Showing metabocard for N-(o)-Hydroxyarginine (BMDB0004224)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:08:35 UTC
Update Date2020-05-21 16:26:55 UTC
BMDB IDBMDB0004224
Secondary Accession Numbers
  • BMDB0095935
  • BMDB04224
  • BMDB95935
Metabolite Identification
Common NameN-(o)-Hydroxyarginine
DescriptionN(omega)-Hydroxyarginine, also known as N(ω)-hydroxy-L-arginine or 6-NOHA, belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N(omega)-Hydroxyarginine is a very strong basic compound (based on its pKa). N(omega)-Hydroxyarginine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-OMEGA-hydroxy-L-arginineChEBI
N(Omega)-hydroxy-L-arginineKegg
N(Ω)-hydroxy-L-arginineHMDB
N(Ω)-hydroxyarginineHMDB
6-NOHAHMDB
N(g)-Hydroxy-L-arginineHMDB
N5-[(Hydroxyamino)iminomethyl]-L-ornithineHMDB
NG-Hydroxy-L-arginineHMDB
Nω-hydroxy-L-arginineHMDB
N(Omega)-hydroxyarginineMeSH
Chemical FormulaC6H14N4O3
Average Molecular Weight190.2004
Monoisotopic Molecular Weight190.106590334
IUPAC Name(2S)-2-amino-5-[(Z)-N''-hydroxycarbamimidamido]pentanoic acid
Traditional Name(2S)-2-amino-5-[(Z)-N''-hydroxycarbamimidamido]pentanoic acid
CAS Registry Number53054-07-2
SMILES
N[C@@H](CCCNC(=N)NO)C(O)=O
InChI Identifier
InChI=1S/C6H14N4O3/c7-4(5(11)12)2-1-3-9-6(8)10-13/h4,13H,1-3,7H2,(H,11,12)(H3,8,9,10)/t4-/m0/s1
InChI KeyFQWRAVYMZULPNK-BYPYZUCNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentArginine and derivatives
Alternative Parents
Substituents
  • Arginine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty acid
  • N-hydroxyguanidine
  • Guanidine
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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-3.6ALOGPS
logP-3.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.2ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area133.96 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity45.27 m³·mol⁻¹ChemAxon
Polarizability18.89 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9300000000-c0d34ab8e133be65558aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-1900000000-b786caa9f1955646a132View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ba-7900000000-504227bb53f351f75953View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-9000000000-8a2dba3a89dbf383615cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-2900000000-a0e075cbf656b2172f59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-6900000000-7f4da6440196f7107a96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9000000000-fde384449989f2053abbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r6-2900000000-499ec74e9d082befa16aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-d12c71ccee9673ac7328View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-10f3b1c2202ce7bb508eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-2900000000-03238bb7652c1d3f071dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9400000000-929ccd53c2ccb65baf55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-105f0dacd0348edebb58View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004224
DrugBank IDDB03144
Phenol Explorer Compound IDNot Available
FooDB IDFDB031063
KNApSAcK IDNot Available
Chemspider ID110427
KEGG Compound IDC05933
BioCyc IDNot Available
BiGG ID46955
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound43088
PDB IDNot Available
ChEBI ID43088
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Nitric oxide synthase, endothelial
General function:
Inorganic ion transport and metabolism
Specific function:
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.
Gene Name:
NOS3
Uniprot ID:
P29473
Molecular weight:
133287.0
Reactions
2 L-Arginine + 3 NADPH + 4 Oxygen →2 N-(o)-Hydroxyarginine +2 Nitric oxide +3 NADP +4 Waterdetails