Cannabis Compound Database: Showing Compound Card for MG(0:0/18:3(6Z,9Z,12Z)/0:0) (CDB001196)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (8) Show 9 proteins XML

Record Information

Version

1.0

Created at

2020-03-30 18:10:12 UTC

Updated at

2020-12-07 19:07:59 UTC

CannabisDB ID

CDB001196

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

MG(0:0/18:3(6Z,9Z,12Z)/0:0)

Description

MG(0:0/18:3(6Z,9Z,12Z)/0:0) belongs to the family of monoradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at one fatty acyl group is attached. Their general formula is [R1]OCC(CO[R2])O[R3]. MG(0:0/18:3(6Z,9Z,12Z)/0:0) is made up of one 6Z,9Z,12Z-octadecatrienoyl(R2). This compound 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
1-Monoacylglyceride	HMDB
1-Monoacylglycerol	HMDB
2-(6Z,9Z,12Z-Octadecatrienoyl)-rac-glycerol	HMDB
2-g-Linolenoyl-glycerol	HMDB
2-gamma-Linolenoyl-glycerol	HMDB
b-Monoacylglycerol	HMDB
beta-Monoacylglycerol	HMDB
MAG(0:0/18:3)	HMDB
MAG(0:0/18:3n6)	HMDB
MAG(0:0/18:3W6)	HMDB
MAG(18:3)	HMDB
MG(0:0/18:3)	HMDB
MG(0:0/18:3n6)	HMDB
MG(0:0/18:3W6)	HMDB
MG(18:3)	HMDB

Chemical Formula

C₂₁H₃₆O₄

Average Molecular Weight

352.51

Monoisotopic Molecular Weight

352.2614

IUPAC Name

1,3-dihydroxypropan-2-yl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate

Traditional Name

1,3-dihydroxypropan-2-yl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate

CAS Registry Number

Not Available

SMILES

[H]C(CO)(CO)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C21H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h6-7,9-10,12-13,20,22-23H,2-5,8,11,14-19H2,1H3/b7-6-,10-9-,13-12-

InChI Key

BXAXVVVVPFELOK-QNEBEIHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
2-acyl-sn-glycerol
Monoacylglycerol
Monoradylglycerol
Fatty acid ester
Glycerolipid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Tissue and substructures:

All tissues

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	5.16	ALOGPS
logP	4.89	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	106.66 m³·mol⁻¹	ChemAxon
Polarizability	42.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	MG(0:0/18:3(6Z,9Z,12Z)/0:0), 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0i7i-6490100000-a204bb9fa33dd165192c	Spectrum
Predicted GC-MS	MG(0:0/18:3(6Z,9Z,12Z)/0:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dl-9011000000-7837aa5ddbb52eccfe05	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abc-9051000000-490eeba4610222a6246f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9350000000-230be145029de9555164	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-87561ddc849e8cd4e903	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ur0-0009000000-6d16beb5877d971e135e	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ur2-0049000000-33b2c82d332bc81d2766	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-090a59acebb84ada146f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0009000000-090a59acebb84ada146f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0vk9-0009000000-7ab914a8b6d96b9ad417	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-9f4ee23bf0cdb2d85a4b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-0009000000-c83819a1597694039b23	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udk-0079000000-d224bc6b038aba67dcff	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-439417b15b92b5f4ecd8	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ui0-0079000000-7dafb35a2685c76b04e2	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ti-0095000000-df93ed24dab2f02a9b7f	2021-09-25	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Monoglyceride lipase	MGLL		Q99685	details
Hormone-sensitive lipase	LIPE	19q13.2	Q05469	details
2-acylglycerol O-acyltransferase 2	MOGAT2	11q13.5	Q3SYC2	details
2-acylglycerol O-acyltransferase 1	MOGAT1	2q36.1	Q96PD6	details
2-acylglycerol O-acyltransferase 3	MOGAT3	7q22.1	Q86VF5	details
Lysophosphatidic acid phosphatase type 6	ACP6	1q21	Q9NPH0	details
Acylglycerol kinase, mitochondrial	AGK	7q34	Q53H12	details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 6	ENPP6	4q35.1	Q6UWR7	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Acylglycerol kinase, mitochondrial	AGK	7q34	Q53H12	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0011539

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028253

KNApSAcK ID

Not Available

Chemspider ID

9820783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11646044

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Not Available

Enzymes

Enzyme Details

1. Monoglyceride lipase

General function:: Lipid transport and metabolism
Specific function:: Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes the endocannabinoid 2-arachidonoylglycerol, and thereby contributes to the regulation of endocannabinoid signaling, nociperception and perception of pain (By similarity). Regulates the levels of fatty acids that serve as signaling molecules and promote cancer cell migration, invasion and tumor growth.
Gene Name:: MGLL
Uniprot ID:: Q99685
Molecular weight:: Not Available

Enzyme Details

2. Hormone-sensitive lipase

General function:: Involved in hydrolase activity
Specific function:: In adipose tissue and heart, it primarily hydrolyzes stored triglycerides to free fatty acids, while in steroidogenic tissues, it principally converts cholesteryl esters to free cholesterol for steroid hormone production.
Gene Name:: LIPE
Uniprot ID:: Q05469
Molecular weight:: 116596.715

Enzyme Details

3. 2-acylglycerol O-acyltransferase 2

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Has a preference toward monoacylglycerols containing unsaturated fatty acids in an order of C18:3 > C18:2 > C18:1 > C18:0. Plays a central role in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes. May play a role in diet-induced obesity.
Gene Name:: MOGAT2
Uniprot ID:: Q3SYC2
Molecular weight:: 38195.285

Enzyme Details

4. 2-acylglycerol O-acyltransferase 1

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Probably not involved in absorption of dietary fat in the small intestine (By similarity).
Gene Name:: MOGAT1
Uniprot ID:: Q96PD6
Molecular weight:: 38812.19

Enzyme Details

5. 2-acylglycerol O-acyltransferase 3

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the formation of diacylglycerol from 2-monoacylglycerol and fatty acyl-CoA. Also able to catalyze the terminal step in triacylglycerol synthesis by using diacylglycerol and fatty acyl-CoA as substrates. Has a preference toward palmitoyl-CoA and oleoyl-CoA. May be involved in absorption of dietary fat in the small intestine by catalyzing the resynthesis of triacylglycerol in enterocytes.
Gene Name:: MOGAT3
Uniprot ID:: Q86VF5
Molecular weight:: 38729.84

Enzyme Details

6. Lysophosphatidic acid phosphatase type 6

General function:: Involved in acid phosphatase activity
Specific function:: Hydrolyzes lysophosphatidic acid to monoacylglycerol.
Gene Name:: ACP6
Uniprot ID:: Q9NPH0
Molecular weight:: 48853.955

Enzyme Details

7. Acylglycerol kinase, mitochondrial

General function:: Involved in NAD+ kinase activity
Specific function:: Lipid kinase that can phosphorylate both monoacylglycerol and diacylglycerol to form lysophosphatidic acid (LPA) and phosphatidic acid (PA), respectively. Does not phosphorylate sphingosine. Overexpression increases the formation and secretion of LPA, resulting in transactivation of EGFR and activation of the downstream MAPK signaling pathway, leading to increased cell growth
Gene Name:: AGK
Uniprot ID:: Q53H12
Molecular weight:: 47136.8

Enzyme Details

8. Ectonucleotide pyrophosphatase/phosphodiesterase family member 6

General function:: Involved in catalytic activity
Specific function:: Choline-specific glycerophosphodiester phosphodiesterase. The preferred substrate may be lysosphingomyelin (By similarity). Hydrolyzes lysophosphatidylcholine (LPC) to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. Has a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. Also hydrolyzes glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. Hydrolyzes the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine in vitro, while it does not hydrolyze the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. Does not hydrolyze diacyl phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol and phosphatidic acid.
Gene Name:: ENPP6
Uniprot ID:: Q6UWR7
Molecular weight:: 50240.625

Showing Compound Card for MG(0:0/18:3(6Z,9Z,12Z)/0:0) (CDB001196)

Structure for CDB001196 (MG(0:0/18:3(6Z,9Z,12Z)/0:0))

Enzymes