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

• ChemBase ID: 132428
• Molecular Formular: C49H62N10O16S3
• Molecular Mass: 1143.26898
• Monoisotopic Mass: 1142.35073895
• SMILES: CSCC[C@@H](C(=O)NCC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)NC(CCSC)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N)NC(=O)[C@H](Cc1ccc(cc1)OS(=O)(=O)O)NC(=O)[C@H](CC(=O)O)N
• Canonical SMILES: CSCC[C@@H](C(=O)NCC(=O)N[C@H](C(=O)NC(C(=O)N[C@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)CC(=O)O)CCSC)Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@H](CC(=O)O)N)Cc1ccc(cc1)OS(=O)(=O)O
• InChI: InChI=1S/C49H62N10O16S3/c1-76-18-16-34(55-47(69)37(58-44(66)32(50)23-41(61)62)21-28-12-14-30(15-13-28)75-78(72,73)74)45(67)53-26-40(60)54-38(22-29-25-52-33-11-7-6-10-31(29)33)48(70)56-35(17-19-77-2)46(68)59-39(24-42(63)64)49(71)57-36(43(51)65)20-27-8-4-3-5-9-27/h3-15,25,32,34-39,52H,16-24,26,50H2,1-2H3,(H2,51,65)(H,53,67)(H,54,60)(H,55,69)(H,56,70)(H,57,71)(H,58,66)(H,59,68)(H,61,62)(H,63,64)(H,72,73,74)/t32-,34-,35?,36-,37-,38-,39-/m0/s1
• InChIKey: IZTQOLKUZKXIRV-IVVJSLGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-4-(methylsulfanyl)butanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido}-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-{2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carboxypropanamido]-3-[4-(sulfooxy)phenyl]propanamido]-4-(methylsulfanyl)butanamido]acetamido}-3-(1H-indol-3-yl)propanamido]-4-(methylsulfanyl)butanamido}-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}propanoic acid
• Synonyms: CCK-8; Cholecystokinin octapeptide; Pancreozymin C-terminal octapeptide; Sincalide; (Tyr[SO3H]27)Cholecystokinin fragment 26-33 Amide

Database IDs

• CAS Number: 25126-32-3
• EC Number: 246-639-0
• MDL Number: MFCD00079849
• Beilstein Number: 5231801
• PubChem SID: 24892470; 162226705
• PubChem CID: 16219094

CALCULATED PROPERTIES

• Acid pKa: -2.0350966
• H Acceptors: 16
• H Donor: 13
• LogD (pH = 5.5): -6.3377867
• LogD (pH = 7.4): -9.274832
• Log P: -2.414598
• Molar Refractivity: 282.0718 cm^3
• Polarizability: 112.05826 Å^3
• Polar Surface Area: 426.8 Å^2
• Rotatable Bonds: 33
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 0.05 M ammonium hydroxide: soluble1 mg/mL, clear, colorless
• Apperance: powder

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 ... Cckar(24889), Cckbr(25706); rat ... Pomc(24664)

Product Information

• Purity: ≥75% peptide basis; ≥97% (HPLC); ≥97.0% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C49H62N10O16S3

DETAILS

Sigma Aldrich - C2175

Amino Acid Sequence
Asp-Tyr-Met-Gly-Trp-Met-Asp-Phe-NH2
Other Notes
C-Terminal octapeptide of cholecystokinin
Biochem/physiol Actions
Neurotransmitter; predominant form of CCK in CNS and gastrointestinal tract; may play a role in satiety.

Sigma Aldrich - 26690

Amino Acid Sequence
Asp-Tyr-Met-Gly-Trp-Met-Asp-Phe-NH2
Other Notes
Inhibition of CCK-8 release by DAGOL1; Cholecystokinin and substance P in the CNS, review2