Cannabis Compound Database: Showing Compound Card for Docosanoyl-CoA (CDB005311)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5) Show 8 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:30:29 UTC

Updated at

2020-12-07 19:11:56 UTC

CannabisDB ID

CDB005311

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Docosanoyl-CoA

Description

Docosanoyl-CoA, also known as behenoyl-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. Docosanoyl-CoA is a strong basic compound (based on its pKa). Docosanoyl-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
Behenoyl-CoA	HMDB
Behenoyl-coenzyme A	HMDB

Chemical Formula

C₄₃H₇₈N₇O₁₇P₃S

Average Molecular Weight

1090.11

Monoisotopic Molecular Weight

1089.4388

IUPAC Name

{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(docosanoylsulfanyl)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

[5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(docosanoylsulfanyl)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

CCCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C43H78N7O17P3S/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/h30-32,36-38,42,53-54H,4-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)

InChI Key

NDDZLVOCGALPLR-UHFFFAOYSA-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
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Alkyl phosphate
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Pyrimidine
Phosphoric acid ester
Oxolane
Azole
Imidazole
Heteroaromatic compound
Amino acid or derivatives
Carbothioic s-ester
Thiocarboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Organic 1,3-dipolar compound
Thiocarboxylic acid or derivatives
Azacycle
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Primary amine
Alcohol
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Amine
Organonitrogen compound
Organooxygen compound
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

Cell and elements:

Extracellular

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	3.88	ALOGPS
logP	3.27	ChemAxon
logS	-3.8	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	40	ChemAxon
Refractivity	264.25 m³·mol⁻¹	ChemAxon
Polarizability	114.63 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-4901220100-ad430b543fc1cc3c9d1c	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1901340000-36d071c4e3f230a57823	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900010000-ebb26a1d3ef41618acad	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00v0-9615240500-17e4235039f190ce32d3	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-5902220100-09ac1e3e39670fff85a3	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-5900100000-dd56c2d9e9d82a3d3e21	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-937c9f6c24c43db1e431	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9800100415-8f6041d6075a75e901d3	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0000390000-b579264e92d141258210	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-97b2abe320fd4ab2ff9b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9001201300-c011a19f1678d6539427	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-9101200200-3f7fec23cf270a784a23	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Acyl-coenzyme A thioesterase 8	ACOT8	20q13.12	O14734	details
Lysyl oxidase homolog 2	LOXL2	8p21.3	Q9Y4K0	details
Cyclin-dependent kinase 2-interacting protein	CINP	14q32.31	Q9BW66	details
HIRA-interacting protein 3	HIRIP3	16p11.2	Q9BW71	details
Putative acyl-coenzyme A thioesterase 6	ACOT6	14q24.3	Q3I5F7	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Lysyl oxidase homolog 2	LOXL2	8p21.3	Q9Y4K0	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Lysyl oxidase homolog 2	LOXL2	8p21.3	Q9Y4K0	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Lysyl oxidase homolog 2	LOXL2	8p21.3	Q9Y4K0	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0012930

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029210

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74346883

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Not Available

Enzymes

Enzyme Details

1. 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

2. Lysyl oxidase homolog 2

General function:: Involved in copper ion binding
Specific function:: Mediates the post-translational oxidative deamination of lysine residues on target proteins leading to the formation of deaminated lysine (allysine). When secreted in extracellular matrix, promotes cross-linking of extracellular matrix proteins by mediating oxidative deamination of peptidyl lysine residues in precursors to fibrous collagen and elastin. Acts as a regulator of sprouting angiogenesis, probably via collagen IV scaffolding. When nuclear, acts as a transcription corepressor and specifically mediates deamination of trimethylated 'Lys-4' of histone H3 (H3K4me3), a specific tag for epigenetic transcriptional activation. Involved in epithelial to mesenchymal transition (EMT) via interaction with SNAI1 and participates in repression of E-cadherin, probably by mediating deamination of histone H3. Also involved in E-cadherin repression following hypoxia, a hallmark of epithelial to mesenchymal transition believed to amplify tumor aggressiveness, suggesting that it may play a role in tumor progression. Acts as a regulator of chondrocyte differentiation, probably by regulating expression of factors that control chondrocyte differentiation.
Gene Name:: LOXL2
Uniprot ID:: Q9Y4K0
Molecular weight:: 86724.305

Enzyme Details

3. Cyclin-dependent kinase 2-interacting protein

General function:: Involved in cell cycle
Specific function:: Interacts with the components of the replication complex and 2 kinases, CDK2 and CDC7, thereby providing a functional and physical link between CDK2 and CDC7 during firing of the origins of replication. Regulates ATR-mediated checkpoint signaling
Gene Name:: CINP
Uniprot ID:: Q9BW66
Molecular weight:: 24323.6

Enzyme Details

4. HIRA-interacting protein 3

General function:: Translation, ribosomal structure and biogenesis
Specific function:: May play a role in chromatin function and histone metabolism via its interaction with HIRA and histones
Gene Name:: HIRIP3
Uniprot ID:: Q9BW71
Molecular weight:: 61956.5

Enzyme Details

5. Putative acyl-coenzyme A thioesterase 6

General function:: Involved in carboxylesterase activity
Specific function:: Not Available
Gene Name:: ACOT6
Uniprot ID:: Q3I5F7
Molecular weight:: 22990.5

Showing Compound Card for Docosanoyl-CoA (CDB005311)

Structure for CDB005311 (Docosanoyl-CoA)

Enzymes