Basic information
- CAS
53-59-8- 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](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)c1- InChIKey
XJLXINKUBYWONI-NNYOXOHSSA-N- Molecular formula
- C21H28N7O17P3
- Average molar mass
- 743.4 g/mol
- Monoisotopic mass
- 743.07545344
Overview
NADP zwitterion is a NADP. It has a role as a fundamental metabolite. It is a conjugate base of a NADP(+).
Names & identifiers
- Preferred name
- Nadp
- IUPAC
- [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
- English name
- Triphosphopyridine nucleotide
- Molecular formula
- C21H28N7O17P3
- Molecular weight
- 743.41
Names & synonyms
53-59-8triphosphopyridine nucleotidecoenzyme IINADPCodehydrogenase IINAD phosphateCozymase IINadide phosphateTPN (nucleotide)Nicotinamide-adenine dinucleotide phosphateNADP+BY8P107XEP
Show more names
NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATETPNΒ-NADPβ-Nicotinamide adenine dinucleotide phosphateb-Nicotinamide adenine dinucleotide phosphateTPNHnicotinamide adenine dinucleotide-P
beta-nicotinamide adenine dinucleotide phosphateCHEBI:44409DTXSID50889327Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'-5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner saltbeta-NADP+[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphateCHEBI:18009(((2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl) ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl)methyl phosphate
Database identifiers
Properties
Computed structural properties
- XLogP
- -7.1
- Topological polar surface area
- 368 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 21
- Rotatable bonds
- 13
- Heavy atoms
- 48
- Formal charge
- 0
- Complexity
- 1,290
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Other Biomolecules
Physical Description
Grayish-white solid; [Merck Index]
Solid
Physicochemical properties
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- 2 O: · H2O: 50 mg/mL, clear, slightly yellow
- pka
- 1 · pKa1 3.9; pKa2 6.1(at 25℃)
- form
- powder to crystal
- color
- White to Orange to Green
- Water Solubility
- 2 O: · H2O: soluble 50mg/mL, clear, colorless to faintly yellow
- λmax
- 260 nm · 260nm(lit.)
- Merck
- 14 · 14,6348
- InChIKey
- XJLXINKUBYWONI-WFYQBQJJNA-N
- SMILES
- O.NC(=O)c1ccc[n+](c1)[C@@H]2O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](OP(O)(O)=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O
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
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), 5'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium hydroxide, inner salt
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards SummarySee NADPH.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- F
- 10-21
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UU3440000
- hs_code
- 2934.99.9001
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
Chemistry & industry
Pharmacology
Tissue LocationsAll Tissues
Cellular LocationsEndoplasmic reticulum
Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)
Uses & manufacturing
UsesThe active form of nicotinic acid, which functions as a coenzyme; [Merck Index] It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed) [ChemIDplus]
General Manufacturing InformationAdenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium, inner salt: ACTIVE
Applications
DescriptionTriphosphopyridine nucleotide is a coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. Triphosphopyridine nucleotide serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH).
Usesβ-Nicotinamide adenine dinucleotide phosphate hydrate is suitable for use in:the measurement of Glucose-6-phosphate dehydrogenase activitythe Cytochrome P450 3A4 assay as a part of NADPH-regenerating systemthe Cytochrome P450 2D6 assay as a part of NADPH-regenerating systemthe determination of Glucose-6-phosphate content
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…