Sincalide (CHEM019858)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2016-05-22 06:35:22 UTC
Update Date2026-04-14 17:38:52 UTC
Accession NumberCHEM019858
Identification
Common NameSincalide
ClassSmall Molecule
DescriptionSincalide is a medication given by injection to assist in the diagnosis of gallbladder and pancreas disorders. It is identified as the 8-amino acid C-terminal segment of cholecystokinin and is also known as _CCK-8_. Naturally occurring cholecystokinin is a gastrointestinal peptide hormone normally essential for stimulating protein and fat digestion in the body. When injected intravenously, sincalide produces a substantial reduction in gallbladder size by causing this organ to contract. The evacuation of bile that results is similar to that which occurs physiologically in response to endogenous cholecystokinin. Furthermore, sincalide stimulates pancreatic secretion of bicarbonate and enzymes. As the product Kinevac (FDA), sincalide is used for the following indications: 1) to stimulate gallbladder contraction, as may be assessed by various methods of diagnostic imaging, or to obtain by duodenal aspiration a sample of concentrated bile for analysis of cholesterol, bile salts, phospholipids, and crystals; (2) to stimulate pancreatic secretion (especially in conjunction with secretin) prior to obtaining a duodenal aspirate for analysis of enzyme activity, composition, and cytology; (3) to accelerate the transit of a barium meal through the small bowel, thereby decreasing the time and extent of radiation associated with fluoroscopy and x-ray examination of the intestinal tract.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cholecystokinin-pancreozyminKegg
KinevacKegg
CCK-OPMeSH
Cholecystokinin octapeptideMeSH
H-Asp-tyr(so3h)-met-gly-TRP-met-asp-phe-NH2MeSH
SyncalideMeSH
bracco Brand OF sincalideMeSH
Cholecystokinin pancreozymin C terminal octapeptideMeSH
Cholecystokinin pancreozymin C-terminal octapeptideMeSH
CCK-8MeSH
OP-CCKMeSH
(3S)-3-{[(2S)-2-{[(2S)-2-[(2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-3-[4-(sulfooxy)phenyl]propylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-1-hydroxy-4-(methylsulfanyl)butylidene]amino}-3-{[(1S)-1-(C-hydroxycarbonimidoyl)-2-phenylethyl]-C-hydroxycarbonimidoyl}propanoateGenerator
(3S)-3-{[(2S)-2-{[(2S)-2-[(2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-3-[4-(sulphooxy)phenyl]propylidene]amino}-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-3-{[(1S)-1-(C-hydroxycarbonimidoyl)-2-phenylethyl]-C-hydroxycarbonimidoyl}propanoateGenerator
(3S)-3-{[(2S)-2-{[(2S)-2-[(2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-3-[4-(sulphooxy)phenyl]propylidene]amino}-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-1-hydroxy-4-(methylsulphanyl)butylidene]amino}-3-{[(1S)-1-(C-hydroxycarbonimidoyl)-2-phenylethyl]-C-hydroxycarbonimidoyl}propanoic acidGenerator
Chemical FormulaC49H62N10O16S3
Average Molecular Mass1143.270 g/mol
Monoisotopic Mass1142.351 g/mol
CAS Registry Number25126-32-3
IUPAC Name(3S)-3-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-4-(methylsulfanyl)butanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
Traditional Name(3S)-3-[(2S)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-4-(methylsulfanyl)butanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
SMILESCSCC[C@H](NC(=O)[C@H](CC1=CC=C(OS(O)(=O)=O)C=C1)NC(=O)[C@@H](N)CC(O)=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 IdentifierInChI=1S/C49H62N10O16S3/c1-76-18-16-34(55-47(69)37(58-44(66)32(50)23-41(61)62)21-28-12-14-30(15-13-28)75-78(72,73)74)45(67)53-26-40(60)54-38(22-29-25-52-33-11-7-6-10-31(29)33)48(70)56-35(17-19-77-2)46(68)59-39(24-42(63)64)49(71)57-36(43(51)65)20-27-8-4-3-5-9-27/h3-15,25,32,34-39,52H,16-24,26,50H2,1-2H3,(H2,51,65)(H,53,67)(H,54,60)(H,55,69)(H,56,70)(H,57,71)(H,58,66)(H,59,68)(H,61,62)(H,63,64)(H,72,73,74)/t32-,34-,35-,36-,37-,38-,39-/m0/s1
InChI KeyIZTQOLKUZKXIRV-YRVFCXMDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Phenylalanine or derivatives
  • Methionine or derivatives
  • Aspartic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Phenylsulfate
  • N-substituted-alpha-amino acid
  • Arylsulfate
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole or derivatives
  • Indole
  • Phenoxy compound
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Sulfuric acid ester
  • N-acyl-amine
  • Sulfate-ester
  • Sulfuric acid monoester
  • Pyrrole
  • Organic sulfuric acid or derivatives
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Carboxylic acid
  • Thioether
  • Sulfenyl compound
  • Azacycle
  • Dialkylthioether
  • Organoheterocyclic compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
logP0.48ALOGPS
logP-2.4ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area426.8 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity282.07 m³·mol⁻¹ChemAxon
Polarizability112.69 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-5910121100-3340452ed5408c50c8d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imr-9731313000-0e21f4347c59b5da21caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9311200000-94164a1a0b9abf4b2b31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9300000001-2e8bbc02c67fde19fa93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000001-568bf434b6cda55ca098Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9200000001-a551db3f3a2b11c6e4ceSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB09142
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSincalide
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID9833444
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available