(3S)-3-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid

• ChemBase ID: 133909
• Molecular Formular: C29H36N6O6S
• Molecular Mass: 596.69774
• Monoisotopic Mass: 596.2417039
• SMILES: CSCC[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)N
• Canonical 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)N
• InChI: InChI=1S/C29H36N6O6S/c1-42-12-11-22(33-27(39)20(30)14-18-16-32-21-10-6-5-9-19(18)21)28(40)35-24(15-25(36)37)29(41)34-23(26(31)38)13-17-7-3-2-4-8-17/h2-10,16,20,22-24,32H,11-15,30H2,1H3,(H2,31,38)(H,33,39)(H,34,41)(H,35,40)(H,36,37)/t20-,22-,23-,24-/m0/s1
• InChIKey: RGYLYUZOGHTBRF-BIHRQFPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido]-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
• Synonyms: CCK-4; Gastrin Tetrapeptide; Tetragastrin hydrochloride; Trp-Met-Asp-Phe amide; Cholecystokinin Fragment 30-33 Amide

Database IDs

• CAS Number: 1947-37-1
• MDL Number: MFCD00076492
• PubChem SID: 24900382; 162228186
• PubChem CID: 446569

CALCULATED PROPERTIES

• Acid pKa: 3.6962147
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): -1.8366581
• LogD (pH = 7.4): -2.006547
• Log P: -1.8388988
• Molar Refractivity: 157.6603 cm^3
• Polarizability: 62.703262 Å^3
• Polar Surface Area: 209.5 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CCK(885)rat ... Cckbr(25706)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - T6515

Amino Acid Sequence
Trp-Met-Asp-Phe-NH2
Biochem/physiol Actions
CCKB cholecystokinin receptor agonist; anxiogenic.