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Showing Compound Bradykinin hydroxyproline (FDB028409)

Record Information
Version1.0
Creation date2011-09-21 01:39:20 UTC
Update date2017-03-11 23:00:43 UTC
Primary IDFDB028409
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBradykinin hydroxyproline
DescriptionBradykinin hydroxyproline is a bradykinin analog, where the third amino acid, proline, is replaced with hydroxyproline. 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) [HMDB]
CAS Number37642-65-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-(L-4-Hydroxyproline)bradykininChEBI
3-Hydroxy-pro-bradykininChEBI
Arg-3-hyp-bradykininChEBI
Arg-pro-hyp-gly-phe-ser-pro-phe-argChEBI
Bradykinin hydroxy-pro(3)ChEBI
Bradykinin, hydroxy-pro(3)ChEBI
Hydroxy-pro(3)-bradykininChEBI
Hydroxyproline(3)-bradykininChEBI
L-Arg-L-pro-L-hyp-gly-L-phe-L-ser-L-pro-L-phe-L-argChEBI
Arg-hyp(3)-bradykininHMDB
Bradykinin hydroxyprolineChEBI
3-Hydroxyproline-bradykininHMDB
3-L-(trans-4-Hydroxyproline)-bradykininHMDB
L-Arginyl-L-prolyl-(4R)-4-hydroxy-L-prolylglycyl-L-phenylalanyl-L-seryl-L-prolyl-L-phenylalanyl-L-arginineHMDB
arg-hyp(3)-Bradykininhmdb
hydroxy-pro(3)-Bradykininhmdb
hydroxyproline(3)-Bradykininhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.087 g/LALOGPS
logP-2.6ALOGPS
logP-7.9ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)-1ChemAxon
pKa (Strongest Basic)12.34ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area434.01 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity296.4 m³·mol⁻¹ChemAxon
Polarizability111.32 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC50H73N15O12
IUPAC name(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-(2-{[(2S,4R)-1-[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]-4-hydroxypyrrolidin-2-yl]formamido}acetamido)-3-phenylpropanamido]-3-hydroxypropanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanamido]-5-carbamimidamidopentanoic acid
InChI IdentifierInChI=1S/C50H73N15O12/c51-32(15-7-19-56-49(52)53)45(73)64-22-10-18-38(64)47(75)65-27-31(67)25-39(65)43(71)58-26-40(68)59-34(23-29-11-3-1-4-12-29)41(69)62-36(28-66)46(74)63-21-9-17-37(63)44(72)61-35(24-30-13-5-2-6-14-30)42(70)60-33(48(76)77)16-8-20-57-50(54)55/h1-6,11-14,31-39,66-67H,7-10,15-28,51H2,(H,58,71)(H,59,68)(H,60,70)(H,61,72)(H,62,69)(H,76,77)(H4,52,53,56)(H4,54,55,57)/t31-,32+,33+,34+,35+,36+,37+,38+,39+/m1/s1
InChI KeyJXRLHZCEMXTCBN-DIBGMJQNSA-N
Isomeric SMILESN[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N1C[C@H](O)C[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](CCCN=C(N)N)C(O)=O
Average Molecular Weight1076.2079
Monoisotopic Molecular Weight1075.556312875
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
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-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 amide
  • Fatty acyl
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Guanidine
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Azacycle
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Amine
  • Primary alcohol
  • Organopnictogen compound
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6s-9207000011-778bbb0a73405e35634f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-9747101012-b42bd37379fc0239fd492017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01vx-9634000000-898b1109990e39d720e42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03ei-9000000002-518cbf6703868bad51a52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nmi-9100000002-705fbadd909ee3cd89a52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pi3-9101100211-d0a28afc2dea8e0ade642017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-9000010000-3768382c99716ff616a22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r0-9000110040-80ee3c9f32cad674a0892021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00du-9670230000-91b46fbe51940280f3352021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-c21b1d88b052e58559e62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0r70-9000000022-0be97a67b8c9ae9813182021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9003760021-faaf717115ac5976cb442021-09-25View Spectrum
NMRNot Available
ChemSpider ID148618
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID169947
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11728
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference