Cannabis Compound Database: Showing Compound Card for α-Linolenoyl-CoA (CDB005308)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:30:10 UTC

Updated at

2020-12-07 19:11:55 UTC

CannabisDB ID

CDB005308

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

α-Linolenoyl-CoA

Description

Alpha-Linolenoyl-CoA, also known as a-linolenoyl-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. Alpha-Linolenoyl-CoA is a strong basic compound (based on its pKa). α-Linolenoyl-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
a-Linolenoyl-CoA	Generator
Α-linolenoyl-CoA	Generator
(9Z,12Z,15Z)-Octadecatrienoyl-CoA	HMDB
(9Z,12Z,15Z)-Octadecatrienoyl-coenzyme A	HMDB
alpha-Linolenoyl-coenzyme A	HMDB

Chemical Formula

C₃₉H₆₄N₇O₁₇P₃S

Average Molecular Weight

1027.95

Monoisotopic Molecular Weight

1027.3292

IUPAC Name

{[(2R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy((3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(C(=O)NCCC(=O)NCCSC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@@H](O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C39H64N7O17P3S/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/h5-6,8-9,11-12,26-28,32-34,38,49-50H,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)/b6-5-,9-8-,12-11-/t28-,32+,33?,34+,38-/m1/s1

InChI Key

OMKFKBGZHNJNEX-QJTDXEISSA-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

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cell and elements:

Extracellular

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	2.84	ALOGPS
logP	0.4	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	33	ChemAxon
Refractivity	249.2 m³·mol⁻¹	ChemAxon
Polarizability	97.82 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 - n/a 71V, negative	splash10-01p9-0008009000-b19fa83af4283fcd0b89	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 71V, negative	splash10-05n0-0009600000-078cbf77a2f434cd44ed	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 71V, negative	splash10-03di-0019002000-1380de023ce360bf7ec0	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 71V, negative	splash10-0a4i-0279310000-44bf2f31c6db5988d5a7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 71V, negative	splash10-004j-0002149000-861577e53f84f4b2ebb9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 71V, negative	splash10-01ot-0002289000-ffe3ffa5e78e22454bca	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 71V, negative	splash10-004i-9000200000-3cecb69b68b6f9ff8184	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 84V, negative	splash10-056r-7000900000-3d284b943b5b0ebb41bb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 94V, negative	splash10-056r-1000900000-34703ef6e109c21c18e9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 104V, negative	splash10-056r-1000901000-acb57860a878dcc2023d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 125V, negative	splash10-0a6r-1211901000-cc5cc6376dc63c7e796b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 156V, negative	splash10-056r-9833500000-3f06d96e6b56a1c533b8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 189V, negative	splash10-004i-9511000000-856cf20e875260148ebb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 230V, negative	splash10-004i-9400000000-10c923a4025dad9a24ec	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 273V, negative	splash10-004i-9300000000-17dbaea3bd39295e9b7d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 71V, negative	splash10-004j-1000319013-26b2710bf282ad4e0efc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 71V, negative	splash10-00di-0190000000-a3b560dd23c1d54b0740	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 71V, negative	splash10-0a4i-0900000000-55f0257dfa1a12894fde	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 71V, negative	splash10-052r-0019000000-2a83d907ab00b91dacc6	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-3902020200-1184da02054c79f7d943	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1913140000-f435f6bf9df881a42e1b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900010000-a3a909bd9837261df0e1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a7i-9761432401-fd1bbec725c99dd87063	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-4920210000-58e825fa745dd2fb5725	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a7i-5900100000-c18f0f871cf87bcf5fa9	2017-09-01	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/18:3(9Z,12Z,15Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/16:0/18:3(9Z,12Z,15Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:0/16:0/18:3(9Z,12Z,15Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:1(11Z)/16:0/18:3(9Z,12Z,15Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/16:0/18:3(9Z,12Z,15Z))		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
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

HMDB0006290

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023879

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16162

BioCyc ID

Not Available

BiGG ID

2218410

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477815

PDB ID

Not Available

ChEBI ID

Not Available

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. 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 α-Linolenoyl-CoA (CDB005308)

Structure for CDB005308 (α-Linolenoyl-CoA)

Enzymes