NADPH free acid
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MedKoo CAT#: 111527

CAS#: 53-57-6 (free acid)

Description: NADPH, the reduced form of NADP+, is used in anabolic reactions (such as lipid and nucleic acid synthesis) as a reducing agent and cofactor.

Chemical Structure

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NADPH free acid
CAS# 53-57-6 (free acid)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 111527
Name: NADPH free acid
CAS#: 53-57-6 (free acid)
Chemical Formula: C21H30N7O17P3
Exact Mass: 745.09
Molecular Weight: 745.420
Elemental Analysis: C, 33.84; H, 4.06; N, 13.15; O, 36.49; P, 12.47

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to Ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1250 Ready to ship
500mg USD 2250 Ready to ship
1g USD 3650 Ready to ship
2g USD 6450 Ready to ship
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Related CAS #: 53-57-6 (free acid)   604-79-5 (oxidized)   2646-71-1 (sodium)   100929-71-3 (ammonium)   100929-71-3 (Cy4N)    

Synonym: Codehydrase II reduced; Codehydrogenase II reduced; Coenzyme II reduced; Cozymase II reduced; Dihydrocodehydrogenase II.

IUPAC/Chemical Name: Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide

InChi Key: ACFIXJIJDZMPPO-NNYOXOHSSA-N

InChi Code: InChI=1S/C21H30N7O17P3/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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

SMILES Code: NC(C1=CN(C=CC1)[C@@H]2O[C@H](COP(O)(OP(O)(OC[C@H]3O[C@H]([C@H](OP(O)(O)=O)[C@@H]3O)N4C=NC5=C4N=CN=C5N)=O)=O)[C@@H](O)[C@H]2O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: NADPH is the reduced form of NADP+.
In vitro activity: NADPH oxidase 4 (NOX4) has potential as a tumor promoter in patients with an activated TGF-β pathway within hepatocellular carcinoma (HCC) cells. NOX4 was found to be essential for efficient SMAD2/3 phosphorylation, which is part of the canonical pathway. However, non-canonical signals were enhanced in NOX4-silenced cells. NOX4 played a crucial role in multiple tumor-suppressor actions of TGF-β in HCC, including apoptosis, cell proliferation, and migration. Reference: Redox Biol. 2023 Sep;65:102818. https://pubmed.ncbi.nlm.nih.gov/37463530/
In vivo activity: NOX4 represent a potential target to counteract for OA treatment. Whole-body NOX4 deletion reduced experimental osteoarthritis (OA) in mice by lowering disease scores after 8 weeks. While disease progression increased bone parameters in both NOX4-/- and WT mice, only WT mice exhibited additional changes. NOX4 deficiency increased beneficial factors in cartilage and reduced detrimental ones. Overall, NOX4 deletion led to a more favorable response to OA, with reduced synovitis and other harmful markers. Reference: RMD Open. 2023 Feb;9(1):e002856. https://pubmed.ncbi.nlm.nih.gov/36810185/

Preparing Stock Solutions

The following data is based on the product molecular weight 745.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Espinosa-Sotelo R, Fusté NP, Peñuelas-Haro I, Alay A, Pons G, Almodóvar X, Albaladejo J, Sánchez-Vera I, Bonilla-Amadeo R, Dituri F, Serino G, Ramos E, Serrano T, Calvo M, Martínez-Chantar ML, Giannelli G, Bertran E, Fabregat I. Dissecting the role of the NADPH oxidase NOX4 in TGF-beta signaling in hepatocellular carcinoma. Redox Biol. 2023 Sep;65:102818. doi: 10.1016/j.redox.2023.102818. Epub 2023 Jul 13. PMID: 37463530; PMCID: PMC10372458. 2. Ludwig K, Le Belle JE, Muthukrishnan SD, Sperry J, Condro M, Vlashi E, Pajonk F, Kornblum HI. NADPH oxidase promotes glioblastoma radiation resistance in a PTEN-dependent manner. Antioxid Redox Signal. 2023 Jul 20. doi: 10.1089/ars.2022.0086. Epub ahead of print. PMID: 37470216. 3. Renaudin F, Oudina K, Gerbaix M, McGilligan Subilia M, Paccaud J, Jaquet V, Krause KH, Ferrari S, Laumonier T, Hannouche D. NADPH oxidase 4 deficiency attenuates experimental osteoarthritis in mice. RMD Open. 2023 Feb;9(1):e002856. doi: 10.1136/rmdopen-2022-002856. PMID: 36810185; PMCID: PMC9945017.
In vitro protocol: 1. Espinosa-Sotelo R, Fusté NP, Peñuelas-Haro I, Alay A, Pons G, Almodóvar X, Albaladejo J, Sánchez-Vera I, Bonilla-Amadeo R, Dituri F, Serino G, Ramos E, Serrano T, Calvo M, Martínez-Chantar ML, Giannelli G, Bertran E, Fabregat I. Dissecting the role of the NADPH oxidase NOX4 in TGF-beta signaling in hepatocellular carcinoma. Redox Biol. 2023 Sep;65:102818. doi: 10.1016/j.redox.2023.102818. Epub 2023 Jul 13. PMID: 37463530; PMCID: PMC10372458. 2. Ludwig K, Le Belle JE, Muthukrishnan SD, Sperry J, Condro M, Vlashi E, Pajonk F, Kornblum HI. NADPH oxidase promotes glioblastoma radiation resistance in a PTEN-dependent manner. Antioxid Redox Signal. 2023 Jul 20. doi: 10.1089/ars.2022.0086. Epub ahead of print. PMID: 37470216.
In vivo protocol: 1. Renaudin F, Oudina K, Gerbaix M, McGilligan Subilia M, Paccaud J, Jaquet V, Krause KH, Ferrari S, Laumonier T, Hannouche D. NADPH oxidase 4 deficiency attenuates experimental osteoarthritis in mice. RMD Open. 2023 Feb;9(1):e002856. doi: 10.1136/rmdopen-2022-002856. PMID: 36810185; PMCID: PMC9945017.

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1: Sameer H, Victor G, Katalin S, Henrik A. Elucidation of ligand binding and dimerization of NADPH:protochlorophyllide (Pchlide) oxidoreductase (POR) from pea (Pisum sativum L.) by structural analysis and simulations. Proteins. 2021 May 22. doi: 10.1002/prot.26151. Epub ahead of print. PMID: 34021929.

2: Chakraborty T, Polley S, Sinha D, Seal S, Sinha D, Mitra SK, Hazra J, Sau K, Pal M, Sau S. Structurally distinct unfolding intermediates formed from a staphylococcal capsule-producing enzyme retained NADPH binding activity. J Biomol Struct Dyn. 2021 May 12:1-18. doi: 10.1080/07391102.2021.1924269. Epub ahead of print. PMID: 33977860.

3: Dmitrieva VA, Domashkina VV, Ivanova AN, Sukhov VS, Tyutereva EV, Voitsekhovskaja OV. Regulation of plasmodesmata in leaves of Arabidopsis: ATP, NADPH and chlorophyll b levels matter. J Exp Bot. 2021 May 11:erab205. doi: 10.1093/jxb/erab205. Epub ahead of print. PMID: 33974689.

4: Rather GM, Pramono AA, Szekely Z, Bertino JR, Tedeschi PM. In cancer, all roads lead to NADPH. Pharmacol Ther. 2021 Apr 22;226:107864. doi: 10.1016/j.pharmthera.2021.107864. Epub ahead of print. PMID: 33894275.

5: Zhu J, Schwörer S, Berisa M, Kyung YJ, Ryu KW, Yi J, Jiang X, Cross JR, Thompson CB. Mitochondrial NADP(H) generation is essential for proline biosynthesis. Science. 2021 Apr 22:eabd5491. doi: 10.1126/science.abd5491. Epub ahead of print. PMID: 33888598.

6: Shen YP, Liao YL, Lu Q, He X, Yan ZB, Liu JZ. ATP and NADPH engineering of Escherichia coli to improve the production of 4-hydroxyphenylacetic acid using CRISPRi. Biotechnol Biofuels. 2021 Apr 20;14(1):100. doi: 10.1186/s13068-021-01954-6. PMID: 33879249; PMCID: PMC8056492.

7: Abdel-Hady GN, Ikeda T, Ishida T, Funabashi H, Kuroda A, Hirota R. Engineering Cofactor Specificity of a Thermostable Phosphite Dehydrogenase for a Highly Efficient and Robust NADPH Regeneration System. Front Bioeng Biotechnol. 2021 Apr 1;9:647176. doi: 10.3389/fbioe.2021.647176. PMID: 33869158; PMCID: PMC8047080.

8: Zhang J, Liu Z, Tian F, Chen Y. A novel ratiometric fluorescent probe from a hemicyanine derivative for detecting NAD(P)H in a cell microenvironment. Anal Methods. 2021 Apr 14;13(14):1681-1686. doi: 10.1039/d1ay00002k. Epub 2021 Mar 23. PMID: 33861234.

9: Diehl FF, Vander Heiden MG. Mitochondrial NADPH is a pro at Pro synthesis. Nat Metab. 2021 Apr;3(4):453-455. doi: 10.1038/s42255-021-00381-z. PMID: 33833464.

10: Hörl M, Fuhrer T, Zamboni N. Bifunctional Malic/Malolactic Enzyme Provides a Novel Mechanism for NADPH-Balancing in Bacillus subtilis. mBio. 2021 Apr 6;12(2):e03438-20. doi: 10.1128/mBio.03438-20. PMID: 33824210; PMCID: PMC8092299.

11: Milrad Y, Schweitzer S, Feldman Y, Yacoby I. Bi-directional electron transfer between H2 and NADPH mitigates light fluctuation responses in green algae. Plant Physiol. 2021 Feb 4:kiab051. doi: 10.1093/plphys/kiab051. Epub ahead of print. PMID: 33793951.

12: Yoshikawa Y, Nasuno R, Takagi H. An NADPH-independent mechanism enhances oxidative and nitrosative stress tolerance in yeast cells lacking glucose-6-phosphate dehydrogenase activity. Yeast. 2021 Mar 1. doi: 10.1002/yea.3558. Epub ahead of print. PMID: 33648021.

13: Deschoenmaeker F, Mihara S, Niwa T, Taguchi H, Wakabayashi KI, Toyoshima M, Shimizu H, Hisabori T. Thioredoxin pathway in anabaena sp. PCC 7120: activity of NADPH-thioredoxin reductase C. J Biochem. 2021 Feb 4:mvab014. doi: 10.1093/jb/mvab014. Epub ahead of print. PMID: 33537746.

14: Li S, Ye Z, Moreb EA, Hennigan JN, Castellanos DB, Yang T, Lynch MD. Dynamic control over feedback regulatory mechanisms improves NADPH flux and xylitol biosynthesis in engineered E. coli. Metab Eng. 2021 Mar;64:26-40. doi: 10.1016/j.ymben.2021.01.005. Epub 2021 Jan 16. PMID: 33460820.

15: Shlosberg Y, Eichenbaum B, Tóth TN, Levin G, Liveanu V, Schuster G, Adir N. NADPH performs mediated electron transfer in cyanobacterial-driven bio- photoelectrochemical cells. iScience. 2020 Dec 4;24(1):101892. doi: 10.1016/j.isci.2020.101892. PMID: 33364581; PMCID: PMC7750406.

16: Qin N, Li L, Ji X, Li X, Zhang Y, Larsson C, Chen Y, Nielsen J, Liu Z. Rewiring Central Carbon Metabolism Ensures Increased Provision of Acetyl-CoA and NADPH Required for 3-OH-Propionic Acid Production. ACS Synth Biol. 2020 Dec 18;9(12):3236-3244. doi: 10.1021/acssynbio.0c00264. Epub 2020 Nov 13. PMID: 33186034.

17: Assil-Companioni L, Büchsenschütz HC, Solymosi D, Dyczmons-Nowaczyk NG, Bauer KKF, Wallner S, Macheroux P, Allahverdiyeva Y, Nowaczyk MM, Kourist R. Engineering of NADPH Supply Boosts Photosynthesis-Driven Biotransformations. ACS Catal. 2020 Oct 16;10(20):11864-11877. doi: 10.1021/acscatal.0c02601. Epub 2020 Sep 4. PMID: 33101760; PMCID: PMC7574619.

18: Ju HQ, Lin JF, Tian T, Xie D, Xu RH. NADPH homeostasis in cancer: functions, mechanisms and therapeutic implications. Signal Transduct Target Ther. 2020 Oct 7;5(1):231. doi: 10.1038/s41392-020-00326-0. PMID: 33028807; PMCID: PMC7542157.

19: Wei X, Lu Z, Li L, Zhang H, Sun F, Ma H, Wang L, Hu Y, Yan Z, Zheng H, Yang G, Liu D, Tepel M, Gao P, Zhu Z. Reducing NADPH Synthesis Counteracts Diabetic Nephropathy through Restoration of AMPK Activity in Type 1 Diabetic Rats. Cell Rep. 2020 Sep 29;32(13):108207. doi: 10.1016/j.celrep.2020.108207. PMID: 32997989.

20: Moon SJ, Dong W, Stephanopoulos GN, Sikes HD. Oxidative pentose phosphate pathway and glucose anaplerosis support maintenance of mitochondrial NADPH pool under mitochondrial oxidative stress. Bioeng Transl Med. 2020 Sep 8;5(3):e10184. doi: 10.1002/btm2.10184. PMID: 33005744; PMCID: PMC7510474.