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Human Metabolome Database Version 3.5

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Showing metabocard for Bradykinin (HMDB04246)

Record Information
Version 3.5
Creation Date 2006-08-13 09:11:32 -0600
Update Date 2013-02-08 17:13:08 -0700
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 | 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 Comments
Prostate Tissue Detected and Quantified
Article_icon
0.5 (0.0-1.0) umol/g tissue Adult (>18 years old) Both Prostate cancer Estimated concentration
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
    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
    Enzymes
    Name: Angiotensin-converting enzyme
    Reactions:
    • Release of a C-terminal dipeptide, oligopeptide!Xaa-Yaa, when Xaa is not Pro, and Yaa is neither Asp nor Glu. Thus, conversion of angiotensin I to angiotensin II, with increase in vasoconstrictor activity, but no action on angiotensin II COFACTOR Zinc [CPD:C00038] INHIBITOR (S)-N-[3-(3,4-Methylenedioxyphenyl)-2-(mercaptomethyl)-1-oxoprolyl]g lycine [CPD:C01313]
    • (S)-N-[3-(3,4-Methylenedioxyphenyl)-2-(mercaptomethyl)-1-oxoprolyl]- (S)-alanine [CPD:C01314]
    • (S)-N-[3-(3,4-Methylenedioxyphenyl)-2-(acetylthio)methyl-1-oxoprolyl ]glycine benzyl ester [CPD:C01315]
    • (S)-N-[3-(3,4-Methylenedioxyphenyl)-2-(acetylthio)methyl-1-oxoprolyl ]-(S)-alanine benzyl ester [CPD:C01316]
    Gene Name: ACE
    Uniprot ID: P12821 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Coagulation factor XII
    Reactions:
    • Selective cleavage of Arg!Ile bonds in factor VII to form factor VIIa and factor XI to form factor XIa
    Gene Name: F12
    Uniprot ID: P00748 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Kininogen-1
    Reactions:
      Gene Name: KNG1
      Uniprot ID: P01042 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Plasma kallikrein
      Reactions:
      • Selective cleavage of some Arg! and Lys! bonds, including Lys!Arg and Arg!Ser in (human) kininogen to release bradykinin
      Gene Name: KLKB1
      Uniprot ID: P03952 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Type-1 angiotensin II receptor
      Reactions:
        Gene Name: AGTR1
        Uniprot ID: P30556 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: B2 bradykinin receptor
        Reactions:
          Gene Name: BDKRB2
          Uniprot ID: P30411 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Protein MRVI1
          Reactions:
            Gene Name: MRVI1
            Uniprot ID: Q9Y6F6 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Relaxin-3 receptor 2
            Reactions:
              Gene Name: RXFP4
              Uniprot ID: Q8TDU9 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Endoplasmic reticulum aminopeptidase 1
              Reactions:
                Gene Name: ERAP1
                Uniprot ID: Q9NZ08 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Neurolysin, mitochondrial
                Reactions:
                • Preferential cleavage in neurotensin: Pro10!Tyr COFACTOR Zinc [CPD:C00038]
                • Metal [CPD:C00050]
                Gene Name: NLN
                Uniprot ID: Q9BYT8 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: B1 bradykinin receptor
                Reactions:
                  Gene Name: BDKRB1
                  Uniprot ID: P46663 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Bradykinin B1 receptor
                  Reactions:
                    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:
                      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:
                        Gene Name: Not Available
                        Uniprot ID: Q13832 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Putative uncharacterized protein DKFZp686O088
                        Reactions:
                          Gene Name: DKFZp686O088
                          Uniprot ID: Q68DM8 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA