Cannabis Compound Database: Showing Compound Card for TG(22:1(13Z)/18:1(11Z)/22:1(13Z)) (CDB002885)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (27)transporters (7) Show 35 proteins XML

Record Information

Version

1.0

Created at

2020-03-30 20:07:27 UTC

Updated at

2020-12-07 19:10:11 UTC

CannabisDB ID

CDB002885

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

TG(22:1(13Z)/18:1(11Z)/22:1(13Z))

Description

TG(22:1(13Z)/18:1(11Z)/22:1(13Z)) belongs to the family of triradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. Their general formula is [R1]OCC(CO[R2])O[R3]. TG(22:1(13Z)/18:1(11Z)/22:1(13Z)) is made up of one 13Z-docosenoyl(R1), one 11Z-octadecenoyl(R2), and one 13Z-docosenoyl(R3). 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
TG(62:3)	HMDB
Triacylglycerol	HMDB
TAG(22:1/18:1/22:1)	HMDB
Triglyceride	HMDB
TG(22:1/18:1/22:1)	HMDB
Tracylglycerol(22:1/18:1/22:1)	HMDB
1-Erucoyl-2-vaccenoyl-3-erucoyl-glycerol	HMDB
Tracylglycerol(62:3)	HMDB
TAG(62:3)	HMDB
1-(13Z-Docosenoyl)-2-(11Z-octadecenoyl)-3-(13Z-docosenoyl)-glycerol	HMDB
TG(22:1(13Z)/18:1(11Z)/22:1(13Z))	Lipid Annotator

Chemical Formula

C₆₅H₁₂₀O₆

Average Molecular Weight

997.64

Monoisotopic Molecular Weight

996.9085

IUPAC Name

3-[(13Z)-docos-13-enoyloxy]-2-[(11Z)-octadec-11-enoyloxy]propyl (13Z)-docos-13-enoate

Traditional Name

3-[(13Z)-docos-13-enoyloxy]-2-[(11Z)-octadec-11-enoyloxy]propyl (13Z)-docos-13-enoate

CAS Registry Number

Not Available

SMILES

[H]C(COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)(COC(=O)CCCCCCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCC

InChI Identifier

InChI=1S/C65H120O6/c1-4-7-10-13-16-19-22-25-28-30-32-34-37-39-42-45-48-51-54-57-63(66)69-60-62(71-65(68)59-56-53-50-47-44-41-36-27-24-21-18-15-12-9-6-3)61-70-64(67)58-55-52-49-46-43-40-38-35-33-31-29-26-23-20-17-14-11-8-5-2/h21,24-26,28-29,62H,4-20,22-23,27,30-61H2,1-3H3/b24-21-,28-25-,29-26-

InChI Key

HTXRBEDVXNDXBO-HGKIKGFLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Triradylcglycerols

Direct Parent

Triacylglycerols

Alternative Parents

Substituents

Triacyl-sn-glycerol
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Obesity

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Adipose tissue

Biofluid and excreta:

Blood

Subcellular:

Source:

Biological:

Animal

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	24.06	Extrapolated

Predicted Properties

Property	Value	Source
logP	10.77	ALOGPS
logP	24.06	ChemAxon
logS	-8.2	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	61	ChemAxon
Refractivity	309.05 m³·mol⁻¹	ChemAxon
Polarizability	134.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	TG(22:1(13Z)/18:1(11Z)/22:1(13Z)), 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, Positive	splash10-03di-9000000000-559f7a0447bd80459e2d	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-559f7a0447bd80459e2d	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0b91-1000009906-1be46dc21c187dd376a1	2017-10-04	View Spectrum
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, Positive	splash10-03di-9000000000-a62ea8ebe631dd5d7cbf	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-a62ea8ebe631dd5d7cbf	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066s-1011009906-fcced765aa72fdf573db	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-9000000000-8a039aef94d54442a310	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9000000000-8a039aef94d54442a310	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0y4k-9009009900-55a9c59935fb89d12ac1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05mk-4443004379-5e08f607bfda4e559154	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0avi-8473003192-517541f53c66f71d4fed	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016r-2459001200-a2f401e616f5613fdd84	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000b-0029005208-09f2448e75f686061845	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-0009001000-f6be5dfca14d704056ad	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052r-1019000000-cd2011e528668d69a294	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-9000000000-6a9057ca849e5533394d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9000000000-6a9057ca849e5533394d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-6a9057ca849e5533394d	2021-09-25	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(22:1(13Z)/18:1(11Z)/22:1(13Z))		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Pancreatic triacylglycerol lipase	PNLIP	10q26.1	P16233	details
Hepatic triacylglycerol lipase	LIPC	15q21-q23	P11150	details
Lysosomal acid lipase/cholesteryl ester hydrolase	LIPA	10q23.2-q23.3	P38571	details
Inactive pancreatic lipase-related protein 1	PNLIPRP1		P54315	details
Patatin-like phospholipase domain-containing protein 3	PNPLA3	22q13.31	Q9NST1	details
Gastric triacylglycerol lipase	LIPF	10q23.31	P07098	details
Endothelial lipase	LIPG	18q21.1	Q9Y5X9	details
Bile salt-activated lipase	CEL	9q34.3	P19835	details
Diacylglycerol O-acyltransferase 1	DGAT1	8q24.3	O75907	details
Pancreatic lipase-related protein 2	PNLIPRP2	10q25.3	P54317	details
Carnitine O-palmitoyltransferase 1, muscle isoform	CPT1B	22q13.33	Q92523	details
Carnitine O-palmitoyltransferase 1, liver isoform	CPT1A	11q13.2	P50416	details
Lipoprotein lipase	LPL	8p22	P06858	details
Carnitine O-palmitoyltransferase 2, mitochondrial	CPT2	1p32	P23786	details
Monoglyceride lipase	MGLL		Q99685	details
Liver carboxylesterase 1	CES1	16q22.2	P23141	details
Hormone-sensitive lipase	LIPE	19q13.2	Q05469	details
Apolipoprotein A-I	APOA1	11q23-q24	P02647	details
Apolipoprotein E	APOE	19q13.2	P02649	details
Apolipoprotein B-100	APOB	2p24-p23	P04114	details
Protein disulfide-isomerase	P4HB	17q25	P07237	details
2-acylglycerol O-acyltransferase 2	MOGAT2	11q13.5	Q3SYC2	details
Patatin-like phospholipase domain-containing protein 4	PNPLA4	Xp22.3	P41247	details
Diacylglycerol O-acyltransferase 2	DGAT2	11q13.5	Q96PD7	details
2-acylglycerol O-acyltransferase 1	MOGAT1	2q36.1	Q96PD6	details
2-acylglycerol O-acyltransferase 3	MOGAT3	7q22.1	Q86VF5	details
Phospholipase B1, membrane-associated	PLB1	2p23.2	Q6P1J6	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Microsomal triglyceride transfer protein large subunit	MTTP	4q24	P55157	details
Cholesteryl ester transfer protein	CETP	16q21	P11597	details
Apolipoprotein C-III precursor	APOC3	11q23.1-q23.2	P02656	details
Apolipoprotein B-100	APOB	2p24-p23	P04114	details
Apolipoprotein A-IV precursor	APOA4	11q23	P06727	details
Platelet glycoprotein 4	CD36	7q11.2	P16671	details
Long-chain fatty acid transport protein 1	SLC27A1	19p13.11	Q6PCB7	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Pancreatic triacylglycerol lipase	PNLIP	10q26.1	P16233	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0051561

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

131762284

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Not Available

Only showing the first 10 proteins. There are 35 proteins in total.

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Enzymes

Enzyme Details

1. Pancreatic triacylglycerol lipase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: PNLIP
Uniprot ID:: P16233
Molecular weight:: 51156.48

Enzyme Details

2. Hepatic triacylglycerol lipase

General function:: Involved in catalytic activity
Specific function:: Hepatic lipase has the capacity to catalyze hydrolysis of phospholipids, mono-, di-, and triglycerides, and acyl-CoA thioesters. It is an important enzyme in HDL metabolism. Hepatic lipase binds heparin.
Gene Name:: LIPC
Uniprot ID:: P11150
Molecular weight:: 55914.1

Enzyme Details

3. Lysosomal acid lipase/cholesteryl ester hydrolase

General function:: Involved in lipid metabolic process
Specific function:: Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:: LIPA
Uniprot ID:: P38571
Molecular weight:: 45418.71

Enzyme Details

4. Inactive pancreatic lipase-related protein 1

General function:: Involved in catalytic activity
Specific function:: May function as inhibitor of dietary triglyceride digestion. Lacks detectable lipase activity towards triglycerides, diglycerides, phosphatidylcholine, galactolipids or cholesterol esters (in vitro) (By similarity).
Gene Name:: PNLIPRP1
Uniprot ID:: P54315
Molecular weight:: Not Available

Enzyme Details

5. Patatin-like phospholipase domain-containing protein 3

General function:: Involved in metabolic process
Specific function:: Multifunctional enzyme which has both triacylglycerol lipase and acylglycerol O-acyltransferase activities.
Gene Name:: PNPLA3
Uniprot ID:: Q9NST1
Molecular weight:: 52864.64

Enzyme Details

6. Gastric triacylglycerol lipase

General function:: Involved in lipid metabolic process
Specific function:: Not Available
Gene Name:: LIPF
Uniprot ID:: P07098
Molecular weight:: 45237.375

Enzyme Details

7. Endothelial lipase

General function:: Involved in catalytic activity
Specific function:: Has phospholipase and triglyceride lipase activities. Hydrolyzes high density lipoproteins (HDL) more efficiently than other lipoproteins. Binds heparin.
Gene Name:: LIPG
Uniprot ID:: Q9Y5X9
Molecular weight:: 56794.275

Enzyme Details

8. Bile salt-activated lipase

General function:: Lipid transport and metabolism
Specific function:: Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
Gene Name:: CEL
Uniprot ID:: P19835
Molecular weight:: 79666.385

Enzyme Details

9. Diacylglycerol O-acyltransferase 1

General function:: Involved in diacylglycerol O-acyltransferase activity
Specific function:: Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. In liver, plays a role in esterifying exogenous fatty acids to glycerol. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders.
Gene Name:: DGAT1
Uniprot ID:: O75907
Molecular weight:: 55277.735

Enzyme Details

10. Pancreatic lipase-related protein 2

General function:: Involved in catalytic activity
Specific function:: Lipase with broad substrate specificity. Can hydrolyze both phospholipids and galactolipids. Acts preferentially on monoglycerides, phospholipids and galactolipids. Contributes to milk fat hydrolysis.
Gene Name:: PNLIPRP2
Uniprot ID:: P54317
Molecular weight:: 52077.475

Transporters

Enzyme Details

1. Microsomal triglyceride transfer protein large subunit

General function:: Involved in lipid transporter activity
Specific function:: Catalyzes the transport of triglyceride, cholesteryl ester, and phospholipid between phospholipid surfaces. Required for the secretion of plasma lipoproteins that contain apolipoprotein B
Gene Name:: MTTP
Uniprot ID:: P55157
Molecular weight:: 99350.3

Enzyme Details

2. Cholesteryl ester transfer protein

General function:: Involved in lipid binding
Specific function:: Involved in the transfer of insoluble cholesteryl esters in the reverse transport of cholesterol
Gene Name:: CETP
Uniprot ID:: P11597
Molecular weight:: 54755.7

Enzyme Details

3. Apolipoprotein C-III precursor

General function:: Not Available
Specific function:: Inhibits lipoprotein lipase and hepatic lipase and decreases the uptake of lymph chylomicrons by hepatic cells. This suggests that it delays the catabolism of triglyceride-rich particles
Gene Name:: APOC3
Uniprot ID:: P02656
Molecular weight:: 10852.0

Enzyme Details

4. Apolipoprotein B-100

General function:: Involved in lipid transporter activity
Specific function:: Apolipoprotein B is a major protein constituent of chylomicrons (apo B-48), LDL (apo B-100) and VLDL (apo B-100). Apo B-100 functions as a recognition signal for the cellular binding and internalization of LDL particles by the apoB/E receptor
Gene Name:: APOB
Uniprot ID:: P04114
Molecular weight:: 515600.1

Enzyme Details

5. Apolipoprotein A-IV precursor

General function:: Replication, recombination and repair
Specific function:: May have a role in chylomicrons and VLDL secretion and catabolism. Required for efficient activation of lipoprotein lipase by ApoC-II; potent activator of LCAT. Apoa-IV is a major component of HDL and chylomicrons
Gene Name:: APOA4
Uniprot ID:: P06727
Molecular weight:: 45400.0

Enzyme Details

6. Platelet glycoprotein 4

General function:: Not Available
Specific function:: Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:: CD36
Uniprot ID:: P16671
Molecular weight:: 53054.0

Enzyme Details

7. Long-chain fatty acid transport protein 1

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:: SLC27A1
Uniprot ID:: Q6PCB7
Molecular weight:: 71107.5

Only showing the first 10 proteins. There are 35 proteins in total.

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Showing Compound Card for TG(22:1(13Z)/18:1(11Z)/22:1(13Z)) (CDB002885)

Structure for CDB002885 (TG(22:1(13Z)/18:1(11Z)/22:1(13Z)))

Enzymes

Transporters