5-carbamimidamido-2-(2-{2-[3-hydroxy-2-(2-{2-[(4-hydroxypyrrolidin-2-yl)formamido]acetamido}-3-phenylpropanamido)propanamido]-3-phenylpropanamido}-4-methylpentanamido)pentanoyl 1-[2-(2-amino-5-carbamimidamidopentanamido)-5-carbamimidamidopentanoyl]pyrrolidine-2-carboxylate

• ChemBase ID: 105991
• Molecular Formular: C57H89N19O13
• Molecular Mass: 1248.43606
• Monoisotopic Mass: 1247.688724
• SMILES: CC(C)CC(NC(=O)C(Cc1ccccc1)NC(=O)C(CO)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C1CC(O)CN1)C(=O)NC(CCCNC(=N)N)C(=O)OC(=O)C1CCCN1C(=O)C(CCCNC(=N)N)NC(=O)C(N)CCCNC(=N)N
• Canonical SMILES: OCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)OC(=O)C1CCCN1C(=O)C(NC(=O)C(CCCNC(=N)N)N)CCCNC(=N)N)CCCNC(=N)N)CC(C)C)Cc1ccccc1)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C1NCC(C1)O
• InChI: InChI=1S/C57H89N19O13/c1-32(2)25-40(48(82)72-38(19-11-23-67-57(63)64)53(87)89-54(88)44-20-12-24-76(44)52(86)37(18-10-22-66-56(61)62)71-46(80)36(58)17-9-21-65-55(59)60)73-50(84)42(27-34-15-7-4-8-16-34)74-51(85)43(31-77)75-49(83)41(26-33-13-5-3-6-14-33)70-45(79)30-69-47(81)39-28-35(78)29-68-39/h3-8,13-16,32,35-44,68,77-78H,9-12,17-31,58H2,1-2H3,(H,69,81)(H,70,79)(H,71,80)(H,72,82)(H,73,84)(H,74,85)(H,75,83)(H4,59,60,65)(H4,61,62,66)(H4,63,64,67)
• InChIKey: IBUPLVFJDPVVRN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-carbamimidamido-2-(2-{2-[3-hydroxy-2-(2-{2-[(4-hydroxypyrrolidin-2-yl)formamido]acetamido}-3-phenylpropanamido)propanamido]-3-phenylpropanamido}-4-methylpentanamido)pentanoyl 1-[2-(2-amino-5-carbamimidamidopentanamido)-5-carbamimidamidopentanoyl]pyrrolidine-2-carboxylate
• IUPAC Traditional name: 5-carbamimidamido-2-(2-{2-[3-hydroxy-2-(2-{2-[(4-hydroxypyrrolidin-2-yl)formamido]acetamido}-3-phenylpropanamido)propanamido]-3-phenylpropanamido}-4-methylpentanamido)pentanoyl 1-[2-(2-amino-5-carbamimidamidopentanamido)-5-carbamimidamidopentanoyl]pyrrolidine-2-carboxylate
• Synonyms: [D-Arg, Hyp^3, D-Phe^7, Leu^8]-BRADYKININ

Database IDs

• CAS Number: 135701-67-6
• PubChem SID: 162092877
• PubChem CID: 44134585

CALCULATED PROPERTIES

• H Acceptors: 23
• H Donor: 20
• LogD (pH = 5.5): -17.89004
• LogD (pH = 7.4): -14.654364
• Log P: -5.4884963
• Molar Refractivity: 352.9812 cm^3
• Polarizability: 125.44132 Å^3
• Polar Surface Area: 531.59 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 02195630

D-Arg-Arg-Pro-Hyp-Gly-Phe-Ser-D-Phe-Leu-Arg
Potent antagonist used to discriminate B-2 receptors.

REFERENCES

• Rhaleb, N.E., et al., Life Sci., 51: 125, (1992).