Bovine Metabolome Database: Showing metabocard for TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0) (BMDB0062443)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2018-07-17 17:39:23 UTC

Update Date

2020-05-21 16:27:33 UTC

BMDB ID

BMDB0062443

Secondary Accession Numbers

BMDB62443

Metabolite Identification

Common Name

TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0)

Description

TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0), also known as tag(15:0/18:4/24:0) or tag(57:4), 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. TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0) can be biosynthesized from DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) and tetracosanoyl-CoA; which is mediated by the enzyme diacylglycerol O-acyltransferase. In cattle, TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Pentadecanoyl-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-3-tetracosanoyl-glycerol	HMDB
1-Pentadecanoyl-2-stearidonoyl-3-lignoceroyl-glycerol	HMDB
TAG(15:0/18:4/24:0)	HMDB
TAG(57:4)	HMDB
TG(15:0/18:4/24:0)	HMDB
TG(57:4)	HMDB
Tracylglycerol(15:0/18:4/24:0)	HMDB
Tracylglycerol(57:4)	HMDB
Triacylglycerol	HMDB
Triglyceride	HMDB
TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0)	Lipid Annotator

Chemical Formula

C₆₀H₁₀₈O₆

Average Molecular Weight

925.518

Monoisotopic Molecular Weight

924.814591198

IUPAC Name

(2S)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-(pentadecanoyloxy)propyl tetracosanoate

Traditional Name

(2S)-2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]-3-(pentadecanoyloxy)propyl tetracosanoate

CAS Registry Number

Not Available

SMILES

[H][C@](COC(=O)CCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCCCCCCCC)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C60H108O6/c1-4-7-10-13-16-19-22-25-27-28-29-30-31-32-34-35-38-41-44-47-50-53-59(62)65-56-57(55-64-58(61)52-49-46-43-40-37-24-21-18-15-12-9-6-3)66-60(63)54-51-48-45-42-39-36-33-26-23-20-17-14-11-8-5-2/h8,11,17,20,26,33,39,42,57H,4-7,9-10,12-16,18-19,21-25,27-32,34-38,40-41,43-56H2,1-3H3/b11-8-,20-17-,33-26-,42-39-/t57-/m0/s1

InChI Key

GPQRMWGHHPNZPB-RSWNSSALSA-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

Status

Detected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Membrane

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	21.48	Extrapolated

Predicted Properties

Property	Value	Source
logP	10.92	ALOGPS
logP	21.48	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	55	ChemAxon
Refractivity	287.17 m³·mol⁻¹	ChemAxon
Polarizability	124.11 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000009-1da4eef8baf3f0db704f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000009-1da4eef8baf3f0db704f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a8b-0000049003-452264438b0c1bd743d3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xv-0096002001-7fe7423adef141f62d1d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01bd-0098001000-379f49cde8ba1431ff76	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05tg-3095000000-a4286c254bb2418fb8a2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-3011012069-f41cfc97f362e515640d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-4011001091-052a25a64ef29fc8433b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-092c-0493100040-5fdeb7b308855fc885b4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000009-e44212892014ed34493a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000009-e44212892014ed34493a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk0-0004009004-316e5c1bdbf6a2a88f47	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0065016009-eef1d448705e107dbc15	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kwf-0097201000-2caf6f8b77b9c5cab4bc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-2095000000-d5813226c282c76a2826	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000009-86eb9ae4261082c5c659	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000009-86eb9ae4261082c5c659	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a7j-0010049003-7e7bc028f5330a392640	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000000009-f64ee0bc1b8e41506876	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000000009-f64ee0bc1b8e41506876	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0000000009-f64ee0bc1b8e41506876	View in MoNA

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Membrane

Biospecimen Locations

Milk

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 28965405	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0043661

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

131754781

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tang C, Zhang K, Zhan T, Zhao Q, Zhang J: Metabolic Characterization of Dairy Cows Treated with Gossypol by Blood Biochemistry and Body Fluid Untargeted Metabolome Analyses. J Agric Food Chem. 2017 Oct 25;65(42):9369-9378. doi: 10.1021/acs.jafc.7b03544. Epub 2017 Oct 17. [PubMed:28965405 ]

Enzymes

Enzyme Details

1. Diacylglycerol O-acyltransferase 1

General function:: Not Available
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. 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. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:: DGAT1
Uniprot ID:: Q8MK44
Molecular weight:: 55602.0

Reactions

DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Tetracosanoyl-CoA → TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0) + Coenzyme A	details

Showing metabocard for TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0) (BMDB0062443)

Structure for BMDB0062443 (TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0))

Enzymes

Reactions