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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 14:44:13 UTC
Update Date2020-02-26 21:25:03 UTC
HMDB IDHMDB0004224
Secondary Accession Numbers
  • HMDB04224
Metabolite Identification
Common NameN(omega)-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. NOS is a heme protein that catalyzes the oxygenation of L-arginine in the presence of NADPH to form nitric oxide and citrulline. N(omega)-Hydroxyarginine appears to interfere with cell proliferation/cell growth by inhibiting arginase, a binuclear Mn(2+) metalloenzyme that catalyzes the hydrolysis of L-arginine to L-ornithine and urea (99). 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. N(omega)-hydroxyarginine and nitric oxide can be biosynthesized from L-arginine through the action of the enzyme nitric-oxide synthase, brain. Arginase has 6R-tetrahydrobiopterin (H4B) as an enzyme-bound cofactor (PMID: 11259671 , 11258880 , 14504282 , 9735327 ). In humans, N(omega)-hydroxyarginine is involved in the metabolic disorder called hyperornithinemia with gyrate atrophy (hoga). N(omega)-Hydroxyarginine is a product of the arginine-nitric oxide pathway, and is the first intermediate in the process catalyzed by nitric oxide synthase (NOS) (EC1.14.13.99). Outside of the human body, N(omega)-Hydroxyarginine has been detected, but not quantified in, several different foods, such as jutes, root vegetables, sesbania flowers, saskatoon berries, and chayotes. This could make N(omega)-hydroxyarginine a potential biomarker for the consumption of these foods.
Structure
Data?1582752302
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
Disposition

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.567Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.7 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9300000000-c0d34ab8e133be65558aSpectrum
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
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNWHARG
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:11259671 ]
  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. [PubMed:11258880 ]
  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. [PubMed:14504282 ]
  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. [PubMed:9735327 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2.
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular weight:
131116.3
Reactions
NADPH + N(omega)-Hydroxyarginine + Oxygen + Hydrogen Ion → NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion → N(omega)-Hydroxyarginine + NADP + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR.
Gene Name:
NOS1
Uniprot ID:
P29475
Molecular weight:
160969.095
Reactions
NADPH + N(omega)-Hydroxyarginine + Oxygen + Hydrogen Ion → NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion → N(omega)-Hydroxyarginine + NADP + Waterdetails
General function:
Involved in oxidoreductase activity
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. Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
Gene Name:
NOS3
Uniprot ID:
P29474
Molecular weight:
133273.59
Reactions
NADPH + N(omega)-Hydroxyarginine + Oxygen + Hydrogen Ion → NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion → N(omega)-Hydroxyarginine + NADP + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
NOS1
Uniprot ID:
B3VK56
Molecular weight:
160969.1