Name: Ceruletide
Brand: Creative Peptides
SKU: C03003
Availability: MadeToOrder

Ceruletide

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.

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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. Uncarboxylated osteocalcin decreases insulin-stimulated glucose uptake without affecting insulin signaling and regulators of mitochondrial biogenesis in myotubes

2. Immune responses to homocitrulline-and citrulline-containing peptides in rheumatoid arthritis

3. An Isolated TCR αβ Restricted by HLA-A* 02: 01/CT37 Peptide Redirecting CD8+ T Cells to Kill and Secrete IFN-γ in Response to Lung Adenocarcinoma Cell Lines

4. High fat diet and GLP-1 drugs induce pancreatic injury in mice

5. Adipose tissue is a key organ for the beneficial effects of GLP-2 metabolic function

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