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

• ChemBase ID: 132726
• Molecular Formular: C50H73N15O12
• Molecular Mass: 1076.20792
• Monoisotopic Mass: 1075.55631285
• SMILES: c1ccc(cc1)C[C@@H](C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)NC(=O)CNC(=O)[C@@H]1C[C@H](CN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)N)O
• Canonical SMILES: OC[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)Cc1ccccc1)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)N)O
• InChI: InChI=1S/C50H73N15O12/c51-32(15-7-19-56-49(52)53)45(73)64-22-10-18-38(64)47(75)65-27-31(67)25-39(65)43(71)58-26-40(68)59-34(23-29-11-3-1-4-12-29)41(69)62-36(28-66)46(74)63-21-9-17-37(63)44(72)61-35(24-30-13-5-2-6-14-30)42(70)60-33(48(76)77)16-8-20-57-50(54)55/h1-6,11-14,31-39,66-67H,7-10,15-28,51H2,(H,58,71)(H,59,68)(H,60,70)(H,61,72)(H,62,69)(H,76,77)(H4,52,53,56)(H4,54,55,57)/t31-,32+,33+,34+,35+,36+,37+,38+,39+/m1/s1
• InChIKey: JXRLHZCEMXTCBN-DIBGMJQNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-5-carbamimidamidopentanoic acid
• Synonyms: [Hyp3]-Bradykinin

Database IDs

• CAS Number: 37642-65-2
• MDL Number: MFCD00076259
• PubChem SID: 162227003
• PubChem CID: 169947

CALCULATED PROPERTIES

• Acid pKa: -1.0496649
• H Acceptors: 19
• H Donor: 15
• LogD (pH = 5.5): -11.584818
• LogD (pH = 7.4): -9.898229
• Log P: -7.852803
• Molar Refractivity: 296.4011 cm^3
• Polarizability: 106.966125 Å^3
• Polar Surface Area: 434.01 Å^2
• Rotatable Bonds: 27
• 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

Pharmacology Properties

• Gene Information: rat ... Tac1(24806)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - B7775

Amino Acid Sequence
Arg-Pro-Hyp-Gly-Phe-Ser-Pro-Phe-Arg
Biochem/physiol Actions
B2 bradykinin receptor agonist.