Cannabis Compound Database: Showing Compound Card for Glutaryl-CoA (CDB005135)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:12:51 UTC

Updated at

2020-12-07 19:11:38 UTC

CannabisDB ID

CDB005135

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Glutaryl-CoA

Description

Glutaryl-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Glutaryl-coenzyme A	HMDB

Chemical Formula

C₂₆H₄₂N₇O₁₉P₃S

Average Molecular Weight

881.63

Monoisotopic Molecular Weight

881.1469

IUPAC Name

5-{[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 Name

5-({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 Number

103192-48-9

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 Key

SYKWLIJQEHRDNH-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Fatty acyl CoAs (C00154 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Organ and components:

Liver

Biofluid and excreta:

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	-0.48	ALOGPS
logP	-5.6	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	3.84	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	400.93 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	187.7 m³·mol⁻¹	ChemAxon
Polarizability	78.94 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

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-00kr-0005009000-eb3a971b38526182c8ac	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-0a4i-0269300000-b433e45be2e4ddb9b3dd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-05n1-0009700000-d04f275432ce90be4c03	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-0a4l-0691000000-1c9c9dcd3392e14e12d9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-0f80-0009841000-c64bfcd1084f04509fc5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-000i-0009000000-8ef4f57ae35ca24154ac	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-014r-0001920000-f105e4c7bcf62b49d748	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 61V, negative	splash10-001i-0000100090-7e0c0d1ae140f9f6c57c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 77V, negative	splash10-053r-0000920060-2e8ff86ba386000c087e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 100V, negative	splash10-0a6r-1211920000-b87d792a259c80a7b01d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 123V, negative	splash10-056r-9835710000-f9df91f65d08757ed109	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 146V, negative	splash10-004i-9512100000-6725b9c211e210ffa4f9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 169V, negative	splash10-004i-9400000000-3b7b4c8aa8db05827423	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 200V, negative	splash10-004i-9300000000-a481ad1113e5856425ad	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 232V, negative	splash10-004i-9200000000-484261819d8fe28a06bc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 278V, negative	splash10-004i-9100000000-1ced5b391be9b0f5176c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-001i-0001960370-e5f5990aef17b3100ae7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-00di-0190000000-0bdc30775338012cc42f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, negative	splash10-0a4i-0900000000-816bc86479bd970ceed6	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1912000130-9b9c96863df04861fbee	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0913000000-43f2e61c32509ed14b97	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1901000000-4ff7fbc1bd490ad4c020	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-3911030350-425e74ceb7a0a4256402	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01si-2901010010-f93605fcb2512efdd305	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-74a35eb8b1b0810315e4	2015-09-15	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Lysine Degradation
Fatty acid Metabolism
Ethylmalonic Encephalopathy		Not Available
Glutaric Aciduria Type I		Not Available
Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Dihydrolipoyl dehydrogenase, mitochondrial	DLD	7q31-q32	P09622	details
Glutaryl-CoA dehydrogenase, mitochondrial	GCDH	19p13.2	Q92947	details
2-oxoglutarate dehydrogenase, mitochondrial	OGDH	7p14-p13	Q02218	details
Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial	DLST	14q24.3	P36957	details
2-oxoglutarate dehydrogenase-like, mitochondrial	OGDHL		Q9ULD0	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001339

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022563

KNApSAcK ID

Not Available

Chemspider ID

388388

KEGG Compound ID

C00527

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15524

References

General References

Not Available

Enzymes

Enzyme Details

1. Dihydrolipoyl dehydrogenase, mitochondrial

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

Enzyme Details

2. Glutaryl-CoA dehydrogenase, mitochondrial

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

Enzyme Details

3. 2-oxoglutarate dehydrogenase, mitochondrial

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

Enzyme Details

4. Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial

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

Enzyme Details

5. 2-oxoglutarate dehydrogenase-like, mitochondrial

General function:: Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:: Not Available
Gene Name:: OGDHL
Uniprot ID:: Q9ULD0
Molecular weight:: Not Available

Showing Compound Card for Glutaryl-CoA (CDB005135)

Structure for CDB005135 (Glutaryl-CoA)

Enzymes