Showing Compound Card for Acetyl-CoA (CDB005092)

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Record Information
Version1.0
Created at2020-04-17 19:08:31 UTC
Updated at2020-12-07 19:11:33 UTC
CannabisDB IDCDB005092
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAcetyl-CoA
DescriptionAcetyl-CoA, also known as acetyl coenzyme A or accoa, belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. Thus, acetyl-CoA is considered to be a fatty ester lipid molecule. Acetyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Acetyl-CoA exists in all living species, ranging from bacteria to humans. In humans, acetyl-CoA is involved in the metabolic disorder called the long chain acyl-coa dehydrogenase deficiency (lcad) pathway. An acyl-CoA having acetyl as its S-acetyl component. Outside of the human body, Acetyl-CoA has been detected, but not quantified in, several different foods, such as amaranths, lemon verbena, strawberries, lingonberries, and carobs. This could make acetyl-CoA a potential biomarker for the consumption of these foods. Acetyl-CoA is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC23H38N7O17P3S
Average Molecular Weight809.57
Monoisotopic Molecular Weight809.1258
IUPAC Name{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Nameacetyl-CoA
CAS Registry Number72-89-9
SMILES
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/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1
InChI KeyZSLZBFCDCINBPY-ZSJPKINUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Glycosyl compound
  • O-glycosyl compound
  • Pyrrolidinylpyridine
  • Alkaloid or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Pyridine
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxamide group
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.58ALOGPS
logP-5.9ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity172.21 m³·mol⁻¹ChemAxon
Polarizability70.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAcetyl-CoA, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyl-CoA, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyl-CoA, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyl-CoA, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyl-CoA, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyl-CoA, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyl-CoA, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAcetyl-CoA, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Fatty acid synthaseFASN17q25P49327 details
Very long-chain acyl-CoA synthetaseSLC27A215q21.2O14975 details
Fatty acid-binding protein, heartFABP31p33-p32P05413 details
Acetyl-coenzyme A transporter 1SLC33A13q25.31O00400 details
Bile acyl-CoA synthetaseSLC27A519q13.43Q9Y2P5 details
Long-chain fatty acid transport protein 1SLC27A119p13.11Q6PCB7 details
Acyl-CoA synthetase family member 4AASDH4q12Q4L235 details
Fatty acid-binding protein, intestinalFABP24q28-q31P12104 details
Metal Bindings
Receptors
Protein NameGene NameLocusUniprot IDDetails
Histone acetyltransferase p300EP30022q13.2Q09472 details
Nuclear receptor coactivator 3NCOA320q12Q9Y6Q9 details
Histone acetyltransferase KAT5KAT511q13Q92993 details
Nuclear receptor coactivator 1NCOA12p23Q15788 details
Peroxisome proliferator-activated receptor gammaPPARG3p25P37231 details
Peroxisome proliferator-activated receptor alphaPPARA22q12-q13.1|22q13.31Q07869 details
Peroxisome proliferator-activated receptor deltaPPARD6p21.2Q03181 details
Benzodiazepine receptor ligandBRLQ71U42 details
Transcriptional Factors
Concentrations Data
Not Available
HMDB IDHMDB0001206
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022491
KNApSAcK IDC00007259
Chemspider ID392413
KEGG Compound IDC00024
BioCyc IDACETYL-COA
BiGG ID33558
Wikipedia LinkAcetyl-CoA
METLIN ID6082
PubChem Compound444493
PDB IDNot Available
ChEBI ID15351
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 226 proteins in total.

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Enzymes

Enzyme Details
1. Hydroxymethylglutaryl-CoA lyase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Key enzyme in ketogenesis (ketone body formation). Terminal step in leucine catabolism.
Gene Name:
HMGCL
Uniprot ID:
P35914
Molecular weight:
34359.84
Enzyme Details
2. ATP-citrate synthase
General function:
Involved in ATP citrate synthase activity
Specific function:
ATP citrate-lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Has a central role in de novo lipid synthesis. In nervous tissue it may be involved in the biosynthesis of acetylcholine.
Gene Name:
ACLY
Uniprot ID:
P53396
Molecular weight:
120838.27
Enzyme Details
3. Histone acetyltransferase p300
General function:
Involved in transcription cofactor activity
Specific function:
Functions as histone acetyltransferase and regulates transcription via chromatin remodeling. Acetylates all four core histones in nucleosomes. Histone acetylation gives an epigenetic tag for transcriptional activation. Mediates cAMP-gene regulation by binding specifically to phosphorylated CREB protein. Also functions as acetyltransferase for nonhistone targets. Acetylates 'Lys-131' of ALX1 and acts as its coactivator in the presence of CREBBP. Acetylates SIRT2 and is proposed to indirectly increase the transcriptional activity of TP53 through acetylation and subsequent attenuation of SIRT2 deacetylase function. Acetylates HDAC1 leading to its inactivation and modulation of transcription. Acts as a TFAP2A-mediated transcriptional coactivator in presence of CITED2. Plays a role as a coactivator of NEUROD1-dependent transcription of the secretin and p21 genes and controls terminal differentiation of cells in the intestinal epithelium. Promotes cardiac myocyte enlargement. Can also mediate transcriptional repression. Binds to and may be involved in the transforming capacity of the adenovirus E1A protein. In case of HIV-1 infection, it is recruited by the viral protein Tat. Regulates Tat's transactivating activity and may help inducing chromatin remodeling of proviral genes. Acetylates FOXO1 and enhances its transcriptional activity.
Gene Name:
EP300
Uniprot ID:
Q09472
Molecular weight:
264159.725
Enzyme Details
4. Pyruvate dehydrogenase E1 component subunit beta, mitochondrial
General function:
Involved in catalytic activity
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:
PDHB
Uniprot ID:
P11177
Molecular weight:
39233.1
Enzyme Details
5. 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
6. Diamine acetyltransferase 2
General function:
Involved in N-acetyltransferase activity
Specific function:
Enzyme which catalyzes the acetylation of polyamines. Substrate specificity: norspermidine > spermidine = spermine >> N(1)acetylspermine = putrescine.
Gene Name:
SAT2
Uniprot ID:
Q96F10
Molecular weight:
19154.905
Enzyme Details
7. Malonyl-CoA decarboxylase, mitochondrial
General function:
Involved in malonyl-CoA decarboxylase activity
Specific function:
Catalyzes the conversion of malonyl-CoA to acetyl-CoA. In the fatty acid biosynthesis MCD selectively removes malonyl-CoA and thus assures that methyl-malonyl-CoA is the only chain elongating substrate for fatty acid synthase and that fatty acids with multiple methyl side chains are produced. In peroxisomes it may be involved in degrading intraperoxisomal malonyl-CoA, which is generated by the peroxisomal beta-oxidation of odd chain-length dicarboxylic fatty acids.
Gene Name:
MLYCD
Uniprot ID:
O95822
Molecular weight:
55002.94
Enzyme Details
8. Acetyl-CoA carboxylase 2
General function:
Involved in acetyl-CoA carboxylase activity
Specific function:
ACC-beta may be involved in the provision of malonyl-CoA or in the regulation of fatty acid oxidation, rather than fatty acid biosynthesis. Carries out three functions: biotin carboxyl carrier protein, biotin carboxylase and carboxyltransferase.
Gene Name:
ACACB
Uniprot ID:
O00763
Molecular weight:
276538.575
Enzyme Details
9. Pyruvate carboxylase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate.
Gene Name:
PC
Uniprot ID:
P11498
Molecular weight:
129632.565
Enzyme Details
10. Arylamine N-acetyltransferase 1
General function:
Involved in acetyltransferase activity
Specific function:
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:
NAT1
Uniprot ID:
P18440
Molecular weight:
33898.445

Transporters

Enzyme Details
1. Fatty acid synthase
General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06
Enzyme Details
2. Very long-chain acyl-CoA synthetase
General function:
Involved in catalytic activity
Specific function:
Acyl-CoA synthetase probably involved in bile acid metabolism. Proposed to activate C27 precurors of bile acids to their CoA thioesters derivatives before side chain cleavage via peroxisomal beta-oxidation occurs. In vitro, activates 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate (THCA), the C27 precursor of cholic acid deriving from the de novo synthesis from cholesterol. Does not utilize C24 bile acids as substrates. In vitro, also activates long- and branched-chain fatty acids and may have additional roles in fatty acid metabolism. May be involved in translocation of long-chain fatty acids (LFCA) across membranes (By similarity).
Gene Name:
SLC27A2
Uniprot ID:
O14975
Molecular weight:
64614.99
Enzyme Details
3. Fatty acid-binding protein, heart
General function:
Involved in negative regulation of cell proliferation
Specific function:
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters
Gene Name:
FABP3
Uniprot ID:
P05413
Molecular weight:
14857.9
Enzyme Details
4. Acetyl-coenzyme A transporter 1
General function:
Carbohydrate transport and metabolism
Specific function:
Probable acetyl-CoA transporter necessary for O-acetylation of gangliosides.
Gene Name:
SLC33A1
Uniprot ID:
O00400
Molecular weight:
60908.39
Enzyme Details
5. Bile acyl-CoA synthetase
General function:
Involved in catalytic activity
Specific function:
Acyl-CoA synthetase involved in bile acid metabolism. Proposed to catalyze the first step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi by activating them to their CoA thioesters. Seems to activate secondary bile acids entering the liver from the enterohepatic circulation. In vitro, also activates 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate (THCA), the C27 precursor of cholic acid deriving from the de novo synthesis from cholesterol.
Gene Name:
SLC27A5
Uniprot ID:
Q9Y2P5
Molecular weight:
75384.375
Enzyme Details
6. Long-chain fatty acid transport protein 1
General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
SLC27A1
Uniprot ID:
Q6PCB7
Molecular weight:
71107.5
Enzyme Details
7. Acyl-CoA synthetase family member 4
General function:
Involved in acyl carrier activity
Specific function:
Acyl-CoA synthases catalyze the initial reaction in fatty acid metabolism, by forming a thioester with CoA
Gene Name:
AASDH
Uniprot ID:
Q4L235
Molecular weight:
122596.1
Enzyme Details
8. Fatty acid-binding protein, intestinal
General function:
Involved in binding
Specific function:
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds saturated long-chain fatty acids with a high affinity, but binds with a lower affinity to unsaturated long- chain fatty acids. FABP2 may also help maintain energy homeostasis by functioning as a lipid sensor
Gene Name:
FABP2
Uniprot ID:
P12104
Molecular weight:
15207.2

Only showing the first 10 proteins. There are 226 proteins in total.

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