Nω-hydroxy-L-arginine (CHEM042340)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:59:13 UTC
Update Date2016-11-09 01:22:39 UTC
Accession NumberCHEM042340
Identification
Common NameNω-hydroxy-L-arginine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass190.200 g/mol
Monoisotopic Mass190.107 g/mol
CAS Registry NumberNot Available
IUPAC Name(2S)-2-amino-5-[(Z)-N''-hydroxycarbamimidamido]pentanoic acid
Traditional Name(2S)-2-amino-5-[(Z)-N''-hydroxycarbamimidamido]pentanoic acid
SMILESN[C@@H](CCCNC(=N)NO)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.49 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9300000000-c0d34ab8e133be65558aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0005-1900000000-b786caa9f1955646a132Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ba-7900000000-504227bb53f351f75953Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-9000000000-8a2dba3a89dbf383615cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-2900000000-a0e075cbf656b2172f59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-6900000000-7f4da6440196f7107a96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9000000000-fde384449989f2053abbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r6-2900000000-499ec74e9d082befa16aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-d12c71ccee9673ac7328Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-10f3b1c2202ce7bb508eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-2900000000-03238bb7652c1d3f071dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9400000000-929ccd53c2ccb65baf55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-105f0dacd0348edebb58Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03144
HMDB IDHMDB0004224
FooDB IDFDB031063
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID46955
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID110427
ChEBI ID43088
PubChem Compound ID43088
Kegg Compound IDC05933
YMDB IDNot Available
ECMDB IDM2MDB004534
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ignarro LJ, Buga GM, Wei LH, Bauer PM, Wu G, del Soldato P: Role of the arginine-nitric oxide pathway in the regulation of vascular smooth muscle cell proliferation. Proc Natl Acad Sci U S A. 2001 Mar 27;98(7):4202-8. Epub 2001 Mar 20.
2. Cox JD, Cama E, Colleluori DM, Pethe S, Boucher JL, Mansuy D, Ash DE, Christianson DW: Mechanistic and metabolic inferences from the binding of substrate analogues and products to arginase. Biochemistry. 2001 Mar 6;40(9):2689-701.
3. Wei CC, Wang ZQ, Hemann C, Hille R, Stuehr DJ: A tetrahydrobiopterin radical forms and then becomes reduced during Nomega-hydroxyarginine oxidation by nitric-oxide synthase. J Biol Chem. 2003 Nov 21;278(47):46668-73. Epub 2003 Sep 22.
4. Witteveen CF, Giovanelli J, Yim MB, Gachhui R, Stuehr DJ, Kaufman S: Reactivity of the flavin semiquinone of nitric oxide synthase in the oxygenation of arginine to NG-hydroxyarginine, the first step of nitric oxide synthesis. Biochem Biophys Res Commun. 1998 Sep 8;250(1):36-42.