MiMeDB: Showing metabocard for N(omega)-Hydroxyarginine (MMDBc0047945)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:17:57 UTC

Update Date

2024-04-30 20:33:20 UTC

Metabolite ID

MMDBc0047945

Metabolite Identification

Common Name

N(omega)-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 (NOS) (EC 1.14.13.99). 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 (EC 3.5.3.1). Arginase has 6R-tetrahydrobiopterin (H4B) as an enzyme-bound cofactor (PMID: 11259671 , 11258880 , 14504282 , 9735327 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652303102016452D          

 13 12  0  0  0  0            999 V2000
10002.472510001.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.187710001.1780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.900610001.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.615710001.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.900610002.4146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.187710000.3538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.757610001.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.041910001.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.327710001.1780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9999.613210001.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.899010001.1780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9998.182610001.5918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.613210002.4146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047945

> <DATABASE_NAME>
MIME

> <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_KEY>
FQWRAVYMZULPNK-BYPYZUCNSA-N

> <FORMULA>
C6H14N4O3

> <MOLECULAR_WEIGHT>
190.2004

> <EXACT_MASS>
190.106590334

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.892284573839312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-[(Z)-N''-hydroxycarbamimidamido]pentanoic acid

> <ALOGPS_LOGP>
-3.57

> <JCHEM_LOGP>
-3.8536940164346847

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.342214796199041

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1966173561333404

> <JCHEM_PKA_STRONGEST_BASIC>
9.234696953279306

> <JCHEM_POLAR_SURFACE_AREA>
133.95999999999998

> <JCHEM_REFRACTIVITY>
45.2728

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-5-[(Z)-N''-hydroxycarbamimidamido]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0    8671.2828669.634   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8672.6178668.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8673.9488669.634   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8675.2838668.866   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8673.9488671.174   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0    8672.6178667.327   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0    8669.9488668.866   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.6128669.634   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8667.2788668.866   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    8665.9458669.634   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8664.6118668.866   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    8663.2748669.638   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0    8665.9458671.174   0.000  0.00  0.00           N+0
CONECT    1    2    7                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0004224
HETATM    1  N1  UNL     1      -2.389  -1.040  -1.590  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.501  -0.073  -0.760  1.00  0.00           C  
HETATM    3  N2  UNL     1      -3.774   0.414  -0.387  1.00  0.00           N  
HETATM    4  O1  UNL     1      -4.298   1.505  -0.960  1.00  0.00           O  
HETATM    5  N3  UNL     1      -1.337   0.514  -0.213  1.00  0.00           N  
HETATM    6  C2  UNL     1      -0.804  -0.051   1.020  1.00  0.00           C  
HETATM    7  C3  UNL     1       0.432   0.704   1.447  1.00  0.00           C  
HETATM    8  C4  UNL     1       1.529   0.663   0.425  1.00  0.00           C  
HETATM    9  C5  UNL     1       1.984  -0.747   0.128  1.00  0.00           C  
HETATM   10  N4  UNL     1       2.490  -1.439   1.262  1.00  0.00           N  
HETATM   11  C6  UNL     1       2.992  -0.763  -0.947  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.085  -1.330  -0.766  1.00  0.00           O  
HETATM   13  O3  UNL     1       2.714  -0.147  -2.148  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.173  -1.535  -2.045  1.00  0.00           H  
HETATM   15  H2  UNL     1      -4.298  -0.104   0.351  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.132   2.263  -0.345  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.874   1.324  -0.673  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.569  -1.119   0.869  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.553   0.045   1.839  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.779   0.282   2.425  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.106   1.737   1.679  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.411   1.220   0.800  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.181   1.156  -0.506  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.109  -1.310  -0.256  1.00  0.00           H  
HETATM   25  H12 UNL     1       3.117  -0.913   1.871  1.00  0.00           H  
HETATM   26  H13 UNL     1       1.856  -2.098   1.711  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.915   0.843  -2.285  1.00  0.00           H  
CONECT    1    2    2   14
CONECT    2    3    5
CONECT    3    4   15
CONECT    4   16
CONECT    5    6   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   11   24
CONECT   10   25   26
CONECT   11   12   12   13
CONECT   13   27
END

Synonyms

Value	Source
N-OMEGA-hydroxy-L-arginine	ChEBI
N(Omega)-hydroxy-L-arginine	Kegg
N(Ω)-hydroxy-L-arginine	HMDB
N(Ω)-hydroxyarginine	HMDB
6-NOHA	HMDB
N(g)-Hydroxy-L-arginine	HMDB
N5-[(Hydroxyamino)iminomethyl]-L-ornithine	HMDB
NG-Hydroxy-L-arginine	HMDB
Nω-hydroxy-L-arginine	HMDB
N(Omega)-hydroxyarginine	MeSH

Molecular Formula

C₆H₁₄N₄O₃

Average Mass

190.2004

Monoisotopic Mass

190.106590334

IUPAC Name

(2S)-2-amino-5-[(Z)-N''-hydroxycarbamimidamido]pentanoic acid

Traditional Name

(2S)-2-amino-5-[(Z)-N''-hydroxycarbamimidamido]pentanoic acid

CAS Registry Number

53054-07-2

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 Key

FQWRAVYMZULPNK-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Arginine 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 Framework

Aliphatic acyclic compounds

External Descriptors

N(omega)-hydroxy-L-arginine (CHEBI:43088 )
N(5)-[(hydroxyamino)(imino)methyl]ornithine (CHEBI:43088 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.49 g/L	ALOGPS
logP	-3.6	ALOGPS
logP	-3.9	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.2	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	133.96 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	45.27 m³·mol⁻¹	ChemAxon
Polarizability	18.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9300000000-c0d34ab8e133be65558a	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0005-1900000000-b786caa9f1955646a132	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ba-7900000000-504227bb53f351f75953	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00b9-9000000000-8a2dba3a89dbf383615c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0079-2900000000-a0e075cbf656b2172f59	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-6900000000-7f4da6440196f7107a96	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9000000000-fde384449989f2053abb	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r6-2900000000-499ec74e9d082befa16a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9200000000-d12c71ccee9673ac7328	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-10f3b1c2202ce7bb508e	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-2900000000-03238bb7652c1d3f071d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052f-9400000000-929ccd53c2ccb65baf55	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-105f0dacd0348edebb58	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192544	Nitric oxide synthase, inducible	Unknown	P35228	Homo sapiens
MMDBp0192546	Nitric oxide synthase, brain	Unknown	P29475	Homo sapiens
MMDBp0192547	Nitric oxide synthase, endothelial	Unknown	P29474	Homo sapiens
MMDBp0196205	NOS1 mutant	Enzyme	B3VK56	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001770	L-Arginine	N(omega)-Hydroxyarginine	Not Available	VMH	7545544 7558036
MMDBr0001771	N(omega)-Hydroxyarginine	Citrulline	nitric oxide synthase 1 (neuronal)	VMH	7545544 7558036
MMDBr0002439	N(omega)-Hydroxyarginine	Citrulline	nitric oxide synthase 1 (neuronal)	VMH	11125020 7515853
MMDBr0008403	N(omega)-Hydroxyarginine	Citrulline	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	65	Human feces; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria	Actinobacteria	2	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Species	Data Source	Reference
Animal	Chondrus crispus	FooDB	31437929
Animal	Laminaria	FooDB	31437929
Animal	Haliotis	FooDB	31437929
Animal	Strombidae	FooDB	31437929
Animal	Clupea harengus harengus	FooDB	31437929
Animal	Undaria pinnatifida	FooDB	31437929
Animal	Peprilus triacanthus	FooDB	31437929
Animal	Rhodophyta	FooDB	31437929
Animal	Myoxocephalus	FooDB	31437929
Animal	Eucheuma	FooDB	31437929
Animal	Saccharina japonica	FooDB	31437929
Animal	Spirulina	FooDB	31437929
Animal	Lota lota	FooDB	31437929
Animal	Porphyra umbilicalis	FooDB	31437929
Plant	Vaccinium vitis-idaea	FooDB	31437929
Plant	Tilia tomentosa	FooDB	31437929
Plant	Empetrum nigrum	FooDB	31437929
Plant	Typha angustifolia	FooDB	31437929
Plant	Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	31437929
Plant	Valerianella locusta	FooDB	31437929
Plant	Myrica rubra	FooDB	31437929
Plant	Vaccinium angustifolium x vaccinium corymbosum	FooDB	31437929
Plant	Prunus dulcis	FooDB	31437929
Plant	Vigna radiata	FooDB	31437929
Plant	Raphanus sativus	FooDB	31437929
Plant	Sisymbrium	FooDB	31437929
Plant	Vanilla	FooDB	31437929
Plant	Borago officinalis	FooDB	31437929
Plant	Hyssopus officinalis	FooDB	31437929
Plant	Carya	FooDB	31437929
Plant	Beta vulgaris ssp. cicla	FooDB	31437929
Plant	Manihot esculenta	FooDB	31437929
Plant	Physalis philadelphica var. immaculata	FooDB	31437929
Plant	Scorzonera hispanica	FooDB	31437929
Plant	Angelica keiskei	FooDB	31437929
Plant	Musa x paradisiaca	FooDB	31437929
Plant	Vigna unguiculata ssp. sesquipedalis	FooDB	31437929
Plant	Rubus idaeus	FooDB	31437929
Plant	Ipomoea aquatica	FooDB	31437929
Plant	Cuminum cyminum	FooDB	31437929
Plant	Arachis hypogaea	FooDB	31437929
Plant	Rubus spectabilis	FooDB	31437929
Plant	Pyrus communis	FooDB	31437929
Plant	Fragaria x ananassa	FooDB	31437929
Plant	Allium sativum	FooDB	31437929
Plant	Solanum lycopersicum	FooDB	31437929
Plant	Sinapis alba	FooDB	31437929
Plant	Mentha spicata	FooDB	31437929
Plant	Cantharellus cibarius	FooDB	31437929
Plant	Apium graveolens var. secalinum	FooDB	31437929
Plant	Zingiber officinale	FooDB	31437929
Plant	Brassica ruvo	FooDB	31437929
Plant	Moringa oleifera	FooDB	31437929
Plant	Abelmoschus esculentus	FooDB	31437929
Plant	Morus nigra	FooDB	31437929
Plant	Helianthus annuus	FooDB	31437929
Plant	Vigna angularis	FooDB	31437929
Plant	Pisum sativum	FooDB	31437929
Plant	Pinus edulis	FooDB	31437929
Plant	Passiflora edulis	FooDB	31437929
Plant	Ribes nigrum	FooDB	31437929
Plant	Opuntia macrorhiza	FooDB	31437929
Plant	Petroselinum crispum	FooDB	31437929
Plant	Sambucus nigra	FooDB	31437929
Plant	Cucurbita pepo var. clypeata	FooDB	31437929
Plant	Manilkara zapota	FooDB	31437929
Plant	Laurus nobilis	FooDB	31437929
Plant	Corylus	FooDB	31437929
Plant	Malus	FooDB	31437929
Plant	Mangifera indica	FooDB	31437929
Plant	Juglans	FooDB	31437929
Plant	Allium cepa	FooDB	31437929
Plant	Illicium verum	FooDB	31437929
Plant	Chamaemelum nobile	FooDB	31437929
Plant		FooDB	31437929
Plant	Melissa officinalis	FooDB	31437929
Plant	Vaccinium corymbosum	FooDB	31437929
Plant	Auricularia auricula-judae	FooDB	31437929
Plant	Attalea speciosa	FooDB	31437929
Plant	Hippophae rhamnoides	FooDB	31437929
Plant	Spinacia oleracea	FooDB	31437929
Plant	Juglans ailanthifolia	FooDB	31437929
Plant	Thymus vulgaris	FooDB	31437929
Plant	Carica papaya	FooDB	31437929
Plant	Polygonum alpinum	FooDB	31437929
Plant	Actinidia chinensis	FooDB	31437929
Plant	Brassica juncea	FooDB	31437929
Plant		FooDB	31437929
Plant	Pimenta dioica	FooDB	31437929
Plant	Pediomelum esculentum	FooDB	31437929
Plant	Auricularia polytricha	FooDB	31437929
Plant	Camellia oleifera	FooDB	31437929
Plant	Chrysanthemum coronarium	FooDB	31437929
Plant	Eleocharis dulcis	FooDB	31437929
Plant	Medicago sativa	FooDB	31437929
Plant	Vigna mungo	FooDB	31437929
Plant	Hibiscus sabdariffa	FooDB	31437929
Plant	Rubus arcticus	FooDB	31437929
Plant	Foeniculum vulgare	FooDB	31437929
Plant	Origanum majorana	FooDB	31437929
Plant	Agaricus bisporus	FooDB	31437929
Plant	Armoracia rusticana	FooDB	31437929
Plant	Prunus persica	FooDB	31437929
Plant	Brassica oleracea var. gongylodes	FooDB	31437929
Plant	Cajanus cajan	FooDB	31437929
Plant	Phoenix dactylifera	FooDB	31437929
Plant	Rumex articus	FooDB	31437929
Plant	Brassica oleracea var. gemmifera	FooDB	31437929
Plant	Vaccinium macrocarpon	FooDB	31437929
Plant	Benincasa hispida	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Canarium ovatum	FooDB	31437929
Plant	Ribes aureum var. villosum	FooDB	31437929
Plant	Rosmarinus officinalis	FooDB	31437929
Plant	Prunus cerasus	FooDB	31437929
Plant	Arctium lappa	FooDB	31437929
Plant		FooDB	31437929
Plant	Juglans cinerea	FooDB	31437929
Plant	Citrus x paradisi	FooDB	31437929
Plant	Ficus carica	FooDB	31437929
Plant	Artocarpus altilis	FooDB	31437929
Plant	Eruca vesicaria ssp. sativa	FooDB	31437929
Plant	Beta vulgaris var. rubra	FooDB	31437929
Plant	Cynara scolymus	FooDB	31437929
Plant	Psidium cattleianum	FooDB	31437929
Plant	Vigna unguiculata	FooDB	31437929
Plant	Lentinus edodes	FooDB	31437929
Plant	Cyathea	FooDB	31437929
Plant	Metroxylon sagu	FooDB	31437929
Plant	Vitis rotundifolia	FooDB	31437929
Plant	Brosimum alicastrum	FooDB	31437929
Plant	Lepidium sativum	FooDB	31437929
Plant	Castanea mollissima	FooDB	31437929
Plant	Morus	FooDB	31437929
Plant	Helianthus tuberosus	FooDB	31437929
Plant	Grifola frondosa	FooDB	31437929
Plant	Phytolacca americana	FooDB	31437929
Plant	Vitis labrusca	FooDB	31437929
Plant	Artemisia vulgaris	FooDB	31437929
Plant	Corylus avellana	FooDB	31437929
Plant	Tetragonia tetragonioides	FooDB	31437929
Plant	Juglans regia	FooDB	31437929
Plant	Cucumis metuliferus	FooDB	31437929
Plant	Nephelium lappaceum	FooDB	31437929
Plant	Myrica	FooDB	31437929
Plant	Castanea crenata	FooDB	31437929
Plant	Litchi chinensis	FooDB	31437929
Plant	Vaccinium angustifolium	FooDB	31437929
Plant		FooDB	31437929
Plant	Quercus	FooDB	31437929
Plant	Trigonella foenum-graecum	FooDB	31437929
Plant	Brassica oleracea var. sabauda	FooDB	31437929
Plant	Levisticum officinale	FooDB	31437929
Plant	Brassica napus	FooDB	31437929
Plant	Physalis	FooDB	31437929
Plant	Malpighia emarginata	FooDB	31437929
Plant	Malus pumila	FooDB	31437929
Plant	Citrus aurantiifolia	FooDB	31437929
Plant	Artemisia dracunculus	FooDB	31437929
Plant	Thelesperma	FooDB	31437929
Plant	Asparagus officinalis	FooDB	31437929
Plant	Lactuca sativa	FooDB	31437929
Plant	Pimpinella anisum	FooDB	31437929
Plant	Chamerion angustifolium	FooDB	31437929
Plant	Matricaria recutita	FooDB	31437929
Plant	Eragrostis tef	FooDB	31437929
Plant	Vaccinium elliottii	FooDB	31437929
Plant	Punica granatum	FooDB	31437929
Plant	Ziziphus zizyphus	FooDB	31437929
Plant	Pistacia vera	FooDB	31437929
Plant	Dimocarpus longan	FooDB	31437929
Plant	Salvia hispanica	FooDB	31437929
Plant	Vitellaria paradoxa	FooDB	31437929
Plant	Pangium edule	FooDB	31437929
Plant	Cynara cardunculus	FooDB	31437929
Plant	Allium	FooDB	31437929
Plant	Gossypium	FooDB	31437929
Plant	Brassica oleracea var. viridis	FooDB	31437929
Plant	Agave	FooDB	31437929
Plant	Cucumis sativus	FooDB	31437929
Plant	Diospyros	FooDB	31437929
Plant	Hedysarum alpinum	FooDB	31437929
Plant	Vigna aconitifolia	FooDB	31437929
Plant	Amaranthus	FooDB	31437929
Plant	Apium graveolens var. dulce	FooDB	31437929
Plant	Beta vulgaris	FooDB	31437929
Plant	Mammea americana	FooDB	31437929
Plant	Annona squamosa	FooDB	31437929
Plant	Brassica alboglabra	FooDB	31437929
Plant	Vitis	FooDB	31437929
Plant	Carya illinoinensis	FooDB	31437929
Plant	Xanthosoma sagittifolium	FooDB	31437929
Plant	Basella alba	FooDB	31437929
Plant	Citrus latifolia	FooDB	31437929
Plant	Cinnamomum aromaticum	FooDB	31437929
Plant	Capsicum baccatum var. baccatum	FooDB	31437929
Plant	Ribes rubrum	FooDB	31437929
Plant	Solanum lycopersicum var. cerasiforme	FooDB	31437929
Plant	Byrsonima crassifolia	FooDB	31437929
Plant	Mentha arvensis	FooDB	31437929
Plant	Brassica rapa var. chinensis	FooDB	31437929
Plant	Portulaca oleracea	FooDB	31437929
Plant	Capsicum pubescens	FooDB	31437929
Plant	Pastinaca sativa	FooDB	31437929
Plant	Crateva religiosa	FooDB	31437929
Plant		FooDB	31437929
Plant	Ipomoea batatas	FooDB	31437929
Plant	Vitis aestivalis	FooDB	31437929
Plant	Cucurbita maxima	FooDB	31437929
Plant	Eugenia javanica	FooDB	31437929
Plant	Chenopodium album	FooDB	31437929
Plant	Brassica oleracea	FooDB	31437929
Plant	Psophocarpus tetragonolobus	FooDB	31437929
Plant	Vaccinium stamineum	FooDB	31437929
Plant	Allium ampeloprasum	FooDB	31437929
Plant	Sechium edule	FooDB	31437929
Plant	Lactuca sativa l. var. longifolia	FooDB	31437929
Plant	Grataegosorbus mitschurinii	FooDB	31437929
Plant	Diospyros virginiana	FooDB	31437929
Plant	Ananas comosus	FooDB	31437929
Plant	Origanum x majoricum	FooDB	31437929
Plant	Rubus x loganobaccus	FooDB	31437929
Plant	Taraxacum officinale	FooDB	31437929
Plant	Rubus chamaemorus	FooDB	31437929
Plant	Tragopogon porrifolius	FooDB	31437929
Plant	Elettaria cardamomum	FooDB	31437929
Plant	Curcuma longa	FooDB	31437929
Plant	Persea americana	FooDB	31437929
Plant	Rumex	FooDB	31437929
Plant	Allium ascalonicum	FooDB	31437929
Plant	Eugenia uniflora	FooDB	31437929
Plant	Citrullus lanatus var. fistulosus	FooDB	31437929
Plant	Amelanchier alnifolia	FooDB	31437929
Plant	Cinnamomum verum	FooDB	31437929
Plant	Chenopodium quinoa	FooDB	31437929
Plant	Annona reticulata	FooDB	31437929
Plant	Cichorium intybus	FooDB	31437929
Plant	Brassica oleracea var. botrytis	FooDB	31437929
Plant	Glycine max	FooDB	31437929
Plant	Cucumis melo	FooDB	31437929
Plant	Sesbania bispinosa	FooDB	31437929
Plant	Juglans nigra	FooDB	31437929
Plant	Ocimum basilicum	FooDB	31437929
Plant	Ribes x nidigrolaria	FooDB	31437929
Plant	Garcinia mangostana	FooDB	31437929
Plant	Allium tuberosum	FooDB	31437929
Plant	Corchorus olitorius	FooDB	31437929
Plant	Dioscorea pentaphylla	FooDB	31437929
Plant	Mentha x piperita	FooDB	31437929
Plant	Lathyrus sativus	FooDB	31437929
Plant	Petasites japonicus	FooDB	31437929
Plant	Citrus limon	FooDB	31437929
Plant	Gaylussacia baccata	FooDB	31437929
Plant	Prunus tomentosa	FooDB	31437929
Plant	Tilia	FooDB	31437929
Plant	Maranta arundinacea	FooDB	31437929
Plant	Capsicum annuum var. annuum	FooDB	31437929
Plant	Macadamia	FooDB	31437929
Plant	Matteuccia struthiopteris	FooDB	31437929
Plant	Cucurbita moschata	FooDB	31437929
Plant	Sesamum orientale	FooDB	31437929
Plant	Citrus sinensis	FooDB	31437929
Plant	Apium graveolens var. rapaceum	FooDB	31437929
Plant	Papaver	FooDB	31437929
Plant	Vaccinium myrtilloides	FooDB	31437929
Plant	Rosa	FooDB	31437929
Plant	Brassica oleracea var. conica	FooDB	31437929
Plant	Nelumbo	FooDB	31437929
Plant	Annona cherimola	FooDB	31437929
Plant	Brassica rapa var. pekinensis	FooDB	31437929
Plant	Brassica rapa	FooDB	31437929
Plant	Lippia graveolens	FooDB	31437929
Plant	Prunus	FooDB	31437929
Plant	Capparis spinosa	FooDB	31437929
Plant	Citrullus lanatus	FooDB	31437929
Plant	Lens culinaris	FooDB	31437929
Plant	Vaccinium deliciosum	FooDB	31437929
Plant	Prunus armeniaca	FooDB	31437929
Plant	Phaseolus lunatus	FooDB	31437929
Plant	Linum usitatissimum	FooDB	31437929
Plant	Musa acuminata	FooDB	31437929
Plant	Artocarpus heterophyllus	FooDB	31437929
Plant	Citrus reticulata	FooDB	31437929
Plant	Prunus virginiana	FooDB	31437929
Plant	Prunus domestica	FooDB	31437929
Plant	Anethum graveolens	FooDB	31437929
Plant	Carum carvi	FooDB	31437929
Plant	Macadamia tetraphylla	FooDB	31437929
Plant	Vigna unguiculata ssp. unguiculata	FooDB	31437929
Plant	Allium schoenoprasum	FooDB	31437929
Plant	Phyllostachys edulis	FooDB	31437929
Plant	Camellia sinensis	FooDB	31437929
Plant	Lagenaria siceraria	FooDB	31437929
Plant	Brassica rapa var. rapa	FooDB	31437929
Plant	Averrhoa carambola	FooDB	31437929
Plant	Satureja hortensis	FooDB	31437929
Plant	Carissa macrocarpa	FooDB	31437929
Plant	Coriandrum sativum	FooDB	31437929
Plant	Sorbus aucuparia	FooDB	31437929
Plant	Solanum lycopersicum var. lycopersicum	FooDB	31437929
Plant	Bertholletia excelsa	FooDB	31437929
Plant	Nelumbo nucifera	FooDB	31437929
Plant	Cymbopogon citratus	FooDB	31437929
Plant	Brassica oleracea var. costata	FooDB	31437929
Plant	Ceratonia siliqua	FooDB	31437929
Plant	Panax	FooDB	31437929
Plant	Anacardium occidentale	FooDB	31437929
Plant	Carthamus tinctorius	FooDB	31437929
Plant	Rubus occidentalis	FooDB	31437929
Plant	Luffa aegyptiaca	FooDB	31437929
Plant	Cicer arietinum	FooDB	31437929
Plant	Vigna umbellata	FooDB	31437929
Plant	Allium fistulosum	FooDB	31437929
Plant	Capsicum	FooDB	31437929
Plant	Vaccinium alaskaense	FooDB	31437929
Plant	Eriobotrya japonica	FooDB	31437929
Plant	Lupinus	FooDB	31437929
Plant	Phaseolus vulgaris	FooDB	31437929
Plant	Tilia cordata	FooDB	31437929
Plant	Prunus persica var. nucipersica	FooDB	31437929
Plant	Daucus carota ssp. sativus	FooDB	31437929
Plant	Vaccinium myrtillus	FooDB	31437929
Plant	Durio zibethinus	FooDB	31437929
Plant	Oenothera biennis	FooDB	31437929
Plant	Syzygium aromaticum	FooDB	31437929
Plant	Brassica napus var. pabularia	FooDB	31437929
Plant	Theobroma cacao	FooDB	31437929
Plant	Diospyros kaki	FooDB	31437929
Plant	Ribes glandulosum	FooDB	31437929
Plant	Vaccinium oxycoccos	FooDB	31437929
Plant	Virola surinamensis	FooDB	31437929
Plant	Verbena officinalis	FooDB	31437929
Plant	Rumex acetosa	FooDB	31437929
Plant	Brassica oleracea var. capitata	FooDB	31437929
Plant	Vicia faba	FooDB	31437929
Plant	Vaccinium parvifolium	FooDB	31437929
Plant	Vitis vinifera	FooDB	31437929
Plant	Pyrus pyrifolia	FooDB	31437929
Plant	Aloysia triphylla	FooDB	31437929
Plant	Capsicum annuum	FooDB	31437929
Plant	Ginkgo biloba	FooDB	31437929
Plant	Capsicum chinense	FooDB	31437929
Plant	Theobroma grandiflorum	FooDB	31437929
Plant	Vaccinium reticulatum	FooDB	31437929
Plant	Solanum quitoense	FooDB	31437929
Plant	Satureja montana	FooDB	31437929
Plant	Vigna unguiculata ssp. cylindrica	FooDB	31437929
Plant	Flammulina velutipes	FooDB	31437929
Plant	Prunus avium	FooDB	31437929
Plant	Citrus japonica	FooDB	31437929
Plant		FooDB	31437929
Plant	Piper nigrum	FooDB	31437929
Plant	Perideridia oregana	FooDB	31437929
Plant	Origanum onites	FooDB	31437929
Plant	Origanum vulgare	FooDB	31437929
Plant	Vaccinium arboreum	FooDB	31437929
Plant	Pouteria sapota	FooDB	31437929
Plant	Wasabia japonica	FooDB	31437929
Plant	Brassica oleracea var. italica	FooDB	31437929
Plant	Viburnum edule	FooDB	31437929
Plant	Dioscorea	FooDB	31437929
Plant	Momordica charantia	FooDB	31437929
Plant	Vaccinium uliginosum	FooDB	31437929
Plant	Solanum melongena	FooDB	31437929
Plant	Myristica fragrans	FooDB	31437929
Plant	Apium graveolens	FooDB	31437929
Plant	Castanea	FooDB	31437929
Plant	Rubus ursinus x idaeus	FooDB	31437929
Plant	Cirsium	FooDB	31437929
Plant	Raphanus sativus var. sativus	FooDB	31437929
Plant	Prunus persica var. persica	FooDB	31437929
Plant	Pleurotus ostreatus	FooDB	31437929
Plant	Opuntia	FooDB	31437929
Plant	Lupinus albus	FooDB	31437929
Plant	Anthriscus cerefolium	FooDB	31437929
Plant	Colocasia esculenta	FooDB	31437929
Plant	Nuphar lutea	FooDB	31437929
Plant	Pachyrhizus erosus	FooDB	31437929
Plant	Cichorium endivia	FooDB	31437929
Plant	Ribes uva-crispa	FooDB	31437929
Plant	Cinnamomum	FooDB	31437929
Plant	Elaeis	FooDB	31437929
Plant	Salvia officinalis	FooDB	31437929
Plant	Raphanus sativus var. niger	FooDB	31437929
Plant	Crocus sativus	FooDB	31437929
Plant	Photinia melanocarpa	FooDB	31437929
Plant	Feijoa sellowiana	FooDB	31437929
Plant	Dysphania ambrosioides	FooDB	31437929
Plant	Rheum rhabarbarum	FooDB	31437929
Plant	Vaccinium	FooDB	31437929
Plant	Citrus maxima	FooDB	31437929
Plant	Lablab purpureus	FooDB	31437929
Plant	Cydonia oblonga	FooDB	31437929
Plant	Cucurbita	FooDB	31437929
Plant	Castanea sativa	FooDB	31437929
Plant	Syzygium jambos	FooDB	31437929
Plant	Annona muricata	FooDB	31437929
Plant	Salix pulchra	FooDB	31437929
Plant	Fagus	FooDB	31437929
Plant	Tamarindus indica	FooDB	31437929
Plant	Vaccinium ovatum	FooDB	31437929
Plant	Solanum tuberosum	FooDB	31437929
Plant	Opuntia cochenillifera	FooDB	31437929
Plant	Cocos nucifera	FooDB	31437929
Plant	Psidium guajava	FooDB	31437929
Plant	Phaseolus coccineus	FooDB	31437929
Plant	Thymus pulegioides	FooDB	31437929
Plant	Mentha aquatica	FooDB	31437929
Plant	Mespilus germanica	FooDB	31437929
Plant	Cucurbita pepo var. cylindrica	FooDB	31437929
Plant	Olea europaea	FooDB	31437929
Plant	Brassica rapa var. perviridis	FooDB	31437929
Plant	Mentha	FooDB	31437929
Plant	Pinus	FooDB	31437929
Plant	Salvia elegans	FooDB	31437929
Plant	Daucus carota	FooDB	31437929
Plant	Sagittaria latifolia	FooDB	31437929
Plant	Sambucus	FooDB	31437929
Plant	Syzygium cumini	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0004224

DrugBank ID

DB03144

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031063

KNApSAcK ID

Not Available

Chemspider ID

110427

KEGG Compound ID

C05933

BioCyc ID

Not Available

BiGG ID

46955

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

43088

PDB ID

Not Available

ChEBI ID

43088

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1006/bbrc.1998.8807. [PubMed:9735327 ]
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. doi: 10.1021/bi002318+. [PubMed:11258880 ]
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. doi: 10.1073/pnas.071054698. Epub 2001 Mar 20. [PubMed:11259671 ]
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. doi: 10.1074/jbc.M307682200. Epub 2003 Sep 22. [PubMed:14504282 ]

Showing metabocard for N(omega)-Hydroxyarginine (MMDBc0047945)

MOL for #<Metabolite:0x00005634c2a792a0>

3D MOL for #<Metabolite:0x00005634c2a792a0>

3D SDF for #<Metabolite:0x00005634c2a792a0>

3D-SDF for #<Metabolite:0x00005634c2a792a0>

PDB for #<Metabolite:0x00005634c2a792a0>

3D PDB for #<Metabolite:0x00005634c2a792a0>

SMILES for #<Metabolite:0x00005634c2a792a0>

INCHI for #<Metabolite:0x00005634c2a792a0>

Structure for #<Metabolite:0x00005634c2a792a0>

3D Structure for #<Metabolite:0x00005634c2a792a0>