Tetragastrin (CHEM035992)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:07:59 UTC
Update Date2016-11-09 01:21:24 UTC
Accession NumberCHEM035992
Identification
Common NameTetragastrin
ClassSmall Molecule
DescriptionA tetrapeptide composed of L-tryptophan, L-methione, L-aspartic acid and L-phenylalaninamide residues joined in sequence.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CCK-4ChEBI
CCRIS 3246ChEBI
Cholecystokinin tetrapeptideChEBI
Cholecystokinin-4ChEBI
Gastrin tetrapeptideChEBI
Gastrin tetrapeptide amideChEBI
L-TRP-L-Met-L-asp-L-phe-NH(2)ChEBI
L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalaninamideChEBI
TRP-Met-asp-phe-NH(2)ChEBI
WMDF-NH(2)ChEBI
Carbobenzoxy-TRP-met-asp-phe-amideHMDB
GatratetHMDB
L-Tryptophyl-L-methionyl-L-aspartylphenyl-alaninamideHMDB
4, CholecystokininMeSH, HMDB
Cholecystokinin-tetrapeptideMeSH, HMDB
AOC-tetragastrinMeSH, HMDB
CCK (30-33)MeSH, HMDB
Cholecystokinin (30-33)MeSH, HMDB
Cholecystokinin 4MeSH, HMDB
Tetrapeptide, gastrinMeSH, HMDB
AOC-tetrapeptideMeSH, HMDB
CKK-4MeSH, HMDB
AOC tetragastrinMeSH, HMDB
AOC tetrapeptideMeSH, HMDB
Chemical FormulaC29H36N6O6S
Average Molecular Mass596.698 g/mol
Monoisotopic Mass596.242 g/mol
CAS Registry Number1947-37-1
IUPAC Name(3S)-3-[(2S)-2-[(2S)-2-amino-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-amino-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](N)CC1=CNC2=CC=CC=C12)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC1=CC=CC=C1)C(N)=O
InChI IdentifierInChI=1S/C29H36N6O6S/c1-42-12-11-22(33-27(39)20(30)14-18-16-32-21-10-6-5-9-19(18)21)28(40)35-24(15-25(36)37)29(41)34-23(26(31)38)13-17-7-3-2-4-8-17/h2-10,16,20,22-24,32H,11-15,30H2,1H3,(H2,31,38)(H,33,39)(H,34,41)(H,35,40)(H,36,37)/t20-,22-,23-,24-/m0/s1
InChI KeyRGYLYUZOGHTBRF-BIHRQFPBSA-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
  • Aspartic acid or derivatives
  • Methionine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Aralkylamine
  • Monocyclic benzene moiety
  • Fatty amide
  • N-acyl-amine
  • Substituted pyrrole
  • Fatty acyl
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Thioether
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Primary amine
  • 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 Solubility0.0048 g/LALOGPS
logP-0.41ALOGPS
logP-1.8ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.7ChemAxon
pKa (Strongest Basic)7.66ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area209.5 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity157.66 m³·mol⁻¹ChemAxon
Polarizability62.16 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3900120000-5c94753fbda3e8b3ae94Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-4911021000-ac75805ea7132e0d7b7cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Tetragastrin,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0522190000-9147056989212e59b65dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0931010000-037fcba066e60e6dfe64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc3-2910000000-74754045897784a95545Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-4000090000-3fa10e322422852b0d0bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9220030000-d93638019accce0fd9e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9220000000-b6b5d9f3b73597d1954dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0100090000-f757e4d3a27f3a4259bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ogv-0921160000-7e0ca6a777425dc36500Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-3900000000-00beb9fe276ba345777eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000490000-6c1de053b22bf4b121a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w9u-3132490000-21608d2a37764b2671aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6931000000-66c55eea268a548e064fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDNot Available
HMDB IDHMDB0005775
FooDB IDFDB023765
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCCK-4
Chemspider ID393888
ChEBI ID137728
PubChem Compound ID446569
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20198494
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20387390
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22414867
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22632477
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22939006
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23059050
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23463151
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24342768
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24939759
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=25106129
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25522396
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26235955
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26752621
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27871026
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=28328228
16. Hardy, P. M.; Kenner, G. W.; Sheppard, R. C.; MacLeod, J. K.; Morley, J. S. Therapeutical acylated tetrapeptides. (1965), 58 pp. BE 665591 19651217 CAN 64:104706 AN 1966:104706
17. Roosenburg S, Laverman P, van Delft FL, Boerman OC: Radiolabeled CCK/gastrin peptides for imaging and therapy of CCK2 receptor-expressing tumors. Amino Acids. 2011 Nov;41(5):1049-58. doi: 10.1007/s00726-010-0501-y. Epub 2010 Mar 3.
18. Koszycki D, Prichard Z, Fiocco AJ, Shlik J, Kennedy JL, Bradwejn J: CCK-B receptor gene and response to cholecystokinin-tetrapeptide in healthy volunteers. Peptides. 2012 May;35(1):9-13. doi: 10.1016/j.peptides.2012.02.014. Epub 2012 Mar 10.
19. Plag J, Gaudlitz K, Zschucke E, Yassouridis A, Pyrkosch L, Wittmann A, Holsboer F, Strohle A: Distinct panicogenic activity of sodium lactate and cholecystokinin tetrapeptide in patients with panic disorder. Curr Pharm Des. 2012;18(35):5619-26.
20. Toru I, Maron E, Raag M, Vasar V, Nutt DJ, Shlik J: The effect of 6-week treatment with escitalopram on CCK-4 challenge: a placebo-controlled study in CCK-4-sensitive healthy volunteers. Eur Neuropsychopharmacol. 2013 Jul;23(7):645-52. doi: 10.1016/j.euroneuro.2012.08.011. Epub 2012 Aug 29.
21. Leicht G, Mulert C, Eser D, Samann PG, Ertl M, Laenger A, Karch S, Pogarell O, Meindl T, Czisch M, Rupprecht R: Benzodiazepines counteract rostral anterior cingulate cortex activation induced by cholecystokinin-tetrapeptide in humans. Biol Psychiatry. 2013 Feb 15;73(4):337-44. doi: 10.1016/j.biopsych.2012.09.004. Epub 2012 Oct 8.
22. Zwanzger P, Zavorotnyy M, Gencheva E, Diemer J, Kugel H, Heindel W, Ruland T, Ohrmann P, Arolt V, Domschke K, Pfleiderer B: Acute shift in glutamate concentrations following experimentally induced panic with cholecystokinin tetrapeptide--a 3T-MRS study in healthy subjects. Neuropsychopharmacology. 2013 Aug;38(9):1648-54. doi: 10.1038/npp.2013.61. Epub 2013 Mar 5.
23. Agorastos A, Kellner M, Stiedl O, Muhtz C, Becktepe JS, Wiedemann K, Demiralay C: The 5-HTTLPR genotype modulates heart rate variability and its adjustment by pharmacological panic challenge in healthy men. J Psychiatr Res. 2014 Mar;50:51-8. doi: 10.1016/j.jpsychires.2013.11.013. Epub 2013 Dec 7.
24. Maddock RJ: Glutamate changes in anterior cingulate cortex following CCK-4 infusion. Neuropsychopharmacology. 2014 Oct;39(11):2706. doi: 10.1038/npp.2014.93. Epub 2014 Jun 18.
25. Ruland T, Domschke K, Schutte V, Zavorotnyy M, Kugel H, Notzon S, Vennewald N, Ohrmann P, Arolt V, Pfleiderer B, Zwanzger P: Neuropeptide S receptor gene variation modulates anterior cingulate cortex Glx levels during CCK-4 induced panic. Eur Neuropsychopharmacol. 2015 Oct;25(10):1677-82. doi: 10.1016/j.euroneuro.2015.07.011. Epub 2015 Jul 20.
26. Agorastos A, Demiralay C, Stiedl O, Muhtz C, Wiedemann K, Kellner M: Metabotropic glutamate2/3 receptor agonism facilitates autonomic recovery after pharmacological panic challenge in healthy humans. Int Clin Psychopharmacol. 2016 May;31(3):176-8. doi: 10.1097/YIC.0000000000000117.
27. Demiralay C, Agorastos A, Yassouridis A, Jahn H, Wiedemann K, Kellner M: Copeptin - A potential endocrine surrogate marker of CCK-4-induced panic symptoms? Psychoneuroendocrinology. 2017 Feb;76:14-18. doi: 10.1016/j.psyneuen.2016.11.006. Epub 2016 Nov 8.