Nadide

HCID 5892CAS 53-84-9
Substructure searchFind similar structures

Basic information

Standard SMILES
NC(=O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c1
InChIKey
BAWFJGJZGIEFAR-NNYOXOHSSA-N
Molecular formula
C21H27N7O14P2
Average molar mass
663.4 g/mol
Monoisotopic mass
663.10912256

Names & identifiers

Preferred name
Nadide
IUPAC
[[(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 phosphate
English name
β-Nicotinamide adenine dinucleotide
Molecular formula
C21H27N7O14P2
Molecular weight
663.43

Names & synonyms

nadide53-84-9coenzyme Ibeta-NADCodehydrogenase ICodehydrase Inicotinamide adenine dinucleotidediphosphopyridine nucleotideCozymase Ibeta-Diphosphopyridine nucleotideEnzoprideCOZYMASE
Show more names
NADβ-NADbeta-Nicotinamide adenine dinucleotideDPNB-NADβ-nicotinamide adenine dinucleotide hydratecozymaseibeta-diphosphopyridine
NadidumNicotinamide-adenine dinucleotidecodehydrogenaseNadidaPyridine, nucleotide diphosphateAdenine-nicotinamide dinucleotideNicotineamide adenine dinucleotideNadidum [INN-Latin]

Database identifiers

CAS
53-84-9、64417-72-7
PubChem CID
5892
DTXSID
DTXSID2045236
ChEMBL
CHEMBL1234613
ChEBI
CHEBI:44215
UNII
0U46U6E8UK
EC Number
200-184-4、264-884-1
Nikkaji
J136.554A

Properties

Computed structural properties

XLogP
-6
Topological polar surface area
321 Ų
Hydrogen bond donors
7
Hydrogen bond acceptors
18
Rotatable bonds
11
Heavy atoms
44

Experimental & physicochemical properties

Solubility752.5 mg/mL
Melting Point140.0 - 142.0 °C
Physical Description · 2 items

Highly hygroscopic white solid; [Merck Index] White powder; [Sigma-Aldrich MSDS]

Solid

Collision Cross Section · 3 items

222.7 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；230.8 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；223.8 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；227.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

226.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

227 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
140 · 140-142 °C (decomp)
alpha
20 · D20 -31.5° (c = 1.2 in water)
bulk density
200 · 200-300kg/m3
storage temp.
-20 °C · -20°C
solubility
2 O: · H2O: 50 mg/mL
form
Powder

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 99.1% (114 of 115) of all reports.

Not Classified；Reported as not meeting GHS hazard criteria by 114 of 115 companies (only 0.9% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 115 reports by companies from 2 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 114 of 115 reports by companies.；There is 1 notification provided by 1 of 115 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 3 items

Chemical: Adenosine 5'-(trihydrogen diphosphate), 5'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium hydroxide, inner salt

Status: Active Update: 11-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10862

Adenosine 5'-(trihydrogen diphosphate), P'→5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium, inner salt: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazard Classes and CategoriesNot Classified

Regulatory information

Regulatory Information · 3 items

Chemical: Adenosine 5'-(trihydrogen diphosphate), 5'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium hydroxide, inner salt

Status: Active Update: 11-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10862

Adenosine 5'-(trihydrogen diphosphate), P'→5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium, inner salt: Does not have an individual approval but may be used under an appropriate group standard

Safety data

wgk
3
tsca
TSCA listed
rtecs
UU3450000
hs_code
29349990
risk_code
36-68/20/21/22-20/21/22-40-22
Signal word
Warning

Chemistry & industry

Pharmacology

Tissue LocationsAdrenal Gland；Brain；Epidermis；Fibroblasts；Liver；Placenta；Platelet；Prostate；Skeletal Muscle
Cellular LocationsEndoplasmic reticulum；Extracellular；Mitochondria；Nucleus；Peroxisome
Metabolite Pathways · 1 item

11-beta-hydroxylase deficiency (CYP11B1)；17-alpha-hydroxylase deficiency (CYP17)；17-Beta Hydroxysteroid Dehydrogenase III Deficiency；2-aminoadipic 2-oxoadipic aciduria；2-Hydroxyglutric Aciduria (D And L Form)；2-ketoglutarate dehydrogenase complex deficiency；2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency；21-hydroxylase deficiency (CYP21)；27-Hydroxylase Deficiency；3-Beta-Hydroxysteroid Dehydrogenase Deficiency；Total 46223 pathways, visit the HMDB page for details

Uses & manufacturing

Uses · 1 item

A biologically active form of nicotinic acid; [Merck Index] A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed) [ChemIDplus]

General Manufacturing InformationAdenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium, inner salt: ACTIVE
Applications · 4 items

Descriptionβ-Nicotinamide adenine dinucleotide (NAD+) plays a major role in metabolism as a cofactor and mobile electron acceptor. NAD+ is a required oxidizing cosubstrate for many enzymes. It is reduced to NADH (Cat# N-035) which carries electrons to the electron transport chain for subsequent oxidative phorphorylation and ATP production. NAD+ is capable of donating ADP-ribose moieties to a protein, producing nicotinamide in the process. Sirtuin enzymes use NAD+ as a substrate to deacetylate proteins and direct activity between the nucleus and mitochondria. NAD+ is regenerated by fermentation and by oxidative phosphorylation.

Historyβ-Nicotinamide adenine dinucleotide was first discovered by British biochemists Arthur Harden and William John Young in 1906. They observed that the addition of boiled and filtered yeast extract significantly increased the rate of alcoholic fermentation in unboiled yeast extracts. They named the unidentified factor responsible for this effect a coferment. By extensively purifying it from yeast extracts, Hans von Euler-Chelpin identified this heat-stable factor as a nucleotide sugar phosphate. In 1936, German scientist Otto Heinrich Warburg demonstrated the role of this nucleotide coenzyme in hydride transfer and determined the nicotinamide portion as the site of redox reactions. Vitamin precursors of NAD+ were first identified in 1938, when Conrad Elvehjem showed that liver has an "anti-black tongue" activity in the form of nicotinamide. Then, in 1939, he provided the first strong evidence that niacin is used to synthesize NAD+.

Usesβ-Nicotinamide Adenine Dinucleotide is a coeznyme consisting of an adenine base and a nicotinamide base connected by a pair of bridging phosphate group. β-Nicotinamide Adenine Dinucleotide acts as a c oenzyme in redox reactions, as a donor of ADP-ribose moieties in ADP-ribosylation reactions and also as a precursor of the second messenger molecule cyclic ADP-ribose. β-Nicotinamide Adenine Dinucleot ide also acts as a substrate for bacterial DNA ligases and a group of enzymes called sirtuins that use NAD+ to remove acetyl groups from proteins.

General Descriptionβ-Nicotinamide adenine dinucleotide (NAD) is a ubiquitously found electron carrier and a cofactor. NAD+ contains an adenylic acid and a nicotinamide-5′-ribonucleotide group linked together by a pyrophosphate moiety. In NAD+ complexes, the enzyme-cofactor interactions are highly conserved.

Upstream & downstream products

Downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
苏州华赛生物工程技术有限公司0512-89581819; 18915732708 · [email protected]
Additional notes · 1 item

DefinitionChEBI: β-Nicotinamide adenine dinucleotide (NAD) is the oxidized form of β-Nicotinamide Adenine Dinucleotide. It exists as an anion under normal physio-logic conditions. It is functionally related to a deamido-NAD zwitterion. It is a conjugate base of a NAD(+). It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed)

Related reactions

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