D-Aspartic acid (BioDeep_00000014567)

Main id: BioDeep_00000398115

Secondary id: BioDeep_00000405607

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 natural product


代谢物信息卡片


(2R)-2-Aminobutanedioic acid

化学式: C4H7NO4 (133.0375)
中文名称: D-天冬氨酸, D-天门冬氨酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(C(C(=O)O)N)C(=O)O
InChI: InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m1/s1

描述信息

D-Aspartic acid is the D-isomer of aspartic acid. Since its discovery in invertebrates, free D-aspartate (D-Asp) has been identified in a variety of organisms, including microorganisms, plants, and lower animals, mammals and humans. D-Asp in mammalian tissues is present in specific cells, indicating the existence of specific molecular components that regulate D-Asp levels and localization in tissues. In the rat adrenal medulla, D-Asp is closely associated with adrenaline-cells (A-cells), which account for approximately 80\\\\\\% of the total number of chromaffin cells in the tissue, and which make and store adrenaline. D-Asp appears to be absent from noradrenaline-cells (NA-cells), which comprise approximately 20\\\\\\% of the total number of chromaffin cells in the adrenal medulla, and which make and store noradrenaline. D-aspartate oxidase (EC 1.4.3.1, D-AspO), which catalyzes oxidative deamination of D-Asp, appears to be present only in NA-cells, suggesting that the lack of D-Asp in these cells is due to D-Asp oxidase-mediated metabolism of D-Aspecies In the rat adrenal cortex, the distribution of D-Asp changes during development. It has been suggested that developmental changes in the localization of D-Asp reflects the participation of D-Asp in the development and maturation of steroidogenesis in rat adrenal cortical cells. D-Asp is involved in steroid hormone synthesis and secretion in mammals as well. D-Asp is synthesized intracellularly, most likely by Asp racemase (EC 5.1.1.13). Endogenous D-Asp apparently has two different intracellular localization patterns: cytoplasmic and vesicular. D-Asp release can occur through three distinct pathways: 1) spontaneous, continuous release of cytoplasmic D-Asp, which is not associated with a specific stimulus; 2) release of cytoplasmic D-Asp via a volume-sensitive organic anion channel that connects the cytoplasm and extracellular space; 3) exocytotic discharge of vesicular D-Aspecies D-Asp can be released via a mechanism that involves the L-Glu transporter. D-Asp is thus apparently in dynamic flux at the cellular level to carry out its physiological function(s) in mammals. (PMID: 16755369) [HMDB]
D-Aspartic acid is the D-isomer of aspartic acid. Since its discovery in invertebrates, free D-aspartate (D-Asp) has been identified in a variety of organisms, including microorganisms, plants, and lower animals, mammals and humans. D-Asp in mammalian tissues is present in specific cells, indicating the existence of specific molecular components that regulate D-Asp levels and localization in tissues. In the rat adrenal medulla, D-Asp is closely associated with adrenaline-cells (A-cells), which account for approximately 80\\\\\\% of the total number of chromaffin cells in the tissue, and which make and store adrenaline. D-Asp appears to be absent from noradrenaline-cells (NA-cells), which comprise approximately 20\\\\\\% of the total number of chromaffin cells in the adrenal medulla, and which make and store noradrenaline. D-aspartate oxidase (EC 1.4.3.1, D-AspO), which catalyzes oxidative deamination of D-Asp, appears to be present only in NA-cells, suggesting that the lack of D-Asp in these cells is due to D-Asp oxidase-mediated metabolism of D-Asp. In the rat adrenal cortex, the distribution of D-Asp changes during development. It has been suggested that developmental changes in the localization of D-Asp reflects the participation of D-Asp in the development and maturation of steroidogenesis in rat adrenal cortical cells. D-Asp is involved in steroid hormone synthesis and secretion in mammals as well. D-Asp is synthesized intracellularly, most likely by Asp racemase (EC 5.1.1.13). Endogenous D-Asp apparently has two different intracellular localization patterns: cytoplasmic and vesicular. D-Asp release can occur through three distinct pathways: 1) spontaneous, continuous release of cytoplasmic D-Asp, which is not associated with a specific stimulus; 2) release of cytoplasmic D-Asp via a volume-sensitive organic anion channel that connects the cytoplasm and extracellular space; 3) exocytotic discharge of vesicular D-Asp. D-Asp can be released via a mechanism that involves the L-Glu transporter. D-Asp is thus apparently in dynamic flux at the cellular level to carry out its physiological function(s) in mammals (PMID:16755369).
(-)-Aspartic acid is an endogenous NMDA receptor agonist.
(-)-Aspartic acid is an endogenous NMDA receptor agonist.
(-)-Aspartic acid is an endogenous NMDA receptor agonist.
(-)-Aspartic acid is an endogenous NMDA receptor agonist.

同义名列表

29 个代谢物同义名

(2R)-2-Aminobutanedioic acid; (R)-2-Aminobutanedioic acid; (R)-(-)-Aminosuccinic acid; 1-amino-1,2-Carboxyethane; (R)-2-Aminosuccinic acid; (2R)-2-Aminobutanedioate; (R)-2-Aminobutanedioate; delta-(-)-Aspartic acid; delta-Asparaginsaeure; (R)-2-Aminosuccinate; Aspartic acid D-form; D-(-)-Aspartic acid; delta-Aspartic acid; (-)-Aspartic acid; (R)-Aspartic acid; D-Asparaginsaeure; Lopac-alpha-9256; Aspartate D-form; delta-Aspartate; D Aspartic acid; D-Aspartic acid; Aspartic Acid; Tocris-0213; D Aspartate; D-Aspartate; H-D-Asp-OH; DAS; D-Aspartate; D-Aspartic acid



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(3)

BioCyc(0)

PlantCyc(0)

代谢反应

49 个相关的代谢反应过程信息。

Reactome(36)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(12)

PharmGKB(0)

338 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。

亚细胞结构定位 关联基因列表


文献列表

  • Debora Latino, Massimo Venditti, Sara Falvo, Giulia Grillo, Alessandra Santillo, Imed Messaoudi, Mariem Ben Rhouma, Sergio Minucci, Gabriella Chieffi Baccari, Maria Maddalena Di Fiore. Steroidogenesis Upregulation through Mitochondria-Associated Endoplasmic Reticulum Membranes and Mitochondrial Dynamics in Rat Testes: The Role of D-Aspartate. Cells. 2024 Mar; 13(6):. doi: 10.3390/cells13060523. [PMID: 38534366]
  • Chenyu Wang, Le Huang, Shunshun Jin, Ruoxin Hou, Mingzhe Chen, Yonghui Liu, Wenjie Tang, Tiejun Li, Yulong Yin, Liuqin He. d-Aspartate in Low-Protein Diets Improves the Pork Quality by Regulating Energy and Lipid Metabolism via the Gut Microbes. Journal of agricultural and food chemistry. 2023 Aug; 71(33):12417-12430. doi: 10.1021/acs.jafc.3c01974. [PMID: 37578298]
  • Dawei Chen, Yating Liang, Jiaojiao Liang, Feifei Shen, Yue Cheng, Hengxian Qu, Yunchao Wa, Congcong Guo, Ruixia Gu, Jianya Qian, Xia Chen, Chenchen Zhang, Chengran Guan. Beneficial effects of Lactobacillus rhamnosus hsryfm 1301 fermented milk on rats with nonalcoholic fatty liver disease. Journal of dairy science. 2023 Mar; 106(3):1533-1548. doi: 10.3168/jds.2022-22383. [PMID: 36710180]
  • Giulia Murtas, Loredano Pollegioni. D-amino Acids as Novel Blood-based Biomarkers. Current medicinal chemistry. 2022; 29(24):4202-4215. doi: 10.2174/0929867328666211125092438. [PMID: 34823459]
  • Tommaso Nuzzo, Masae Sekine, Daniela Punzo, Mattia Miroballo, Masumi Katane, Yasuaki Saitoh, Alberto Galbusera, Massimo Pasqualetti, Francesco Errico, Alessandro Gozzi, Jean-Pierre Mothet, Hiroshi Homma, Alessandro Usiello. Dysfunctional d-aspartate metabolism in BTBR mouse model of idiopathic autism. Biochimica et biophysica acta. Proteins and proteomics. 2020 12; 1868(12):140531. doi: 10.1016/j.bbapap.2020.140531. [PMID: 32853769]
  • Qixia Shen, Wenyu Xiang, Sen Ye, Xin Lei, Lefeng Wang, Sha Jia, Xue Shao, Chunhua Weng, Xiujin Shen, Yucheng Wang, Shi Feng, Lihui Qu, Cuili Wang, Jianghua Chen, Ping Zhang, Hong Jiang. Plasma metabolite biomarkers related to secondary hyperparathyroidism and parathyroid hormone. Journal of cellular biochemistry. 2019 09; 120(9):15766-15775. doi: 10.1002/jcb.28846. [PMID: 31069832]
  • Blair Crewther, Konrad Witek, Paweł Draga, Piotr Zmijewski, Zbigniew Obmiński. Short-Term d-Aspartic Acid Supplementation Does Not Affect Serum Biomarkers Associated With the Hypothalamic-Pituitary-Gonadal Axis in Male Climbers. International journal of sport nutrition and exercise metabolism. 2019 May; 29(3):259-264. doi: 10.1123/ijsnem.2018-0076. [PMID: 29893592]
  • Jumpei Sasabe, Masataka Suzuki. Distinctive Roles of D-Amino Acids in the Homochiral World: Chirality of Amino Acids Modulates Mammalian Physiology and Pathology. The Keio journal of medicine. 2019 Mar; 68(1):1-16. doi: 10.2302/kjm.2018-0001-ir. [PMID: 29794368]
  • Mahdi Goudarzvand, Yaser Panahi, Reza Yazdani, Hosein Miladi, Saeed Tahmasebi, Amin Sherafat, Sanaz Afraei, Kosar Abouhamzeh, Mahnaz Jamee, Kawthar Jasim Mohammad Rida Al-Hussieni, Hamed Mohammadi, Ali Mohebbi, Nikoo Hossein-Khannazer, Majid Zaki-Dizaji, Maria Maddalena Di Fiore, Antimo D'Aniello, Gholamreza Azizi. The Effects of D-aspartate on Neurosteroids, Neurosteroid Receptors, and Inflammatory Mediators in Experimental Autoimmune Encephalomyelitis. Endocrine, metabolic & immune disorders drug targets. 2019; 19(3):316-325. doi: 10.2174/1871530318666181005093459. [PMID: 30289086]
  • Mahdi Ansari, Mahdi Zhandi, Hamid Kohram, Mojtaba Zaghari, Mostafa Sadeghi, Maedeh Gholami, Hamid Deldar, Maria Maddalena Di Fiore, Andrew Parks Benson. D-Aspartate amends reproductive performance of aged roosters by changing gene expression and testicular histology. Reproduction, fertility, and development. 2018 Jun; 30(7):1038-1048. doi: 10.1071/rd17072. [PMID: 31039968]
  • Kazuma Ogawa, Atsushi Ishizaki, Kenichiro Takai, Yoji Kitamura, Akira Makino, Takashi Kozaka, Yasushi Kiyono, Kazuhiro Shiba, Akira Odani. Evaluation of Ga-DOTA-(D-Asp)n as bone imaging agents: D-aspartic acid peptides as carriers to bone. Scientific reports. 2017 10; 7(1):13971. doi: 10.1038/s41598-017-14149-7. [PMID: 29070853]
  • P H Do, P V Tran, M A Bahry, H Yang, G Han, A Tsuchiya, Y Asami, M Furuse, V S Chowdhury. Oral administration of a medium containing both D-aspartate-producing live bacteria and D-aspartate reduces rectal temperature in chicks. British poultry science. 2017 Oct; 58(5):569-577. doi: 10.1080/00071668.2017.1335858. [PMID: 28548864]
  • Sanaz Afraei, Antimo D'Aniello, Reza Sedaghat, Parvin Ekhtiari, Gholamreza Azizi, Nakisa Tabrizian, Laura Magliozzi, Zahra Aghazadeh, Abbas Mirshafiey. Therapeutic effects of D-aspartate in a mouse model of multiple sclerosis. Journal of food and drug analysis. 2017 Jul; 25(3):699-708. doi: 10.1016/j.jfda.2016.10.025. [PMID: 28911655]
  • Filippo Giacone, Rosita A Condorelli, Laura M Mongioì, Valentina Bullara, Sandro La Vignera, Aldo E Calogero. In vitro effects of zinc, D-aspartic acid, and coenzyme-Q10 on sperm function. Endocrine. 2017 May; 56(2):408-415. doi: 10.1007/s12020-016-1013-7. [PMID: 27422792]
  • Vincenza Barbato, Riccardo Talevi, Sabrina Braun, Anna Merolla, Sam Sudhakaran, S Longobardi, Roberto Gualtieri. Supplementation of sperm media with zinc, D-aspartate and co-enzyme Q10 protects bull sperm against exogenous oxidative stress and improves their ability to support embryo development. Zygote (Cambridge, England). 2017 Apr; 25(2):168-175. doi: 10.1017/s0967199416000459. [PMID: 28264757]
  • Mahdi Ansari, Mahdi Zhandi, Hamid Kohram, Mojtaba Zaghari, Mostafa Sadeghi, Mohsen Sharafi. Improvement of post-thawed sperm quality and fertility of Arian rooster by oral administration of d-aspartic acid. Theriogenology. 2017 Apr; 92(?):69-74. doi: 10.1016/j.theriogenology.2017.01.014. [PMID: 28237346]
  • Zhenxia Qin, Jeff X Zhu, Dana W Aswad. The D-isoAsp-25 variant of histone H2B is highly enriched in active chromatin: potential role in the regulation of gene expression?. Amino acids. 2016 Feb; 48(2):599-603. doi: 10.1007/s00726-015-2140-9. [PMID: 26666674]
  • Sachise Karakawa, Kazutaka Shimbo, Naoyuki Yamada, Toshimi Mizukoshi, Hiroshi Miyano, Masashi Mita, Wolfgang Lindner, Kenji Hamase. Simultaneous analysis of D-alanine, D-aspartic acid, and D-serine using chiral high-performance liquid chromatography-tandem mass spectrometry and its application to the rat plasma and tissues. Journal of pharmaceutical and biomedical analysis. 2015 Nov; 115(?):123-9. doi: 10.1016/j.jpba.2015.05.024. [PMID: 26186615]
  • Satsuki Matsuda, Masumi Katane, Kazuhiro Maeda, Yuusuke Kaneko, Yasuaki Saitoh, Tetsuya Miyamoto, Masae Sekine, Hiroshi Homma. Biosynthesis of D-aspartate in mammals: the rat and human homologs of mouse aspartate racemase are not responsible for the biosynthesis of D-aspartate. Amino acids. 2015 May; 47(5):975-85. doi: 10.1007/s00726-015-1926-0. [PMID: 25646960]
  • A Gholizadeh. The possible involvement of D-amino acids or their metabolites in Arabidopsis cysteine proteinase/cystatin N-dependent proteolytic pathway. TSitologiia i genetika. 2015 Mar; 49(2):3-10. doi: ". [PMID: 26030967]
  • D D P Ferreira, B Stutz, F G de Mello, R A M Reis, R C C Kubrusly. Caffeine potentiates the release of GABA mediated by NMDA receptor activation: Involvement of A1 adenosine receptors. Neuroscience. 2014 Dec; 281(?):208-15. doi: 10.1016/j.neuroscience.2014.09.060. [PMID: 25286387]
  • R Gualtieri, V Barbato, I Fiorentino, S Braun, D Rizos, S Longobardi, R Talevi. Treatment with zinc, d-aspartate, and coenzyme Q10 protects bull sperm against damage and improves their ability to support embryo development. Theriogenology. 2014 Sep; 82(4):592-8. doi: 10.1016/j.theriogenology.2014.05.028. [PMID: 24999011]
  • Edi Erwan, Vishwajit Sur Chowdhury, Mao Nagasawa, Ryosei Goda, Tsuyoshi Otsuka, Shinobu Yasuo, Mitsuhiro Furuse. Oral administration of D-aspartate, but not L-aspartate, depresses rectal temperature and alters plasma metabolites in chicks. Life sciences. 2014 Jul; 109(1):65-71. doi: 10.1016/j.lfs.2014.05.015. [PMID: 24881518]
  • Franca Raucci, Antimo D'Aniello, Maria Maddalena Di Fiore. Stimulation of androgen production by D-aspartate through the enhancement of StAR, P450scc and 3β-HSD mRNA levels in vivo rat testis and in culture of immature rat Leydig cells. Steroids. 2014 Jun; 84(?):103-10. doi: 10.1016/j.steroids.2014.03.016. [PMID: 24713504]
  • Darryn S Willoughby, Brian Leutholtz. D-aspartic acid supplementation combined with 28 days of heavy resistance training has no effect on body composition, muscle strength, and serum hormones associated with the hypothalamo-pituitary-gonadal axis in resistance-trained men. Nutrition research (New York, N.Y.). 2013 Oct; 33(10):803-10. doi: 10.1016/j.nutres.2013.07.010. [PMID: 24074738]
  • Mao Horio, Tamaki Ishima, Yuko Fujita, Ran Inoue, Hisashi Mori, Kenji Hashimoto. Decreased levels of free D-aspartic acid in the forebrain of serine racemase (Srr) knock-out mice. Neurochemistry international. 2013 May; 62(6):843-7. doi: 10.1016/j.neuint.2013.02.015. [PMID: 23439386]
  • Miki Senda, Atsushi Yamamoto, Hiroyuki Tanaka, Tetsuo Ishida, Kihachiro Horiike, Toshiya Senda. Crystallization and preliminary crystallographic analysis of D-aspartate oxidase from porcine kidney. Acta crystallographica. Section F, Structural biology and crystallization communications. 2012 Jun; 68(Pt 6):644-6. doi: 10.1107/s1744309112013243. [PMID: 22684060]
  • Hans Christian Helms, Rasmus Madelung, Helle Sønderby Waagepetersen, Carsten Uhd Nielsen, Birger Brodin. In vitro evidence for the brain glutamate efflux hypothesis: brain endothelial cells cocultured with astrocytes display a polarized brain-to-blood transport of glutamate. Glia. 2012 May; 60(6):882-93. doi: 10.1002/glia.22321. [PMID: 22392649]
  • Silvia Holmseth, Yvette Dehnes, Yanhua H Huang, Virginie V Follin-Arbelet, Nina J Grutle, Maria N Mylonakou, Celine Plachez, Yun Zhou, David N Furness, Dwight E Bergles, Knut P Lehre, Niels C Danbolt. The density of EAAC1 (EAAT3) glutamate transporters expressed by neurons in the mammalian CNS. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2012 Apr; 32(17):6000-13. doi: 10.1523/jneurosci.5347-11.2012. [PMID: 22539860]
  • Hai Han, Yurika Miyoshi, Kyoko Ueno, Chieko Okamura, Yosuke Tojo, Masashi Mita, Wolfgang Lindner, Kiyoshi Zaitsu, Kenji Hamase. Simultaneous determination of D-aspartic acid and D-glutamic acid in rat tissues and physiological fluids using a multi-loop two-dimensional HPLC procedure. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Nov; 879(29):3196-202. doi: 10.1016/j.jchromb.2011.01.023. [PMID: 21371949]
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  • Alessandra Santillo, Lavinia Burrone, Rosalba Senese, Federica Cioffi, Antonia Lanni, Gabriella Chieffi Baccari. Effect of D-aspartate uptake on uncoupling protein-3 and α-tubulin expressions in rat Harderian gland. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Nov; 879(29):3344-8. doi: 10.1016/j.jchromb.2011.04.001. [PMID: 21524945]
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