Ceruletide is a decapeptide comprising 5-oxoprolyl, glutamyl, aspartyl, O-sulfotyrosyl, threonyl, glycyl, tryptopyl, methionyl, aspartyl and phenylalaninamide residues in sequence. Found in the skins of certain Australian amphibians, it is an analogue of the gastrointestinal peptide hormone cholecystokinin and stimulates gastric, biliary, and pancreatic secretion. It is used in cases of paralysis of the intestine (paralytic ileus) and as a diagnostic aid in pancreatic malfunction. It has a role as a diagnostic agent and a gastrointestinal drug.
CAT No: C03003
CAS No: 17650-98-5
Synonyms/Alias: Caerulein;Ceruletide;17650-98-5;Cerulein;Ceruletida;Ceruletidum;Ceruletidum [INN-Latin];Ceruletida [INN-Spanish];Ceruletide [USAN:INN:BAN];CCRIS 3063;5-Oxo-L-prolyl-L-glutaminyl-L-alpha-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-alpha-aspartyl-L-phenylalaninamide;CHEBI:59219;CERULETIDE [MI];CERULETIDE [INN];CERULETIDE [USAN];5-Oxo-L-prolyl-L-glutaminyl-L-aspartyl-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-aspartylphenyl-L-alaninamide 4-(hydrogen sulfate) (ester);CERULETIDE [MART.];CERULETIDE [WHO-DD];888Y08971B;DTXSID8040434;Caerulein (~85%);Ceruletidum (INN-Latin);Ceruletida (INN-Spanish);CERULETIDE (MART.);(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;pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2;Ceruletid;5-OXO-L-PROLYL-L-GLUTAMINYL-L-A-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-.ALPHA.-ASPARTYL-L-PHENYLALANINAMIDE;5-oxo-L-prolyl-L-glutaminyl-L-a-aspartyl-O-sulfo-L-tyrosyl-L-threonylglycyl-L-tryptophyl-L-methionyl-L-a-aspartyl-L-phenylalaninamide;Ceruletide (USAN/INN);UNII-888Y08971B;(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;Caerulein, sulfated;Caerulein triammonium;MFCD00076478;ceruletide diethylamide;Ceruletide (Standard);SCHEMBL29520;GTPL7589;CHEMBL1201355;DTXCID6020434;HY-A0190R;V04CC04;YRALAIOMGQZKOW-HYAOXDFASA-N;HY-A0190;AKOS030529560;CS-5876;DB00403;AS-56061;FC108931;NS00004791;C73362;D03442;EN300-23248418;Q5065299;(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-(indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]propanoic acid;5-OXO-L-PROLYL-L-GLUTAMINYL-L-A-ASPARTYL-O-SULFO-L-TYROSYL-L-THREONYLGLYCYL-L-TRYPTOPHYL-L-METHIONYL-L-ALPHA-ASPARTYL-L-PHENYLALANINAMIDE;
Chemical Name: (3S)-3-[[(2S)-5-amino-5-oxo-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]pentanoyl]amino]-4-[[(2S)-1-[[(2S,3R)-1-[[2-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-(4-sulfooxyphenyl)propan-2-yl]amino]-4-oxobutanoic acid
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M.F/Formula | C58H73N13O21S2 |
M.W/Mr. | 1352.4 |
Sequence | One Letter Code:XQDXTGWMDF Three Letter Code:H-Pyr-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2 |
Activity | Agonist |
Biological Activity | CCK agonist. Stimulates biosynthesis of pancreatic enzymes in AR4-2J pancreatic cells in vitro. Induces acute pancreatitis in mice. Also enhances proteasome activity in Gdeg mice. |
Target | CCK receptor |
Long-term Storage Conditions | Soluble to 1 mg/ml in water |
Shipping Condition | Evaluation sample solution : ship with blue ice All other available size: ship with RT , or blue ice upon request |
InChI | 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 Key | YRALAIOMGQZKOW-HYAOXDFASA-N |
Canonical SMILES | CC(C(C(=O)NCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CCSC)C(=O)NC(CC(=O)O)C(=O)NC(CC3=CC=CC=C3)C(=O)N)NC(=O)C(CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)C(CC(=O)O)NC(=O)C(CCC(=O)N)NC(=O)C5CCC(=O)N5)O |
Isomeric SMILES | C[C@H]([C@@H](C(=O)NCC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N)NC(=O)[C@H](CC4=CC=C(C=C4)OS(=O)(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]5CCC(=O)N5)O |
1. Myotropic activity of allatostatins in tenebrionid beetles
3. The spatiotemporal control of signalling and trafficking of the GLP-1R
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