Human Metabolome Database Version 3.5

Showing metabocard for N-(o)-Hydroxyarginine (HMDB04224)

Record Information
Version 3.5
Creation Date 2006-08-13 08:44:13 -0600
Update Date 2013-05-29 13:39:57 -0600
HMDB ID HMDB04224
Secondary Accession Numbers None
Metabolite Identification
Common Name N-(o)-Hydroxyarginine
Description 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 (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 Link_out, 11258880 Link_out, 14504282 Link_out, 9735327 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. N-(G)-Hydroxyarginine
  2. N-(Omega)-Hydroxyarginine
Chemical Formula C6H14N4O3
Average Molecular Weight 190.2004
Monoisotopic Molecular Weight 190.106590334
IUPAC Name 2-amino-5-[(E)-[amino(hydroxyamino)methylidene]amino]pentanoic acid
Traditional IUPAC Name 2-amino-5-[(E)-[amino(hydroxyamino)methylidene]amino]pentanoic acid
CAS Registry Number Not 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 Key FQWRAVYMZULPNK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha 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 Parent Alpha Amino Acids and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -2.567 Not Available
Predicted Properties
Property Value Source
Water Solubility 5.7 g/L ALOGPS
LogP -3.58 ALOGPS
LogP -3.5 ChemAxon
LogS -1.52 ALOGPS
pKa (strongest acidic) 2.2 ChemAxon
pKa (strongest basic) 10.05 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 133.96 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 55.89 ChemAxon
Polarizability 18.89 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Arginine and Proline Metabolism SMP00020 map00330 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023337
KNApSAcK ID Not Available
Chemspider ID 389691 Link_out
KEGG Compound ID C05933 Link_out
BioCyc ID Not Available
BiGG ID 46955 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB04224 Link_out
Metagene Link HMDB04224 Link_out
METLIN ID Not Available
PubChem Compound 440849 Link_out
PDB ID Not Available
ChEBI ID 7101 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Nitric oxide synthase, inducible
Reactions:
NADPH + N-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion unknown NADP + Nitric oxide + Citrulline + Water details
L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown N-(o)-Hydroxyarginine + NADP + Water details
Gene Name: NOS2
Uniprot ID: P35228 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nitric oxide synthase, brain
Reactions:
NADPH + N-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion unknown NADP + Nitric oxide + Citrulline + Water details
L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown N-(o)-Hydroxyarginine + NADP + Water details
Gene Name: NOS1
Uniprot ID: P29475 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nitric oxide synthase, endothelial
Reactions:
NADPH + N-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion unknown NADP + Nitric oxide + Citrulline + Water details
L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown N-(o)-Hydroxyarginine + NADP + Water details
Gene Name: NOS3
Uniprot ID: P29474 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: NOS1 mutant
Reactions: Not Available
Gene Name: NOS1
Uniprot ID: B3VK56 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA