1-(1-{2-[2-({1-[5-carbamimidamido-2-({1-[3-(1H-indol-3-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanoyl]pyrrolidin-2-yl}formamido)pentanoyl]pyrrolidin-2-yl}formamido)-4-carbamoylbutanamido]-3-methylpentanoyl}pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid

• ChemBase ID: 103747
• Molecular Formular: C53H76N14O12
• Molecular Mass: 1101.25714
• Monoisotopic Mass: 1100.57671394
• SMILES: CCC(C)C(NC(=O)C(CCC(=O)N)NC(=O)C1CCCN1C(=O)C(CCCNC(=N)N)NC(=O)C1CCCN1C(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C1CCC(=O)N1)C(=O)N1CCCC1C(=O)N1CCCC1C(=O)O
• Canonical SMILES: CCC(C(C(=O)N1CCCC1C(=O)N1CCCC1C(=O)O)NC(=O)C(NC(=O)C1CCCN1C(=O)C(NC(=O)C1CCCN1C(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C1CCC(=O)N1)CCCNC(=N)N)CCC(=O)N)C
• InChI: InChI=1S/C53H76N14O12/c1-3-29(2)43(51(77)66-25-9-16-39(66)50(76)67-26-10-17-40(67)52(78)79)63-45(71)34(18-20-41(54)68)60-46(72)37-14-7-23-64(37)48(74)35(13-6-22-57-53(55)56)61-47(73)38-15-8-24-65(38)49(75)36(62-44(70)33-19-21-42(69)59-33)27-30-28-58-32-12-5-4-11-31(30)32/h4-5,11-12,28-29,33-40,43,58H,3,6-10,13-27H2,1-2H3,(H2,54,68)(H,59,69)(H,60,72)(H,61,73)(H,62,70)(H,63,71)(H,78,79)(H4,55,56,57)
• InChIKey: UUUHXMGGBIUAPW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(1-{2-[2-({1-[5-carbamimidamido-2-({1-[3-(1H-indol-3-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanoyl]pyrrolidin-2-yl}formamido)pentanoyl]pyrrolidin-2-yl}formamido)-4-carbamoylbutanamido]-3-methylpentanoyl}pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: 1-(1-{2-[2-({1-[5-carbamimidamido-2-({1-[3-(1H-indol-3-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanoyl]pyrrolidin-2-yl}formamido)pentanoyl]pyrrolidin-2-yl}formamido)-4-carbamoylbutanamido]-3-methylpentanoyl}pyrrolidine-2-carbonyl)pyrrolidine-2-carboxylic acid
• Synonyms: Bradykinin Potentiating Factor; SQ 20881; pyroGlu-Trp-Pro-Arg-Pro-Gln-Ile-Pro-Pro; ANGIOTENSIN-CONVERTING ENZYME INHIBITOR

Database IDs

• CAS Number: 35115-60-7
• PubChem SID: 162102908
• PubChem CID: 37056

CALCULATED PROPERTIES

• Acid pKa: 3.3789575
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -4.721985
• LogD (pH = 7.4): -4.7193704
• Log P: -4.7193804
• Molar Refractivity: 292.5639 cm^3
• Polarizability: 110.612175 Å^3
• Polar Surface Area: 384.82 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

REFERENCES

• Greene, L.J., et al., Adv. Exp. Med. Biol., 8: 81, (1970).
• Ondetti, M.A., et al., Biochemistry, 10: 4033, (1971).
• Cheung, D.W. and Cushman, D.W.; Biochim. Biophys. Acta, 293: 451, (1973).
• Martin, L.C., et al.Biochem. J., 184: 713, (1979).
• Malborough, D.I., et al., Arch. Biochem. Biophys., 210: 43, (1981).