N(omega)-Hydroxyarginine (BioDeep_00000006006)
Secondary id: BioDeep_00001869001
human metabolite Endogenous
代谢物信息卡片
化学式: C6H14N4O3 (190.1066)
中文名称: L-羟基精氨酸
谱图信息:
最多检出来源 Homo sapiens(otcml) 10.32%
分子结构信息
SMILES: C(CC(C(=O)O)N)CN=C(N)NO
InChI: 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)
描述信息
N-omega-hydroxy-l-arginine, also known as 6-noha, belongs to arginine and derivatives class of compounds. Those 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. N-omega-hydroxy-l-arginine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). N-omega-hydroxy-l-arginine can be found in a number of food items such as chinese cinnamon, chervil, sugar apple, and safflower, which makes N-omega-hydroxy-l-arginine a potential biomarker for the consumption of these food products.
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).
同义名列表
17 个代谢物同义名
(2S)-2-amino-5-[(Z)-N-hydroxycarbamimidamido]pentanoic acid; N5-[(Hydroxyamino)iminomethyl]-L-ornithine; N(Omega)-hydroxy-L-arginine; N-OMEGA-hydroxy-L-arginine; N-(omega)-Hydroxyarginine; N(omega)-Hydroxyarginine; N(Ω)-hydroxy-L-arginine; N(g)-Hydroxy-L-arginine; Nomega-hydroxyarginine; NG-Hydroxy-L-arginine; Nω-hydroxy-L-arginine; N-(o)-Hydroxyarginine; N-(G)-Hydroxyarginine; N(Ω)-hydroxyarginine; 6-NOHA; N(omega)-Hydroxyarginine; L-Hydroxyarginine
数据库引用编号
29 个数据库交叉引用编号
- ChEBI: CHEBI:47822
- ChEBI: CHEBI:47825
- ChEBI: CHEBI:47826
- ChEBI: CHEBI:43088
- ChEBI: CHEBI:47819
- ChEBI: CHEBI:47821
- ChEBI: CHEBI:47827
- ChEBI: CHEBI:7101
- KEGG: C05933
- PubChem: 123895
- PubChem: 440849
- PubChem: 43088
- HMDB: HMDB0004224
- Metlin: METLIN58229
- DrugBank: DB03144
- ChEMBL: CHEMBL323186
- ChEMBL: CHEMBL260629
- MetaCyc: CPD-13518
- foodb: FDB031063
- chemspider: 110427
- CAS: 53054-07-2
- PMhub: MS000018926
- PubChem: 8221
- PDB-CCD: HAR
- 3DMET: B05141
- NIKKAJI: J390.553E
- KNApSAcK: 7101
- LOTUS: LTS0248676
- wikidata: Q27088084
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
38 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(38)
- Arginine and Proline Metabolism:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Prolidase Deficiency (PD):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperprolinemia Type II:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperprolinemia Type I:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Prolinemia Type II:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Ornithine Aminotransferase Deficiency (OAT Deficiency):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Creatine Deficiency, Guanidinoacetate Methyltransferase Deficiency:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperornithinemia with Gyrate Atrophy (HOGA):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome]:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- L-Arginine:Glycine Amidinotransferase Deficiency:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Arginine and Proline Metabolism:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Arginine and Proline Metabolism:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperprolinemia Type I:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperprolinemia Type II:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Ornithine Aminotransferase Deficiency (OAT Deficiency):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Prolinemia Type II:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Prolidase Deficiency (PD):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Creatine Deficiency, Guanidinoacetate Methyltransferase Deficiency:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperornithinemia with Gyrate Atrophy (HOGA):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome]:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- L-Arginine:Glycine Amidinotransferase Deficiency:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Arginine and Proline Metabolism:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Arginine and Proline Metabolism:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperprolinemia Type I:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperprolinemia Type II:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Ornithine Aminotransferase Deficiency (OAT Deficiency):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Prolinemia Type II:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Prolidase Deficiency (PD):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Creatine Deficiency, Guanidinoacetate Methyltransferase Deficiency:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperornithinemia with Gyrate Atrophy (HOGA):
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome]:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
- L-Arginine:Glycine Amidinotransferase Deficiency:
Guanidoacetic acid + S-Adenosylmethionine ⟶ Creatine + S-Adenosylhomocysteine
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
文献列表
- Rym Attia, Andy Zedet, Mélanie Bourjot, Eya Skhiri, Chokri Messaoud, Corine Girard. Thin-layer chromatography-bioautographic method for the detection of arginase inhibitors.
Journal of separation science.
2020 Jun; 43(12):2477-2486. doi:
10.1002/jssc.201901210
. [PMID: 32233066] - Alexander Bollenbach, Stephan J L Bakker, Dimitrios Tsikas. GC-MS measurement of biological NG-hydroxy-L-arginine, a stepmotherly investigated endogenous nitric oxide synthase substrate and arginase inhibitor.
Amino acids.
2019 Apr; 51(4):627-640. doi:
10.1007/s00726-018-02695-x
. [PMID: 30610471] - Alexander Bollenbach, Dimitrios Tsikas. Pharmacological activation of dimethylarginine dimethylaminohydrolase (DDAH) activity by inorganic nitrate and DDAH inhibition by NG-hydroxy-L-arginine, Nω,Nω-dimethyl-L-citrulline and Nω,Nω-dimethyl-Nδ-hydroxy-L-citrulline: results and overview.
Amino acids.
2019 Mar; 51(3):483-494. doi:
10.1007/s00726-018-2684-6
. [PMID: 30536052] - Alexander Bollenbach, Erik Hanff, Dimitrios Tsikas. Investigation of NG-hydroxy-l-arginine interference in the quantitative determination of nitrite and nitrate in human plasma and urine by GC-NICI-MS.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2018 Nov; 1100-1101(?):174-178. doi:
10.1016/j.jchromb.2018.10.007
. [PMID: 30340066] - Qingzhi Zhang, Philip Milliken, Agnieszka Kulczynska, Alex M Z Slawin, Adele Gordon, Nicholas S Kirkby, David J Webb, Nigel P Botting, Ian L Megson. Development and characterization of glutamyl-protected N-hydroxyguanidines as reno-active nitric oxide donor drugs with therapeutic potential in acute renal failure.
Journal of medicinal chemistry.
2013 Jul; 56(13):5321-34. doi:
10.1021/jm400146r
. [PMID: 23782349] - Nasser Samadi, Raie T Bekele, Ing Swie Goping, Luis M Schang, David N Brindley. Lysophosphatidate induces chemo-resistance by releasing breast cancer cells from taxol-induced mitotic arrest.
PloS one.
2011; 6(5):e20608. doi:
10.1371/journal.pone.0020608
. [PMID: 21647386] - Gregory J Kato, Zeneng Wang, Roberto F Machado, William C Blackwelder, James G Taylor, Stanley L Hazen. Endogenous nitric oxide synthase inhibitors in sickle cell disease: abnormal levels and correlations with pulmonary hypertension, desaturation, haemolysis, organ dysfunction and death.
British journal of haematology.
2009 May; 145(4):506-13. doi:
10.1111/j.1365-2141.2009.07658.x
. [PMID: 19344390] - David J Tate, Derek J Vonderhaar, Yupanqui A Caldas, Toye Metoyer, John R Patterson, Diego H Aviles, Arnold H Zea. Effect of arginase II on L-arginine depletion and cell growth in murine cell lines of renal cell carcinoma.
Journal of hematology & oncology.
2008 Sep; 1(?):14. doi:
10.1186/1756-8722-1-14
. [PMID: 18817562] - Hui Chen, Bonnie C McCaig, Maeli Melotto, Sheng Yang He, Gregg A Howe. Regulation of plant arginase by wounding, jasmonate, and the phytotoxin coronatine.
The Journal of biological chemistry.
2004 Oct; 279(44):45998-6007. doi:
10.1074/jbc.m407151200
. [PMID: 15322128] - David E Ash. Structure and function of arginases.
The Journal of nutrition.
2004 10; 134(10 Suppl):2760S-2764S; discussion 2765S. doi:
10.1093/jn/134.10.2760s
. [PMID: 15465781] - Johan A Kers, Michael J Wach, Stuart B Krasnoff, Joanne Widom, Kimberly D Cameron, Raghida A Bukhalid, Donna M Gibson, Brian R Crane, Rosemary Loria. Nitration of a peptide phytotoxin by bacterial nitric oxide synthase.
Nature.
2004 May; 429(6987):79-82. doi:
10.1038/nature02504
. [PMID: 15129284] - N Yasuda, K Moriwaki, S Furuyama. Distribution and properties of arginase in the salivary glands of four species of laboratory mammals.
Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology.
2004 Apr; 174(3):237-42. doi:
10.1007/s00360-003-0407-z
. [PMID: 14712329] - Mona Lotfy Zamzam, Manal Mohamed Yassin, Maha Mohamed Sallam. Implication of intercellular adhesion molecule-1 (ICAM-1) and serum N(G)-hydroxy-L-arginine (L-NHA) in the pathogenesis of systemic sclerosis.
The Egyptian journal of immunology.
2003; 10(2):27-38. doi:
. [PMID: 15719609]
- R B Muijsers, N H ten Hacken, I Van Ark, G Folkerts, F P Nijkamp, D S Postma. L-Arginine is not the limiting factor for nitric oxide synthesis by human alveolar macrophages in vitro.
The European respiratory journal.
2001 Oct; 18(4):667-71. doi:
10.1183/09031936.01.00101301
. [PMID: 11716172] - C D Garlichs, J Beyer, H Zhang, A Schmeisser, K Plötze, A Mügge, S Schellong, W G Daniel. Decreased plasma concentrations of L-hydroxy-arginine as a marker of reduced NO formation in patients with combined cardiovascular risk factors.
The Journal of laboratory and clinical medicine.
2000 May; 135(5):419-25. doi:
10.1067/mlc.2000.105975
. [PMID: 10811058] - S N Waddington, F W Tam, H T Cook, V Cattell. Arginase activity is modulated by IL-4 and HOArg in nephritic glomeruli and mesangial cells.
The American journal of physiology.
1998 03; 274(3):F473-80. doi:
10.1152/ajprenal.1998.274.3.f473
. [PMID: 9530263] - R Wigand, J Meyer, R Busse, M Hecker. Increased serum NG-hydroxy-L-arginine in patients with rheumatoid arthritis and systemic lupus erythematosus as an index of an increased nitric oxide synthase activity.
Annals of the rheumatic diseases.
1997 May; 56(5):330-2. doi:
10.1136/ard.56.5.330
. [PMID: 9175936] - J Meyer, N Richter, M Hecker. High-performance liquid chromatographic determination of nitric oxide synthase-related arginine derivatives in vitro and in vivo.
Analytical biochemistry.
1997 Apr; 247(1):11-6. doi:
10.1006/abio.1997.2008
. [PMID: 9126364] - M Hecker, C Schott, B Bucher, R Busse, J C Stoclet. Increase in serum NG-hydroxy-L-arginine in rats treated with bacterial lipopolysaccharide.
European journal of pharmacology.
1995 Feb; 275(1):R1-3. doi:
10.1016/0014-2999(95)00046-n
. [PMID: 7539764] - K L Campos, J Giovanelli, S Kaufman. Characteristics of the nitric oxide synthase-catalyzed conversion of arginine to N-hydroxyarginine, the first oxygenation step in the enzymic synthesis of nitric oxide.
The Journal of biological chemistry.
1995 Jan; 270(4):1721-8. doi:
10.1074/jbc.270.4.1721
. [PMID: 7530247]