NADPH

Base Information

• Chemical Name: NADPH
• CAS No.: 53-57-6
• Deprecated CAS: 22046-90-8,3545-01-5
• Molecular Formula: C21H30 N7 O17 P3
• Molecular Weight: 745.427
• European Community (EC) Number: 200-177-6,220-163-3
• UNII: 381Q4X082D
• DSSTox Substance ID: DTXSID001018921
• Nikkaji Number: J213.537J
• Wikidata: Q26841327
• Metabolomics Workbench ID: 50514
• ChEMBL ID: CHEMBL407009
• Mol file: 53-57-6.mol

Synonyms:Coenzyme II;Dinucleotide Phosphate, Nicotinamide-Adenine;NADP;NADPH;Nicotinamide Adenine Dinucleotide Phosphate;Nicotinamide-Adenine Dinucleotide Phosphate;Nucleotide, Triphosphopyridine;Phosphate, Nicotinamide-Adenine Dinucleotide;Triphosphopyridine Nucleotide

Chemical Property of NADPH

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1175.1°Cat760mmHg
• PKA: 1.13±0.50(Predicted)
• Flash Point: 664.5°C
• PSA: 394.57000
• Density: 2.28g/cm³
• LogP: -0.90060
• XLogP3: -6.8
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 22
• Rotatable Bond Count: 13
• Exact Mass: 745.09110351
• Heavy Atom Count: 48
• Complexity: 1410

Purity/Quality:

99% ^*data from raw suppliers

β-NADPH-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Other Biomolecules
• Canonical 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)OP(=O)(O)O)O)O)O
• 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
• Uses: β-NADPH-d4 is the isotope labelled analog of β-NADPH. One of the biologically active forms of nicotinic acid. Differs from NAD by an additional phosphate group at the 2’-position of the adenosine moiety. Serves as a coenzyme of hydrogenases and dehydrogenases. Present in living cells primarily in the reduced form (NADPH) and is involved in synthetic reactions.

Technology Process of NADPH

There total 11 articles about NADPH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 55.0%

NADPH (53-59-8) → NADPH (53-57-6)

Guidance literature:

With chloro-[η⁵-(pentamethyl)-cyclopentadienyl]-(2,2′-bipyridyl)-rhodium(III) chloride; triethanolamine; In aq. phosphate buffer; N,N-dimethyl-formamide; at 20 ℃; for 2.5h; pH=Ca. 7; Reagent/catalyst; Inert atmosphere; Irradiation;

DOI:10.1039/c4gc00885e

Reference yield: 40.0%

NADP (53-59-8) → NADPH (53-57-6)

Guidance literature:

With triethanolamine; zinc protoporphyrin reconstituted horse myoglobin; In phosphate buffer; at 20 ℃; for 5.5h; pH=8.5; Irradiation;

DOI:10.1246/cl.1999.357

Reference yield:

L-glutamine (56-85-9,26700-71-0) + NADP (53-59-8) → 2-keto-glutaramic acid (18465-19-5) + NADPH (53-57-6)

Guidance literature:

With glutamate dehydrogenase; ethylenediaminetetraacetic acid; Pyrococcus horikoshii OT₃ ATP pyrophosphatase; Pyrococcus horikoshii OT₃ glutamine amidotransferase; XMP; ATP; magnesium chloride; pH=8; aq. buffer;

DOI:10.1016/j.jmb.2009.10.053

upstream raw materials:

NADP

nicotinamide adenine dinucleotide phosphate

D-glucose 6-phosphate

L-glutamine

Downstream raw materials:

NADP

NADPH

D-sorbitol

pregnanedione

Refernces

• 1、 Wong, Chi-Huey,Daniels, Lacy,Orme-Johnson, William H.,Whitesides, George M.. "Enzyme-Catalyzed Organic Synthesis: NAD(P)H Regeneration Using Dihydrogen and the Hydrogenase from Methanobacterium thermoautotrophicum". . p. 6227 - 6228. Retrieved 1981.
• 2、 Cordeiro, Artur T.,Thiemann, Otavio H.. "16-Bromoepiandrosterone, an activator of the mammalian immune system, inhibits glucose 6-phosphate dehydrogenase from Trypanosoma cruzi and is toxic to these parasites grown in culture". . p. 4762 - 4768. Retrieved 2010.
• 3、 Honjoh, Ken-Ichi,Mimura, Ayano,Kuroiwa, Eiko,Hagisako, Takahiro,Suga, Koushirou,Shimizu, Hideyuki,Dubey, Rama Shanker,Miyamoto, Takahisa,Hatano, Shoji,Iio, Masayoshi. "Purification and characterization of two isoforms of glucose 6-phosphate dehydrogenase (G6PDH) from Chlorella vulgaris C-27". . p. 1888 - 1896. Retrieved 2003.
• 4、 Zhang, Yugang,Lin, Zhewang,Wang, Miao,Lin, Hening. "Selective Usage of Isozymes for Stress Response". . p. 3059 - 3064. Retrieved 2018/11/23.
• 5、 Morra, Simone,Pordea, Anca. "Biocatalyst-artificial metalloenzyme cascade based on alcohol dehydrogenase". . p. 7447 - 7454. Retrieved 2018/10/21.