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NAD+ (Nicotinamide adenine dinucleotide)

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Identification
Molecular formula
C21H27N7O14P2
CAS number
53-84-9
IUPAC name
[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl hydrogen phosphate
State
State
NAD+ is typically a solid at room temperature, usually encountered as a crystalline powder that is white or off-white in color.
Melting point (Celsius)
140.00
Melting point (Kelvin)
413.15
Boiling point (Celsius)
953.00
Boiling point (Kelvin)
1 226.15
General information
Molecular weight
663.43g/mol
Molar mass
663.4250g/mol
Density
1.7600g/cm3
Appearence

NAD+ is typically found as a white crystalline powder. In its oxidized form, it is stable and can readily interact with enzymes to partake in redox reactions. It is hygroscopic and thus can absorb moisture from the air.

Comment on solubility

Solubility of Compound

The compound with the formula C21H27N7O14P2 exhibits unique solubility characteristics influenced by its intricate structure. This compound is a hybrid of nucleobase and carbohydrate moieties, contributing to its behavior in solvents:

  • Aqueous Solubility: Due to the presence of multiple hydroxyl groups and phosphate functionalities, it tends to be water-soluble.
  • Organic Solvents: It may show limited solubility in organic solvents like ethanol or acetone, which can be attributed to its polar groups.
  • pH Dependence: Solubility could be affected by pH; at very acidic or basic conditions, solubility may increase or decrease based on ionization states of the phosphoric acid moieties.
  • Temperature Effect: Higher temperatures generally enhance solubility, making thermal conditions a consideration for its applications.

In summary, the solubility profile of this compound can be described as primarily hydrophilic due to the presence of functional groups that interact favorably with water molecules.

Interesting facts

Intriguing Insights into a Complex Compound

The compound with the intricate name and formula, a unique derivative of nucleosides, holds remarkable significance in the field of biochemistry and pharmaceutical research. Here are some fascinating aspects to consider:

  • Structural Complexity: This compound is notable for its complex structure, featuring a tetrahydrofuran ring that incorporates multiple functional groups, including hydroxy and phosphonooxy groups. This architecture plays a critical role in its biological activity.
  • Biological Relevance: It is related to nucleosides, which are fundamental building blocks of nucleic acids. Compounds like this can influence various biological processes, making them potential candidates for drug development, especially in targeting RNA mechanisms.
  • Mechanism of Action: The presence of an aminopurine moiety suggests a relationship to purine metabolism, which is crucial in cellular energy transfer and signaling pathways.
  • Phosphorylation Role: The phosphoryl groups contribute to the compound's ability to participate in key biochemical reactions, notably in phosphorylation processes, which are vital for enzyme activity and energy storage.
  • Potential Applications: Given its structural features, this compound may be explored further in the realms of antiviral and anticancer research, where modulation of nucleic acid synthesis is essential. Its unique properties could lead to breakthroughs in treating various diseases.

In summary, this compound encapsulates the beauty and complexity of biochemical systems, reflecting how small structural variations can lead to significant changes in biological function. As scientists continue to investigate compounds like this one, the promise of new therapeutic strategies remains a compelling avenue for research.

Synonyms
NADPH
53-57-6
TPNH
Dihydronicotinamide-adenine dinucleotide phosphate
2646-71-1
UNII-381Q4X082D
CHEBI:16474
NADP REDUCED FOM
beta-NADPH
EINECS 200-177-6
COENZYME II, REDUCED
NADP REDUCED FORM [MI]
REDUCED CODEHYDROGENASE II
Reduced Nicotinamide Adenine Dinucleotide Phosphate
dihydronicotinamide adenine dinucleotide phosphate
DTXSID001018921
reduced nicotinamide-adenine dinucleotide phosphate
Nicotinamide-adenine dinucleotide phosphate, reduced
Reduced triphosphopyridine nucleotide
381Q4X082D
[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
reduced NADP
dihydronicotinamide adenine dinucleotide-P
NADPH DIHYDRO-NICOTINAMIDE-ADENINE-DINUCLEOTIDE PHOSPHATE
Dihydrocodehydrogenase II
NADP-red
NADPH2
2'-O-phosphonoadenosine 5'-{3-[1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl] dihydrogen diphosphate}
Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
dihydrotriphosphopyridine nucleotide
reduced dihydrotriphosphopyridine nucleotide
nadph hydride
NADP-reduced
dihydronicotinamide adenine dinucleotide phosphate reduced
beta-TPNH
(((2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl) ((2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl)methyl phosphate
(((2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl) ((2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl)methyl hydrogen phosphate
(((2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-((((((((2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)methyl)-4-hydroxyoxolan-3-yl)oxy)phosphonic acid
[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
2'-O-phosphonoadenosine 5'-(3-(1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl) dihydrogen diphosphate)
reduced Coenzyme II
reduced Cozymase II
b-NADPH
reduced Codehydrase II
beta-NADPH Tetrasodium
NADP REDUCED FORM
.BETA.-NADPH
bmse000055
SCHEMBL2041
Nucleotide, Triphosphopyridine
CHEMBL407009
DTXCID201476935
((2S,3S,4S,5S)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl)methyl (((2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl) hydrogen phosphate
[(2S,3S,4S,5S)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methyl [[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
Triphosphopyridine nucleotide reduced
Triphosphopyridine nucleotide, reduced
DB02338
DA-55982
dihydrotriphosphopyridine nucleotide reduced
Dinucleotide Phosphate, Nicotinamide-Adenine
HY-113324
Nicotinamide-adenine-dinucleotide-phosphorate
Phosphate, Nicotinamide-Adenine Dinucleotide
CS-0059609
NS00015230
b-Nicotinamide-adenine-dinucleotide-phosphorate
C00005
Dihydronicotinamideadenine dinucleotide phosphate
beta-Nicotinamide-adenine-dinucleotide-phosphorate
Nicotinamide-adenine-dinucleotide-phosphoric acid
reducednicotinamide-adenine dinucleotide phosphate
b-Nicotinamide-adenine-dinucleotide-phosphoric acid
Nicotinamide adenine dinucleotide phosphate - reduced
beta-Nicotinamide-adenine-dinucleotide-phosphoric acid
Q26841327
Dihydronicotinamide-adenine dinucleotide phosphoric acid
Reduced nicotinamide adenine dinucleotide phosphoric acid
Reduced nicotinamide-adenine dinucleotide phosphoric acid
.BETA.-NICOTINAMIDE-ADENINE-DINUCLEOTIDE-PHOSPHORIC ACID
NADPH dihydro-nicotinamide-adenine-dinucleotide phosphoric acid
Nadph dihydro-nicotinamide-adenine-dinucleotidephosphoric acid
[(2R,3R,4R,5R)-2-(6-Aminopurin-9-yl)-5-[[[[(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxymethyl]-4-hydroxy-oxolan-3-yl]oxyphosphonic acid
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide
Adenosine 5'(trihydrogen diphosphate), 2'(dihydrogen phosphate), P'.fwdarw.5'ester with 1,4dihydro1betaDribofuranosyl3pyridinecarboxamide
Adenosine 5'(trihydrogen diphosphate), 2'(dihydrogen phosphate), P'>5'ester with 1,4dihydro1betaDribofuranosyl3pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide
ADENOSINE 5'-(TRIHYDROGEN DIPHOSPHATE), 2'-(DIHYDROGEN PHOSPHATE), P'->5'-ESTER WITH 1,4-DIHYDRO-1-.BETA.-D-RIBOFURANOSYL-3-PYRIDINECARBOXAMIDE
Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'.fwdarw.5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogenphosphate), P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide