NADPH - ≥93% , CAS No.2646-71-1

CAS: 2646-71-1 Cat. No.: N276326 Molecular Weight: 833.35 (anhydrous basis) EC Number: 220-163-3

GRADE & PURITY ≥93%

Synonyms

NADPH Na4 | TPNH2 Na4 | AS-10522 | C21H26N7O17P3Na4 | A-NADPH | HB4469 | C74369 | MFCD00036263 | beta-Nicotinamide adenine dinucleotide phosphate reduced tetrasodium salt | NADPH tetrasodium salt (reduced form) | Dihydronicotinamide-adenine dinucleotide p

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C. It is important to note that this product is reported to be light sensitive. Store In the Dark. Store under desiccating conditions.

Specifications

Synonyms

NADPH Na4 | TPNH2 Na4 | AS-10522 | C21H26N7O17P3Na4 | A-NADPH | HB4469 | C74369 | MFCD00036263 | beta-Nicotinamide adenine dinucleotide phosphate reduced tetrasodium salt | NADPH tetrasodium salt (reduced form) | Dihydronicotinamide-adenine dinucleotide p

Specifications & Purity

≥93%

Biochemical and Physiological Mechanisms

Ubiquitous coenzyme and biological reducing agent that acts as an electron donor for many redox enzymes including nitric oxide synthetase. Generated by reduction of the electron acceptor NADP+.

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥93%

Names and Identifiers

• Pubchem Sid: 488201525
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488201525
• Canonical Smiles: [Na+].[Na+].[Na+].[Na+].NC(=O)C1=CN(C=CC1)[C@H]2O[C@@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@H](O)[C@@H]2O
• IUPAC Name: tetrasodium;[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-5-[[[[(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl] phosphate
• InChIKey: WYWWVJHQDVCHKF-ITGWJZMWSA-J
• INCHI: 1S/C21H30N7O17P3.4Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;;;;/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35);;;;/q;4*+1/p-4/t10-,11-,13-,14-,15-,16-,20-,21-;;;;/m1..../s1
• 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)OP(=O)([O-])[O-])O)O)O.[Na+].[Na+].[Na+].[Na+]
• Molecular Weight: 833.35 (anhydrous basis)

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class (5'->5')-dinucleotides

• 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 2',5'-bisphosphates Nicotinamide nucleotides Pentose phosphates Glycosylamines Monosaccharide phosphates 6-aminopurines N-substituted nicotinamides Organic pyrophosphates Aminopyrimidines and derivatives Dihydropyridines Alkyl phosphates Imidolactams N-substituted imidazoles Heteroaromatic compounds Vinylogous amides Oxolanes Primary carboxylic acid amides Secondary alcohols Amino acids and derivatives Enamines Oxacyclic compounds Azacyclic compounds Organic oxides Hydrocarbon derivatives Organic zwitterions Carbonyl compounds Primary amines Organic sodium salts
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: (5'->5')-dinucleotide - Purine nucleotide sugar - Purine ribonucleoside 2',5'-bisphosphate - Purine ribonucleoside bisphosphate - Purine ribonucleoside diphosphate - 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 - Imidolactam - Alkyl phosphate - Hydropyridine - Pyrimidine - Monosaccharide - N-substituted imidazole - Organic phosphoric acid derivative - Phosphoric acid ester - Vinylogous amide - Azole - Imidazole - Heteroaromatic compound - Oxolane - Carboxamide group - Primary carboxylic acid amide - Secondary alcohol - Amino acid or derivatives - Organoheterocyclic compound - Carboxylic acid derivative - Enamine - Organic alkali metal salt - Azacycle - Oxacycle - Alcohol - Organic zwitterion - Organic sodium salt - Organic salt - Organic oxygen compound - Primary amine - Carbonyl group - Organic oxide - Organooxygen compound - Amine - Organic nitrogen compound - Organonitrogen compound - Hydrocarbon derivative - 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

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: 10 mM NaOH: soluble 50 mg/mL, clear
• Sensitivity: light sensitive;Heat sensitive
• Molecular Weight: 833.300 g/mol
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 22
• Rotatable Bond Count: 12
• Exact Mass: 833.019 Da
• Monoisotopic Mass: 833.019 Da
• Topological Polar Surface Area: 375.000 Ų
• Heavy Atom Count: 52
• Formal Charge: 0
• Complexity: 1380.000
• 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: 5

XLogP3

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52. Ximei Li, Lihua Xin, Lan Yang, Yi Yang, Wei Li, Mingyu Zhang, Yufen Liao, Chen Sun, Weiwei Li, Ying Peng, Jiang Zheng.  (2024)  Identification of an Epoxide Metabolite of Amitriptyline In Vitro and In Vivo.  CHEMICAL RESEARCH IN TOXICOLOGY,      [PMID:38761382] [10.1021/acs.chemrestox.4c00008]

53. Yuxin Shen, Fengsheng Hong, Hualu Wu, Xiaohai Chen, Hailun Xia, Ren-ai Xu, Guanyang Lin, Lu Shi.  (2025)  Inhibitory effect of luteolin on the metabolism of vandetanib in vivo and in vitro.  Frontiers in Pharmacology,      [PMID:40098621] [10.3389/fphar.2025.1526159]

54. Xia Hailun, Xu Xinhao, Chen Jie, Wu Hualu, Shen Yuxin, Chen Xiaohai, Xu Ren-ai, Wu Wenzhi.  (2024)  Inhibitory effects of calcium channel blockers nisoldipine and nimodipine on ivacaftor metabolism and their underlying mechanism.  Frontiers in Pharmacology,      [PMID:39329117] [10.3389/fphar.2024.1403649]

55. Xiaohai Chen, Fengsheng Hong, Yuxin Shen, Hailun Xia, Lu Shi, Zheli Jiang, Ren-ai Xu.  (2025)  Inhibitory effects of nimodipine, nitrendipine and felodipine on tamoxifen metabolism and molecular docking.  BIOCHEMICAL PHARMACOLOGY,      [PMID:40054784] [10.1016/j.bcp.2025.116854]

56. Wan Xinyi, Zeng Weiwu, Fan Haonan, Wang Chenliang, Han Shixun, Sun Zhongxing, Tang Mei, Shao Juejia, Liu Yu, Fang Yuan, Jia Junqi, Tang Yin, Zhang Yanjun, Zhao Bin, Fang Dong.  (2024)  MAT2B regulates the protein level of MAT2A to preserve RNA N6-methyladenosine.  Cell Death & Disease,  15  (10): (1-16).  [PMID:39353892] [10.1038/s41419-024-07093-8]

57. Xuecai Wei, Xiaoyang Yue, Quan Yuan, Ying He, Li Ma, Liya Zhou, Guanhua Liu, Yunting Liu, Yanjun Jiang.  (2024)  Multigram synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate in a monophasic aqueous system using a robust NADH-dependent alcohol dehydrogenase from Pseudomonas bacterium.  Molecular Catalysis,      [PMID:] [10.1016/j.mcat.2024.114067]

58. Tingmin Ye, Chunping Tang, Dandan Yang, Qing Zhang, Yufen Liao, Jie Dai, Hong Tang, Changqiang Ke, Ying Peng, Yang Ye, Weiwei Li, Jiang Zheng.  (2025)  Metabolic activation and cytotoxicity of bavachin mediated by CYP3A in mice.  CHEMICO-BIOLOGICAL INTERACTIONS,      [PMID:40609922] [10.1016/j.cbi.2025.111630]

59. Yan Hai, Yunxing Zhao, Yao Wang, Zhiqiang Wang, Ting Li, Jianfeng Zhang, Jing Liang.  (2025)  Construction of a Cold-Resistant Shelter: Assembly of Bacteria on Hierarchical Porous Material for Low-Temperature Phenol Bio-degradation and Machine Learning Prediction.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2025.137840]

60. Chenjian Zhou, Peiqi Wang, Jie Chen, Hualu Wu, Yige Yu.  (2025)  Development and validation of a UPLC-MS/MS method for the quantification of parsaclisib and its application to pharmacokinetics and metabolic stability studies.  BMC Chemistry,  19  (1): (194).  [PMID:40611338] [10.1186/s13065-025-01569-0]

61. Qian Zhu, Kangning Wei, Kaihua Pan, Gang Hu, Weihao Zhu, Yanni Huang, Changchang Wang, Qian Li, Mingliang Zhang, Jiguo Qiu, Qing Hong.  (2025)  Identification of a novel ipp gene cluster responsible for 2-isopropylphenol degradation in strain Rhodococcus sp. D-6.  APPLIED AND ENVIRONMENTAL MICROBIOLOGY,      [PMID:40810535] [10.1128/aem.00995-25]

62. Jinzhao Yang, Hailun Xia, Qingqing Li, Ruibin Li, Lu Cao, Congrong Tang.  (2025)  Evaluation the inhibitory effect of nicardipine on the metabolism of quetiapine.  Frontiers in Pharmacology,      [PMID:41064448] [10.3389/fphar.2025.1567044]

63. Jianfeng Zhang, Wenrong Bing, Tiancheng Hu, Xu Zhou, Jiejing Zhang, Jing Liang, Yongguang Li.  (2023)  Enhanced biodegradation of phenol by microbial collaboration: Resistance, metabolite utilization, and pH stabilization.  ENVIRONMENTAL RESEARCH,      [PMID:37776942] [10.1016/j.envres.2023.117269]

64. Chunyan Liao, Xiang Wang, Xueying Zhou, Dequan Wang, Ziyin Zhang, Yan Liu, Xiao Wu, Ying Chen, Yifeng Tan, Xin Dai, Pei Jing, Jie Pang, Xiao Xiao, Jie Liu, Xiaoming Liao, Shiyong Zhang.  (2022)  Dietary Antioxidant-Constructed Nanodrugs Can High-Efficiently Kill Cancer Cells while Protecting Noncancer Cells.  ACS Applied Materials & Interfaces,      [PMID:36315104] [10.1021/acsami.2c12043]

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68. Jiali Chen, Chen Huang, Yuqing Zhang, Liya Zhou, Li Ma, Lihui Wang, Yanjun Jiang, Yunting Liu.  (2025)  Continuous-flow chemoenzymatic conversion of racemic alcohols to enantiopure alcohols and amines.  Molecular Catalysis,      [PMID:] [10.1016/j.mcat.2025.115094]

69. Hualu Wu, Haoxin Fu, Fangyuan Xia, Jun Wu, Peiqi Wang, Lu Cao, Ren-ai Xu, Lu Shi.  (2025)  Effect of ponatinib on the metabolism of cariprazine in vitro and in vivo and the underlying mechanism.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:40286877] [10.1016/j.taap.2025.117353]

70. Hualu Wu, Qian Liu, Yuxin Shen, He Qi, Jiade Zhao, Qiaoying Li, Hailun Xia, Ren-Ai Xu, Lu Shi.  (2025)  Drug Interactions of Imperatorin and Curcumin on Macitentan in vitro and in vivo.  Drug Design Development and Therapy,      [PMID:40322036] [10.2147/DDDT.S505960]

71. Hulin Qiu, Wenzhong Gong, Huilin Huang, Heng Guo, Zhizeng Gao, Lan Liu, Xinjian Yin.  (2025)  Rosetta-Driven Rapid Evolution of meso-Diaminopimelate Dehydrogenases for Structurally Diverse D-Amino Acid Production.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:40494826] [10.1021/acs.jafc.5c03073]

72. Xiaomin Tan, Yanjuan Huang, Yong Luo, Zijun Lin, Xianmin Shi, Zishan Zeng, Jie Chen, Chunshun Zhao.  (2025)  A molecular-size sieve-inspired metal-organic cage-based hydrogen sulfide probe for colon cancer diagnosis.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.164859]

73. Jiawei Guo, Qiaoyu Zhang, Yang Shen, Fangyuan Cheng, Moli Sang, Xuan Wang, Yunjun Pan, Mingyu Liu, Hao-Bing Yu, Bo Hu, Sheng Wang, Liangzhen Zheng, Ce Geng, Chaofan Yang, Lianzhong Luo, Gang Zhang, Lei Du, Yuanning Li, Wei Zhang, Yandong Zhang, Binju Wang, Shengying Li, Xingwang Zhang.  (2025)  Deciphering the Thiolactonization Mechanism in Thiolactomycin Biosynthesis.  Journal of the American Chemical Society,      [PMID:40537968] [10.1021/jacs.4c14296]

74. Yan Sun, Tayyab Shaheen, Jiali Guo, Bingjie Shi, Miaohan Li, Xiaoyan Li, Yongqiang Li, Gunghui Tang.  (2025)  Laboratory selection, resistance risk assessment, fitness costs and biochemical mechanism of Aphis gossypii to flonicamid.  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:41326073] [10.1016/j.pestbp.2025.106757]

75. Yuxin Shen, Ruibin Li, Lu Cao, Jun Wu, Haoxin Fu, Peiqi Wang, Ren-ai Xu, Ling Ji.  (2025)  Development of an UPLC-MS/MS method for quantification of donafenib and its metabolite in rat plasma: application to drug–drug interaction.  BIOCHEMICAL PHARMACOLOGY,      [PMID:41241015] [10.1016/j.bcp.2025.117540]

76. Shoufang Tang, Yi Wu, Rongjin Wang, Yuwen Li, Jing Li, Yuxin Peng, Shu Liu, Lihui Men, Zong Hou, Zhiqiang Liu, Zhongying Liu.  (2025)  Revealing the Formula Pattern of Congming Decoction by Ultra-High-Performance Liquid Chromatography Coupled With Quadrupole-Orbitrap Mass Spectrometry From the Perspective of Chemical Constituents, In Vitro, and In Vivo Properties.  JOURNAL OF SEPARATION SCIENCE,  48  (10): (e70306).  [PMID:41122827] [10.1002/jssc.70306]

77. Hailun Xia, Jun Wu, Yingying Hu, Peiqi Wang, Lu Cao, Ruibin Li, Haoxin Fu, Ren-ai Xu, Saili Xie.  (2025)  Effects of CYP2C9 genetic polymorphism and drug-drug interactions on trimethoprim metabolism.  BIOCHEMICAL PHARMACOLOGY,      [PMID:41308926] [10.1016/j.bcp.2025.117558]

78. Chen Xiaohai, Chen Dongxin, Wu Hualu, Xia Hailun, Lan Tian, Xu Ren-ai.  (2025)  Simultaneous determination of iloperidone and its metabolites in rat plasma using a novel UPLC-MS/MS method: an application for drug-drug interaction.  BMC Pharmacology & Toxicology,  26  (1): (200).  [PMID:41291928] [10.1186/s40360-025-01037-4]

79. Shuling Zhang, Jiajing Yan, Quan Yuan, Yanjun Jiang, Lihui Wang, Yunting Liu.  (2025)  Integration of Medium Engineering, Immobilization, and Rotating Bed Reactor for Intensifying Enzymatic Reduction of Halogenated Aryl Ketones.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.5c12396]

80. Wenhao Hou, Qian Xu, Yuqing Niu, Yaqi Liu, Yun Ju, Jing He, Jie Jiang, Lina Qiao, Hongbin Xie, Hong Zhang.  (2026)  Regulating CO and CC reduction by positively charged ions in water microdroplets.  Journal of Environmental Chemical Engineering,  14  (1): (121009).  [PMID:] [10.1016/j.jece.2025.121009]

81. Jinyu Hu, Haoxin Fu, Ruibin Li, Peiqi Wang, Jun Wu, Lu Cao, Chenjian Zhou, Ren-ai Xu.  (2026)  Effects of CYP3A4 variants and drug–drug interactions on the metabolism of fexinidazole.  BIOCHEMICAL PHARMACOLOGY,      [PMID:41571200] [10.1016/j.bcp.2026.117730]

82. Hailun Xia, Haoxin Fu, Lu Cao, Ruibin Li, Jun Wu, Peiqi Wang, Ren-ai Xu, Weihong Lin.  (2026)  Effect of apatinib on albendazole metabolism in vitro and in vivo.  BIOORGANIC CHEMISTRY,      [PMID:41610585] [10.1016/j.bioorg.2026.109550]

83. Zhiheng Feng, Peijun Li, Guang Yang, Yining Wang, Mengqi Li, Jiangting Wu, Nan Chao, Li Liu.  (2026)  Characterization of two reductases MaLAR and MaANR revealed their roles in proanthocyanidin biosynthesis in mulberry.  Frontiers in Plant Science,      [PMID:41647646] [10.3389/fpls.2025.1760417]

84. Peiqi Wang, Haoxin Fu, Jun Wu, Ruibin Li, Lu Cao, Ren-Ai Xu, Weihong Lin.  (2026)  Inhibition of acalabrutinib metabolism by finerenone and its molecular docking studies.  CELL BIOLOGY AND TOXICOLOGY,      [PMID:41673329] [10.1007/s10565-026-10148-5]

85. Zhuoda Liu, Yifei Zhou, Dongliang Wang, Ruichi Li, Zhen Tian, Yifan Li, Jiyuan Liu.  (2026)  From Field Overexpression to Biochemical Function: PxCYP6B4-Mediated Hydroxylation Confers Pyrethroid Resistance in Plutella xylostella.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41645610] [10.1021/acs.jafc.6c00843]

86. Shijie Du, Shujing Yan, Muyasaer Aisana, Huan Xu, Hanjing Xue, Chunhong Zhong, Xiaoli Gao, Chunli Chen.  (2026)  Heterologous Expression of 20α-Hydroxysteroid Dehydrogenase in Escherichia coli for the Production of 20α-Hydroxyprogesterone.  JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY,      [PMID:] [10.1016/j.jsbmb.2026.106975]

87. Wu Hualu, Cao Lu, Wang Peiqi, Li Ruibin, Wu Jun, Fu Haoxin, Chen Yan, Jiang Shiqi, Xu Ren-ai.  (2026)  Mechanism-based inactivation of CYP2D6 by imperatorin and drug-drug interaction in vitro and in vivo.  ARCHIVES OF TOXICOLOGY,      [PMID:] [10.1007/s00204-026-04367-2]

88. Wenzhi Wu, Xiaohai Chen, Weiyi Zhang, Haoxin Fu, Jie Chen, Chenchen Qian, Saili Xie, Congcong Zeng.  (2026)  Apatinib inhibits CYP1A2-mediated melatonin metabolism: in vitro, in vivo and molecular docking studies.  CHEMICO-BIOLOGICAL INTERACTIONS,      [PMID:] [10.1016/j.cbi.2026.112038]