Coa disulfide
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Basic information
- CAS
31664-36-5- Standard SMILES
CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCSSCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O- InChIKey
YAISMNQCMHVVLO-ODFVJXNFSA-N- Molecular formula
- C42H70N14O32P6S2
- Average molar mass
- 1,533.1 g/mol
- Monoisotopic mass
- 1,532.2147704
Overview
CoA-disulfide is an organic disulfide obtained via oxidative dimerisation of coenzyme A. It is a conjugate acid of a CoA-disulfide(8-).
Names & identifiers
- Preferred name
- Coa disulfide
- IUPAC
- [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-4-[[3-[2-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyldisulfanyl]ethylamino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl] hydrogen phosphate
- English name
- coenzyme A disulfide
- Molecular formula
- C42H70N14O32P6S2
- Molecular weight
- 1533.05
Names & synonyms
CoA-disulfideCoa disulfideCoenzyme A disulfide31664-36-5CHEBI:16161DTXSID401317672RefChem:127193DTXCID601747477(((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl) ((3R)-4-((3-(2-(2-(3-(((2R)-4-((((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl)oxy-hydroxyphosphoryl)oxy-2-hydroxy-3,3-dimethylbutanoyl)amino)propanoylamino)ethyldisulfanyl)ethylamino)-3-oxopropyl)amino)-3-hydroxy-2,2-dimethyl-4-oxobutyl) hydrogen phosphate(CoA)2Oxidized CoA5NG
Show more names
Coenzyme A Impurity 27
orb2564170SCHEMBL29390522TN7656Q27098407Adenosine, 3'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate), 5'-->4:5'''-->4'-diester with N,N'-[dithiobis(ethyleneiminocarbonylethylene)]bis[2,4-dihydroxy-3,3-dimethylbutyramide]Adenosine, 3'-phosphate 5'-pyrophosphate, 5',5'''-diester with N,N'-[dithiobis(ethyleneiminocarbonylethylene)]bis[2,4-dihydroxy-3,3-dimethylbutyramide]Bis{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} (3R,22R)-3,22-dihydroxy-2,2,23,23-tetramethyl-4,8,17,21-tetraoxo-12,13-dithia-5,9,16,20-tetraazatetracosane-1,24-diyl bis[dihydrogen (diphosphate)]Butyramide, N,N'-[dithiobis(ethyleneiminocarbonylethylene)]bis[2,4-dihydroxy-3,3-dimethyl-, 5',5'''-->4,4'-diester with adenosine 3'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate)
Properties
Computed structural propertiesFilling in
- XLogP
- -11.7
- Topological polar surface area
- 744 Ų
- Hydrogen bond donors
- 18
- Hydrogen bond acceptors
- 42
- Rotatable bonds
- 39
- Heavy atoms
- 96
- Formal charge
- 0
- Complexity
- 2,760
Physicochemical properties
- Density
- 2.02 · 2.02±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- pka
- 1.16 · 1.16±0.50(Predicted)
- form
- solid
- InChIKey
- YAISMNQCMHVVLO-ODFVJXNFSA-N
- UNSPSC Code
- 41106305 · 41106305
- NACRES
- 51 · NA.51
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 315 · H315-H318
- Precautionary statements
- 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P362+P364
- WGK Germany
- 3 · 3
- Storage Class
- 4.1 B · 4.1B - Flammable solid hazardous materials
- Hazard Classifications
- 1 Skin · Eye Dam. 1Skin Irrit. 2
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- Storage Class
- 4.1B - Flammable solid hazardous materials
- Hazard statements
- H315-H318
- Hazard Classifications
- Eye Dam. 1Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P362+P364
Chemistry & industry
Applications
UsesCoenzyme A (CoA, CoASH, HSCoA) is a coenzyme that facilitates enzymatic acyl-group transfer reactions and supports the synthesis and oxidation of fatty acids. CoA is involved in the mechanisms of a wide variety of enzymes. CoA is a thiol compound subject to oxidation. Oxidized CoA may be used to study reduction systems (CoA disulfide reductase (CoADR) systems) that regenerate reduced CoA in vivo. Furthermore, oxidized CoA may be used to study unique functions of this molecule in vivo.
Additional notes
DefinitionChEBI: An organic disulfide obtained via oxidative dimerisation of coenzyme A.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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