Human Metabolome Database Version 3.5

Showing metabocard for Bradykinin (HMDB04246)

Record Information
Version 3.5
Creation Date 2006-08-13 09:11:32 -0600
Update Date 2013-05-29 13:40:05 -0600
HMDB ID HMDB04246
Secondary Accession Numbers None
Metabolite Identification
Common Name Bradykinin
Description Bradykinin is a vasoactive kinin that is liberated from its substrate kininogen by the action of kallikrein, and is known to be involved in a wide range of biologic processes. It may play an important role in blood pressure regulation and the maintenance of normal blood flow. Moreover, in various pathologic states of the cardiovascular system, it appears to provide protective actions against ischemic injury, ventricular hypertrophy, congestive heart failure, and thrombosis. Bradykinin is a potent vasodilator that acts through endothelial B2 kinin receptors to stimulate the release of nitric oxide and endothelium-derived hyperpolarizing factor. Bradykinin deficiency states may play a role in some forms of hypertension, and a relative deficiency in bradykinin may be a contributing factor to worsening heart failure. Experimental studies revealed that mice lacking the B2 receptor gene were more likely to develop hypertension, cardiac hypertrophy, and myocardial damage. Kinins exert several biologic actions. They are involved in nociception, inflammation, capillary permeability, reactive hyperemia, and stimulation of cellular glucose uptake. Bradykinin is a polypeptide that circulates in the plasma in very low concentrations in comparison with the amount of bradykinin found in various body tissues. Kininogens ([alpha] 2 globulins) are synthesized in the liver and circulate at high concentrations in the plasma. There are two kininogenases that convert kininogens into bradykinin: plasma kallikrein, also known as Fletcher factor, and glandular kallikrein, also known as tissue kallikrein. (PMID: 11975815 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Callidin I
  2. Kallidin 9
  3. Kallidin I
  4. L-Arginyl-L-prolyl-L-prolylglycyl-L-phenylalanyl-L-seryl-L-prolyl-L-phenylalanyl-L-Arginine
  5. L-Bradykinin
Chemical Formula C50H73N15O11
Average Molecular Weight 1060.2085
Monoisotopic Molecular Weight 1059.561398253
IUPAC Name (2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S)-1-{[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl]carbonyl}pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-5-carbamimidamidopentanoic acid
Traditional IUPAC Name bradykinin
CAS Registry Number 58-82-2
SMILES N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O
InChI Identifier InChI=1S/C50H73N15O11/c51-32(16-7-21-56-49(52)53)45(72)65-25-11-20-39(65)47(74)64-24-9-18-37(64)43(70)58-28-40(67)59-34(26-30-12-3-1-4-13-30)41(68)62-36(29-66)46(73)63-23-10-19-38(63)44(71)61-35(27-31-14-5-2-6-15-31)42(69)60-33(48(75)76)17-8-22-57-50(54)55/h1-6,12-15,32-39,66H,7-11,16-29,51H2,(H,58,70)(H,59,67)(H,60,69)(H,61,71)(H,62,68)(H,75,76)(H4,52,53,56)(H4,54,55,57)/t32-,33-,34-,35-,36-,37-,38-,39-/m0/s1
InChI Key QXZGBUJJYSLZLT-FDISYFBBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Bradykinin [KO:K03898](KEGG)
  • oligopeptide(ChEBI)
Substituents
  • Alpha Amino Acid Or Derivative
  • Amphetamine Or Derivative
  • Carboxamide Group
  • Carboxylic Acid
  • Guanidine
  • N Acyl Alpha Amino Acid
  • N Substituted Alpha Amino Acid
  • Primary Alcohol
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrolidine
  • Secondary Carboxylic Acid Amide
  • Tertiary Carboxylic Acid Amide
Direct Parent Peptides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.057 g/L ALOGPS
LogP -2.14 ALOGPS
LogP -6.4 ChemAxon
LogS -4.27 ALOGPS
pKa (strongest acidic) 3.39 ChemAxon
pKa (strongest basic) 12.44 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 14 ChemAxon
Polar Surface Area 413.78 A2 ChemAxon
Rotatable Bond Count 27 ChemAxon
Refractivity 295.08 ChemAxon
Polarizability 109.98 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Prostate Tissue
Tissue Location
  • Prostate
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Prostate Tissue Detected and Quantified 0.5 (0.0-1.0) umol/g tissue Adult (>18 years old) Both Comment Prostate cancer
Associated Disorders and Diseases
Disease References
Prostate cancer
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB023350
      KNApSAcK ID Not Available
      Chemspider ID 388341 Link_out
      KEGG Compound ID C00306 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB04246 Link_out
      Metagene Link HMDB04246 Link_out
      METLIN ID Not Available
      PubChem Compound 439201 Link_out
      PDB ID Not Available
      ChEBI ID 3165 Link_out
      References
      Synthesis Reference Postnov, V. N. Some aspects of the synthesis of organic functional groups on inorganic matrices. Napravl. Sintez Tverd. Veshchestv (1987), (2), 109-20.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
      2. Palkhiwala SA, Frishman WH, Warshafsky S: Bradykinin for the treatment of cardiovascular disease. Heart Dis. 2001 Sep-Oct;3(5):333-9. Pubmed: 11975815 Link_out

      Enzymes
      Name: Angiotensin-converting enzyme
      Reactions: Not Available
      Gene Name: ACE
      Uniprot ID: P12821 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Coagulation factor XII
      Reactions: Not Available
      Gene Name: F12
      Uniprot ID: P00748 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Kininogen-1
      Reactions: Not Available
      Gene Name: KNG1
      Uniprot ID: P01042 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Plasma kallikrein
      Reactions: Not Available
      Gene Name: KLKB1
      Uniprot ID: P03952 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Type-1 angiotensin II receptor
      Reactions: Not Available
      Gene Name: AGTR1
      Uniprot ID: P30556 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: B2 bradykinin receptor
      Reactions: Not Available
      Gene Name: BDKRB2
      Uniprot ID: P30411 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Protein MRVI1
      Reactions: Not Available
      Gene Name: MRVI1
      Uniprot ID: Q9Y6F6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Relaxin-3 receptor 2
      Reactions: Not Available
      Gene Name: RXFP4
      Uniprot ID: Q8TDU9 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Endoplasmic reticulum aminopeptidase 1
      Reactions: Not Available
      Gene Name: ERAP1
      Uniprot ID: Q9NZ08 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Neurolysin, mitochondrial
      Reactions: Not Available
      Gene Name: NLN
      Uniprot ID: Q9BYT8 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: B1 bradykinin receptor
      Reactions: Not Available
      Gene Name: BDKRB1
      Uniprot ID: P46663 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Bradykinin B1 receptor
      Reactions: Not Available
      Gene Name: Not Available
      Uniprot ID: Q71U72 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: B2 bradykinin receptor basal promoter, allele BP-58-T
      Reactions: Not Available
      Gene Name: Not Available
      Uniprot ID: Q13833 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: B2 bradykinin receptor basal promoter, allele BP-58-C
      Reactions: Not Available
      Gene Name: Not Available
      Uniprot ID: Q13832 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Putative uncharacterized protein DKFZp686O088
      Reactions: Not Available
      Gene Name: DKFZp686O088
      Uniprot ID: Q68DM8 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA