You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-08-13 15:11:32 UTC
Update Date2013-05-29 19:40:05 UTC
HMDB IDHMDB04246
Secondary Accession NumbersNone
Metabolite Identification
Common NameBradykinin
DescriptionBradykinin 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 ).
Structure
Thumb
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 FormulaC50H73N15O11
Average Molecular Weight1060.2085
Monoisotopic Molecular Weight1059.561398253
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 Namebradykinin
CAS Registry Number58-82-2
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 KeyQXZGBUJJYSLZLT-FDISYFBBSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassPeptides
Sub ClassN/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 ParentPeptides
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.057 g/LALOGPS
logP-2.1ALOGPS
logP-6.4ChemAxon
logS-4.3ALOGPS
pKa (strongest acidic)3.39ChemAxon
pKa (strongest basic)12.44ChemAxon
physiological charge2ChemAxon
hydrogen acceptor count18ChemAxon
hydrogen donor count14ChemAxon
polar surface area413.78ChemAxon
rotatable bond count27ChemAxon
refractivity295.08ChemAxon
polarizability109.98ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Prostate Tissue
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Prostate TissueDetected and Quantified0.5 (0.0-1.0) umol/g tissueAdult (>18 years old)Both
Prostate cancer
details
Associated Disorders and Diseases
Disease References
Prostate cancer
  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
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023350
KNApSAcK IDNot Available
Chemspider ID388341
KEGG Compound IDC00306
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04246
Metagene LinkHMDB04246
METLIN IDNot Available
PubChem Compound439201
PDB IDNot Available
ChEBI ID3165
References
Synthesis ReferencePostnov, 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
  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

Enzymes

General function:
Involved in metallopeptidase activity
Specific function:
Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:
ACE
Uniprot ID:
P12821
Molecular weight:
149713.7
General function:
Involved in serine-type endopeptidase activity
Specific function:
Factor XII is a serum glycoprotein that participates in the initiation of blood coagulation, fibrinolysis, and the generation of bradykinin and angiotensin. Prekallikrein is cleaved by factor XII to form kallikrein, which then cleaves factor XII first to alpha-factor XIIa and then trypsin cleaves it to beta- factor XIIa. Alpha-factor XIIa activates factor XI to factor XIa
Gene Name:
F12
Uniprot ID:
P00748
Molecular weight:
67817.6
General function:
Involved in cysteine-type endopeptidase inhibitor activity
Specific function:
(1) Kininogens are inhibitors of thiol proteases; (2) HMW-kininogen plays an important role in blood coagulation by helping to position optimally prekallikrein and factor XI next to factor XII; (3) HMW-kininogen inhibits the thrombin- and plasmin- induced aggregation of thrombocytes; (4) the active peptide bradykinin that is released from HMW-kininogen shows a variety of physiological effects:(4A) influence in smooth muscle contraction, (4B) induction of hypotension, (4C) natriuresis and diuresis, (4D) decrease in blood glucose level, (4E) it is a mediator of inflammation and causes (4E1) increase in vascular permeability, (4E2) stimulation of nociceptors (4E3) release of other mediators of inflammation (e.g. prostaglandins), (4F) it has a cardioprotective effect (directly via bradykinin action, indirectly via endothelium-derived relaxing factor action); (5) LMW-kininogen inhibits the aggregation of thrombocytes; (6) LMW- kininogen is in contrast to HMW-kininogen not involved in blood clotting
Gene Name:
KNG1
Uniprot ID:
P01042
Molecular weight:
71957.0
General function:
Involved in serine-type endopeptidase activity
Specific function:
The enzyme cleaves Lys-Arg and Arg-Ser bonds. It activates, in a reciprocal reaction, factor XII after its binding to a negatively charged surface. It also releases bradykinin from HMW kininogen and may also play a role in the renin-angiotensin system by converting prorenin into renin
Gene Name:
KLKB1
Uniprot ID:
P03952
Molecular weight:
71369.2
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
AGTR1
Uniprot ID:
P30556
Molecular weight:
41060.5
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for bradykinin. It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
BDKRB2
Uniprot ID:
P30411
Molecular weight:
44460.2
General function:
Not Available
Specific function:
Play a role as NO/PRKG1-dependent regulator of IP3- induced calcium release; its phosphorylation by PRKG1 inhibits bradykinin and IP3-induced calcium release from intracellular stores. Recruits PRKG1 to the endoplasmic reticulum and may mediate the assembly of PRKG1 and ITPR1 in a macrocomplex. Involved in PRKG1 signaling cascade leading to inhibition of platelet activation and aggregation. Mediates also NO-dependent inhibition of calcium signaling in gastrointestinal smooth muscle contributing to NO-dependent relaxation
Gene Name:
MRVI1
Uniprot ID:
Q9Y6F6
Molecular weight:
96144.2
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
High affinity receptor for INSL5. Also acts as receptor for RLN3/relaxin-3, as well as bradykinin and kallidin. Binding of the ligand inhibit cAMP accumulation
Gene Name:
RXFP4
Uniprot ID:
Q8TDU9
Molecular weight:
41141.0
General function:
Involved in proteolysis
Specific function:
Aminopeptidase that plays a central role in peptide trimming, a step required for the generation of most HLA class I- binding peptides. Peptide trimming is essential to customize longer precursor peptides to fit them to the correct length required for presentation on MHC class I molecules. Strongly prefers substrates 9-16 residues long. Rapidly degrades 13-mer to a 9-mer and then stops. Preferentially hydrolyzes the residue Leu and peptides with a hydrophobic C-terminus, while it has weak activity toward peptides with charged C-terminus. May play a role in the inactivation of peptide hormones. May be involved in the regulation of blood pressure through the inactivation of angiotensin II and/or the generation of bradykinin in the kidney
Gene Name:
ERAP1
Uniprot ID:
Q9NZ08
Molecular weight:
107233.9
General function:
Involved in metalloendopeptidase activity
Specific function:
Hydrolyzes oligopeptides such as neurotensin, bradykinin and dynorphin A
Gene Name:
NLN
Uniprot ID:
Q9BYT8
Molecular weight:
80651.1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is a receptor for bradykinin. Could be a factor in chronic pain and inflammation
Gene Name:
BDKRB1
Uniprot ID:
P46663
Molecular weight:
40494.3
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q71U72
Molecular weight:
2216.5
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q13833
Molecular weight:
4152.5
General function:
Involved in receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q13832
Molecular weight:
4140.4
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Not Available
Gene Name:
DKFZp686O088
Uniprot ID:
Q68DM8
Molecular weight:
41493.8