Coenzyme A

HCID 87642CAS 85-61-0
Substructure searchFind similar structures

Basic information

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)NCCS
InChIKey
RGJOEKWQDUBAIZ-IBOSZNHHSA-N
Molecular formula
C21H36N7O16P3S
Average molar mass
767.5 g/mol
Monoisotopic mass
767.11520896

Overview

Coenzyme A is a thiol comprising a panthothenate unit in phosphoric anhydride linkage with a 3',5'-adenosine diphosphate unit; and an aminoethanethiol unit. It has a role as a coenzyme, a mouse metabolite and an Escherichia coli metabolite. It is a secondary carboxamide, a member of 6-aminopurines, a nucleotide derivative and a thiol. It is functionally related to a 3'-phosphate-adenosine-5'-diphosphate. It is a conjugate acid of a coenzyme A(4-).

Names & identifiers

Preferred name
Coenzyme A
IUPAC
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-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
Coenzyme A
Molecular formula
C21H36N7O16P3S
Molecular weight
767.53

Names & synonyms

coenzyme ACoASH85-61-0CoA-SHZeelHSCoACOENZYME_ASAA04E81UXDTXSID90483023'-phosphoadenosine-(5')diphospho(4')pantatheineCHEBI:15346[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate
Show more names
COACOENZYME A HYDRATECoalipLucinaAluzimeThiol-CoASHUIRUJIECONENZYME A
3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl] dihydrogen diphosphate}NSC20274(((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl) ((3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-((3-oxo-3-(2-sulfanylethylamino)propyl)amino)butyl) hydrogen phosphate((2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl)methyl (hydroxy-((3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-((3-oxo-3-(2-sulfanylethylamino)propyl)amino)butoxy)phosphoryl) hydrogen phosphate[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methyl [hydroxy-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butoxy]phosphoryl] hydrogen phosphate3'-phosphoadenosine 5'-(3-((3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-((3-oxo-3-((2-sulfanylethyl)amino)propyl)amino)butyl) dihydrogen diphosphate)RefChem:127396DTXCID7028277

Database identifiers

CAS
85-61-0
PubChem CID
87642
DTXSID
DTXSID9048302
ChEMBL
CHEMBL1213327
ChEBI
CHEBI:15346
UNII
SAA04E81UX
EC Number
201-619-0
Nikkaji
J192.630F

Properties

Computed structural properties

XLogP
-5.8
Topological polar surface area
348 Ų
Hydrogen bond donors
10
Hydrogen bond acceptors
21
Rotatable bonds
18
Heavy atoms
48

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Other Biomolecules
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsEmollient; Solvent
Physical Description · 2 items

White solid; [Merck Index] White powder; [Avanti Polar Lipids MSDS]

Solid

Collision Cross Section · 2 items

255.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

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

Physicochemical properties

Density
1.96 · 1.96±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility
PBS (pH 7.2): 10 mg/ml
form
A crystalline solid
pka
9.6 · 9.6 (thiol); pK 6.4 (secondary phosphate); pK 4.0 (adenine NH3+)
color
White to light yellow

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 6.2% (2 of 32) of reports.

Warning

H315 (93.8%): 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 32 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationCoenzyme A: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards SummaryRapidly oxidizes in air forming the catalytically inactive disulfide; [Merck Index] May cause irritation; [Avanti Polar Lipids MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (93.8%)

Safety data

F
1-10
wgk
3
tsca
TSCA listed
hs_code
2933299090
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

Tissue LocationsAdipose Tissue
Cellular LocationsEndoplasmic reticulum
Metabolite Pathways2-aminoadipic 2-oxoadipic aciduria

Uses & manufacturing

UsesEssential cofactor in acetyl transfer reactions found in mammalian cells and many microorganisms; [Merck Index]
Use ClassificationCosmetics -> Emollient; Solvent
General Manufacturing InformationCoenzyme A: ACTIVE
Applications · 4 items

DescriptionCoenzyme A (CoA) is an essential cofactor functioning as an acyl group carrier and carbonyl-activating group for the citric acid cycle and fatty acid metabolism. About 4% of cellular enzymes utilize CoA as a substrate. It is synthesized from pantothenic acid in a 5-step process that requires ATP. The pantothenate kinase step of the CoA biosynthetic pathway has been identified as a target for the development of antibacterial compounds.

UsesA hydrated form of Coenzyme A (CoA) is a useful biochemical research chemical, used in the preparation of high-yielding cell-free protein synthesis platforms.

UsesCoenzyme A hydrate has been used in the thiolase enzyme assay of recombinant acetoacetyl-CoA thiolase (rACAT) in Clonorchis sinensis. It may be used as a reference standard in Raman spectra measurements.

General DescriptionCoenzyme A (CoA) is a cofactor with a molecular weight of 797 Da. Its biological structure is formed from pantothenic acid (vitamin B5), cysteine and adenosine triphosphate through an evolutionarily conserved pathway. CoA is primarily involved in cellular oxidative pathways, including fatty acid beta-oxidation, carbohydrate, amino acid oxidation, and the Krebs cycle; as well as in lipid synthesis, protein modification, and membrane transport. CoA serves as a carrier for the activation of acyl groups, which can be transferred to amides, esters, or acid anhydrides. CoA can also be regulate a variety of metabolic processes at different levels as substrates, allosteric regulators, and through post-translational modifications of histones and other non-histone proteins. It is an essential cofactor in all organisms.

Upstream & downstream products

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
湖北博杰生物科技有限公司0713-2060728 15629612610
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Coenzyme A is a thiol comprising a panthothenate unit in phosphoric anhydride linkage with a 3',5'-adenosine diphosphate unit; and an aminoethanethiol unit. It has a role as an Escherichia coli metabolite, a mouse metabolite and a coenzyme. It is functionally related to an ADP. It is a conjugate acid of a coenzyme A(4-).

Related reactions

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Linked notes

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