Nadide
Completing data — refresh the page later to see the latest
Basic information
- CAS
53-84-9- 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 propertiesFilling in
- XLogP
- -6
- Topological polar surface area
- 321 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 18
- Rotatable bonds
- 11
- Heavy atoms
- 44
- Formal charge
- 0
- Complexity
- 1,120
Experimental & physicochemical properties
Solubility752.5 mg/mL
Melting Point140.0 - 142.0 °C
Physical Description
Highly hygroscopic white solid; [Merck Index] White powder; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
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
- pka
- 5.25 · 5.25
- color
- White
- PH
- 3 · ~3.0 (50mg/mL in water)
- Odor
- Odorless
- biological source
- yeast
- Water Solubility
- 50 mg/ml · Soluble in water at 50mg/ml
- λmax
- 260 nm · 260 nm
- Merck
- 14 · 14,6344
- BRN
- 3584133 · 3584133
- Stability
- Stable. Hygroscopic. Incompatible with strong oxidizing agents.
- Major Application
- metabolomics
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChIKey
- BAWFJGJZGIEFAR-WWRWIPRPSA-N
- SMILES
- NC1=NC=NC2=C1N=CN2.O[C@@H]3[C@@H](COP(O)(OP(OC[C@@H](O4)[C@@H](O)[C@@H](O)[C@H]4[N+]5=CC=CC(C(N)=O)=C5)([O-])=O)=O)OC[C@@H]3O
- FDA UNII
- 0 U46U6E8UK · 0U46U6E8UK
- EPA Substance Registry System
- 5 · Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium, inner salt (53-84-9)
- UNSPSC Code
- 41106305 · 41106305
- NACRES
- 21 · NB.21
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 371 · H371
- Precautionary statements
- 260 · P260-P264-P270-P308+P311-P405-P501
- Hazard Codes
- Xn,F,Xi
- Risk Statements
- 36 · 36-68/20/21/22-20/21/22-40-22
- Safety Statements
- 36 · 36-26-36/37-24/25
- WGK Germany
- 3 · 3
- RTECS
- 3450000 · UU3450000
- TSCA
- TSCA listed
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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
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'â5'-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
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'â5'-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
- Symbol(GHS)
- GHS08
- hazard_code
- Xn,F,Xi
- safety_code
- 36-26-36/37-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H371
- REACH Registrations
- Active
- Precautionary statements
- P260-P264-P270-P308+P311-P405-P501
Chemistry & industry
Pharmacology
Tissue LocationsAdrenal Gland；Brain；Epidermis；Fibroblasts；Liver；Placenta；Platelet；Prostate；Skeletal Muscle
Cellular LocationsEndoplasmic reticulum；Extracellular；Mitochondria；Nucleus；Peroxisome
Metabolite Pathways
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
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
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
Upstream raw materials
Downstream products
Additional notes
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
40 records
Compound notes
Loading…