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NAD+

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Identification
Molecular formula
C21H27N7O14P2
CAS number
53-84-9
IUPAC name
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl hydrogen phosphate
State
State

At room temperature, NAD+ is in a solid state.

Melting point (Celsius)
140.00
Melting point (Kelvin)
413.15
Boiling point (Celsius)
180.00
Boiling point (Kelvin)
453.15
General information
Molecular weight
663.43g/mol
Molar mass
663.4250g/mol
Density
1.5749g/cm3
Appearence

NAD+ is typically a white to off-white powder. It is visually characterized by uniformity and may appear slightly crystalline.

Comment on solubility

Solubility of the Compound

The solubility of the chemical compound with the formula C21H27N7O14P2 is influenced by several factors, including its molecular structure and the presence of various functional groups. Here are some key considerations regarding its solubility:

  • Functional Groups: The presence of hydroxyl groups (–OH) and the phosphorus-containing groups greatly enhances its solubility in polar solvents, particularly water. This is due to hydrogen bonding capabilities.
  • Ionic Nature: The compound has a pyridinium moiety, which may contribute to its ionic character, making it more soluble in polar solvents.
  • Hydrogen Bonding: The ability to form hydrogen bonds with solvent molecules can significantly increase solubility. Given the multiple hydroxyls and nitrogen atoms, this compound likely demonstrates increased solubility.
  • Temperature Effects: As with many compounds, higher temperatures typically enhance solubility. It’s important to consider solubility changes across different temperature ranges.

In conclusion, it's reasonable to assert that this compound is likely to be soluble in polar solvents due to its structure and functional groups. As with all solubility assessments, experimental verification remains crucial to draw definitive conclusions.

Interesting facts

Exploring the Fascinating Compound: A Complex Nucleotide Analog

This compound is a prime example of the intricate world of nucleotide analogs, which play a significant role in molecular biology and pharmaceutical applications. Its structure reveals a rich tapestry of functional groups that contribute to its unique properties and biological activities.

Key Features of the Compound:

  • Structural Complexity: The presence of a tetrahydrofuran moiety contributes to the stereochemistry that can affect how this compound interacts with biological targets.
  • Amino Group Interaction: The 6-aminopurine and 3-carbamoylpyridine components grant the molecule a unique surface for interaction with enzymes and receptors, opening pathways for immunotherapy and antiviral research.
  • Phosphate Backbone: The addition of the phosphate functionality is critical, as it mimics natural nucleotides and can potentially disrupt nucleotide metabolism in pathogens.

Applications in Research and Medicine:

This compound is not just a synthetic curiosity; it holds significant promise in various fields. Researchers are particularly interested in its potential applications in:

  1. Antiviral Agents: Given its structural similarities to nucleotides, it is being investigated for its ability to inhibit viral replication.
  2. Cancer Treatments: Its unique amino and phosphoramide groups suggest potential mechanisms for targeting and disrupting cancer cell growth.
  3. Biochemical Research: Scientists utilize such compounds to understand enzyme mechanisms and the role of nucleotides in cellular processes.

In the words of a leading medicinal chemist, “Nucleotide analogs can be the key to unlocking novel therapeutic strategies” – reflecting the excitement surrounding this class of compounds. Their ability to influence biological activity while mimicking natural molecules emphasizes their importance in health sciences. The synthesis and exploration of this compound underscore the ongoing quest for effective treatments and the deepening understanding of molecular interactions in living systems.

Synonyms
nicotinamide adenine dinucleotide
NAD+
151411-04-0
53-84-9
NAD(+)
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
CHEBI:15846
Nicotinamide-Adenine-Dinucleotide
beta-nicotinamide adenine dinucleotide
121053-11-0
Adenine Dinucleotide, Dihydronicotinamide
SR-05000001677
65085-09-8
Nadide [USAN:BAN:INN:JAN]
NAD cation
[[(2R,3S,4R,5R)-5-[(3R)-3-aminocarbonyl-3,4-dihydro-2H-pyridin-1-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanidyl-ph osphoryl] [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl phosphate
NAJ
TXE
Spectrum_000973
[[(2~{R},3~{S},4~{R},5~{R})-5-(3-aminocarbonylpyridin-1-ium-1-yl)-4-[[5-[4-cyano-2-[(~{E})-hydroxyiminomethyl]phenoxy]-1-oxidanyl-3~{H}-2,1$l^{4}-benzoxaborol-1-yl]oxy]-3-oxidanyl-oxolan-2-yl]methoxy-oxidanyl-phosphoryl] [(2~{R},3~{S},4~{R},5~{R})-5-(6-aminopurin-9-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl hydrogen phosphate
9JM
Adenosine 5'-(trihydrogen diphosphate), P'-5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt
Prestwick3_000741
Spectrum2_001056
Spectrum3_000511
Spectrum4_000065
Spectrum5_001291
bmse000053
Nadide (JAN/USAN/INN)
BSPBio_000722
BSPBio_002061
KBioGR_000589
KBioSS_001453
DivK1c_000189
SPBio_001012
BPBio1_000796
CHEMBL3039307
SCHEMBL14478781
KBio1_000189
KBio2_001453
KBio2_004021
KBio2_006589
KBio3_001561
NINDS_000189
IDI1_000189
Nicotinamide adenine dinucleotide (NAD+)
PD062453
C00003
D00002
SR-05000001677-1
SR-05000001677-3
BRD-A11132253-001-01-7
BRD-A11132253-001-08-2
Q26987253
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1??-pyridin-1-ylium
865-05-4
adenosine 5'-{3-[1-(3-carbamoylpyridinio)-1,4-anhydro-D-ribitol-5-yl] dihydrogen diphosphate}