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coenzyme A   Click here for help

GtoPdb Ligand ID: 3044

Synonyms: co-enzyme-A | CoA
PDB Ligand
Compound class: Metabolite

coenzyme A is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 22
Hydrogen bond donors 9
Rotatable bonds 20
Topological polar surface area 414.79
Molecular weight 767.12
XLogP -5.83
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES SCCNC(=O)CCNC(=O)C(C(COP(=O)(OP(=O)(OCC1OC(C(C1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O
Isomeric SMILES SCCNC(=O)CCNC(=O)[C@@H](C(COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O
InChI InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1
InChI Key RGJOEKWQDUBAIZ-IBOSZNHHSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
acetyl-CoA acetyltransferase 1 2.3.1.9 2acetyl CoA = acetoacetyl CoA + coenzyme A 1
ceramide synthase 6 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
ceramide synthase 3 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
hydroxymethylglutaryl-CoA reductase 1.1.1.34 (S)-3-hydroxy-3-methylglutaryl-CoA + NADPH -> (R)-mevalonate + coenzyme A + NADP+
serine palmitoyltransferase long chain base subunit 3 2.3.1.50 L-serine + palmitoyl-CoA -> 3-ketosphinganine + coenzyme A + CO2
ceramide synthase 2 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
ceramide synthase 4 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
ceramide synthase 5 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
choline O-acetyltransferase 2.3.1.6 Acetyl CoA + choline = acetylcholine + coenzyme A
ceramide synthase 1 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
acetyl-CoA acetyltransferase 2 2.3.1.9 2acetyl CoA = acetoacetyl CoA + coenzyme A
hydroxymethylglutaryl-CoA synthase 2 2.3.3.10 Acetyl CoA + H2O + acetoacetyl CoA -> (S)-3-hydroxy-3-methylglutaryl-CoA + coenzyme A
serine palmitoyltransferase long chain base subunit 2 2.3.1.50 L-serine + palmitoyl-CoA -> 3-ketosphinganine + coenzyme A + CO2
hydroxymethylglutaryl-CoA synthase 1 2.3.3.10 Acetyl CoA + H2O + acetoacetyl CoA -> (S)-3-hydroxy-3-methylglutaryl-CoA + coenzyme A
serine palmitoyltransferase long chain base subunit 1 2.3.1.50 L-serine + palmitoyl-CoA -> 3-ketosphinganine + coenzyme A + CO2
Ligand mentioned in the following text fields
Eicosanoid turnover overview
SLC27 family of fatty acid transporters comments
SLC33 acetylCoA transporter comments