Cannabis Compound Database: Showing Compound Card for Linoleoyl-CoA (CDB005306)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:29:57 UTC

Updated at

2020-12-07 19:11:55 UTC

CannabisDB ID

CDB005306

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Linoleoyl-CoA

Description

Linoleoyl-CoA, also known as CoA(18:2(9Z,12Z)) or linoleyl-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. Thus, linoleoyl-CoA is considered to be a fatty ester lipid molecule. Linoleoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Linoleoyl-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
(9Z,12Z)-Octadecadienoyl-CoA	ChEBI
Linoleoyl-coenzyme A	HMDB
Linoleoyl-coenzyme A, (Z,Z)-isomer	HMDB
(Z,Z)-9,12-Octadecadienoyl-CoA	HMDB
CoA(18:2(9Z,12Z))	HMDB
Linoleic coenzyme A	HMDB
Linoleoyl coenzyme A	HMDB
Linoleyl-CoA	HMDB
Linoleyl-coenzyme A	HMDB
(9Z,12Z)-Octadecadienoyl-coenzyme A	HMDB
Linoleoyl-CoA	HMDB

Chemical Formula

C₃₉H₆₆N₇O₁₇P₃S

Average Molecular Weight

1029.97

Monoisotopic Molecular Weight

1029.3449

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-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

linoleoyl-coa

CAS Registry Number

6709-57-5

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=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/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-/t28-,32-,33-,34+,38-/m1/s1

InChI Key

YECLLIMZHNYFCK-RRNJGNTNSA-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

unsaturated fatty acyl-CoA (CHEBI:15530 )
linoleoyl bioconjugate (CHEBI:15530 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Role

Biological role:

Industrial application:

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	2.83	ALOGPS
logP	0.76	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	248.08 m³·mol⁻¹	ChemAxon
Polarizability	103.13 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 - Orbitrap 123V, negative	splash10-056r-1100903000-97979bc4426e696ca500	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 133V, negative	splash10-0a6r-2211903000-4df18afe923088dccc9d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 135V, negative	splash10-0a6r-2311904000-084368125746db9a1a8d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 160V, negative	splash10-056r-9834804000-ca985ff7e3a0a2cf068c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 168V, negative	splash10-056r-9723402000-1ea9fba94f19b641305d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 185V, negative	splash10-056r-9622100000-4bcd035304dec49a3add	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 199V, negative	splash10-004i-9511000000-1f5c4a5c6b6d8b944e54	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 218V, negative	splash10-004i-9410000000-cdcfa205f52edfcda7f1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 232V, negative	splash10-004i-9400000000-678749dd033055882657	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 253V, negative	splash10-004i-9400000000-dcd823851fb7d4ad77a7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 273V, negative	splash10-004i-9300000000-2e76dfce41f4d4f8fea5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 304V, negative	splash10-004i-9300000000-6a4626bbeafb9da35d70	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 72V, negative	splash10-001i-1000209003-f68430866c04428bfb90	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 47V, positive	splash10-001i-9000200000-2cabae93047abe4a748d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 65V, positive	splash10-00fr-3000970000-f399f99de6048f888713	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 100V, positive	splash10-00di-0100590000-9dc110d2f0daecf49e4d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 133V, positive	splash10-00dr-1930160000-1caa8491ab78bfd3d5a9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 168V, positive	splash10-000i-2920000000-c8b0b7ed0a3db1633f65	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 247V, positive	splash10-000i-4900000000-70e58b576b80fd6196af	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 72V, positive	splash10-00di-0000490000-7f3332450575be86b2d1	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9000000000-08cf5e6d7b995d0cb8cd	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-7900200548-53d677114eea1a3495ee	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0200890000-1142d1b46c4936109361	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-47a1be0b9f32d430c281	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010201300-d0da1a5320d13a306df8	2021-09-25	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Plasmalogen Synthesis		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Bile acid-CoA:amino acid N-acyltransferase	BAAT	9q22.3	Q14032	details
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	1p36	O00154	details
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	14q24.3	P49753	details
Acyl-coenzyme A thioesterase 4	ACOT4	14q24.3	Q8N9L9	details
Acyl-coenzyme A thioesterase 8	ACOT8	20q13.12	O14734	details
Lysocardiolipin acyltransferase 1	LCLAT1	2p23.1	Q6UWP7	details
Acyl-coenzyme A thioesterase 1	ACOT1	14q24.3	Q86TX2	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001064

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4593690

KEGG Compound ID

C02050

BioCyc ID

CPD-18

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5497112

PDB ID

Not Available

ChEBI ID

15530

References

General References

Not Available

Enzymes

Enzyme Details

1. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Enzyme Details

2. Cytosolic acyl coenzyme A thioester hydrolase

General function:: Lipid transport and metabolism
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:: ACOT7
Uniprot ID:: O00154
Molecular weight:: 40454.945

Enzyme Details

3. Acyl-coenzyme A thioesterase 2, mitochondrial

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:: ACOT2
Uniprot ID:: P49753
Molecular weight:: 53218.02

Enzyme Details

4. Acyl-coenzyme A thioesterase 4

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:: ACOT4
Uniprot ID:: Q8N9L9
Molecular weight:: 46326.09

Enzyme Details

5. Acyl-coenzyme A thioesterase 8

General function:: Involved in acyl-CoA thioesterase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:: ACOT8
Uniprot ID:: O14734
Molecular weight:: 35914.02

Enzyme Details

6. Lysocardiolipin acyltransferase 1

General function:: Involved in acyltransferase activity
Specific function:: Acyl-CoA:lysocardiolipin acyltransferase. Possesses both lysophosphatidylinositol acyltransferase (LPIAT) and lysophosphatidylglycerol acyltransferase (LPGAT) activities. Recognizes both monolysocardiolipin and dilysocardiolipin as substrates with a preference for linoleoyl-CoA and oleoyl-CoA as acyl donors. Acts as a remodeling enzyme for cardiolipin, a major membrane polyglycerophospholipid. Converts lysophosphatidic acid (LPA) into phosphatidic acid (PA) with a relatively low activity. Required for establishment of the hematopoietic and endothelial lineages.
Gene Name:: LCLAT1
Uniprot ID:: Q6UWP7
Molecular weight:: 44560.815

Enzyme Details

7. Acyl-coenzyme A thioesterase 1

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:: ACOT1
Uniprot ID:: Q86TX2
Molecular weight:: 46276.96

Showing Compound Card for Linoleoyl-CoA (CDB005306)

Structure for CDB005306 (Linoleoyl-CoA)

Enzymes