Cannabis Compound Database: Showing Compound Card for Glycerol trihexadecanoate (CDB000795)

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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 17:43:17 UTC

Updated at

2020-12-07 19:07:46 UTC

CannabisDB ID

CDB000795

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Glycerol trihexadecanoate

Description

TG(16:0/16:0/16:0) 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(16:0/16:0/16:0) is made up of one hexadecanoyl(R1), one hexadecanoyl(R2), and one hexadecanoyl(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
1,2,3-Propanetriol trihexadecanoate	ChEBI
1,2,3-Propanetriyl trihexadecanoate	ChEBI
1,2,3-Trihexadecanoylglycerol	ChEBI
Glycerin tripalmitate	ChEBI
Glycerol tripalmitate	ChEBI
Glyceryl trihexadecanoate	ChEBI
Glyceryl tripalmitate	ChEBI
Hexadecanoic acid, 1,2,3-propanetriyl ester	ChEBI
Palmitic acid triglycerin ester	ChEBI
Palmitic triglyceride	ChEBI
TG 16:0/16:0/16:0	ChEBI
Triglyceryl palmitate	ChEBI
Trihexadecanoylglycerol	ChEBI
Tripalmitoylglycerol	ChEBI
1,2,3-Propanetriol trihexadecanoic acid	Generator
1,2,3-Propanetriyl trihexadecanoic acid	Generator
Glycerin tripalmitic acid	Generator
Glycerol tripalmitic acid	Generator
Glyceryl trihexadecanoic acid	Generator
Glyceryl tripalmitic acid	Generator
Hexadecanoate, 1,2,3-propanetriyl ester	Generator
Palmitate triglycerin ester	Generator
Triglyceryl palmitic acid	Generator
1,2,3-Trihexadecanoyl-sn-glycerol	HMDB
Barolub LCD	HMDB
Dynasan 116	HMDB
Dynosan 114	HMDB
Spezialfett 116	HMDB
Triglyceride PPP	HMDB
Tripalmitate	HMDB
Tripalmitin	HMDB
Tripalmitoyl glycerol	HMDB
Glycero-tripalmitate	HMDB
Tripalmitylglycerol	HMDB
1-Palmitoyl-2-palmitoyl-3-palmitoyl-glycerol	HMDB
TG(48:0)	HMDB
Triglyceride	HMDB
Tracylglycerol(48:0)	HMDB
TAG(16:0/16:0/16:0)	HMDB
Tracylglycerol(16:0/16:0/16:0)	HMDB
TAG(48:0)	HMDB
1-Hexadecanoyl-2-hexadecanoyl-3-hexadecanoyl-glycerol	HMDB
Triacylglycerol	HMDB
TG(16:0/16:0/16:0)	Lipid Annotator, ChEBI

Chemical Formula

C₅₁H₉₈O₆

Average Molecular Weight

807.32

Monoisotopic Molecular Weight

806.7363

IUPAC Name

1,3-bis(hexadecanoyloxy)propan-2-yl hexadecanoate

Traditional Name

tripalmitin

CAS Registry Number

555-44-2

SMILES

[H]C(COC(=O)CCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C51H98O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-49(52)55-46-48(57-51(54)45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)47-56-50(53)44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h48H,4-47H2,1-3H3

InChI Key

PVNIQBQSYATKKL-UHFFFAOYSA-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:77393 )
Triacylglycerols (LMGL03010001 )
a triacylglycerol (CPD66-35 )

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Obesity

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Adipose tissue

Biofluid and excreta:

Blood

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	10.59	ALOGPS
logP	18.92	ChemAxon
logS	-7.8	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	50	ChemAxon
Refractivity	241.29 m³·mol⁻¹	ChemAxon
Polarizability	109.39 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
GC-MS	Glycerol trihexadecanoate, non-derivatized, GC-MS Spectrum	splash10-0udr-4266090000-d72def42ee8b15e7d8ab	Spectrum
GC-MS	Glycerol trihexadecanoate, non-derivatized, GC-MS Spectrum	splash10-0udi-5255090000-f2b69e4c01f94e964a8e	Spectrum
GC-MS	Glycerol trihexadecanoate, non-derivatized, GC-MS Spectrum	splash10-0udr-4266090000-d72def42ee8b15e7d8ab	Spectrum
GC-MS	Glycerol trihexadecanoate, non-derivatized, GC-MS Spectrum	splash10-0udi-5255090000-f2b69e4c01f94e964a8e	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0udr-4266090000-d72def42ee8b15e7d8ab	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0udi-5255090000-08a84d0a82ce5839332e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (ACQUITY UPLC System, Waters) 30V, Positive	splash10-0udi-0000090000-b971f7be0932cc17d4fc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (ACQUITY UPLC System, Waters) 30V, Positive	splash10-0udi-0000090000-ba2f475d5deb56cbcb0f	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000090-2dcd9d1c90fb060e2d76	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000000090-2dcd9d1c90fb060e2d76	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-0000090070-5e4488c43f4273c179dd	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0070080190-e59a843e2ac9eb401541	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-0090020000-1e6cc9453781ea6f2f0e	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-1090010000-52dbd7332c4689b8becb	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000090-497b97a123d4ddbee56b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000090-497b97a123d4ddbee56b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fr-0090090090-3d1ee4df7694f2a67b63	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000090-feacb9716f0cce2e39b9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000000090-feacb9716f0cce2e39b9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-0000000090-feacb9716f0cce2e39b9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000090-c9b5cf0ac5a5011ec584	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000000090-c9b5cf0ac5a5011ec584	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-0010090070-13293a79e092976cb1e0	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-4130052390-48f5c7a747823dfa0644	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-059i-9150123400-dde2539447879b15fbf1	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000l-4496013000-d20d940fe1d4244aa3e7	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycerolipid Metabolism
Glycerol Kinase Deficiency		Not Available
D-glyceric acidura		Not Available
Familial lipoprotein lipase deficiency		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/16:0/16:0)		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

HMDB0005356

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002911

KNApSAcK ID

Not Available

Chemspider ID

10674

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

3857

PubChem Compound

11147

PDB ID

Not Available

ChEBI ID

77393

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 Glycerol trihexadecanoate (CDB000795)

Structure for CDB000795 (Glycerol trihexadecanoate)

Enzymes

Transporters