4-[2-(2-aminopropanamido)acetamido]-4-({[(1-{[1-({1-[2-({1-[(1-{[1-({1-[(1-{[1-(2-{[1-({4-carbamimidamido-1-[(1-carbamoyl-2-phenylethyl)carbamoyl]butyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}pyrrolidin-1-yl)-1-oxopropan-2-yl]carbamoyl}ethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]-2-phenylethyl}carbamoyl)pyrrolidin-1-yl]-3-hydroxy-1-oxopropan-2-yl}carbamoyl)-2-hydroxyethyl]carbamoyl}-3-methylbutyl)carbamoyl]methyl}carbamoyl)butanoic acid

• ChemBase ID: 132081
• Molecular Formular: C89H130N24O24
• Molecular Mass: 1920.1309
• Monoisotopic Mass: 1918.96898116
• SMILES: CC(C)CC(C(=O)NC(CO)C(=O)NC(CO)C(=O)N1CCCC1C(=O)NC(Cc1ccccc1)C(=O)NC(Cc1c[nH]c2c1cccc2)C(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(C)C(=O)N1CCCC1C(=O)NC(CCC(=O)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(Cc1ccccc1)C(=O)N)NC(=O)CNC(=O)C(CCC(=O)O)NC(=O)CNC(=O)C(C)N
• Canonical SMILES: OCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)Cc1ccccc1)CCCNC(=N)N)CCC(=O)N)C)C)CC(C)C)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C1CCCN1C(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)CNC(=O)C(N)C)CCC(=O)O)CC(C)C)CO)CO)Cc1ccccc1
• InChI: InChI=1S/C89H130N24O24/c1-46(2)35-60(102-71(119)42-98-76(125)57(29-31-72(120)121)101-70(118)41-97-74(123)48(5)90)80(129)109-65(44-115)84(133)111-66(45-116)88(137)113-34-18-27-68(113)86(135)108-62(38-52-21-12-9-13-22-52)81(130)107-63(39-53-40-96-55-24-15-14-23-54(53)55)82(131)110-64(43-114)83(132)106-61(36-47(3)4)79(128)99-49(6)75(124)100-50(7)87(136)112-33-17-26-67(112)85(134)104-58(28-30-69(91)117)78(127)103-56(25-16-32-95-89(93)94)77(126)105-59(73(92)122)37-51-19-10-8-11-20-51/h8-15,19-24,40,46-50,56-68,96,114-116H,16-18,25-39,41-45,90H2,1-7H3,(H2,91,117)(H2,92,122)(H,97,123)(H,98,125)(H,99,128)(H,100,124)(H,101,118)(H,102,119)(H,103,127)(H,104,134)(H,105,126)(H,106,132)(H,107,130)(H,108,135)(H,109,129)(H,110,131)(H,111,133)(H,120,121)(H4,93,94,95)
• InChIKey: GNNFMZHECHAEGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(2-aminopropanamido)acetamido]-4-({[(1-{[1-({1-[2-({1-[(1-{[1-({1-[(1-{[1-(2-{[1-({4-carbamimidamido-1-[(1-carbamoyl-2-phenylethyl)carbamoyl]butyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}pyrrolidin-1-yl)-1-oxopropan-2-yl]carbamoyl}ethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]-2-phenylethyl}carbamoyl)pyrrolidin-1-yl]-3-hydroxy-1-oxopropan-2-yl}carbamoyl)-2-hydroxyethyl]carbamoyl}-3-methylbutyl)carbamoyl]methyl}carbamoyl)butanoic acid
• IUPAC Traditional name: 4-[2-(2-aminopropanamido)acetamido]-4-({[(1-{[1-({1-[2-({1-[(1-{[1-({1-[(1-{[1-(2-{[1-({4-carbamimidamido-1-[(1-carbamoyl-2-phenylethyl)carbamoyl]butyl}carbamoyl)-3-carbamoylpropyl]carbamoyl}pyrrolidin-1-yl)-1-oxopropan-2-yl]carbamoyl}ethyl)carbamoyl]-3-methylbutyl}carbamoyl)-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]-2-phenylethyl}carbamoyl)pyrrolidin-1-yl]-3-hydroxy-1-oxopropan-2-yl}carbamoyl)-2-hydroxyethyl]carbamoyl}-3-methylbutyl)carbamoyl]methyl}carbamoyl)butanoic acid
• Synonyms: A-18-F-NH2; Ala-Gly-Glu-Gly-Leu-Ser-Ser-Pro-Phe-Trp-Ser-Leu-Ala-Ala-Pro-Gln-Arg-Phe amide

Database IDs

• CAS Number: 99588-52-0
• MDL Number: MFCD00076703
• PubChem SID: 24890965; 162226358
• PubChem CID: 16133278

CALCULATED PROPERTIES

• Log P: -10.757198
• Molar Refractivity: 496.5163 cm^3
• Polarizability: 190.74083 Å^3
• Polar Surface Area: 765.0 Å^2
• Rotatable Bonds: 56
• Lipinski's Rule of Five: false
• Acid pKa: 3.494106
• H Acceptors: 28
• H Donor: 26
• LogD (pH = 5.5): -13.191358
• LogD (pH = 7.4): -11.499031

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

DETAILS

Sigma Aldrich - A5296

Biochem/physiol Actions
Attenuates analgesic effects of morphine
Other Notes
Endogenous peptide found in periaqueductal grey and in dorsal spinal cord