1-[5-carbamimidamido-2-(2-{2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]propanamido}-4-methylpentanamido)pentanoyl]-N-ethylpyrrolidine-2-carboxamide

• ChemBase ID: 103807
• Molecular Formular: C56H78N16O12
• Molecular Mass: 1167.31852
• Monoisotopic Mass: 1166.59851202
• SMILES: CCNC(=O)C1CCCN1C(=O)C(CCCNC(=N)N)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CO)NC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)C(Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1
• Canonical SMILES: CCNC(=O)C1CCCN1C(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(Cc1ccc(cc1)O)NC(=O)C(NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1)CO)C)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/C56H78N16O12/c1-5-60-54(83)45-13-9-21-72(45)55(84)39(12-8-20-61-56(57)58)66-50(79)40(22-30(2)3)67-47(76)31(4)64-49(78)41(23-32-14-16-35(74)17-15-32)68-53(82)44(28-73)71-51(80)42(24-33-26-62-37-11-7-6-10-36(33)37)69-52(81)43(25-34-27-59-29-63-34)70-48(77)38-18-19-46(75)65-38/h6-7,10-11,14-17,26-27,29-31,38-45,62,73-74H,5,8-9,12-13,18-25,28H2,1-4H3,(H,59,63)(H,60,83)(H,64,78)(H,65,75)(H,66,79)(H,67,76)(H,68,82)(H,69,81)(H,70,77)(H,71,80)(H4,57,58,61)
• InChIKey: QLGKMLRGKPKGKI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[5-carbamimidamido-2-(2-{2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]propanamido}-4-methylpentanamido)pentanoyl]-N-ethylpyrrolidine-2-carboxamide
• IUPAC Traditional name: 1-[5-carbamimidamido-2-(2-{2-[2-(3-hydroxy-2-{2-[3-(3H-imidazol-4-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]propanamido}-4-methylpentanamido)pentanoyl]-N-ethylpyrrolidine-2-carboxamide
• Synonyms: pyroGlu-His-Trp-Ser-Tyr-D-Ala-Leu-Arg-Pro-NH-ethyl; [D-Ala^6,Des-Gly^10]-LH-RH Ethylamide

Database IDs

• CAS Number: 79561-22-1
• PubChem SID: 162090441
• PubChem CID: 12821050

CALCULATED PROPERTIES

• Acid pKa: 9.489627
• H Acceptors: 16
• H Donor: 16
• LogD (pH = 5.5): -6.439026
• LogD (pH = 7.4): -5.691966
• Log P: -3.9936347
• Molar Refractivity: 314.1338 cm^3
• Polarizability: 118.41493 Å^3
• Polar Surface Area: 429.04 Å^2
• Rotatable Bonds: 30
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 02152917

An LH-RH antagonist with a marked stimulatory effect on spawning in fish.

REFERENCES

• Barnabe, G. and Barnabe-Quet, R., Aquaculture, 49: 125, (1985).