Record Information
Version1.0
Created at2020-04-17 19:12:51 UTC
Updated at2020-12-07 19:11:38 UTC
CannabisDB IDCDB005135
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGlutaryl-CoA
DescriptionGlutaryl-CoA belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Glutaryl-CoA is a very strong basic compound (based on its pKa). Glutaryl-CoA is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
Glutaryl-coenzyme AHMDB
Chemical FormulaC26H42N7O19P3S
Average Molecular Weight881.63
Monoisotopic Molecular Weight881.1469
IUPAC Name5-{[2-(3-{3-[({[({[(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)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-5-oxopentanoic acid
Traditional Name5-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-5-oxopentanoic acid
CAS Registry Number103192-48-9
SMILES
CC(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)C(O)C(=O)NCCC(=O)NCCSC(=O)CCCC(O)=O
InChI Identifier
InChI=1S/C26H42N7O19P3S/c1-26(2,21(39)24(40)29-7-6-15(34)28-8-9-56-17(37)5-3-4-16(35)36)11-49-55(46,47)52-54(44,45)48-10-14-20(51-53(41,42)43)19(38)25(50-14)33-13-32-18-22(27)30-12-31-23(18)33/h12-14,19-21,25,38-39H,3-11H2,1-2H3,(H,28,34)(H,29,40)(H,35,36)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/t14-,19-,20-,21?,25-/m1/s1
InChI KeySYKWLIJQEHRDNH-KRPIADGTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain fatty acyl 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.48ALOGPS
logP-5.6ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)3.84ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity187.7 m³·mol⁻¹ChemAxon
Polarizability78.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-00kr-0005009000-eb3a971b38526182c8acSpectrum
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-0a4i-0269300000-b433e45be2e4ddb9b3ddSpectrum
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-05n1-0009700000-d04f275432ce90be4c03Spectrum
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-0a4l-0691000000-1c9c9dcd3392e14e12d9Spectrum
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-0f80-0009841000-c64bfcd1084f04509fc5Spectrum
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-000i-0009000000-8ef4f57ae35ca24154acSpectrum
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-014r-0001920000-f105e4c7bcf62b49d748Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 61V, negativesplash10-001i-0000100090-7e0c0d1ae140f9f6c57cSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 77V, negativesplash10-053r-0000920060-2e8ff86ba386000c087eSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 100V, negativesplash10-0a6r-1211920000-b87d792a259c80a7b01dSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 123V, negativesplash10-056r-9835710000-f9df91f65d08757ed109Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 146V, negativesplash10-004i-9512100000-6725b9c211e210ffa4f9Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 169V, negativesplash10-004i-9400000000-3b7b4c8aa8db05827423Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 200V, negativesplash10-004i-9300000000-a481ad1113e5856425adSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 232V, negativesplash10-004i-9200000000-484261819d8fe28a06bcSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 278V, negativesplash10-004i-9100000000-1ced5b391be9b0f5176cSpectrum
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-001i-0001960370-e5f5990aef17b3100ae7Spectrum
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-00di-0190000000-0bdc30775338012cc42fSpectrum
MS/MSLC-MS/MS Spectrum - n/a 61V, negativesplash10-0a4i-0900000000-816bc86479bd970ceed6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000130-9b9c96863df04861fbeeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913000000-43f2e61c32509ed14b97Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1901000000-4ff7fbc1bd490ad4c020Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-3911030350-425e74ceb7a0a4256402Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-2901010010-f93605fcb2512efdd305Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-74a35eb8b1b0810315e4Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Dihydrolipoyl dehydrogenase, mitochondrialDLD7q31-q32P09622 details
Glutaryl-CoA dehydrogenase, mitochondrialGCDH19p13.2Q92947 details
2-oxoglutarate dehydrogenase, mitochondrialOGDH7p14-p13Q02218 details
Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrialDLST14q24.3P36957 details
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001339
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022563
KNApSAcK IDNot Available
Chemspider ID388388
KEGG Compound IDC00527
BioCyc IDNot Available
BiGG ID35255
Wikipedia LinkGlutaryl-CoA
METLIN ID6173
PubChem Compound439252
PDB IDNot Available
ChEBI ID15524
References
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes. Involved in the hyperactivation of spermatazoa during capacitation and in the spermatazoal acrosome reaction.
Gene Name:
DLD
Uniprot ID:
P09622
Molecular weight:
54176.91
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the oxidative decarboxylation of glutaryl-CoA to crotonyl-CoA and CO(2) in the degradative pathway of L-lysine, L-hydroxylysine, and L-tryptophan metabolism. It uses electron transfer flavoprotein as its electron acceptor. Isoform Short is inactive.
Gene Name:
GCDH
Uniprot ID:
Q92947
Molecular weight:
48126.715
General function:
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
OGDH
Uniprot ID:
Q02218
Molecular weight:
48179.59
General function:
Involved in acyltransferase activity
Specific function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of 3 enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
DLST
Uniprot ID:
P36957
Molecular weight:
48754.87
General function:
Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
Not Available
Gene Name:
OGDHL
Uniprot ID:
Q9ULD0
Molecular weight:
Not Available