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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 14:44:13 UTC
Update Date2017-10-23 19:04:11 UTC
HMDB IDHMDB0004224
Secondary Accession Numbers
  • HMDB04224
Metabolite Identification
Common NameN-(o)-Hydroxyarginine
DescriptionN(omega)-hydroxyarginine is a product of the arginine-Nitric Oxide pathway, and is the first intermediate in the process catalyzed by nitric oxide synthase (EC 1.14.13.99, NOS, a heme protein that catalyzes the oxygenation of L-arginine in the presence of NADPH to form nitric oxide + citrulline). N(omega)-hydroxyarginine appears to interfere with cell proliferation/cell growth by inhibiting arginase (EC 3.5.3.1, a binuclear Mn (2+) metalloenzyme that catalyzes the hydrolysis of L-arginine to L-ornithine and urea), and that has 6R-tetrahydrobiopterin (H4B) as an enzyme-bound cofactor. (PMID: 11259671 , 11258880 , 14504282 , 9735327 ).
Structure
Thumb
Synonyms
ValueSource
N-(Omega)-hydroxyarginineChEBI
N-(g)-HydroxyarginineHMDB
6-NOHAMeSH
N(g)-Hydroxy-L-arginineMeSH
N(Omega)-hydroxy-L-arginineMeSH
N(Omega)-hydroxyarginineMeSH
N-Omega-hydroxy-L-arginineMeSH
Chemical FormulaC6H14N4O3
Average Molecular Weight190.2004
Monoisotopic Molecular Weight190.106590334
IUPAC Name2-amino-5-[(E)-[amino(hydroxyamino)methylidene]amino]pentanoic acid
Traditional Name2-amino-5-[(E)-[amino(hydroxyamino)methylidene]amino]pentanoic acid
CAS Registry NumberNot Available
SMILES
NC(CCC\N=C(/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)
InChI KeyFQWRAVYMZULPNK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • N-hydroxyguanidine
  • Fatty acid
  • Guanidine
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

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-3.5ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.2ChemAxon
pKa (Strongest Basic)10.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area133.96 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity55.89 m³·mol⁻¹ChemAxon
Polarizability18.89 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0c33-9200000000-4be199a7b3c6d73cc546View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9210000000-0e67aba5b5f149ed554eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006w-0900000000-80a793692d9e7c60a2e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ba-6900000000-7d238c63e5173148098aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-9000000000-9ae3cfb7d4b6d1d77f0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0080-1900000000-1ee422060ea005d25dccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-5900000000-1d442b980e4227c71a26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9000000000-28cfe991ad7920e78c1fView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Arginine and Proline MetabolismPw000010Pw000010 greyscalePw000010 simpleMap00330
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)Pw000084Pw000084 greyscalePw000084 simpleNot Available
Creatine deficiency, guanidinoacetate methyltransferase deficiencyPw000480Pw000480 greyscalePw000480 simpleNot Available
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)Pw000088Pw000088 greyscalePw000088 simpleNot Available
Hyperornithinemia with gyrate atrophy (HOGA)Pw000481Pw000481 greyscalePw000481 simpleNot Available
Displaying entries 1 - 5 of 12 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023337
KNApSAcK IDNot Available
Chemspider ID389691
KEGG Compound IDC05933
BioCyc IDNot Available
BiGG ID46955
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440849
PDB IDNot Available
ChEBI ID7101
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-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion → NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion → N-(o)-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-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion → NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion → N-(o)-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-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion → NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion → N-(o)-Hydroxyarginine + NADP + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
NOS1
Uniprot ID:
B3VK56
Molecular weight:
160969.1