Showing Compound Card for Crotonoyl-CoA (CDB005139)

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Record Information
Version1.0
Created at2020-04-17 19:13:15 UTC
Updated at2020-12-07 19:11:39 UTC
CannabisDB IDCDB005139
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCrotonoyl-CoA
Description(E)-but-2-enoyl-CoA, also known as trans-but-2-enoyl-CoA or crotonyl-CoA, belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain. Thus, (e)-but-2-enoyl-CoA is considered to be a fatty ester lipid molecule (E)-but-2-enoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Crotonoyl-CoA is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Crotonyl-CoAChEBI
trans-But-2-enoyl-CoAChEBI
trans-Butyr-2-enoyl-CoAChEBI
2-Butenoyl-CoAKegg
But-2-enoyl-CoAKegg
(2E)-But-2-enoyl-CoAKegg
Crotonyl-coenzyme AHMDB
(e)-But-2-enoyl-CoAChEBI
Crotonoyl-CoAHMDB
Crotonoyl-coenzyme AHMDB
Crotonyl coenzyme AHMDB
trans-2-Butenoyl-CoAHMDB
trans-2-Butenoyl-coenzyme AHMDB
trans-Crotonoyl-CoAHMDB
trans-Crotonoyl-coenzyme AHMDB
trans-Crotonyl CoAHMDB
Chemical FormulaC25H40N7O17P3S
Average Molecular Weight835.61
Monoisotopic Molecular Weight835.1414
IUPAC Name(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid
Traditional Name(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-N-[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid
CAS Registry Number992-67-6
SMILES
C\C=C\C(=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/C25H40N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h4-5,12-14,18-20,24,35-36H,6-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/b5-4+/t14-,18-,19-,20+,24-/m1/s1
InChI KeyKFWWCMJSYSSPSK-PAXLJYGASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent2-enoyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.03ALOGPS
logP-4.2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)6.43ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area370.61 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity183.57 m³·mol⁻¹ChemAxon
Polarizability75.89 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Very long-chain acyl-CoA synthetaseSLC27A215q21.2O14975 details
Fatty acid-binding protein, heartFABP31p33-p32P05413 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
Protein NameGene NameLocusUniprot IDDetails
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrialBCKDHA19q13.1-q13.2P12694 details
Acyl-CoA desaturaseSCD10q24.31O00767 details
Trans-2-enoyl-CoA reductase, mitochondrialMECR1p35.3Q9BV79 details
Peroxisome proliferator-activated receptor gammaPPARG3p25P37231 details
Peroxisome proliferator-activated receptor alphaPPARA22q12-q13.1|22q13.31Q07869 details
Peroxisome proliferator-activated receptor deltaPPARD6p21.2Q03181 details
Acyl-coenzyme A synthetase ACSM1, mitochondrialACSM116p12.3Q08AH1 details
Lysophosphatidylcholine acyltransferase 1LPCAT15p15.33Q8NF37 details
Acyl-coenzyme A synthetase ACSM6, mitochondrialACSM610q23.33Q6P461 details
Acyl-coenzyme A synthetase ACSM2A, mitochondrialACSM2A16p12.3Q08AH3 details
Acyl-coenzyme A synthetase ACSM2B, mitochondrialACSM2B16p12.3Q68CK6 details
Acyl-coenzyme A synthetase ACSM3, mitochondrialACSM316p13.11Q53FZ2 details
Acyl-coenzyme A synthetase ACSM5, mitochondrialACSM516p12.3Q6NUN0 details
Peroxisomal coenzyme A diphosphatase NUDT7NUDT716q23.1P0C024 details
Acyl-coenzyme A synthetase ACSM4, mitochondrialACSM412p13.31P0C7M7 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
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
Protein NameGene NameLocusUniprot IDDetails
Peroxisome proliferator-activated receptor gammaPPARG3p25P37231 details
Peroxisome proliferator-activated receptor alphaPPARA22q12-q13.1|22q13.31Q07869 details
Peroxisome proliferator-activated receptor deltaPPARD6p21.2Q03181 details
Isobutyryl-CoA dehydrogenase, mitochondrialACAD811q25Q9UKU7 details
Concentrations Data
Not Available
HMDB IDHMDB0002009
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022792
KNApSAcK IDNot Available
Chemspider ID4593713
KEGG Compound IDC00877
BioCyc IDCROTONYL-COA
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5497143
PDB IDNot Available
ChEBI ID15473
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 125 proteins in total.

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Enzymes

Enzyme Details
1. 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
2. 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
3. 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
4. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:
ALDH6A1
Uniprot ID:
Q02252
Molecular weight:
57839.31
Enzyme Details
5. Long-chain specific acyl-CoA dehydrogenase, mitochondrial
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
ACADL
Uniprot ID:
P28330
Molecular weight:
47655.275
Enzyme Details
6. Short-chain specific acyl-CoA dehydrogenase, mitochondrial
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
ACADS
Uniprot ID:
P16219
Molecular weight:
44296.705
Enzyme Details
7. Medium-chain specific acyl-CoA dehydrogenase, mitochondrial
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:
ACADM
Uniprot ID:
P11310
Molecular weight:
46587.98
Enzyme Details
8. Peroxisomal acyl-coenzyme A oxidase 1
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:
ACOX1
Uniprot ID:
Q15067
Molecular weight:
70135.205
Enzyme Details
9. Peroxisomal acyl-coenzyme A oxidase 2
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:
ACOX2
Uniprot ID:
Q99424
Molecular weight:
76826.14
Enzyme Details
10. Isovaleryl-CoA dehydrogenase, mitochondrial
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Not Available
Gene Name:
IVD
Uniprot ID:
P26440
Molecular weight:
43055.325

Transporters

Enzyme Details
1. 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
2. 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
3. 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
4. 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
5. 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
6. 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 125 proteins in total.

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