N-(5-carbamimidamido-1-{2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl}-1-oxopentan-2-yl)-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-methylpentanamide

• ChemBase ID: 103804
• Molecular Formular: C56H77N17O13
• Molecular Mass: 1196.31668
• Monoisotopic Mass: 1195.58867561
• SMILES: CC(C)CC(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)C(=O)NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)NCC(=O)N
• Canonical SMILES: OCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NCC(=O)N)CCCNC(=N)N)CC(C)C)C)Cc1ccc(cc1)O)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C(NC(=O)C1CCC(=O)N1)Cc1[nH]cnc1
• InChI: InChI=1S/C56H77N17O13/c1-29(2)20-39(50(81)67-38(10-6-18-61-56(58)59)55(86)73-19-7-11-44(73)54(85)63-26-45(57)76)68-47(78)30(3)65-49(80)40(21-31-12-14-34(75)15-13-31)69-53(84)43(27-74)72-51(82)41(22-32-24-62-36-9-5-4-8-35(32)36)70-52(83)42(23-33-25-60-28-64-33)71-48(79)37-16-17-46(77)66-37/h4-5,8-9,12-15,24-25,28-30,37-44,62,74-75H,6-7,10-11,16-23,26-27H2,1-3H3,(H2,57,76)(H,60,64)(H,63,85)(H,65,80)(H,66,77)(H,67,81)(H,68,78)(H,69,84)(H,70,83)(H,71,79)(H,72,82)(H4,58,59,61)
• InChIKey: SESQMDHICVIJCF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(5-carbamimidamido-1-{2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl}-1-oxopentan-2-yl)-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-methylpentanamide
• IUPAC Traditional name: N-{5-carbamimidamido-1-[2-(carbamoylmethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl}-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-methylpentanamide
• Synonyms: pyroGlu-His-Trp-Ser-Tyr-D-Ala-Leu-Arg-Pro-Gly-NH₂; [D-Ala^6]-LH-RH

Database IDs

• CAS Number: 51230-19-4
• PubChem SID: 162103281
• PubChem CID: 4673165

CALCULATED PROPERTIES

• Acid pKa: 9.489627
• H Acceptors: 17
• H Donor: 17
• LogD (pH = 5.5): -8.124793
• LogD (pH = 7.4): -7.377733
• Log P: -5.679402
• Molar Refractivity: 317.292 cm^3
• Polarizability: 119.69103 Å^3
• Polar Surface Area: 472.13 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 02152907

A potent LH-RH analog.

REFERENCES

• Monahan, M.W., et al., Biochem., 12, 4616 (1973).