Record Information
Version1.0
Creation date2011-09-21 00:28:30 UTC
Update date2015-07-21 06:57:39 UTC
Primary IDFDB023350
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number58-82-2
Structure
Thumb
Synonyms
SynonymSource
Arg-pro-pro-gly-phe-ser-pro-phe-argChEBI
BKChEBI
L-Arg-L-pro-L-pro-gly-L-phe-L-ser-L-pro-L-phe-L-argChEBI
L-BradykininChEBI
RPPGFSPFRChEBI
Callidin IHMDB
Kallidin 9HMDB
Kallidin IHMDB
L-Arginyl-L-prolyl-L-prolylglycyl-L-phenylalanyl-L-seryl-L-prolyl-L-phenylalanyl-L-arginineHMDB
Bradykinin acetate, (9-D-arg)-isomerHMDB
Bradykinin hydrochlorideHMDB
Bradykinin triacetateHMDB
Bradykinin, (2-D-pro-7-D-pro)-isomerHMDB
Bradykinin, (8-D-phe)-isomerHMDB
Arg pro pro gly phe ser pro phe argHMDB
Bradykinin, (1-D-arg)-isomerHMDB
Bradykinin, (2-D-pro-3-D-pro-7-D-pro)-isomerHMDB
Bradykinin, (3-D-pro-7-D-pro)-isomerHMDB
Bradykinin, (5-D-phe)-isomerHMDB
Bradykinin, (5-D-phe-8-D-phe)-isomerHMDB
Bradykinin, (6-D-ser)-isomerHMDB
Bradykinin, (7-D-pro)-isomerHMDB
Bradykinin, (9-D-arg)-isomerHMDB
Bradykinin diacetateHMDB
Bradykinin, (2-D-pro)-isomerHMDB
Bradykinin, (3-D-pro)-isomerHMDB
L-arginyl-L-prolyl-L-prolylglycyl-L-phenylalanyl-L-seryl-L-prolyl-L-phenylalanyl-L-Argininehmdb
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 Area413.78 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity295.08 m³·mol⁻¹ChemAxon
Polarizability109.98 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC50H73N15O11
IUPAC name(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S)-1-[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-5-carbamimidamidopentanoic acid
InChI IdentifierInChI=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
Isomeric SMILESN[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
Average Molecular Weight1060.2085
Monoisotopic Molecular Weight1059.561398253
Classification
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Phenylalanine or derivatives
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid or derivatives
  • Guanidine
  • Amino acid
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alcohol
  • Primary aliphatic amine
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9605021310-963d37a5c0a6a8c3b581JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-4914021100-da28e55acbc5e55e7615JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9824010200-b5b2c55602c29375ed1aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ard-9000000008-70e85b5126294f4866f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4m-8001001009-d8431ee82b28629bac33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9001111000-9de36ae5c0196bc1ca98JSpectraViewer
ChemSpider ID388341
ChEMBL IDCHEMBL406291
KEGG Compound IDC00306
Pubchem Compound ID439201
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB04246
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Neurolysin, mitochondrialNLNQ9BYT8
Coagulation factor XIIF12P00748
Kininogen-1KNG1P01042
Plasma kallikreinKLKB1P03952
Endoplasmic reticulum aminopeptidase 1ERAP1Q9NZ08
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference