Record Information
Version3.6
Creation Date2006-08-13 14:44:13 UTC
Update Date2013-05-29 19:39:57 UTC
HMDB IDHMDB04224
Secondary Accession NumbersNone
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
  1. N-(G)-Hydroxyarginine
  2. N-(Omega)-Hydroxyarginine
Chemical FormulaC6H14N4O3
Average Molecular Weight190.2004
Monoisotopic Molecular Weight190.106590334
IUPAC Name2-amino-5-[(E)-[amino(hydroxyamino)methylidene]amino]pentanoic acid
Traditional IUPAC 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
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • N(omega)-hydroxyarginine(ChEBI)
Substituents
  • Carboxylic Acid
  • Guanidine
  • Organic Hyponitrite
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locationsNot Available
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 area133.96ChemAxon
rotatable bond count5ChemAxon
refractivity55.89ChemAxon
polarizability18.89ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020map00330
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
NuGOwiki LinkHMDB04224
Metagene LinkHMDB04224
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

Gene Name:
NOS2
Uniprot ID:
P35228
Reactions
NADPH + N-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion unknown NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown N-(o)-Hydroxyarginine + NADP + Waterdetails
Gene Name:
NOS1
Uniprot ID:
P29475
Reactions
NADPH + N-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion unknown NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown N-(o)-Hydroxyarginine + NADP + Waterdetails
Gene Name:
NOS3
Uniprot ID:
P29474
Reactions
NADPH + N-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion unknown NADP + Nitric oxide + Citrulline + Waterdetails
L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown N-(o)-Hydroxyarginine + NADP + Waterdetails
Gene Name:
NOS1
Uniprot ID:
B3VK56