Showing metabocard for Bradykinin (BMDB0004246)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (6) Show 6 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:08:51 UTC
Update Date2020-05-11 20:49:31 UTC
BMDB IDBMDB0004246
Secondary Accession Numbers
  • BMDB04246
Metabolite Identification
Common NameBradykinin
DescriptionBradykinin, also known as BK or RPPGFSPFR, 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. Bradykinin is a very strong basic compound (based on its pKa). Bradykinin exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
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]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-5-carbamimidamidopentanoic acid
Traditional NameL-bradykinin
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
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
StatusExpected but not 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
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9605021310-963d37a5c0a6a8c3b581View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-4914021100-da28e55acbc5e55e7615View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9824010200-b5b2c55602c29375ed1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ard-9000000008-70e85b5126294f4866f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4m-8001001009-d8431ee82b28629bac33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9001111000-9de36ae5c0196bc1ca98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-eb21ccd98d434e431a1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000210241-b63ee10d53ba3efc65cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-022l-9780340000-45c697c4a631655e2811View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-6f7d24ea48539f7cd9fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000100016-0338af4c69622fd514d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-9003871073-646bd5ef5605a552ce67View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004246
DrugBank IDDB12126
Phenol Explorer Compound IDNot Available
FooDB IDFDB023350
KNApSAcK IDNot Available
Chemspider ID388341
KEGG Compound IDC00306
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBradykinin
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Kininogen-2
General function:
Inorganic ion transport and metabolism
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:
KNG2
Uniprot ID:
P01045
Molecular weight:
68710.0
Enzyme Details
2. Kininogen-1
General function:
Inorganic ion transport and metabolism
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:
P01044
Molecular weight:
68890.0
Enzyme Details
3. Protein MRVI1
General function:
Not Available
Specific function:
Plays 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:
Q9N1F0
Molecular weight:
98375.0
Enzyme Details
4. Plasma kallikrein
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 (By similarity).
Gene Name:
KLKB1
Uniprot ID:
Q2KJ63
Molecular weight:
70994.0
Enzyme Details
5. Bradykinin B1 receptor
General function:
Involved in bradykinin receptor activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q3SAL2
Molecular weight:
39508.0
Enzyme Details
6. Bradykinin receptor B2
General function:
Involved in bradykinin receptor activity
Specific function:
Not Available
Gene Name:
BDKRB2
Uniprot ID:
Q9N1D0
Molecular weight:
29002.0