5-carbamimidamido-2-{2-[(1-{3-hydroxy-2-[3-phenyl-2-(2-{[1-(pyrrolidine-2-carbonyl)pyrrolidin-2-yl]formamido}acetamido)propanamido]propanoyl}pyrrolidin-2-yl)formamido]-3-phenylpropanamido}pentanoic acid

• ChemBase ID: 103768
• Molecular Formular: C44H61N11O10
• Molecular Mass: 904.02284
• Monoisotopic Mass: 903.46028721
• SMILES: NC(=N)NCCCC(NC(=O)C(Cc1ccccc1)NC(=O)C1CCCN1C(=O)C(CO)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C1CCCN1C(=O)C1CCCN1)C(=O)O
• Canonical SMILES: OCC(C(=O)N1CCCC1C(=O)NC(C(=O)NC(C(=O)O)CCCNC(=N)N)Cc1ccccc1)NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C1CCCN1C(=O)C1CCCN1
• InChI: InChI=1S/C44H61N11O10/c45-44(46)48-20-8-16-30(43(64)65)51-38(59)32(24-28-13-5-2-6-14-28)52-40(61)35-18-10-22-55(35)42(63)33(26-56)53-37(58)31(23-27-11-3-1-4-12-27)50-36(57)25-49-39(60)34-17-9-21-54(34)41(62)29-15-7-19-47-29/h1-6,11-14,29-35,47,56H,7-10,15-26H2,(H,49,60)(H,50,57)(H,51,59)(H,52,61)(H,53,58)(H,64,65)(H4,45,46,48)
• InChIKey: ZZHVXIPXTCBVBE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-carbamimidamido-2-{2-[(1-{3-hydroxy-2-[3-phenyl-2-(2-{[1-(pyrrolidine-2-carbonyl)pyrrolidin-2-yl]formamido}acetamido)propanamido]propanoyl}pyrrolidin-2-yl)formamido]-3-phenylpropanamido}pentanoic acid
• IUPAC Traditional name: 5-carbamimidamido-2-{2-[(1-{3-hydroxy-2-[3-phenyl-2-(2-{[1-(pyrrolidine-2-carbonyl)pyrrolidin-2-yl]formamido}acetamido)propanamido]propanoyl}pyrrolidin-2-yl)formamido]-3-phenylpropanamido}pentanoic acid
• Synonyms: Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg; [Des-Arg1]-BRADYKININ; BRADYKININ, FRAGMENT 2-9; Bradykinin Fragment 2-9

Database IDs

• CAS Number: 16875-11-9
• MDL Number: MFCD00076264
• PubChem SID: 162103278; 24891619
• PubChem CID: 4140859

CALCULATED PROPERTIES

• Acid pKa: 3.4041288
• H Acceptors: 14
• H Donor: 11
• LogD (pH = 5.5): -7.343026
• LogD (pH = 7.4): -6.2536693
• Log P: -4.3020706
• Molar Refractivity: 244.2379 cm^3
• Polarizability: 90.98154 Å^3
• Polar Surface Area: 317.58 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... KNG1 (includes EG:3827)(3827)

Product Information

• Purity: ≥97% (HPLC); 98%

DETAILS

MP Biomedicals - 02159896

Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg
Purity: 98%

Sigma Aldrich - B1901

Amino Acid Sequence
Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg
Biochem/physiol Actions
The des-arginine-1 bradykinin (BK) peptide (2-9) has no detectable contractile activity, inhibits ACE (angiotensin converting enzyme) and potentiates BK.

REFERENCES

• Nicolaides, E.D., et al., J. Med. Chem., 6: 739, (1963).