4-[(1-{[1-({[(1-{[1-({1-[(1-carbamoyl-2-phenylethyl)carbamoyl]-2-carboxyethyl}carbamoyl)-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]methyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl)carbamoyl]-4-(4-carboxy-2-{4-carboxy-2-[4-carboxy-2-(4-carboxy-2-{2-[3-(1H-indol-3-yl)-2-[(1-{2-[(5-oxopyrrolidin-2-yl)formamido]acetyl}pyrrolidin-2-yl)formamido]propanamido]-4-methylpentanamido}butanamido)butanamido]butanamido}butanamido)butanoic acid

• ChemBase ID: 103798
• Molecular Formular: C98H126N20O31
• Molecular Mass: 2080.16444
• Monoisotopic Mass: 2078.88978735
• SMILES: CC(C)CC(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C1CCCN1C(=O)CNC(=O)C1CCC(=O)N1)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(C)C(=O)NC(Cc1ccc(O)cc1)C(=O)NCC(=O)NC(Cc1c[nH]c2c1cccc2)C(=O)NC(CC(C)C)C(=O)NC(CC(=O)O)C(=O)NC(Cc1ccccc1)C(=O)N
• Canonical SMILES: CC(CC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)Cc1ccccc1)CC(=O)O)CC(C)C)Cc1c[nH]c2c1cccc2)Cc1ccc(cc1)O)C)CCC(=O)O)CCC(=O)O)CCC(=O)O)CCC(=O)O)CCC(=O)O)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C1CCCN1C(=O)CNC(=O)C1CCC(=O)N1)C
• InChI: InChI=1S/C98H126N20O31/c1-49(2)38-68(115-96(147)72(43-55-46-101-60-19-12-10-17-58(55)60)117-98(149)74-20-13-37-118(74)77(122)48-103-86(137)61-25-31-75(120)105-61)93(144)111-66(30-36-82(131)132)92(143)110-65(29-35-81(129)130)91(142)109-64(28-34-80(127)128)90(141)108-63(27-33-79(125)126)89(140)107-62(26-32-78(123)124)88(139)104-51(5)85(136)113-70(41-53-21-23-56(119)24-22-53)87(138)102-47-76(121)106-71(42-54-45-100-59-18-11-9-16-57(54)59)95(146)114-69(39-50(3)4)94(145)116-73(44-83(133)134)97(148)112-67(84(99)135)40-52-14-7-6-8-15-52/h6-12,14-19,21-24,45-46,49-51,61-74,100-101,119H,13,20,25-44,47-48H2,1-5H3,(H2,99,135)(H,102,138)(H,103,137)(H,104,139)(H,105,120)(H,106,121)(H,107,140)(H,108,141)(H,109,142)(H,110,143)(H,111,144)(H,112,148)(H,113,136)(H,114,146)(H,115,147)(H,116,145)(H,117,149)(H,123,124)(H,125,126)(H,127,128)(H,129,130)(H,131,132)(H,133,134)
• InChIKey: CMVMLPDUAGUTOC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1-{[1-({[(1-{[1-({1-[(1-carbamoyl-2-phenylethyl)carbamoyl]-2-carboxyethyl}carbamoyl)-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]methyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl)carbamoyl]-4-(4-carboxy-2-{4-carboxy-2-[4-carboxy-2-(4-carboxy-2-{2-[3-(1H-indol-3-yl)-2-[(1-{2-[(5-oxopyrrolidin-2-yl)formamido]acetyl}pyrrolidin-2-yl)formamido]propanamido]-4-methylpentanamido}butanamido)butanamido]butanamido}butanamido)butanoic acid
• IUPAC Traditional name: 4-[(1-{[1-({[(1-{[1-({1-[(1-carbamoyl-2-phenylethyl)carbamoyl]-2-carboxyethyl}carbamoyl)-3-methylbutyl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]methyl}carbamoyl)-2-(4-hydroxyphenyl)ethyl]carbamoyl}ethyl)carbamoyl]-4-(4-carboxy-2-{4-carboxy-2-[4-carboxy-2-(4-carboxy-2-{2-[3-(1H-indol-3-yl)-2-[(1-{2-[(5-oxopyrrolidin-2-yl)formamido]acetyl}pyrrolidin-2-yl)formamido]propanamido]-4-methylpentanamido}butanamido)butanamido]butanamido}butanamido)butanoic acid
• Synonyms: pyroGlu-Gly-Pro-Trp-Leu-Glu-Glu-Glu-Glu-Glu-Ala-Tyr-Gly-Trp-Leu-Asp-Phe-NH₂; [Leu^15]-GASTRIN I; LHG-17; [15-Leucine]-Gastrin I, human heptadecapeptide; [18-Pyroglutamic acid, 32-leucine]-Big gastrin I-(18-34)-peptide amide, human; [Leu15]-Gastrin I, human; [Leu15]-HG-17; [Leucine15]-Gastrin I heptadecapeptide; [Leucine15]-Little gastrin I; [Leu15]-Gastrin I human

Database IDs

• CAS Number: 39024-57-2; 71526-06-2
• EC Number: 254-250-2
• MDL Number: MFCD00076502
• Beilstein Number: 5227423
• PubChem SID: 162090957; 24895364
• PubChem CID: 16133230

CALCULATED PROPERTIES

• Acid pKa: 3.2714012
• H Acceptors: 31
• H Donor: 26
• LogD (pH = 5.5): -13.275812
• LogD (pH = 7.4): -23.289192
• Log P: -4.5258603
• Molar Refractivity: 515.3342 cm^3
• Polarizability: 203.10173 Å^3
• Polar Surface Area: 804.61 Å^2
• Rotatable Bonds: 61
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• 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 ... GAST(2520)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 02152872

Source/Species: Human
Useful for biological and immunological studies.
A potent stimulator of gastric secretion.

Sigma Aldrich - G9145

Amino Acid Sequence
Glp-Gly-Pro-Trp-Leu-Glu-Glu-Glu-Glu-Glu-Ala-Tyr-Gly-Trp-Leu-Asp-Phe-NH2
Biochem/physiol Actions
Gastrin I analog with full biological activity and improved stability in aqueous solutions. Leu15 replaces Met15, that is readily oxidized resulting in loss of biological activity.

REFERENCES

• Walsh, J.H. and Grossman M.I., New Engl. J. Med., 292: 1324, (1975).