2-(2-{2-[2-(2-{2-[(1-{1-[2-(2-amino-5-carbamimidamidopentanamido)-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl}-4-hydroxypyrrolidin-2-yl)formamido]acetamido}-3-phenylpropanamido)-3-hydroxypropanamido]-3-phenylpropanamido}-3-phenylpropanamido)-5-carbamimidamidopentanoic acid

• ChemBase ID: 103765
• Molecular Formular: C60H87N19O13
• Molecular Mass: 1282.45228
• Monoisotopic Mass: 1281.67307394
• SMILES: NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)N1CC(O)CC1C(=O)NCC(=O)NC(Cc1ccccc1)C(=O)NC(CO)C(=O)NC(Cc1ccccc1)C(=O)NC(Cc1ccccc1)C(=O)NC(CCCNC(=N)N)C(=O)O
• Canonical SMILES: OCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)CCCNC(=N)N)Cc1ccccc1)Cc1ccccc1)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C1CC(CN1C(=O)C1CCCN1C(=O)C(NC(=O)C(CCCNC(=N)N)N)CCCNC(=N)N)O
• InChI: InChI=1S/C60H87N19O13/c61-39(20-10-24-68-58(62)63)49(83)73-40(21-11-25-69-59(64)65)55(89)78-27-13-23-46(78)56(90)79-33-38(81)31-47(79)54(88)71-32-48(82)72-42(28-35-14-4-1-5-15-35)50(84)77-45(34-80)53(87)76-44(30-37-18-8-3-9-19-37)52(86)75-43(29-36-16-6-2-7-17-36)51(85)74-41(57(91)92)22-12-26-70-60(66)67/h1-9,14-19,38-47,80-81H,10-13,20-34,61H2,(H,71,88)(H,72,82)(H,73,83)(H,74,85)(H,75,86)(H,76,87)(H,77,84)(H,91,92)(H4,62,63,68)(H4,64,65,69)(H4,66,67,70)
• InChIKey: RBIXVHPHNGXTCI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-{2-[2-(2-{2-[(1-{1-[2-(2-amino-5-carbamimidamidopentanamido)-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl}-4-hydroxypyrrolidin-2-yl)formamido]acetamido}-3-phenylpropanamido)-3-hydroxypropanamido]-3-phenylpropanamido}-3-phenylpropanamido)-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: 2-(2-{2-[2-(2-{2-[(1-{1-[2-(2-amino-5-carbamimidamidopentanamido)-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl}-4-hydroxypyrrolidin-2-yl)formamido]acetamido}-3-phenylpropanamido)-3-hydroxypropanamido]-3-phenylpropanamido}-3-phenylpropanamido)-5-carbamimidamidopentanoic acid
• Synonyms: D-Arg-Arg-Pro-Hyp-Gly-Phe-Ser-D-Phe-Phe-Arg; [D-Arg^0,Hyp^3,D-Phe^7]-BRADYKININ

Database IDs

• CAS Number: 109333-26-8
• PubChem SID: 162102935
• PubChem CID: 44134584

CALCULATED PROPERTIES

• Acid pKa: 3.4846163
• H Acceptors: 23
• H Donor: 20
• LogD (pH = 5.5): -14.045126
• LogD (pH = 7.4): -12.358167
• Log P: -7.4583287
• Molar Refractivity: 364.0542 cm^3
• Polarizability: 128.85284 Å^3
• Polar Surface Area: 533.8 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

REFERENCES

• Vavrek, R.J. and Stewart, J.M., Peptides, 6: 161, (1985);
• Stewart, J.M. and Vavrek, R.J., Proceedings of the 34th Colloquium Protides of the Biological Fluids