2,3-cGAMP sodium salt (BioDeep_00000013583)
Secondary id: BioDeep_00001869981
代谢物信息卡片
Cyclic guanosine monophosphate-adenosine monophosphate
化学式: C20H24N10O13P2 (674.0999514)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 37.5%
分子结构信息
SMILES: C1C2C(C(C(O2)N3C=NC4=C3N=C(NC4=O)N)OP(=O)(OCC5C(C(C(O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)O)O)O
InChI: InChI=1S/C20H24N10O13P2/c21-14-8-15(24-3-23-14)29(4-25-8)18-11(32)12-7(41-18)2-39-45(36,37)43-13-10(31)6(1-38-44(34,35)42-12)40-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:75947
- KEGG: C20640
- PubChem: 135564529
- ChEMBL: CHEMBL4465054
- CAS: 1441190-66-4
- PMhub: MS000028073
- PubChem: 172232364
- PDB-CCD: 1SY
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 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(0)
PharmGKB(0)
0 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
- Yanfei Hou, Zhimeng Wang, Peiyuan Liu, Xubiao Wei, Zhengyin Zhang, Shilong Fan, Lulu Zhang, Fangping Han, Yikang Song, Ling Chu, Conggang Zhang. SMPDL3A is a cGAMP-degrading enzyme induced by LXR-mediated lipid metabolism to restrict cGAS-STING DNA sensing.
Immunity.
2023 Nov; 56(11):2492-2507.e10. doi:
10.1016/j.immuni.2023.10.001. [PMID: 37890481] - Zhiwen Hu, Xi Li, Yangjun Yang, Zhe Zhang, Shuzhe Ding. High-Intensity Interval Training Ameliorates High-Fat Diet-Induced Metabolic Disorders via the Cyclic GMP-AMP Synthase-Stimulator of Interferon Gene Signaling Pathway.
International journal of molecular sciences.
2023 Sep; 24(18):. doi:
10.3390/ijms241813840. [PMID: 37762143] - Yuan Wang, Feng Li, Zexu Wang, Xiaowei Song, Zhe Ren, Xiao Wang, Yifei Wang, Kai Zheng. Luteolin inhibits herpes simplex virus 1 infection by activating cyclic guanosine monophosphate-adenosine monophosphate synthase-mediated antiviral innate immunity.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2023 Aug; 120(?):155020. doi:
10.1016/j.phymed.2023.155020. [PMID: 37632997] - Xiaobo Li, Yuanyuan Zhu, Xiao Zhang, Xiang An, Mingjiao Weng, Jiaqi Shi, Song Wang, Caiqi Liu, Shengnan Luo, Tongsen Zheng. An alternatively spliced STING isoform localizes in the cytoplasmic membrane and directly senses extracellular cGAMP.
The Journal of clinical investigation.
2022 02; 132(3):. doi:
10.1172/jci144339. [PMID: 34905508] - Zhesen Tan, Chi Ho Chan, Michael Maleska, Bryan Banuelos Jara, Brian K Lohman, Nathan J Ricks, Daniel R Bond, Ming C Hammond. The Signaling Pathway That cGAMP Riboswitches Found: Analysis and Application of Riboswitches to Study cGAMP Signaling in Geobacter sulfurreducens.
International journal of molecular sciences.
2022 Jan; 23(3):. doi:
10.3390/ijms23031183. [PMID: 35163114] - Wenwen Jiang, Li Shi, Lukui Cai, Xiaoyu Wang, Jingyan Li, Heng Li, Jiangli Liang, Qin Gu, Guang Ji, Jing Li, Longding Liu, Mingbo Sun. A two-adjuvant multiantigen candidate vaccine induces superior protective immune responses against SARS-CoV-2 challenge.
Cell reports.
2021 12; 37(11):110112. doi:
10.1016/j.celrep.2021.110112. [PMID: 34863353] - Peerapat Visitchanakun, Warerat Kaewduangduen, Awirut Chareonsappakit, Paweena Susantitaphong, Prapaporn Pisitkun, Patcharee Ritprajak, Natavudh Townamchai, Asada Leelahavanichkul. Interference on Cytosolic DNA Activation Attenuates Sepsis Severity: Experiments on Cyclic GMP-AMP Synthase (cGAS) Deficient Mice.
International journal of molecular sciences.
2021 Oct; 22(21):. doi:
10.3390/ijms222111450. [PMID: 34768881] - Lise Chauveau, Anne Bridgeman, Tiong K Tan, Ryan Beveridge, Joe N Frost, Pramila Rijal, Isabela Pedroza-Pacheco, Thomas Partridge, Javier Gilbert-Jaramillo, Michael L Knight, Xu Liu, Rebecca A Russell, Persephone Borrow, Hal Drakesmith, Alain R Townsend, Jan Rehwinkel. Inclusion of cGAMP within virus-like particle vaccines enhances their immunogenicity.
EMBO reports.
2021 08; 22(8):e52447. doi:
10.15252/embr.202152447. [PMID: 34142428] - Hiroki Nunokawa, Yusuke Murakami, Takashi Ishii, Tomoya Narita, Haruyuki Ishii, Hajime Takizawa, Naomi Yamashita. Crucial role of stimulator of interferon genes-dependent signaling in house dust mite extract-induced IgE production.
Scientific reports.
2021 06; 11(1):13157. doi:
10.1038/s41598-021-92561-w. [PMID: 34162937] - Xia Chen, Li Wang, Limin Cao, Tiantian Li, Zhihong Li, Yumeng Sun, Jinqiu Ding, Chun Zhou, Yadong Xie, Nan Yue, Jing Nan, Xin-Ming Jia, Chao Peng, Huabin Li, Jinbo Yang, Hui Xiao. Regulation of Anion Channel LRRC8 Volume-Regulated Anion Channels in Transport of 2'3'-Cyclic GMP-AMP and Cisplatin under Steady State and Inflammation.
Journal of immunology (Baltimore, Md. : 1950).
2021 05; 206(9):2061-2074. doi:
10.4049/jimmunol.2000989. [PMID: 33827893] - Zaidatul Akmal Othman, Zaida Zakaria, Joseph Bagi Suleiman, Victor Udo Nna, Aminah Che Romli, Wan Syaheedah Wan Ghazali, Mahaneem Mohamed. Bee Bread Ameliorates Vascular Inflammation and Impaired Vasorelaxation in Obesity-Induced Vascular Damage Rat Model: The Role of eNOS/NO/cGMP-Signaling Pathway.
International journal of molecular sciences.
2021 Apr; 22(8):. doi:
10.3390/ijms22084225. [PMID: 33921777] - Bin Wang, Ke-Wu Zeng, Zi-Fu Hong, Gui-Xiang Ti, Li-Yun Wang, Pin Lu, Zhen Liu. Banxia Xiexin Decoction () Treats Diabetic Gastroparesis through PLC-IP3-Ca2+/NO-cGMP-PKG Signal Pathway.
Chinese journal of integrative medicine.
2020 Nov; 26(11):833-838. doi:
10.1007/s11655-020-3077-8. [PMID: 32418177] - Jing Chen, Youxiu Zhong, Yu Liu, Chongfa Tang, Yanbin Zhang, Bo Wei, Wangxue Chen, Meiying Liu. Parenteral immunization with a cyclic guanosine monophosphate-adenosine monophosphate (cGAMP) adjuvanted Helicobacter pylori vaccine induces protective immunity against H. pylori infection in mice.
Human vaccines & immunotherapeutics.
2020 11; 16(11):2849-2854. doi:
10.1080/21645515.2020.1744364. [PMID: 32298215] - Karl-Peter Hopfner, Veit Hornung. Molecular mechanisms and cellular functions of cGAS-STING signalling.
Nature reviews. Molecular cell biology.
2020 09; 21(9):501-521. doi:
10.1038/s41580-020-0244-x. [PMID: 32424334] - Zhen Zhao, Zhixing Ma, Bo Wang, Yukun Guan, Xiao-Dong Su, Zhengfan Jiang. Mn2+ Directly Activates cGAS and Structural Analysis Suggests Mn2+ Induces a Noncanonical Catalytic Synthesis of 2'3'-cGAMP.
Cell reports.
2020 08; 32(7):108053. doi:
10.1016/j.celrep.2020.108053. [PMID: 32814054] - Chun Zhou, Xia Chen, Rosa Planells-Cases, Jiachen Chu, Li Wang, Limin Cao, Zhihong Li, Karen I López-Cayuqueo, Yadong Xie, Shiwei Ye, Xiang Wang, Florian Ullrich, Shixin Ma, Yiyuan Fang, Xiaoming Zhang, Zhikang Qian, Xiaozheng Liang, Shi-Qing Cai, Zhengfan Jiang, Dongming Zhou, Qibin Leng, Tsan S Xiao, Ke Lan, Jinbo Yang, Huabin Li, Chao Peng, Zhaozhu Qiu, Thomas J Jentsch, Hui Xiao. Transfer of cGAMP into Bystander Cells via LRRC8 Volume-Regulated Anion Channels Augments STING-Mediated Interferon Responses and Anti-viral Immunity.
Immunity.
2020 05; 52(5):767-781.e6. doi:
10.1016/j.immuni.2020.03.016. [PMID: 32277911] - Rutger D Luteijn, Shivam A Zaver, Benjamin G Gowen, Stacia K Wyman, Nick E Garelis, Liberty Onia, Sarah M McWhirter, George E Katibah, Jacob E Corn, Joshua J Woodward, David H Raulet. SLC19A1 transports immunoreactive cyclic dinucleotides.
Nature.
2019 09; 573(7774):434-438. doi:
10.1038/s41586-019-1553-0. [PMID: 31511694] - Takuya Yamamoto, Tomohiro Kanuma, Shokichi Takahama, Tomotaka Okamura, Eiko Moriishi, Ken J Ishii, Kazutaka Terahara, Yasuhiro Yasutomi. STING agonists activate latently infected cells and enhance SIV-specific responses ex vivo in naturally SIV controlled cynomolgus macaques.
Scientific reports.
2019 04; 9(1):5917. doi:
10.1038/s41598-019-42253-3. [PMID: 30976083] - Zachary F Hallberg, Chi Ho Chan, Todd A Wright, Philip J Kranzusch, Kevin W Doxzen, James J Park, Daniel R Bond, Ming C Hammond. Structure and mechanism of a Hypr GGDEF enzyme that activates cGAMP signaling to control extracellular metal respiration.
eLife.
2019 04; 8(?):. doi:
10.7554/elife.43959. [PMID: 30964001] - Koji Ozasa, Burcu Temizoz, Takato Kusakabe, Shingo Kobari, Masatoshi Momota, Cevayir Coban, Shuichi Ito, Kouji Kobiyama, Etsushi Kuroda, Ken J Ishii. Cyclic GMP-AMP Triggers Asthma in an IL-33-Dependent Manner That Is Blocked by Amlexanox, a TBK1 Inhibitor.
Frontiers in immunology.
2019; 10(?):2212. doi:
10.3389/fimmu.2019.02212. [PMID: 31616416] - Ming-Jing Deng, Jianli Tao, Chao E, Zhao-Yang Ye, Zhengfan Jiang, Jin Yu, Xiao-Dong Su. Novel Mechanism for Cyclic Dinucleotide Degradation Revealed by Structural Studies of Vibrio Phosphodiesterase V-cGAP3.
Journal of molecular biology.
2018 12; 430(24):5080-5093. doi:
10.1016/j.jmb.2018.10.010. [PMID: 30365951] - Naihan Chen, Matthew D Gallovic, Pamela Tiet, Jenny P-Y Ting, Kristy M Ainslie, Eric M Bachelder. Investigation of tunable acetalated dextran microparticle platform to optimize M2e-based influenza vaccine efficacy.
Journal of controlled release : official journal of the Controlled Release Society.
2018 11; 289(?):114-124. doi:
10.1016/j.jconrel.2018.09.020. [PMID: 30261204] - Geoffrey B Severin, Miriam S Ramliden, Lisa A Hawver, Kun Wang, Macy E Pell, Ann-Katrin Kieninger, Atul Khataokar, Brendan J O'Hara, Lara V Behrmann, Matthew B Neiditch, Christoph Benning, Christopher M Waters, Wai-Leung Ng. Direct activation of a phospholipase by cyclic GMP-AMP in El Tor Vibrio cholerae.
Proceedings of the National Academy of Sciences of the United States of America.
2018 06; 115(26):E6048-E6055. doi:
10.1073/pnas.1801233115. [PMID: 29891656] - Xin Guo, Chang Shu, Honggui Li, Ya Pei, Shih-Lung Woo, Juan Zheng, Mengyang Liu, Hang Xu, Rachel Botchlett, Ting Guo, Yuli Cai, Xinsheng Gao, Jing Zhou, Lu Chen, Qifu Li, Xiaoqiu Xiao, Linglin Xie, Ke K Zhang, Jun-Yuan Ji, Yuqing Huo, Fanyin Meng, Gianfranco Alpini, Pingwei Li, Chaodong Wu. Cyclic GMP-AMP Ameliorates Diet-induced Metabolic Dysregulation and Regulates Proinflammatory Responses Distinctly from STING Activation.
Scientific reports.
2017 07; 7(1):6355. doi:
10.1038/s41598-017-05884-y. [PMID: 28743914] - Ya Zhang, Hang Zhao, Hua Li, Wei Cao, Fang Wang, Tian Zhang, Si-Wang Wang. Protective Effects of Amarogentin against Carbon Tetrachloride-Induced Liver Fibrosis in Mice.
Molecules (Basel, Switzerland).
2017 May; 22(5):. doi:
10.3390/molecules22050754. [PMID: 28481234] - Tara L Martin, Junbae Jee, Eunsoo Kim, Haley E Steiner, Estelle Cormet-Boyaka, Prosper N Boyaka. Sublingual targeting of STING with 3'3'-cGAMP promotes systemic and mucosal immunity against anthrax toxins.
Vaccine.
2017 04; 35(18):2511-2519. doi:
10.1016/j.vaccine.2017.02.064. [PMID: 28343781] - Jianli Tao, Xiang Zhou, Zhengfan Jiang. cGAS-cGAMP-STING: The three musketeers of cytosolic DNA sensing and signaling.
IUBMB life.
2016 11; 68(11):858-870. doi:
10.1002/iub.1566. [PMID: 27706894] - Eunjoo Lee, Hyo-Eun Jang, Yoon Young Kang, Jihyun Kim, Joong-Hoon Ahn, Hyejung Mok. Submicron-sized hydrogels incorporating cyclic dinucleotides for selective delivery and elevated cytokine release in macrophages.
Acta biomaterialia.
2016 Jan; 29(?):271-281. doi:
10.1016/j.actbio.2015.10.025. [PMID: 26485167] - Heng Zhang, Min-Jie Han, Jianli Tao, Zhao-Yang Ye, Xiao-Xia Du, Ming-Jing Deng, Xiao-Yan Zhang, Lan-Fen Li, Zheng-Fan Jiang, Xiao-Dong Su. Rat and human STINGs profile similarly towards anticancer/antiviral compounds.
Scientific reports.
2015 Dec; 5(?):18035. doi:
10.1038/srep18035. [PMID: 26669264] - Juyi Gao, Jianli Tao, Weili Liang, Meng Zhao, Xiaoxia Du, Shan Cui, Haifeng Duan, Biao Kan, Xiaodong Su, Zhengfan Jiang. Identification and characterization of phosphodiesterases that specifically degrade 3'3'-cyclic GMP-AMP.
Cell research.
2015 May; 25(5):539-50. doi:
10.1038/cr.2015.40. [PMID: 25837739] - Lingyin Li, Qian Yin, Pia Kuss, Zoltan Maliga, José L Millán, Hao Wu, Timothy J Mitchison. Hydrolysis of 2'3'-cGAMP by ENPP1 and design of nonhydrolyzable analogs.
Nature chemical biology.
2014 Dec; 10(12):1043-8. doi:
10.1038/nchembio.1661. [PMID: 25344812] - Zhenhua Ming, Wei Wang, Yuchen Xie, Pengfei Ding, Yuchao Chen, Dazhi Jin, Yuna Sun, Bin Xia, Liming Yan, Zhiyong Lou. Crystal structure of the novel di-nucleotide cyclase from Vibrio cholerae (DncV) responsible for synthesizing a hybrid cyclic GMP-AMP.
Cell research.
2014 Oct; 24(10):1270-3. doi:
10.1038/cr.2014.123. [PMID: 25245040]