, and chymotrypsin. Together these pancreatic enzymes catalyze the digestion of fat and protein. Cholecystokinin also stimulates both the contraction of the gall bladder, and the relaxtion of the Sphincter of Oddi (Glisson's Sphinctor), which delivers, (not secretes) bile into the small intestine. Bile salts serve to emulsify fats, thereby increasing the effectiveness with which enzymes can digest them.
Chemical FormulaC58H73N13O21S2
Average Molecular Weight1352.405
Monoisotopic Molecular Weight1351.448537843
IUPAC Name(3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-[(2S)-2-[(2S)-4-carbamoyl-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}butanamido]-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid
Traditional Nameceruletide
CAS Registry Number17650-98-5
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
  • Polypeptide
  • Alpha peptide
  • Phenylalanine or derivatives
  • Glutamine or derivatives
  • Aspartic acid or derivatives
  • Methionine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Phenylsulfate
  • Arylsulfate
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • N-substituted-alpha-amino acid
  • Indole or derivatives
  • Indole
  • Phenoxy compound
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Pyrrolidone
  • 2-pyrrolidone
  • Substituted pyrrole
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Pyrrole
  • Organic sulfuric acid or derivatives
  • Heteroaromatic compound
  • Pyrrolidine
  • Primary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Dialkylthioether
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP-0.9Not Available
Predicted Properties
Water Solubility0.012 g/LALOGPS
pKa (Strongest Acidic)-2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area551.4 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity325.74 m³·mol⁻¹ChemAxon
Polarizability129.96 ųChemAxon
Number of Rings5ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ai-1229101200-f236abd5d600dc274dffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0in9-4596214001-86c3444750a04d4b4457Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03gi-9553211000-675164f70438039ea3f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0541-3049001000-188268018c0d37130249Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-9177001001-8549ab2b2a723df0586eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9311001102-db91298f6a5f52343f0bSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00403 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00403 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00403
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10481982
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCeruletide
METLIN IDNot Available
PubChem Compound16129675
PDB IDNot Available
ChEBI ID59219
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available


General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for cholecystokinin. Mediates pancreatic growth and enzyme secretion, smooth muscle contraction of the gall bladder and stomach. Has a 1000-fold higher affinity for CCK rather than for gastrin. It modulates feeding and dopamine-induced behavior in the central and peripheral nervous system. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
Uniprot ID:
Molecular weight:
  1. Ishikawa Y, Shimatsu A, Murakami Y, Imura H: Barrel rotation in rats induced by SMS 201-995: suppression by ceruletide. Pharmacol Biochem Behav. 1990 Nov;37(3):523-6. [PubMed:2087492 ]
  2. Katsuura G, Ibii N, Matsushita A: Activation of CCK-A receptors induces elevation of plasma corticosterone in rats. Peptides. 1992 Jan-Feb;13(1):203-5. [PubMed:1620654 ]
  3. Maurice T, Hiramatsu M, Kameyama T, Hasegawa T, Nabeshima T: Cholecystokinin-related peptides, after systemic or central administration, prevent carbon monoxide-induced amnesia in mice. J Pharmacol Exp Ther. 1994 May;269(2):665-73. [PubMed:8182534 ]
  4. Shinohara S, Katsuura G, Eigyo M, Shintaku H, Ibii N, Matsushita A: Inhibitory effect of CCK-8 and ceruletide on glutamate-induced rises in intracellular free calcium concentrations in rat neuron cultures. Brain Res. 1992 Aug 21;588(2):223-8. [PubMed:1356589 ]
  5. Ibii N, Ikeda M, Takahara Y, Eigyo M, Akiyoshi T, Matsushita A: Inhibitory effect of ceruletide on haloperidol-induced catalepsy in rats. Peptides. 1989 Jul-Aug;10(4):779-83. [PubMed:2587420 ]
  6. Makovec F, Bani M, Cereda R, Chiste R, Pacini MA, Revel L, Rovati LA, Rovati LC, Setnikar I: Pharmacological properties of lorglumide as a member of a new class of cholecystokinin antagonists. Arzneimittelforschung. 1987 Nov;37(11):1265-8. [PubMed:3440035 ]