Cannabis Compound Database: Showing Compound Card for TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso] (CDB001607)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (23)transporters (1) Show 25 proteins XML

Record Information

Version

1.0

Created at

2020-03-30 18:38:22 UTC

Updated at

2020-12-07 19:08:51 UTC

CannabisDB ID

CDB001607

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso]

Description

TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) 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(18:1(9Z)/18:1(9Z)/18:1(9Z)) is made up of one 9Z-octadecenoyl(R1), one 9Z-octadecenoyl(R2), and one 9Z-octadecenoyl(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
(Z)-9-Octadecenoic acid, 1,2,3-propanetriyl ester	ChEBI
1,2,3-Tri-(9Z-octadecenoyl)-glycerol	ChEBI
Glycerin trioleate	ChEBI
Glycerol trioleate	ChEBI
Glycerol triolein	ChEBI
Glycerol, tri(cis-9-octadecenoate)	ChEBI
Glyceryl trioleate	ChEBI
Glyceryl-1,2,3-trioleate	ChEBI
Oleic acid triglyceride	ChEBI
Oleic triglyceride	ChEBI
Olein	ChEBI
Oleyl triglyceride	ChEBI
Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoate	ChEBI
TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso]	ChEBI
Trioleoylglyceride	ChEBI
Trioleoylglycerol	ChEBI
(Z)-9-Octadecenoate, 1,2,3-propanetriyl ester	Generator
Glycerin trioleic acid	Generator
Glycerol trioleic acid	Generator
Glycerol, tri(cis-9-octadecenoic acid)	Generator
Glyceryl trioleic acid	Generator
Glyceryl-1,2,3-trioleic acid	Generator
Oleate triglyceride	Generator
Propane-1,2,3-triyl (9Z,9'z,9''z)tris-octadec-9-enoic acid	Generator
Trielaidin	HMDB
Trioleate glycerin	HMDB
Trioleyl glycerol	HMDB
Glycerol, trioleyl	HMDB
Trioleate, glycerol	HMDB
Trioleate-glycerin	HMDB
Triacylglycerol	HMDB
TG(18:1/18:1/18:1)	HMDB
TG(54:3)	HMDB
Tracylglycerol(18:1/18:1/18:1)	HMDB
Triglyceride	HMDB
Tracylglycerol(54:3)	HMDB
1-Oleoyl-2-oleoyl-3-oleoyl-glycerol	HMDB
TAG(54:3)	HMDB
1-(9Z-Octadecenoyl)-2-(9Z-octadecenoyl)-3-(9Z-octadecenoyl)-glycerol	HMDB
TAG(18:1/18:1/18:1)	HMDB
TG(18:1(9Z)/18:1(9Z)/18:1(9Z))	Lipid Annotator
Triolein	MeSH

Chemical Formula

C₅₇H₁₀₄O₆

Average Molecular Weight

885.43

Monoisotopic Molecular Weight

884.7833

IUPAC Name

1,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate

Traditional Name

triolein

CAS Registry Number

122-32-7

SMILES

[H]C(COC(=O)CCCCCCC\C=C/CCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C57H104O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h25-30,54H,4-24,31-53H2,1-3H3/b28-25-,29-26-,30-27-

InChI Key

PHYFQTYBJUILEZ-IUPFWZBJSA-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

triglyceride (CHEBI:53753 )
Triacylglycerols (LMGL03010250 )

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Obesity

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Adipose tissue

Biofluid and excreta:

Blood

Subcellular:

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-32 °C	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	10.82	ALOGPS
logP	20.51	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	53	ChemAxon
Refractivity	272.25 m³·mol⁻¹	ChemAxon
Polarizability	116.96 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

Not Available

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, positive	splash10-000i-0000000090-91d6e8bb3820a2b9ebde	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 46V, positive	splash10-000i-0025004090-32e831ad9bb94e656965	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 61V, positive	splash10-00kr-4689024020-7527d97fb03536363c5b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 77V, positive	splash10-00lb-6942000000-37f17691e5732c6d232b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 93V, positive	splash10-000t-7920000000-8d53f79404c44a257cbc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 109V, positive	splash10-0532-9800000000-5ddd79d8af2c416bab4d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 123V, positive	splash10-0532-9700000000-e96406e89785ef71e711	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, positive	splash10-0udi-0000019030-5f72f64cb14b99025263	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, positive	splash10-03di-0158960000-bad288273f5f0ef006e8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, positive	splash10-00or-0054190000-2d9cb5e1963a459c8830	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, positive	splash10-0002-3940000000-daf7601cc0abe13d83fa	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 31V, positive	splash10-0udi-0000009000-6d75632a4c7e9871410c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, positive	splash10-0uxr-5671009000-a4a6beef3d7f47884d90	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, positive	splash10-015a-9830001000-493c7832f4a4288ca519	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 63V, positive	splash10-00l2-9510000000-48886ae654cd58f8e05d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 74V, positive	splash10-05o1-9400000000-50d3f5f119ff86e93d72	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 84V, positive	splash10-05o1-9300000000-c9f83ff0d877bf07548b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 95V, positive	splash10-067j-9200000000-362946f8ec43e2da1de6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 106V, positive	splash10-067j-9100000000-3cbc32304732b7cd617e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 127V, positive	splash10-067i-9100000000-975bad5ee71e2769d5a6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, positive	splash10-014i-0094041000-972891f073da867b3319	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 61V, positive	splash10-0072-2900000000-23da0caf841c568c5920	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000009-7ebc474373ce1c8c3388	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000000009-7ebc474373ce1c8c3388	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-0000009061-c361cdac983d0cdffd59	2017-10-04	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z))		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
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
Lipoprotein lipase	LPL	8p22	P06858	details
Monoglyceride lipase	MGLL		Q99685	details
Liver carboxylesterase 1	CES1	16q22.2	P23141	details
Hormone-sensitive lipase	LIPE	19q13.2	Q05469	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
Glycerol-3-phosphate acyltransferase 3	AGPAT9	4q21.23	Q53EU6	details
Patatin-like phospholipase domain-containing protein 2	PNPLA2	11p15.5	Q96AD5	details
Pancreatic lipase-related protein 3	PNLIPRP3	10q25.3	Q17RR3	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Microsomal triglyceride transfer protein large subunit	MTTP	4q24	P55157	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

HMDB0005453

DrugBank ID

DB13038

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB094046

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-11691

BiGG ID

Not Available

Wikipedia Link

Triolein

METLIN ID

Not Available

PubChem Compound

5497163

PDB ID

Not Available

ChEBI ID

53753

References

General References

Not Available

Only showing the first 10 proteins. There are 25 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. 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

4. 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

5. 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

6. 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

7. 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

8. 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

9. 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

Enzyme Details

10. Lipoprotein lipase

General function:: Involved in catalytic activity
Specific function:: The primary function of this lipase is the hydrolysis of triglycerides of circulating chylomicrons and very low density lipoproteins (VLDL). Binding to heparin sulfate proteogylcans at the cell surface is vital to the function. The apolipoprotein, APOC2, acts as a coactivator of LPL activity in the presence of lipids on the luminal surface of vascular endothelium (By similarity).
Gene Name:: LPL
Uniprot ID:: P06858
Molecular weight:: 53162.07

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

Only showing the first 10 proteins. There are 25 proteins in total.

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Showing Compound Card for TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso] (CDB001607)

Structure for CDB001607 (TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso])

Enzymes

Transporters