(3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(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

• ChemBase ID: 133387
• Molecular Formular: C58H73N13O21S2
• Molecular Mass: 1352.40472
• Monoisotopic Mass: 1351.44853842
• SMILES: C[C@H](C(C(=O)NCC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@@H](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)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@@H]1CCC(=O)N1)O
• 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)NC(=O)CNC(=O)C([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
• InChIKey: YRALAIOMGQZKOW-HJMGKOKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(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
• IUPAC Traditional name: (3S)-3-{[(1S)-1-carbamoyl-2-phenylethyl]carbamoyl}-3-[(2S)-2-[(2S)-2-{2-[(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
• Synonyms: Caerulein Sulfated; Cerulein; Ceruletide; [Tyr(SO3H)4]Caerulein; pGlu-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2; Caerulein

Database IDs

• CAS Number: 17650-98-5
• MDL Number: MFCD00076478
• Beilstein Number: 5422487
• PubChem SID: 24893129; 162227664
• PubChem CID: 16219178

CALCULATED PROPERTIES

• Acid pKa: -2.035095
• H Acceptors: 20
• H Donor: 17
• LogD (pH = 5.5): -10.784196
• LogD (pH = 7.4): -14.010771
• Log P: -5.227809
• Molar Refractivity: 325.7435 cm^3
• Polarizability: 129.04381 Å^3
• Polar Surface Area: 551.4 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

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

Safety Information

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

Product Information

• Purity: ≥80% peptide basis; ≥97% (HPLC); ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C58H73N13O21S2

DETAILS

Sigma Aldrich - C9026

Amino Acid Sequence
Glp-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Effects on perception of pain are conflicting. It prevents gall bladder pain, renal colic, and the pain of intermittent claudication; however, in general, it is seen as an antagonist of endogenous opioids.1

Sigma Aldrich - 21026

Amino Acid Sequence
Glp-Gln-Asp-Tyr(SO3H)-Thr-Gly-Trp-Met-Asp-Phe-NH2
Other Notes
A cholecystokinin analog. Review2; In studies on protease zymogens3
Biochem/physiol Actions
Effects on perception of pain are conflicting. It prevents gall bladder pain, renal colic, and the pain of intermittent claudication; however, in general, it is seen as an antagonist of endogenous opioids.1