CCK-8   Click here for help

GtoPdb Ligand ID: 864

Synonyms: CCK-8 (sulphated) | cholecystokinin 8 | cholecystokinin fragment 26-33 amide (sulphated)
Comment: The sulphated form of CCK-8. A synthetic variant, desulphated CCK-8 also exists.
Species: Human, Mouse, Rat
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: cck-8, cholecystokinin

2D Structure
Click here for help
Click here for structure editor
Click here for help
Canonical SMILES CSCCC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)Cc1ccccc1)CC(=O)O)CCSC)Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C(CC(=O)O)N)Cc1ccc(cc1)OS(=O)(=O)O
Isomeric SMILES CSCC[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)CC(=O)O)CCSC)Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)N)Cc1ccc(cc1)OS(=O)(=O)O
InChI InChI=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
1. Goto Y, Hattori A, Ishii Y, Mizutani S, Tsujimoto M. (2006)
Enzymatic properties of human aminopeptidase A. Regulation of its enzymatic activity by calcium and angiotensin IV.
J Biol Chem, 281 (33): 23503-13. [PMID:16790432]
2. Hughes J, Boden P, Costall B, Domeney A, Kelly E, Horwell DC, Hunter JC, Pinnock RD, Woodruff GN. (1990)
Development of a class of selective cholecystokinin type B receptor antagonists having potent anxiolytic activity.
Proc Natl Acad Sci USA, 87 (17): 6728-32. [PMID:1975695]
3. Ito M, Matsui T, Taniguchi T, Tsukamoto T, Murayama T, Arima N, Nakata H, Chiba T, Chihara K. (1993)
Functional characterization of a human brain cholecystokinin-B receptor. A trophic effect of cholecystokinin and gastrin.
J Biol Chem, 268 (24): 18300-5. [PMID:8349705]
4. Lee YM, Beinborn M, McBride EW, Lu M, Kolakowski Jr LF, Kopin AS. (1993)
The human brain cholecystokinin-B/gastrin receptor. Cloning and characterization.
J Biol Chem, 268 (11): 8164-9. [PMID:7681836]
5. Migaud M, Durieux C, Viereck J, Soroca-Lucas E, FourniĆ©-Zaluski MC, Roques BP. (1996)
The in vivo metabolism of cholecystokinin (CCK-8) is essentially ensured by aminopeptidase A.
Peptides, 17 (4): 601-7. [PMID:8804068]
6. Zini S, Fournie-Zaluski MC, Chauvel E, Roques BP, Corvol P, Llorens-Cortes C. (1996)
Identification of metabolic pathways of brain angiotensin II and III using specific aminopeptidase inhibitors: predominant role of angiotensin III in the control of vasopressin release.
Proc Natl Acad Sci USA, 93 (21): 11968-73. [PMID:8876246]