Symmetric dimethylarginine (BioDeep_00000018367)
Secondary id: BioDeep_00000600559
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Chemicals and Drugs
代谢物信息卡片
化学式: C8H18N4O2 (202.1429688)
中文名称: 对称N,N-二甲基精氨酸, (对称+非对称)二甲基精氨酸, 对称二甲基精氨酸
谱图信息:
最多检出来源 Homo sapiens(blood) 1.56%
分子结构信息
SMILES: CN/C(=N/C)/NCCC[C@@H](C(=O)O)N
InChI: InChI=1S/C8H18N4O2/c1-10-8(11-2)12-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/t6-/m0/s1
描述信息
Symmetric dimethylarginine, also known as N,n-dimethylarginine or SDMA, is a L-arginine derivative having two methyl groups at the N(omega)- and N(omega)-positions It has a role as an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a member of guanidines, a non-proteinogenic L-alpha-amino acid, a L-arginine derivative and a dimethylarginine. It is a tautomer of a N(omega),N(omega)-dimethyl-L-arginine zwitterion. It 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. Symmetric dimethylarginine is a drug. Outside of the human body, symmetric dimethylarginine has been detected, but not quantified in pulses. Symmetric dimethylarginine (SDMA) is an endogenously produced inhibitor of nitric oxide synthase (EC-Number 1.14.13.39). However, elevated levels of Symmetric dimethylarginine occur in patients with vascular disease, especially suffering end-stage renal disease.
Isolated from broad bean (Vicia faba) seed proteins
SDMA (Symmetric dimethylarginine) is an endogenous inhibitor of nitric oxide (NO) synthase activity. SDMA, a novel kidney biomarker, permits earlier diagnosis of kidney disease than traditional creatinine testing.
同义名列表
27 个代谢物同义名
(2S)-2-amino-5-[(E)-N,N-dimethylcarbamimidamido]pentanoic acid; (2S)-2-Amino-5-(n,n-dimethylcarbamimidamido)pentanoic acid; (2S)-2-Amino-5-(n,n-dimethylcarbamimidamido)pentanoate; Symmetric dimethylarginine; NG,NG-Dimethyl-L-arginine; (S)-2-Amino-5-(n,n-dimethylguanidino)pentanoic acid; N5-((Methylamino)(methylimino)methyl)-L-ornithine; (S)-2-Amino-5-(n,n-dimethylguanidino)pentanoate; N(5)-[Bis(methylamino)methylene]-L-ornithine; N(5)-(N,N-dimethylcarbamimidoyl)-L-ornithine; N5-[Bis(methylamino)methylene]-L-ornithine; N(5)-(N,N-dimethylamidino)-L-ornithine; Guanidino-N(1),N(2)-dimethylarginine; N5-(N,N-dimethylamidino)-L-ornithine; Omega-N(g),n(g)-dimethylarginine; N(g),N(g)-dimethyl-L-arginine; N(3),N(4)-Dimethyl-L-arginine; N(g1),N(g2)-Dimethylarginine; N(g),N(g)-dimethylarginine; Symmetric dimethylarginine; N(3),N(4)-Dimethylarginine; NG,NG-dimethyl-L-arginine; N3, N4-dimethylarginine; NG,NG-dimethylarginine; N,N-dimethylarginine; SDMA arginine; SDMA; NG,NG'-Dimethyl-L-arginine
数据库引用编号
12 个数据库交叉引用编号
- ChEBI: CHEBI:25682
- PubChem: 4469587
- PubChem: 169148
- HMDB: HMDB0003334
- DrugBank: DB02302
- KNApSAcK: C00052415
- foodb: FDB000509
- chemspider: 147942
- CAS: 30344-00-4
- PMhub: MS000007259
- RefMet: Symmetric dimethylarginine
- medchemexpress: HY-101410
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
15 个相关的代谢反应过程信息。
Reactome(14)
- eNOS activation and regulation:
dihydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH4 ⟶ Tetrahydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH2
- eNOS activation and regulation:
dihydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH4 ⟶ Tetrahydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH2
- eNOS activation and regulation:
H+ + TPNH + sepiapterin ⟶ TPN + dihydrobiopterin
- eNOS activation and regulation:
dihydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH4 ⟶ Tetrahydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH2
- eNOS activation and regulation:
H+ + TPNH + sepiapterin ⟶ TPN + dihydrobiopterin
- eNOS activation and regulation:
dihydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH4 ⟶ Tetrahydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH2
- eNOS activation and regulation:
dihydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH4 ⟶ Tetrahydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH2
- eNOS activation and regulation:
dihydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH4 ⟶ Tetrahydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH2
- eNOS activation and regulation:
dihydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH4 ⟶ Tetrahydrobiopterin + p-S1177-eNOS:CaM:HSP90:p-AKT1:BH2
- Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA
- Metabolism of nitric oxide:
ADMA + H2O ⟶ DMA + L-Cit
- eNOS activation and regulation:
ADMA + H2O ⟶ DMA + L-Cit
- eNOS activation:
ADMA + H2O ⟶ DMA + L-Cit
- eNOS activation and regulation:
H+ + TPNH + sepiapterin ⟶ TPN + dihydrobiopterin
BioCyc(0)
WikiPathways(1)
- Nitric oxide metabolism in cystic fibrosis:
N ,N - dimethyl- L- arginine ⟶ Dimethylamine
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
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
- Yanzhe Wang, Ming Wu, Dongping Chen, Bo Tan, Pinglan Lin, Di Huang, Chaoyang Ye. SDMA attenuates renal tubulointerstitial fibrosis through inhibition of STAT4.
Journal of translational medicine.
2023 05; 21(1):326. doi:
10.1186/s12967-023-04181-9
. [PMID: 37194066] - Carolina Zaghi Cavalcante, Pedro Vicente Michelotto, Luiz Guilherme Achnar Capriglione, Andressa Thais Roncoski, Anita Nishiyama. Weight loss modifies lipid peroxidation and symmetric dimethylarginine levels in obese dogs.
Canadian journal of veterinary research = Revue canadienne de recherche veterinaire.
2023 Jan; 87(1):29-34. doi:
"
. [PMID: 36606041] - Ceren Eyileten, Aleksandra Gasecka, Anna Nowak, Joanna Jarosz-Popek, Marta Wolska, Al-Medina Dizdarevic, Irene M Lang, Marek Postula, Marcin Ufnal, Jolanta M Siller-Matula. High concentration of symmetric dimethylarginine is associated with low platelet reactivity and increased bleeding risk in patients with acute coronary syndrome.
Thrombosis research.
2022 05; 213(?):195-202. doi:
10.1016/j.thromres.2022.03.025
. [PMID: 35398728] - Helen Michael, Donald Szlosek, Celeste Clements, Rebekah Mack. Symmetrical Dimethylarginine: Evaluating Chronic Kidney Disease in the Era of Multiple Kidney Biomarkers.
The Veterinary clinics of North America. Small animal practice.
2022 May; 52(3):609-629. doi:
10.1016/j.cvsm.2022.01.003
. [PMID: 35379500] - Beata Csiszar, Zsolt Marton, Janos Riba, Peter Csecsei, Lajos Nagy, Kalman Toth, Robert Halmosi, Barbara Sandor, Peter Kenyeres, Tihamer Molnar. L-arginine, asymmetric and symmetric dimethylarginine for early outcome prediction in unselected cardiac arrest victims: a prospective cohort study.
Internal and emergency medicine.
2022 03; 17(2):525-534. doi:
10.1007/s11739-021-02767-z
. [PMID: 34080121] - Andrew C Cushing, Rachel Murphy, Donald Szlosek, Vanessa Gauger, Michael J Coyne, Edward Obare. METHOD COMPARISON FOR MEASUREMENT OF SYMMETRIC DIMETHYLARGININE IN TIGERS (PANTHERA TIGRIS).
Journal of zoo and wildlife medicine : official publication of the American Association of Zoo Veterinarians.
2022 Mar; 53(1):200-203. doi:
10.1638/2021-0067
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Kidney360.
2022 02; 3(2):341-356. doi:
10.34067/kid.0006542020
. [PMID: 35373128] - Beatrice Hanusch, Kathrin Sinningen, Folke Brinkmann, Stefanie Dillenhöfer, Mirjam Frank, Karl-Heinz Jöckel, Cordula Koerner-Rettberg, Martin Holtmann, Tanja Legenbauer, Christian Langrock, Thomas Reinehr, Patricia Maasjosthusmann, Bibiana Beckmann, Eckard Hamelmann, Dimitrios Tsikas, Thomas Lücke. Characterization of the L-Arginine/Nitric Oxide Pathway and Oxidative Stress in Pediatric Patients with Atopic Diseases.
International journal of molecular sciences.
2022 Feb; 23(4):. doi:
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. [PMID: 35216250] - Youssef M Y Elgazzar, Mohamed M Ghanem, Yassein M Abdel-Raof, Mohamed M M Kandiel, Mahmoud A Y Helal. Evaluation of symmetric dimethylarginine and Doppler ultrasonography in the diagnosis of gentamicin-induced acute kidney injury in dogs.
Environmental science and pollution research international.
2022 Feb; 29(6):8779-8789. doi:
10.1007/s11356-021-16086-5
. [PMID: 34490572] - Rebecca Kohnken, Lauren Himmel, Michael Logan, Richard Peterson, Sabyasachi Biswas, Christina Dunn, Bruce LeRoy. Symmetric Dimethylarginine Is a Sensitive Biomarker of Glomerular Injury in Rats.
Toxicologic pathology.
2022 02; 50(2):176-185. doi:
10.1177/01926233211045341
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Cardiovascular diabetology.
2022 01; 21(1):4. doi:
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PloS one.
2022; 17(5):e0269085. doi:
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. [PMID: 35622875] - Jose I Casado Díaz, Nadja S Sieber-Ruckstuhl, Felicitas S Boretti, Federico Fracassi, Claudia E Reusch. Evaluation of symmetric dimethylarginine and creatinine in dogs with primary hypoadrenocorticism receiving long-term mineralocorticoid replacement therapy.
The Veterinary record.
2022 Jan; 190(1):e242. doi:
10.1002/vetr.242
. [PMID: 33870518] - Rana Bozorgmanesh, Jessica Thornton, Jackie Snyder, Caitlin Fletcher, Rebekah Mack, Michael Coyne, Rachel Murphy, Evan Hegarty, Nathan Slovis. Symmetric dimethylarginine concentrations in healthy neonatal foals and mares.
Journal of veterinary internal medicine.
2021 Nov; 35(6):2891-2896. doi:
10.1111/jvim.16295
. [PMID: 34738665] - C Guillermo Couto, Rachel Murphy, Michael Coyne, Corie Drake. Serum Symmetric Dimethylarginine Concentration in Greyhound Pups and Adults.
Topics in companion animal medicine.
2021 Nov; 45(?):100558. doi:
10.1016/j.tcam.2021.100558
. [PMID: 34246821] - Hüseyin Korkmaz, Mehmet Asıl, Tuncer Temel, Bahadır Öztürk, Levent Kebapçılar. Evaluation of serum neutrophil gelatinase-associated lipocalin (NGAL), asymmetric dimethylarginine (ADMA) and symmetric dimethylarginine (SDMA) levels, and their relations with disease type and activity in inflammatory bowel diseases.
Turkish journal of medical sciences.
2021 10; 51(5):2403-2412. doi:
10.3906/sag-2103-220
. [PMID: 33984894] - R M Mack, E Hegarty, D J McCrann, H T Michael, G F Grauer. Longitudinal evaluation of symmetric dimethylarginine and concordance of kidney biomarkers in cats and dogs.
Veterinary journal (London, England : 1997).
2021 Oct; 276(?):105732. doi:
10.1016/j.tvjl.2021.105732
. [PMID: 34391920] - Randolph M Baral, Kathleen P Freeman, Bente Flatland. Comparison of serum and plasma SDMA measured with point-of-care and reference laboratory analysers: implications for interpretation of SDMA in cats.
Journal of feline medicine and surgery.
2021 10; 23(10):906-920. doi:
10.1177/1098612x20983260
. [PMID: 33544013] - Juliette Raulic, Benjamin Lamglait, Claire Vergneau-Grosset. USE OF SYMMETRIC DIMETHYLARGININE TO DETECT RENAL LESIONS IN FISH: A PRELIMINARY STUDY IN BROOK TROUT (SALVELINUS FONTINALIS).
Journal of zoo and wildlife medicine : official publication of the American Association of Zoo Veterinarians.
2021 Sep; 52(3):1024-1029. doi:
10.1638/2020-0218
. [PMID: 34687520] - Mark A McEvoy, John R Attia, Christopher Oldmeadow, Elizabeth Holliday, Wayne T Smith, Arduino A Mangoni, Roseanne Peel, Stephen J Hancock, Marjorie M Walker, Nicholas J Talley. Serum L-arginine and endogenous methylarginine concentrations predict irritable bowel syndrome in adults: A nested case-control study.
United European gastroenterology journal.
2021 09; 9(7):809-818. doi:
10.1002/ueg2.12137
. [PMID: 34431615] - Marius M Mader, Rainer Böger, Daniel Appel, Edzard Schwedhelm, Munif Haddad, Malte Mohme, Katrin Lamszus, Manfred Westphal, Patrick Czorlich, Juliane Hannemann. Intrathecal and systemic alterations of L-arginine metabolism in patients after intracerebral hemorrhage.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism.
2021 08; 41(8):1964-1977. doi:
10.1177/0271678x20983216
. [PMID: 33461409] - Stéphanie M Mota, João Brandão, Amanda Guthrie. COMPARISON OF BLOOD SYMMETRIC DIMETHYLARGININE AND CREATININE AS ENDOGENOUS MARKERS OF KIDNEY FUNCTION IN CAPTIVE TIGERS (PANTHERA TIGRIS).
Journal of zoo and wildlife medicine : official publication of the American Association of Zoo Veterinarians.
2021 Jun; 52(2):628-637. doi:
10.1638/2020-0032
. [PMID: 34130406] - Juliane Hannemann, Paul Balfanz, Edzard Schwedhelm, Bojan Hartmann, Johanna Ule, Dirk Müller-Wieland, Edgar Dahl, Michael Dreher, Nikolaus Marx, Rainer Böger. Elevated serum SDMA and ADMA at hospital admission predict in-hospital mortality of COVID-19 patients.
Scientific reports.
2021 05; 11(1):9895. doi:
10.1038/s41598-021-89180-w
. [PMID: 33972591] - Hannah J Harjen, Tove V Nicolaysen, Tale Negard, Hege Lund, Bente K Sævik, Kristin P Anfinsen, Elena R Moldal, Karin E Zimmer, Runa Rørtveit. Serial serum creatinine, SDMA and urinary acute kidney injury biomarker measurements in dogs envenomated by the European adder (Vipera berus).
BMC veterinary research.
2021 Apr; 17(1):154. doi:
10.1186/s12917-021-02851-8
. [PMID: 33845861] - Adrian Post, Alexander Bollenbach, Stephan J L Bakker, Dimitrios Tsikas. Whole-body arginine dimethylation is associated with all-cause mortality in adult renal transplant recipients.
Amino acids.
2021 Apr; 53(4):541-554. doi:
10.1007/s00726-021-02965-1
. [PMID: 33651245] - Petr Tůma, Blanka Sommerová, Dušan Koval, François Couderc. Electrophoretic Determination of Symmetric and Asymmetric Dimethylarginine in Human Blood Plasma with Whole Capillary Sample Injection.
International journal of molecular sciences.
2021 Mar; 22(6):. doi:
10.3390/ijms22062970
. [PMID: 33804011] - Corie Drake, Michael Coyne, Donald J McCrann, Jesse Buch, Rebekah Mack. Risk of Development of Chronic Kidney Disease After Exposure to Borrelia burgdorferi and Anaplasma spp.
Topics in companion animal medicine.
2021 Mar; 42(?):100491. doi:
10.1016/j.tcam.2020.100491
. [PMID: 33152525] - Harold C Schott, Lisanne R Gallant, Michael Coyne, Rachel Murphy, Julie Cross, Marilyn Strong-Townsend, Donald Szlosek, Maha Yerramilli, Jun Li. Symmetric dimethylarginine and creatinine concentrations in serum of healthy draft horses.
Journal of veterinary internal medicine.
2021 Mar; 35(2):1147-1154. doi:
10.1111/jvim.16042
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Acta biochimica Polonica.
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Journal of veterinary cardiology : the official journal of the European Society of Veterinary Cardiology.
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The Journal of small animal practice.
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Hormone molecular biology and clinical investigation.
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Acta veterinaria Scandinavica.
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PloS one.
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Viruses.
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Microvascular research.
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Veterinary clinical pathology.
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. [PMID: 32677951] - Lucia Yu, Lauren Lacorcia, Sue Finch, Thurid Johnstone. Assessment of serum symmetric dimethylarginine and creatinine concentrations in hyperthyroid cats before and after a fixed dose of orally administered radioiodine.
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. [PMID: 32506701] - N Speight, M Gates, J Scriven, T Stephenson, L Woolford. Symmetric dimethylarginine values in koalas (Phascolarctos cinereus) based on oxalate nephrosis status.
Australian veterinary journal.
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. [PMID: 32189333] - Stefanie M DeMonaco, David L Panciera, Wendy A Morre, Tina Conway, Stephen Werre. Symmetric dimethylarginine in hyperthyroid cats before and after treatment with radioactive iodine.
Journal of feline medicine and surgery.
2020 06; 22(6):531-538. doi:
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. [PMID: 31290362] - Yaya Goïta, Juan Manuel Chao de la Barca, Asmaou Keïta, Mamadou Bocary Diarra, Klétigui Casimir Dembélé, Floris Chabrun, Boubacar Sidiki Ibrahim Dramé, Yaya Kassogué, Mahamadou Diakité, Delphine Mirebeau-Prunier, Bakary Mamadou Cissé, Gilles Simard, Pascal Reynier. Sexual Dimorphism of Metabolomic Profile in Arterial Hypertension.
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