(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid

• ChemBase ID: 133143
• Molecular Formular: C50H73N13O11
• Molecular Mass: 1032.19512
• Monoisotopic Mass: 1031.55525022
• 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)O)NC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)O)Cc1ccccc1)CO)Cc1ccccc1)CCCNC(=N)N)N
• InChI: InChI=1S/C50H73N13O11/c51-22-8-7-17-33(52)42(66)58-34(18-9-23-55-50(53)54)46(70)63-26-12-21-40(63)48(72)62-25-10-19-38(62)44(68)56-29-41(65)57-35(27-31-13-3-1-4-14-31)43(67)60-37(30-64)47(71)61-24-11-20-39(61)45(69)59-36(49(73)74)28-32-15-5-2-6-16-32/h1-6,13-16,33-40,64H,7-12,17-30,51-52H2,(H,56,68)(H,57,65)(H,58,66)(H,59,69)(H,60,67)(H,73,74)(H4,53,54,55)/t33-,34-,35-,36-,37-,38-,39-,40-/m0/s1
• InChIKey: AILVBOHFGXNHCC-TZPCGENMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid
• Synonyms: des-Arg10-Kallidin; [Lys-des-Arg9]-Bradykinin

Database IDs

• CAS Number: 71800-36-7
• MDL Number: MFCD00079826
• PubChem SID: 162227420
• PubChem CID: 122227

CALCULATED PROPERTIES

• Acid pKa: 3.4127889
• H Acceptors: 16
• H Donor: 12
• LogD (pH = 5.5): -10.543952
• LogD (pH = 7.4): -8.433671
• Log P: -5.2253256
• Molar Refractivity: 278.9696 cm^3
• Polarizability: 104.77026 Å^3
• Polar Surface Area: 377.9 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: human ... KNG1 (includes EG:3827)(3827)

Product Information

• Purity: ≥95% (HPLC)

DETAILS

Sigma Aldrich - B1542

Amino Acid Sequence
Lys-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe
Biochem/physiol Actions
[Des-Arg10]-kallidin is a bradykinin B1 receptor agonist. It strongly upregulates the B1 receptor and is blocked by a specific protein kinase C inhibitor. The upregulation is correlated with the induction of transcription factor nuclear factor κB (NF-κB).