Cannabis Compound Database: Showing Compound Card for Erucoyl-CoA (CDB005312)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References XML

Record Information

Version

1.0

Created at

2020-04-17 19:30:34 UTC

Updated at

2020-12-07 19:11:56 UTC

CannabisDB ID

CDB005312

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Erucoyl-CoA

Description

Erucoyl-CoA, also known as C22:1(N-9) -CoA, belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. Thus, erucoyl-CoA is considered to be a fatty ester lipid molecule. Erucoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Erucoyl-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
13cis-Docosenoyl-CoA	ChEBI
13Z-Docosenoyl-CoA	ChEBI
13Z-Docosenoyl-coenzyme A	ChEBI
C22:1(N-9) -CoA	ChEBI
C22:1(N-9)-CoA	ChEBI
(13Z)-Docosenoyl-CoA	Kegg
erucoyl-coenzyme A	SMPDB, HMDB
CoA(22:1(13Z))	SMPDB, HMDB
Erucoyl-CoA	SMPDB, HMDB
Ercoyl-coenzyme A	HMDB
Erucyl-CoA	HMDB
Erucyl-coenzyme A	HMDB
S-Erucyl-coenzyme A	HMDB

Chemical Formula

C₄₃H₇₆N₇O₁₇P₃S

Average Molecular Weight

1088.09

Monoisotopic Molecular Weight

1087.4231

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(13Z)-docos-13-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-{[2-({2-[(13Z)-docos-13-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCC\C=C/CCCCCCCCCCCC(=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/C43H76N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h11-12,30-32,36-38,42,53-54H,4-10,13-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/b12-11-/t32-,36-,37-,38+,42-/m1/s1

InChI Key

OWGHRDKRIGXBJM-SPZFTOIUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Very 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

long-chain fatty acyl-CoA (CHEBI:74106 )
11,12-saturated fatty acyl-CoA (CHEBI:74106 )
unsaturated fatty acyl-CoA (CHEBI:74106 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Subcellular:

Biofluid and excreta:

Urine

Role

Biological role:

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.22 g/l	ALOGPS
logP	3.86	ALOGPS

Predicted Properties

Property	Value	Source
logP	3.86	ALOGPS
logP	2.9	ChemAxon
logS	-3.7	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	39	ChemAxon
Refractivity	265.37 m³·mol⁻¹	ChemAxon
Polarizability	113.45 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
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-4905410200-d7662bef08112b18e968	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-1907320000-9be1850c12af81b98dfc	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1902200000-d87b7c020265a9ee1c6d	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0159-9614241500-3e1e081f8b9434222d3a	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4901120100-b92c7e2df324d0815adc	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900000000-e1501365528673f27dee	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-38d20f359bfc30364b0e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9001201300-149177059c950b6b2d38	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05r9-9101200200-f6608e3e006c17a3074e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-0414ba2d564c9c9a538b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-8900100417-2dd3aced04cb2fcca127	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0000390000-7263bd026c116d95c0ce	2021-09-23	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:1(13Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:0/14:0/22:1(13Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:0/15:0/22:1(13Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:0/16:0/22:1(13Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:0/18:0/22:1(13Z))		Not Available