ceruletide   Click here for help

GtoPdb Ligand ID: 7589

Synonyms: caerulein | cerulein | ceruletide diethylamine | Tymtran®
Approved drug
ceruletide is an approved drug
Compound class: Synthetic organic
Comment: Ceruletide is a decapeptide derivative of cholecystokinin with the amino acid sequence is Pglu-Gln-Asp-Tyr[SO3H]-Thr-Gly-Trp-Met-Asp-Phe-NH2 and originally isolated from the skin of the Australian green tree frog, Litoria caerulea. In the research setting ceruletide can be used to induce pancreatitis in experimental animal models.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 32
Hydrogen bond donors 17
Rotatable bonds 47
Topological polar surface area 585.08
Molecular weight 1351.45
XLogP -5.33
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CSCCC(C(=O)NC(C(=O)NC(C(=O)N)Cc1ccccc1)CC(=O)O)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)CNC(=O)C(C(O)C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C1CCC(=O)N1)CCC(=O)N)CC(=O)O)Cc1ccc(cc1)OS(=O)(=O)O
Isomeric SMILES CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)CC(=O)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)CNC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCC(=O)N1)CCC(=O)N)CC(=O)O)Cc1ccc(cc1)OS(=O)(=O)O
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
3351 ceruletide
Synonyms Click here for help
caerulein | cerulein | ceruletide diethylamine | Tymtran®
Database Links Click here for help
CAS Registry No. 17650-98-5
ChEBI CHEBI:59219
ChEMBL Ligand CHEMBL1201355
DrugBank Ligand DB00403
DrugCentral Ligand 579
GtoPdb PubChem SID 223365924
PubChem CID 16129675
Search Google for chemical match using the InChIKey YRALAIOMGQZKOW-HYAOXDFASA-N
Search Google for chemicals with the same backbone YRALAIOMGQZKOW
Search PubMed clinical trials ceruletide
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Search PubMed titles/abstracts ceruletide
UniChem Compound Search for chemical match using the InChIKey YRALAIOMGQZKOW-HYAOXDFASA-N
UniChem Connectivity Search for chemical match using the InChIKey YRALAIOMGQZKOW-HYAOXDFASA-N
Wikipedia Ceruletide