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

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

Theoretical Analysis

MedKoo Cat#: 111527
Name: NADPH free acid
CAS#: 53-57-6 (free acid)
Chemical Formula: C21H30N7O17P3
Exact Mass: 745.09
Molecular Weight: 745.42
Elemental Analysis: C, 33.84; H, 4.06; N, 13.15; O, 36.49; P, 12.47

Price and Availability

Size Price Availability Quantity
50.0mg USD 350.0 2 Weeks
100.0mg USD 550.0 2 Weeks
200.0mg USD 950.0 2 Weeks
500.0mg USD 1650.0 2 Weeks
1.0g USD 2950.0 2 Weeks
2.0g USD 5250.0 2 Weeks
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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 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

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

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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.