Basic information
- CAS
3633-59-8- Standard SMILES
CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O)[C@@H](O)C(=O)NCCC(=O)NCCS- InChIKey
KDTSHFARGAKYJN-IBOSZNHHSA-N- Molecular formula
- C21H35N7O13P2S
- Average molar mass
- 687.6 g/mol
- Monoisotopic mass
- 687.14887844
Overview
3'-dephospho-CoA is an adenosine 5'-phosphate that is coenzyme A in which the phosphate group at position 3' has been replaced by a hydrogen atom. It is an intermediate metabolite in pantothenate and CoA biosynthesis. It has a role as a mouse metabolite, an Escherichia coli metabolite and a human metabolite. It is functionally related to a coenzyme A. It is a conjugate acid of a 3'-dephospho-CoA(2-).
Names & identifiers
- Preferred name
- Dephospho-coa
- IUPAC
- [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate
- English name
- 3'-DEPHOSPHOCOENZYME A
- Molecular formula
- C21H35N7O13P2S
- Molecular weight
- 687.55
Names & synonyms
dephospho-CoA3633-59-8dephosphocoenzyme A3'-dephospho-CoADephospho coaDesphospho-CoA3'-desphospho-coenzyme ACHEBI:15468dpCoARefChem:585761(((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(3-hydroxy-2,2-dimethyl-3-((2-((2-sulfanylethyl)carbamoyl)ethyl)carbamoyl)propoxy)phosphinic acid[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphinic acid
Show more names
3'-DEPHOSPHOCOENZYME A FREE ACID3'-Dephosphocoenzyme A >=90% (HPLC)Coenzyme A Impurity 26 (3′-O-dephosphono Coenzyme A)
(((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)((3R)-3-hydroxy-2,2-dimethyl-3-((2-((2-sulfanylethyl)carbamoyl)ethyl)carbamoyl)propoxy)phosphinic acid2'-(5''-triphosphoribosyl)-3'-dephospho-CoAdephospho coenzyme a3-DEPHOSPHOCOENZYMEA3'-Dephosphocoenzyme A3'-dephospho cOa3'-O-dephosphono-Coenzyme ACoenzyme A, 3'-O-dephosphono-
Database identifiers
- CAS
3633-59-8- PubChem CID
- 444485
- DTXSID
DTXSID101355526- ChEBI
CHEBI:15468- Nikkaji
- J1.407.433C
Properties
Computed structural properties
- XLogP
- -4.7
- Topological polar surface area
- 301 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 18
- Rotatable bonds
- 16
- Heavy atoms
- 44
- Formal charge
- 0
- Complexity
- 1,100
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Fatty acyl CoAs [FA0705]
Physical DescriptionSolid
Collision Cross Section232.51 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Density
- 1.85 · 1.85±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 50 mg/ml · Water: 50 mg/ml
- form
- A crystalline solid
- pka
- 1.16 · 1.16±0.50(Predicted)
- color
- White to off-white
- InChIKey
- KDTSHFARGAKYJN-UHFFFAOYSA-N
- SMILES
- CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)n2cnc3c(N)ncnc23)C(O)C(=O)NCCC(=O)NCCS
- UNSPSC Code
- 41106305 · 41106305
- NACRES
- 51 · NA.51
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Metabolite PathwaysPantothenate and CoA Biosynthesis
Applications
Description3''-Dephosphocoenzyme A is an intermediate in the biosynthesis of coenzyme A (CoA; Item Nos. 16147 | 21499 | 21722) from pantothenic acid (vitamin B5; ). It is phosphorylated by CoA synthase in humans to form CoA. 3''-Dephosphocoenzyme A can be used as a transcription initiator in the synthesis of CoA-RNA by in vitro transcription.
UsesDephosphocoenzyme A is the direct precursor of coenzyme A. It is used for the synthesis of coenzyme A by bifunctional CoA Synthase (CoASy, 4′-phosphopantetheine adenylyltransferase/dephospho-CoA kinase) which performs the transfer of the γ-phosphate of ATP to dephosphocoenzyme A.
Suppliers24 total
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Additional notes
DefinitionChEBI: An adenosine 5'-phosphate that is coenzyme A in which the phosphate group at position 3' has been replaced by a hydrogen atom. It is an intermediate metabolite in pantothenate and CoA biosynthesis
Related reactions
2 records
Compound notes
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