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

• ChemBase ID: 133835
• Molecular Formular: C57H89N19O13
• Molecular Mass: 1248.43606
• Monoisotopic Mass: 1247.688724
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H]1C[C@H](CN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](CCCNC(=N)N)N)O
• Canonical SMILES: OC[C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)CC(C)C)Cc1ccccc1)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H]1C[C@H](CN1C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](CCCNC(=N)N)N)CCCNC(=N)N)O
• InChI: InChI=1S/C57H89N19O13/c1-32(2)25-39(47(81)71-38(54(88)89)19-11-23-67-57(63)64)72-49(83)41(27-34-15-7-4-8-16-34)73-50(84)42(31-77)74-48(82)40(26-33-13-5-3-6-14-33)69-45(79)29-68-51(85)44-28-35(78)30-76(44)53(87)43-20-12-24-75(43)52(86)37(18-10-22-66-56(61)62)70-46(80)36(58)17-9-21-65-55(59)60/h3-8,13-16,32,35-44,77-78H,9-12,17-31,58H2,1-2H3,(H,68,85)(H,69,79)(H,70,80)(H,71,81)(H,72,83)(H,73,84)(H,74,82)(H,88,89)(H4,59,60,65)(H4,61,62,66)(H4,63,64,67)/t35-,36-,37+,38+,39+,40+,41-,42+,43+,44+/m1/s1
• InChIKey: GGYJNSXTTQXAET-MZZKDSRGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-[(2R)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanamido]-3-phenylpropanamido]-4-methylpentanamido]-5-carbamimidamidopentanoic acid
• Synonyms: D-Arg-[Hyp3, D-Phe7, Leu8]-Bradykinin

Database IDs

• CAS Number: 135701-67-6
• MDL Number: MFCD00236889
• PubChem SID: 162228112
• PubChem CID: 5311060

CALCULATED PROPERTIES

• Acid pKa: 3.5867338
• H Acceptors: 23
• H Donor: 20
• LogD (pH = 5.5): -14.448254
• LogD (pH = 7.4): -12.760385
• Log P: -7.8602495
• Molar Refractivity: 353.1088 cm^3
• Polarizability: 124.82673 Å^3
• Polar Surface Area: 533.8 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - B4916

Amino Acid Sequence
D-Arg-Arg-Pro-Hyp-Gly-Phe-Ser-D-Phe-Leu-Arg
Biochem/physiol Actions
Short-acting competitive antagonist that discriminates between B2a and B2b bradykinin receptors; weak B1 bradykinin receptor antagonist.