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

Plant

Animal

Pharmaceutical

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:17:57 UTC

Update Date

2024-10-15 18:21:01 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 SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₆H₁₄N₄O₃

Average Mass

190.2004

Monoisotopic Mass

190.106590334

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

53054-07-2

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	520.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	409.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	45.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	233.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	305.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	297.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	371.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	933.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (retained)	2025-10-24	713.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	174.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	613.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	181.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	30.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	414.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	992.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	74.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	311.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	611.7
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	592.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_1	C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=N)NO	standard non polar	2025-10-24	1738.91
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_2	C[Si](C)(C)N[C@@H](CCCNC(=N)NO)C(=O)O	standard non polar	2025-10-24	2369.79
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_3	C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=N)NO	standard non polar	2025-10-24	1914.16
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_4	C[Si](C)(C)N=C(NO)NCCC[C@H](N)C(=O)O	standard non polar	2025-10-24	1817.2
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_5	C[Si](C)(C)N(O)C(=N)NCCC[C@H](N)C(=O)O	standard non polar	2025-10-24	2095.35
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_6	C[Si](C)(C)N[C@@H](CCCNC(=N)NO)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2448.03
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_7	C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=N)NO)[Si](C)(C)C	standard non polar	2025-10-24	1756.42
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_8	C[Si](C)(C)N=C(NO)NCCC[C@H](N)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2445.59
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_9	C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=N)N(O)[Si](C)(C)C	standard non polar	2025-10-24	2286.96
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_10	C[Si](C)(C)N([C@@H](CCCNC(=N)NO)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2031.27
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_11	C[Si](C)(C)N[C@@H](CCCN(C(=N)NO)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1857.79
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_12	C[Si](C)(C)N=C(NO)NCCC[C@H](N[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	1940.56
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_13	C[Si](C)(C)N[C@@H](CCCNC(=N)N(O)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	2348.82
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_14	C[Si](C)(C)N=C(NO)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1685.7
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_15	C[Si](C)(C)N(O)C(=N)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2449.13
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_16	C[Si](C)(C)N=C(NCCC[C@H](N)C(=O)O)N(O)[Si](C)(C)C	standard non polar	2025-10-24	2301.47
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_17	C[Si](C)(C)OC(=O)[C@H](CCCNC(=N)NO)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1937.51
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_18	C[Si](C)(C)N[C@@H](CCCN(C(=N)NO)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1561.58
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_19	C[Si](C)(C)N=C(NO)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2207.8
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_20	C[Si](C)(C)N[C@@H](CCCNC(=N)N(O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1641.46
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_21	C[Si](C)(C)N=C(NO)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2109.34
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_22	C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=N)N(O)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2308.52
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_23	C[Si](C)(C)N=C(NCCC[C@H](N)C(=O)O[Si](C)(C)C)N(O)[Si](C)(C)C	standard non polar	2025-10-24	2573.96
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_24	C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=N)NO	standard non polar	2025-10-24	2388.28
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_25	C[Si](C)(C)N=C(NO)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2075.74
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_26	C[Si](C)(C)N(O)C(=N)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1827.52
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_27	C[Si](C)(C)N=C(NO)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	2235.06
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_28	C[Si](C)(C)N[C@@H](CCCN(C(=N)N(O)[Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard non polar	2025-10-24	2348.48
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_29	C[Si](C)(C)N=C(NCCC[C@H](N[Si](C)(C)C)C(=O)O)N(O)[Si](C)(C)C	standard non polar	2025-10-24	2094.7
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_30	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1335.09
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_31	C[Si](C)(C)OC(=O)[C@H](CCCN(C(=N)NO)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2765.94
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_32	C[Si](C)(C)N=C(NO)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2110.65
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_33	C[Si](C)(C)OC(=O)[C@H](CCCNC(=N)N(O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2118.92
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_34	C[Si](C)(C)N=C(NO)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2307.72
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_35	C[Si](C)(C)N[C@@H](CCCN(C(=N)N(O)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	2136.15
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_36	C[Si](C)(C)N=C(NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N(O)[Si](C)(C)C	standard non polar	2025-10-24	1817.41
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_37	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1940.16
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_38	C[Si](C)(C)N=C(NO)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1966.03
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_39	C[Si](C)(C)N(O)C(=N)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2220.35
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_40	C[Si](C)(C)N=C(NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N(O)[Si](C)(C)C	standard non polar	2025-10-24	2450.14
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_41	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1997.82
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_42	C[Si](C)(C)N=C(NO)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1484.59
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_43	C[Si](C)(C)OC(=O)[C@H](CCCN(C(=N)N(O)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2221.58
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_44	C[Si](C)(C)N=C(NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N(O)[Si](C)(C)C	standard non polar	2025-10-24	2049.66
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_45	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	804.819
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_46	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2129.23
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_47	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	1907.4
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_1	C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=N)NO	standard polar	2025-10-24	1949.22
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_2	C[Si](C)(C)N[C@@H](CCCNC(=N)NO)C(=O)O	standard polar	2025-10-24	1964.45
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_3	C[Si](C)(C)N(CCC[C@H](N)C(=O)O)C(=N)NO	standard polar	2025-10-24	1540.63
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_4	C[Si](C)(C)N=C(NO)NCCC[C@H](N)C(=O)O	standard polar	2025-10-24	1773.04
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_5	C[Si](C)(C)N(O)C(=N)NCCC[C@H](N)C(=O)O	standard polar	2025-10-24	1909.63
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_6	C[Si](C)(C)N[C@@H](CCCNC(=N)NO)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2459.57
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_7	C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=N)NO)[Si](C)(C)C	standard polar	2025-10-24	1352.37
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_8	C[Si](C)(C)N=C(NO)NCCC[C@H](N)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2223.85
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_9	C[Si](C)(C)OC(=O)[C@@H](N)CCCNC(=N)N(O)[Si](C)(C)C	standard polar	2025-10-24	1952.12
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_10	C[Si](C)(C)N([C@@H](CCCNC(=N)NO)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1983.31
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_11	C[Si](C)(C)N[C@@H](CCCN(C(=N)NO)[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	1831.0
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_12	C[Si](C)(C)N=C(NO)NCCC[C@H](N[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2189.12
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_13	C[Si](C)(C)N[C@@H](CCCNC(=N)N(O)[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2233.23
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_14	C[Si](C)(C)N=C(NO)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2371.28
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_15	C[Si](C)(C)N(O)C(=N)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2348.93
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_16	C[Si](C)(C)N=C(NCCC[C@H](N)C(=O)O)N(O)[Si](C)(C)C	standard polar	2025-10-24	2222.57
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_17	C[Si](C)(C)OC(=O)[C@H](CCCNC(=N)NO)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2275.08
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_18	C[Si](C)(C)N[C@@H](CCCN(C(=N)NO)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2171.39
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_19	C[Si](C)(C)N=C(NO)NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1963.93
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_20	C[Si](C)(C)N[C@@H](CCCNC(=N)N(O)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	1866.04
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_21	C[Si](C)(C)N=C(NO)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1705.54
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_22	C[Si](C)(C)OC(=O)[C@@H](N)CCCN(C(=N)N(O)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2228.42
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_23	C[Si](C)(C)N=C(NCCC[C@H](N)C(=O)O[Si](C)(C)C)N(O)[Si](C)(C)C	standard polar	2025-10-24	1966.91
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_24	C[Si](C)(C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=N)NO	standard polar	2025-10-24	1866.11
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_25	C[Si](C)(C)N=C(NO)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1854.8
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_26	C[Si](C)(C)N(O)C(=N)NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2663.55
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_27	C[Si](C)(C)N=C(NO)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	1898.15
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_28	C[Si](C)(C)N[C@@H](CCCN(C(=N)N(O)[Si](C)(C)C)[Si](C)(C)C)C(=O)O	standard polar	2025-10-24	2329.42
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_29	C[Si](C)(C)N=C(NCCC[C@H](N[Si](C)(C)C)C(=O)O)N(O)[Si](C)(C)C	standard polar	2025-10-24	1789.67
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_30	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2197.08
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_31	C[Si](C)(C)OC(=O)[C@H](CCCN(C(=N)NO)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1512.14
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_32	C[Si](C)(C)N=C(NO)NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2191.94
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_33	C[Si](C)(C)OC(=O)[C@H](CCCNC(=N)N(O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2559.88
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_34	C[Si](C)(C)N=C(NO)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1184.59
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_35	C[Si](C)(C)N[C@@H](CCCN(C(=N)N(O)[Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2236.71
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_36	C[Si](C)(C)N=C(NCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)N(O)[Si](C)(C)C	standard polar	2025-10-24	2310.79
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_37	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@H](N)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2431.04
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_38	C[Si](C)(C)N=C(NO)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2094.67
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_39	C[Si](C)(C)N(O)C(=N)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2285.09
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_40	C[Si](C)(C)N=C(NCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)N(O)[Si](C)(C)C	standard polar	2025-10-24	905.553
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_41	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2349.93
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_42	C[Si](C)(C)N=C(NO)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2494.13
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_43	C[Si](C)(C)OC(=O)[C@H](CCCN(C(=N)N(O)[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2306.37
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_44	C[Si](C)(C)N=C(NCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)N(O)[Si](C)(C)C	standard polar	2025-10-24	1765.65
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_45	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2395.68
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_46	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1736.42
Gas Chromatography	N(omega)-Hydroxyarginine_TMS_47	C[Si](C)(C)N=C(N(O)[Si](C)(C)C)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	1695.92

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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/Eubacteria	Firmicutes	65	Human feces; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	1	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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:0x00007f2dfca5d5a8>

3D MOL for #<Metabolite:0x00007f2dfca5d5a8>

3D SDF for #<Metabolite:0x00007f2dfca5d5a8>

3D-SDF for #<Metabolite:0x00007f2dfca5d5a8>

PDB for #<Metabolite:0x00007f2dfca5d5a8>

3D PDB for #<Metabolite:0x00007f2dfca5d5a8>

SMILES for #<Metabolite:0x00007f2dfca5d5a8>

INCHI for #<Metabolite:0x00007f2dfca5d5a8>

Structure for #<Metabolite:0x00007f2dfca5d5a8>

3D Structure for #<Metabolite:0x00007f2dfca5d5a8>