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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014547
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.
Structure
Data?1582753191
Synonyms
ValueSource
CaeruleinChEBI
CeruleinChEBI
CeruletidaChEBI
CeruletidumChEBI
CeruletidHMDB
TakusHMDB
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
SMILES
[H][C@](NC(=O)[C@H](CC1=CC=C(OS(O)(=O)=O)C=C1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H]1CCC(=O)N1)([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CC1=CNC2=CC=CC=C12)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O
InChI Identifier
InChI=1S/C58H73N13O21S2/c1-29(72)49(71-57(87)40(23-31-12-14-33(15-13-31)92-94(89,90)91)68-56(86)43(26-48(78)79)69-52(82)37(16-18-44(59)73)65-51(81)36-17-19-45(74)63-36)58(88)62-28-46(75)64-41(24-32-27-61-35-11-7-6-10-34(32)35)54(84)66-38(20-21-93-2)53(83)70-42(25-47(76)77)55(85)67-39(50(60)80)22-30-8-4-3-5-9-30/h3-15,27,29,36-43,49,61,72H,16-26,28H2,1-2H3,(H2,59,73)(H2,60,80)(H,62,88)(H,63,74)(H,64,75)(H,65,81)(H,66,84)(H,67,85)(H,68,86)(H,69,82)(H,70,83)(H,71,87)(H,76,77)(H,78,79)(H,89,90,91)/t29-,36+,37+,38+,39+,40+,41+,42+,43+,49+/m1/s1
InChI KeyYRALAIOMGQZKOW-HYAOXDFASA-N
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
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 g/LNot Available
LogP-0.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP-0.19ALOGPS
logP-5.2ChemAxon
logS-5.1ALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-381.930932474
DeepCCS[M+Na]+355.67530932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 10V, Positive-QTOFsplash10-02ai-1229101200-f236abd5d600dc274dff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 20V, Positive-QTOFsplash10-0in9-4596214001-86c3444750a04d4b44572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 40V, Positive-QTOFsplash10-03gi-9553211000-675164f70438039ea3f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 10V, Negative-QTOFsplash10-0541-3049001000-188268018c0d371302492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 20V, Negative-QTOFsplash10-000t-9177001001-8549ab2b2a723df0586e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 40V, Negative-QTOFsplash10-0005-9311001102-db91298f6a5f52343f0b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 10V, Positive-QTOFsplash10-0ul9-0519012001-0a24572c1b25506ede442021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 20V, Positive-QTOFsplash10-001i-0369021100-318f6a06faeb0c3d238b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 40V, Positive-QTOFsplash10-01qc-5953001001-9ebb539eef3a1656b9c02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 10V, Negative-QTOFsplash10-0udi-0039002000-0df329c5b537eb032b192021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 20V, Negative-QTOFsplash10-01pd-2294000000-f34d67fd7c08e23c14292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ceruletide 40V, Negative-QTOFsplash10-00kg-9342000276-d43876d739c08f99e43a2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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:
CCKAR
Uniprot ID:
P32238
Molecular weight:
47840.6
References
  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 ]