2-{[1-(6-amino-2-{[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidin-2-yl]formamido}hexanoyl)pyrrolidin-2-yl]formamido}-N-{3-carbamoyl-1-[(1-{[1-({1-[(1-{[1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl)carbamoyl]-2-(1H-indol-3-yl)ethyl}carbamoyl)-2-phenylethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]propyl}pentanediamide

• ChemBase ID: 103834
• Molecular Formular: C74H106N20O13S
• Molecular Mass: 1515.82464
• Monoisotopic Mass: 1514.79689455
• SMILES: CSCCC(NC(=O)C(CC(C)C)NC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)C(Cc1ccccc1)NC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)C(CCC(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C1CCCN1C(=O)C(CCCCN)NC(=O)C1CCCN1C(=O)C(N)CCCNC(=N)N)C(=O)N
• Canonical SMILES: NCCCCC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N)CCSC)CC(C)C)Cc1c[nH]c2c1cccc2)Cc1ccccc1)Cc1c[nH]c2c1cccc2)CCC(=O)N)CCC(=O)N)NC(=O)C1CCCN1C(=O)C(CCCNC(=N)N)N
• InChI: InChI=1S/C74H106N20O13S/c1-42(2)36-55(66(100)85-51(63(79)97)30-35-108-3)89-68(102)58(39-45-41-84-50-22-10-8-19-47(45)50)92-67(101)56(37-43-16-5-4-6-17-43)90-69(103)57(38-44-40-83-49-21-9-7-18-46(44)49)91-65(99)52(26-28-61(77)95)86-64(98)53(27-29-62(78)96)87-70(104)60-25-15-34-94(60)73(107)54(23-11-12-31-75)88-71(105)59-24-14-33-93(59)72(106)48(76)20-13-32-82-74(80)81/h4-10,16-19,21-22,40-42,48,51-60,83-84H,11-15,20,23-39,75-76H2,1-3H3,(H2,77,95)(H2,78,96)(H2,79,97)(H,85,100)(H,86,98)(H,87,104)(H,88,105)(H,89,102)(H,90,103)(H,91,99)(H,92,101)(H4,80,81,82)
• InChIKey: ARZXOJGZBACSSO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[1-(6-amino-2-{[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidin-2-yl]formamido}hexanoyl)pyrrolidin-2-yl]formamido}-N-{3-carbamoyl-1-[(1-{[1-({1-[(1-{[1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl)carbamoyl]-2-(1H-indol-3-yl)ethyl}carbamoyl)-2-phenylethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]propyl}pentanediamide
• IUPAC Traditional name: 2-{[1-(6-amino-2-{[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidin-2-yl]formamido}hexanoyl)pyrrolidin-2-yl]formamido}-N-{3-carbamoyl-1-[(1-{[1-({1-[(1-{[1-carbamoyl-3-(methylsulfanyl)propyl]carbamoyl}-3-methylbutyl)carbamoyl]-2-(1H-indol-3-yl)ethyl}carbamoyl)-2-phenylethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl)carbamoyl]propyl}pentanediamide
• Synonyms: Arg-D-Pro-Lys-Pro-Gln-Gln-D-Trp-Phe-D-Trp-Leu-Met-NH₂; [D-Pro^2,D-Trp^7,9]-SUBSTANCE P

Database IDs

• CAS Number: 80434-86-2
• PubChem SID: 162090960
• PubChem CID: 25077352

CALCULATED PROPERTIES

• LogD (pH = 7.4): -8.028257
• Log P: -3.1346886
• Molar Refractivity: 413.4272 cm^3
• Polarizability: 159.15698 Å^3
• Polar Surface Area: 548.21 Å^2
• Rotatable Bonds: 44
• Lipinski's Rule of Five: false
• Acid pKa: 11.534295
• H Acceptors: 18
• H Donor: 18
• LogD (pH = 5.5): -10.132784

DETAILS

MP Biomedicals - 02153010

A CNS antagonist of substance P.
Long-term administration to the eye inhibits ocular response to infrared irradiation of the iris.

REFERENCES

• Engberg, G., et al., Nature, 293: 222, (1981).
• Bynke, G., et al., Experentia, 40: 368, (1984).