Cannabis Compound Database: Showing Compound Card for Acetoacetyl-CoA (CDB005141)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (13) Show 14 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:13:28 UTC

Updated at

2020-12-07 19:11:39 UTC

CannabisDB ID

CDB005141

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Acetoacetyl-CoA

Description

Acetoacetyl-CoA belongs to the class of organic compounds known as aminopiperidines. Aminopiperidines are compounds containing a piperidine that carries an amino group. A 3-oxoacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of acetoacetic acid. Acetoacetyl-CoA is a strong basic compound (based on its pKa). In humans, acetoacetyl-CoA is involved in the metabolic disorder called the short-chain 3-hydroxyacyl-coa dehydrogenase deficiency (hadh) pathway. Acetoacetyl-CoA is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Acetoacetyl-CoA	ChEBI
Acetoacetyl coenzyme A	ChEBI
S-Acetoacetyl-CoA	ChEBI
S-Acetoacetyl-coenzym a	ChEBI
S-Acetoacetyl-coenzyme A	ChEBI
Acetoacetyl CoA	MeSH

Chemical Formula

C₂₅H₄₀N₇O₁₈P₃S

Average Molecular Weight

851.61

Monoisotopic Molecular Weight

851.1363

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxobutanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

acetoacetyl-coa

CAS Registry Number

1420-36-6

SMILES

CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1

InChI Key

OJFDKHTZOUZBOS-CITAKDKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminopiperidines. Aminopiperidines are compounds containing a piperidine that carries an amino group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Aminopiperidines

Direct Parent

Aminopiperidines

Alternative Parents

Substituents

4-aminopiperidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

bipiperidine (CHEBI:40117 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Cell:

Fibroblast

Subcellular:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.24	ALOGPS
logP	-5.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	380.7 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	182.1 m³·mol⁻¹	ChemAxon
Polarizability	76.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-000i-0004009000-9559fa356f1bae03b7ca	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0a4i-0269300000-d5574d3fd84812c0057d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-05n1-0009600000-a29b94fc4d454c655bab	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-000i-0001209000-21979fdba010c3871c5a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, negative	splash10-0udi-0000000090-aa1f97ad009df4ad9439	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 57V, negative	splash10-0udi-0000100490-97b56edeb43a5d82ba85	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 71V, negative	splash10-014i-0000910830-9d7a9bb5d2817f98fbf1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 93V, negative	splash10-0ar9-0101901000-ee3c1d5ebb3142f3c5af	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 115V, negative	splash10-0a6r-5524900000-2d745cfa452462059e2c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 136V, negative	splash10-056r-9513200000-037d88669e973d0dff1c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 158V, negative	splash10-004i-9400000000-fca9f3020e4e007e8164	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 187V, negative	splash10-004i-9300000000-13ad94b2682d99b6234d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 216V, negative	splash10-004i-9200000000-32dfa0b8d343e2eb7b7b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 260V, negative	splash10-004i-9100000000-6461ef6280ce0db781b2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-014i-0000000900-727bb0c3c925e7bbeba4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-00di-0190000000-0e093fb5398057b2093d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0a4i-0900000000-b4c90f8c858e783159b8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0udl-0018900000-91aaf6888a10aac16f57	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-00xr-0092000000-2dd3c44dfb7a39ee9a59	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0670-0000904200-f3bcbcab3db17ae6a02a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-00di-0190000000-3a982abdcfdcfe6b0420	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, negative	splash10-0udr-0027900000-0d41e18ae4bea1b5b7eb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, positive	splash10-0002-6900000000-959cba779002108c94cc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, positive	splash10-00di-9000000000-9fd58d8b09e3b71e5e6f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 59V, positive	splash10-03di-0190000000-aa6e0456b3c35ec78a6a	2020-07-22	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Butyrate Metabolism
Fatty acid Metabolism
Valine, Leucine and Isoleucine Degradation
Propanoate Metabolism
Steroid Biosynthesis

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Acetyl-CoA acetyltransferase, cytosolic	ACAT2	6q25.3	Q9BWD1	details
3-ketoacyl-CoA thiolase, mitochondrial	ACAA2	18q21.1	P42765	details
Acetyl-CoA acetyltransferase, mitochondrial	ACAT1	11q22.3	P24752	details
Hydroxymethylglutaryl-CoA synthase, mitochondrial	HMGCS2	1p13-p12	P54868	details
3-ketoacyl-CoA thiolase, peroxisomal	ACAA1	3p22.2	P09110	details
Trifunctional enzyme subunit beta, mitochondrial	HADHB	2p23	P55084	details
Hydroxymethylglutaryl-CoA synthase, cytoplasmic	HMGCS1	5p14-p13	Q01581	details
3-hydroxyacyl-CoA dehydrogenase type-2	HSD17B10	Xp11.2	Q99714	details
Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial	HADH	4q22-q26	Q16836	details
Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrial	OXCT1	5p13.1	P55809	details
Succinyl-CoA:3-ketoacid coenzyme A transferase 2, mitochondrial	OXCT2	1p34	Q9BYC2	details
Acetoacetyl-CoA synthetase	AACS	12q24.31	Q86V21	details
Estradiol 17-beta-dehydrogenase 12	HSD17B12	11p11.2	Q53GQ0	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Acetyl-CoA acetyltransferase, mitochondrial	ACAT1	11q22.3	P24752	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001484

DrugBank ID

DB03059

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Acetoacetyl-CoA

METLIN ID

Not Available

PubChem Compound

92153

PDB ID

Not Available

ChEBI ID

15345

References

General References

Not Available

Only showing the first 10 proteins. There are 14 proteins in total.

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Enzymes

Enzyme Details

1. Acetyl-CoA acetyltransferase, cytosolic

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: ACAT2
Uniprot ID:: Q9BWD1
Molecular weight:: 41350.5

Enzyme Details

2. 3-ketoacyl-CoA thiolase, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:: ACAA2
Uniprot ID:: P42765
Molecular weight:: 41923.82

Enzyme Details

3. Acetyl-CoA acetyltransferase, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Plays a major role in ketone body metabolism.
Gene Name:: ACAT1
Uniprot ID:: P24752
Molecular weight:: 45199.2

Enzyme Details

4. Hydroxymethylglutaryl-CoA synthase, mitochondrial

General function:: Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:: This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:: HMGCS2
Uniprot ID:: P54868
Molecular weight:: 52481.065

Enzyme Details

5. 3-ketoacyl-CoA thiolase, peroxisomal

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: ACAA1
Uniprot ID:: P09110
Molecular weight:: 34664.46

Enzyme Details

6. Trifunctional enzyme subunit beta, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: HADHB
Uniprot ID:: P55084
Molecular weight:: 51293.955

Enzyme Details

7. Hydroxymethylglutaryl-CoA synthase, cytoplasmic

General function:: Involved in hydroxymethylglutaryl-CoA synthase activity
Specific function:: This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:: HMGCS1
Uniprot ID:: Q01581
Molecular weight:: 57293.105

Enzyme Details

8. 3-hydroxyacyl-CoA dehydrogenase type-2

General function:: Involved in oxidoreductase activity
Specific function:: Functions in mitochondrial tRNA maturation. Part of mitochondrial ribonuclease P, an enzyme composed of MRPP1/TRMT10C, MRPP2/HSD17B10 and MRPP3/KIAA0391, which cleaves tRNA molecules in their 5'-ends. By interacting with intracellular amyloid-beta, it may contribute to the neuronal dysfunction associated with Alzheimer disease (AD).
Gene Name:: HSD17B10
Uniprot ID:: Q99714
Molecular weight:: 25983.695

Enzyme Details

9. Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name:: HADH
Uniprot ID:: Q16836
Molecular weight:: 36035.11

Enzyme Details

10. Succinyl-CoA:3-ketoacid coenzyme A transferase 1, mitochondrial

General function:: Involved in CoA-transferase activity
Specific function:: Key enzyme for ketone body catabolism. Transfers the CoA moiety from succinate to acetoacetate. Formation of the enzyme-CoA intermediate proceeds via an unstable anhydride species formed between the carboxylate groups of the enzyme and substrate.
Gene Name:: OXCT1
Uniprot ID:: P55809
Molecular weight:: 56157.175

Only showing the first 10 proteins. There are 14 proteins in total.

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Showing Compound Card for Acetoacetyl-CoA (CDB005141)

Structure for CDB005141 (Acetoacetyl-CoA)

Enzymes