(3S)-3-[(2R)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-amino-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-indol-3-yl)propanamido]hexanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid

• ChemBase ID: 286
• Molecular Formular: C45H57N9O14S
• Molecular Mass: 980.05098
• Monoisotopic Mass: 979.37456855
• SMILES: S(=O)(=O)(Oc1ccc(C[C@H](N)C(=O)N[C@@H]([C@H](O)C)C(=O)NCC(=O)N[C@@H](Cc2c3c([nH]c2)cccc3)C(=O)N[C@H](CCCC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc2ccccc2)C(=O)N)cc1)O
• Canonical SMILES: CCCC[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](Cc1ccc(cc1)OS(=O)(=O)O)N
• InChI: InChI=1S/C45H57N9O14S/c1-3-4-13-33(42(61)53-36(22-38(57)58)44(63)52-34(40(47)59)20-26-10-6-5-7-11-26)51-43(62)35(21-28-23-48-32-14-9-8-12-30(28)32)50-37(56)24-49-45(64)39(25(2)55)54-41(60)31(46)19-27-15-17-29(18-16-27)68-69(65,66)67/h5-12,14-18,23,25,31,33-36,39,48,55H,3-4,13,19-22,24,46H2,1-2H3,(H2,47,59)(H,49,64)(H,50,56)(H,51,62)(H,52,63)(H,53,61)(H,54,60)(H,57,58)(H,65,66,67)/t25-,31+,33-,34+,35+,36+,39+/m1/s1
• InChIKey: GZCDGEPFXQGWOW-RMNOTBJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2R)-2-[(2S)-2-{2-[(2S,3R)-2-[(2S)-2-amino-3-[4-(sulfooxy)phenyl]propanamido]-3-hydroxybutanamido]acetamido}-3-(1H-indol-3-yl)propanamido]hexanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: tymtran
• Synonyms: Ceruletide

Database IDs

• CAS Number: 17650-98-5
• PubChem SID: 160963749
• PubChem CID: 168399

CALCULATED PROPERTIES

JChem

• Acid pKa: -2.0331511
• H Acceptors: 14
• H Donor: 12
• LogD (pH = 5.5): -3.5011067
• LogD (pH = 7.4): -5.251442
• Log P: -1.755828
• Molar Refractivity: 244.2501 cm^3
• Polarizability: 97.376465 Å^3
• Polar Surface Area: 380.63 Å^2
• Rotatable Bonds: 27
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.35
• LOG S: -5.24
• Solubility (Water): 5.67e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.9

DETAILS

DrugBank - DB00403

• Drug Groups: approved
• Description: Caerulein is a specific decapeptide similar in action and composition to the natural gastrointestinal peptide hormone cholecystokinin. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle.
• Indication: Caerulein stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle. As such, it is used in paralytic ileus and as diagnostic aid in pancreatic malfunction.
• Pharmacology: Caerulein is a specific decapeptide similar in action and composition to the natural gastrointestinal peptide hormone cholecystokinin. It stimulates gastric, biliary, and pancreatic secretion; and certain smooth muscle.
• Affected Organisms: Humans and other mammals
• Absorption: Absorbed following intravenous administration.