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Basic Description
| Synonyms | 606-68-8 | Disodium nicotinamide adenine dinucleotide | Disodium NADH | NADH disodium salt | beta-Nicotinamide Adenine Dinucleotide Disodium Salt | NADH, disodium salt hydrate | NADH (disodium salt) | 8295030YNC | disodium;[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydr |
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| Specifications & Purity | 10mM in DMSO |
| Storage Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Product Description |
β-Nicotinamide adenine dinucleotide (NAD+) and β-Nicotinamide adenine dinucleotide, reduced (NADH) comprise a coenzyme redox pair (NAD+:NADH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. In addition to its redox function, NAD+/NADH is a donor of ADP-ribose units in ADP-ribosylaton (ADP-ribosyltransferases; poly(ADP-ribose) polymerases ) reactions and a precursor of cyclic ADP-ribose (ADP-ribosyl cyclases). |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Nucleosides, nucleotides, and analogues
- Class (5'->5')-dinucleotides
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Superclass
Nucleosides, nucleotides, and analogues
| Kingdom | Organic compounds |
|---|---|
| Superclass | Nucleosides, nucleotides, and analogues |
| Class | (5'->5')-dinucleotides |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | (5'->5')-dinucleotides |
| Alternative Parents | Purine nucleotide sugars Purine ribonucleoside diphosphates Purine ribonucleoside monophosphates Nicotinamide nucleotides Pentose phosphates Glycosylamines 6-aminopurines Monosaccharide phosphates N-substituted nicotinamides Organic pyrophosphates Aminopyrimidines and derivatives Dihydropyridines Alkyl phosphates Imidolactams N-substituted imidazoles Vinylogous amides Heteroaromatic compounds Tetrahydrofurans Amino acids and derivatives Secondary alcohols Primary carboxylic acid amides Oxacyclic compounds Enamines Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives Primary amines Carbonyl compounds Organic oxides Organic zwitterions Organic sodium salts |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | (5'->5')-dinucleotide - Purine nucleotide sugar - Purine ribonucleoside diphosphate - Purine ribonucleoside monophosphate - Nicotinamide-nucleotide - Pentose phosphate - Pentose-5-phosphate - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Monosaccharide phosphate - N-substituted nicotinamide - Organic pyrophosphate - Imidazopyrimidine - Purine - Aminopyrimidine - Dihydropyridine - Alkyl phosphate - Hydropyridine - Pyrimidine - Monosaccharide - N-substituted imidazole - Organic phosphoric acid derivative - Imidolactam - Phosphoric acid ester - Azole - Tetrahydrofuran - Imidazole - Heteroaromatic compound - Vinylogous amide - Primary carboxylic acid amide - Carboxamide group - Amino acid or derivatives - Secondary alcohol - Carboxylic acid derivative - Enamine - Oxacycle - Organic alkali metal salt - Organoheterocyclic compound - Azacycle - Primary amine - Amine - Alcohol - Organic sodium salt - Organic nitrogen compound - Organic zwitterion - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic salt - Organooxygen compound - Organic oxygen compound - Organopnictogen compound - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. |
| External Descriptors | Not available |
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Names and Identifiers
| IUPAC Name | disodium;[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate |
|---|---|
| INCHI | InChI=1S/C21H29N7O14P2.2Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33;;/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25);;/q;2*+1/p-2/t10-,11-,13-,14-,15-,16-,20-,21-;;/m1../s1 |
| InChIKey | QRGNQKGQENGQSE-WUEGHLCSSA-L |
| Smiles | C1C=CN(C=C1C(=O)N)C2C(C(C(O2)COP(=O)([O-])OP(=O)([O-])OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O.[Na+].[Na+] |
| Isomeric SMILES | C1C=CN(C=C1C(=O)N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)([O-])OP(=O)([O-])OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O.[Na+].[Na+] |
| WGK Germany | 3 |
| Alternate CAS | 58-68-4 |
| Molecular Weight | 709.4 |
| Beilstein | 5230241 |
| Reaxy-Rn | 5230241 |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
| Sensitivity | Air Sensitive,Heat Sensitive |
|---|---|
| Molecular Weight | 709.400 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 19 |
| Rotatable Bond Count | 11 |
| Exact Mass | 709.089 Da |
| Monoisotopic Mass | 709.089 Da |
| Topological Polar Surface Area | 323.000 Ų |
| Heavy Atom Count | 46 |
| Formal Charge | 0 |
| Complexity | 1210.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 8 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 3 |
Citations of This Product
| 1. Mengge Feng, Xuelian Zeng, Quan Lin, Yunxiao Wang, Hongjiang Wei, Shanyi Yang, Guangwei Wang, Xingyu Chen, Mengqin Guo, Xin Yang, Jun Hu, Yangge Du, Yanbing Zhao, Yufeng Zhang, Xiangliang Yang. (2023) Characterization of Chitosan-Gallic Acid Graft Copolymer for Periodontal Dressing Hydrogel Application. Advanced Healthcare Materials, (2302877). |
| 2. Qiao Chen, Xinmei Duan, Yao Yu, Rongrong Ni, Guojing Song, Xu Yang, Li Zhu, Yuan Zhong, Kun Zhang, Kai Qu, Xian Qin, Wei Wu. (2023) Target Functionalized Carbon Dot Nanozymes with Dual-Model Photoacoustic and Fluorescence Imaging for Visual Therapy in Atherosclerosis. Advanced Science, (2307441). |
| 3. Min-Yu Wang, Shun-Ju Cai, Jia-Chun Lin, Xiao-Jun Ji, Zhi-Gang Zhang. (2023) New Anti-Prelog Stereospecific Whole-Cell Biocatalyst for Asymmetric Reduction of Prochiral Ketones. MOLECULES, 28 (3): (1422). |
| 4. Shunzhang Chen, Junyuan Gong, Yanxia Cheng, Yuqi Guo, Feize Li, Tu Lan, Yuanyou Yang, Jijun Yang, Ning Liu, Jiali Liao. (2024) The biochemical behavior and mechanism of uranium(Ⅵ) bioreduction induced by natural Bacillus thuringiensis. Journal of Environmental Sciences, 136 (372). |
| 5. Hao Fei, Xie Xing, Feng Zhixin, Chen Rong, Wei Yanna, Liu Jin, Xiong Qiyan, Shao Guoqing, Lin Johnson. (2022) NADH oxidase of Mycoplasma hyopneumoniae functions as a potential mediator of virulence. BMC Veterinary Research, 18 (1): (1-14). |
| 6. Xie Xing, Hao Fei, Chen Rong, Wang Jingjing, Wei Yanna, Liu Jin, Wang Haiyan, Zhang Zhenzhen, Bai Yun, Shao Guoqing, Xiong Qiyan, Feng Zhixin. (2021) Nicotinamide Adenine Dinucleotide-Dependent Flavin Oxidoreductase of Mycoplasma hyopneumoniae Functions as a Potential Novel Virulence Factor and Not Only as a Metabolic Enzyme. Frontiers in Microbiology, 12 |
| 7. Zhang Qianqian, Zheng Shanshan, Zhang Jinli, Li Wei, Fu Yan. (2021) Peroxidase Mimicking Activity of Palladium Nanocluster Altered by Heparin. CATALYSIS LETTERS, 151 (9): (2537-2546). |
| 8. Jing Wang, Yongqin Lv. (2021) An enzyme-loaded reactor using metal-organic framework-templated polydopamine microcapsule. CHINESE JOURNAL OF CHEMICAL ENGINEERING, 29 (317). |
| 9. Simin Cao, Haoyang Li, Yangyi Liu, Mengyu Wang, Mengjie Zhang, Sanjun Zhang, Jinquan Chen, Jianhua Xu, Jay R. Knutson, Ludwig Brand. (2020) Dehydrogenase Binding Sites Abolish the “Dark” Fraction of NADH: Implication for Metabolic Sensing via FLIM. JOURNAL OF PHYSICAL CHEMISTRY B, 124 (31): (6721–6727). |
| 10. Simin Cao, Haoyang Li, Yangyi Liu, Mengjie Zhang, Mengyu Wang, Zhongneng Zhou, Jinquan Chen, Sanjun Zhang, Jianhua Xu, Jay R. Knutson. (2020) Femtosecond Fluorescence Spectra of NADH in Solution: Ultrafast Solvation Dynamics. JOURNAL OF PHYSICAL CHEMISTRY B, 124 (5): (771–776). |
| 11. Fanpeng Kong, Ying Li, Chao Yang, Xiao Li, Junlin Wu, Xiaojun Liu, Xiaonan Gao, Kehua Xu, Bo Tang. (2019) A fluorescent probe for simultaneously sensing NTR and hNQO1 and distinguishing cancer cells. Journal of Materials Chemistry B, 7 (43): (6822-6827). |
| 12. Xiaohong Pan, Yuehui Zhao, Tingting Cheng, Aishan Zheng, Anbin Ge, Lixin Zang, Kehua Xu, Bo Tang. (2019) Monitoring NAD(P)H by an ultrasensitive fluorescent probe to reveal reductive stress induced by natural antioxidants in HepG2 cells under hypoxia. Chemical Science, 10 (35): (8179-8186). |
| 13. Ni Zeng, Guowen Zhang, Xing Hu, Junhui Pan, Deming Gong. (2019) Mechanism of fisetin suppressing superoxide anion and xanthine oxidase activity. Journal of Functional Foods, 58 (1). |
| 14. Simin Cao, Zhongneng Zhou, Haoyang Li, Menghui Jia, Yangyi Liu, Mengyu Wang, Mengjie Zhang, Sanjun Zhang, Jinquan Chen, Jianhua Xu, Jay R. Knutson. (2019) A fraction of NADH in solution is “dark”: Implications for metabolic sensing via fluorescence lifetime. CHEMICAL PHYSICS LETTERS, 726 (18). |
| 15. Ni Zeng, Guowen Zhang, Xing Hu, Junhui Pan, Zhisheng Zhou, Deming Gong. (2018) Inhibition mechanism of baicalein and baicalin on xanthine oxidase and their synergistic effect with allopurinol. Journal of Functional Foods, 50 (172). |
| 16. Yan Li,Liyin Wen,Tianwei Tan,Yongqin Lv. (2019-12-24) Sequential Co-immobilization of Enzymes in Metal-Organic Frameworks for Efficient Biocatalytic Conversion of Adsorbed CO2 to Formate.. Frontiers in bioengineering and biotechnology, 7 (394-394). |
| 17. Guorong Cheng,Zifeng Pi,Zhong Zheng,Shu Liu,Zhiqiang Liu,Fengrui Song. (2020-01-02) Magnetic nanoparticles-based lactate dehydrogenase microreactor as a drug discovery tool for rapid screening inhibitors from natural products.. Talanta, 209 (120554-120554). |
| 18. Zhang Zhiqi, Li Lin, Wang Xinyang, Liu Liyan. (2024) An analytical method for the determination of flavonoids in Houttuynia cordata Thunb. by UPLC-TQ-MS and analysis of its antioxidant activity. Journal of Food Measurement and Characterization, (1-12). |
| 19. Chaoqiang Wu, Xin Zhang, Wei Liu, Chengyong Wang, Qianqian Jiang, Feifei Chen, Quanzhen Liu, Fei Cao, Gaowei Zheng, Alei Zhang, Kequan Chen. (2024) Biocatalytic Synthesis of Two Furan-Based Amino Compounds 2-Acetyl-4-aminofuran and 3-Acetylamino-5-(α-aminoethyl)-furan from Chitin Resources. ACS Sustainable Chemistry & Engineering, 12 (30): (11145-11154). |
| 20. Qiao Chen, Xu Yang, Yao Yu, Xinmei Duan, Rongrong Ni, Guojing Song, Li Zhu, Yuan Zhong, Kai Qu, Xian Qin, Kun Zhang, Yang Luo, Wei Wu. (2025) Biomimetic Cerium-Assisted Supra-Carbon Dots Assembly for Reactive Oxygen Species-Activated Atherosclerosis Theranostic. Small, (2408980). |
| 21. Shuwen Zhou, Huijuan Cai, Zhiyong Tang, Siyu Lu. (2024) Carbon dots encapsulated zeolitic imidazolate framework-8 as an enhanced multi-antioxidant for efficient cytoprotection to HK-2 cells. JOURNAL OF COLLOID AND INTERFACE SCIENCE, 676 (726). |
| 22. Henggang Wang, Shan Sun, Ye Zhao, Peng Wang, Yonghua Zhou, Haoyi Sun, Jin Yang, Ke Cheng, Si Li, Hengwei Lin. (2024) Carbon Dots with Integrated Photothermal Antibacterial and Heat-Enhanced Antioxidant Properties for Diabetic Wound Healing. Small, (2403160). |
| 23. Ying Chen, Guanglian Zhou, Yitong Li, Shuxian Liu, Qianru Xu, Xiumei Liu. (2025) Construction of nitroreductase-responsive near-infrared composite nanoprobe and its application in tumor hypoxia imaging. TALANTA, 289 (127750). |
| 24. Likun Luan, Yingfang Zhang, Xiuling Ji, Boxia Guo, Shaoyu Song, Yuhong Huang, Suojiang Zhang. (2024) Electro-Driven Multi-Enzymatic Cascade Conversion of CO2 to Ethylene Glycol in Nano-Reactor. Advanced Science, (2407204). |
| 25. Panpan Xue, Huilan Zhuang, Sijie Shao, Tingjie Bai, Xuemei Zeng, Shuangqian Yan. (2024) Engineering Biodegradable Hollow Silica/Iron Composite Nanozymes for Breast Tumor Treatment through Activation of the “Ferroptosis Storm”. ACS Nano, 18 (37): (25795-25812). |
| 26. Pengjie Zhang, Jiwei Xu, Bin Du, Qianyu Yang, Bing Liu, Jianjie Xu, Zhaoyang Tong. (2024) Improved Classification Performance of Bacteria in Interference Using Raman and Fourier-Transform Infrared Spectroscopy Combined with Machine Learning. MOLECULES, 29 (13): (2966). |
| 27. Xinmei Duan, Xu Yang, Nianlian Mou, Yu Cao, Zhigui He, Li Zhu, Yuan Zhong, Kun Zhang, Kai Qu, Xian Qin, Qiao Chen, Yang Luo, Wei Wu. (2024) Reactive Oxygen Species-Triggered Carbon Dots-Based Biomimetic Nanotheranostic Agents for Atherosclerosis Management. ADVANCED FUNCTIONAL MATERIALS, (2405629). |
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