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
BiofluidStatusValueAgeSexConditionReference
Prostate TissueDetected and Quantified0.5 (0.0-1.0) umol/g tissueAdult (>18 years old)BothCommentProstate 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
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)Not Available
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

Gene Name:
ACE
Uniprot ID:
P12821
Gene Name:
F12
Uniprot ID:
P00748
Gene Name:
KNG1
Uniprot ID:
P01042
Gene Name:
KLKB1
Uniprot ID:
P03952
Gene Name:
AGTR1
Uniprot ID:
P30556
Gene Name:
BDKRB2
Uniprot ID:
P30411
Gene Name:
MRVI1
Uniprot ID:
Q9Y6F6
Gene Name:
RXFP4
Uniprot ID:
Q8TDU9
Gene Name:
NLN
Uniprot ID:
Q9BYT8
Gene Name:
BDKRB1
Uniprot ID:
P46663
Gene Name:
Not Available
Uniprot ID:
Q71U72
Gene Name:
DKFZp686O088
Uniprot ID:
Q68DM8