TG(10:0/16:1(9Z)/20:1(13Z)) (YMDB15734)

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Identification

YMDB ID

YMDB15734

Name

TG(10:0/16:1(9Z)/20:1(13Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

TG(10:0/16:1(9Z)/20:1(13Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). TG(10:0/16:1(9Z)/20:1(13Z)) may be a unique S. cerevisiae (yeast) metabolite. Within yeast, TG(10:0/16:1(9Z)/20:1(13Z)) participates in a number of enzymatic reactions. In particular, TG(10:0/16:1(9Z)/20:1(13Z)) can be biosynthesized from DG(10:0/20:1(13Z)/0:0) through its interaction with the enzyme diacylglycerol O-acyltransferase 1. In addition, TG(10:0/16:1(9Z)/20:1(13Z)) can be converted into DG(10:0/20:1(13Z)/0:0); which is mediated by the enzyme triacylglycerol lipase complex. In yeast, TG(10:0/16:1(9Z)/20:1(13Z)) is involved in the metabolic pathway called the triacylglycerol metabolism tg(10:0/16:1(9z)/20:1(13z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

CAS number

Not Available

Weight

Average: 775.253
Monoisotopic: 774.673740618

InChI Key

XVYPJSNIFQTBBE-XIXXCSPQSA-N

InChI

InChI=1S/C49H90O6/c1-4-7-10-13-16-18-20-22-23-24-25-27-28-30-33-36-39-42-48(51)54-45-46(44-53-47(50)41-38-35-32-15-12-9-6-3)55-49(52)43-40-37-34-31-29-26-21-19-17-14-11-8-5-2/h18-21,46H,4-17,22-45H2,1-3H3/b20-18-,21-19-/t46-/m0/s1

IUPAC Name

(2S)-3-(decanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl (13Z)-icos-13-enoate

Traditional IUPAC Name

(2S)-3-(decanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propyl (13Z)-icos-13-enoate

Chemical Formula

C₄₉H₉₀O₆

SMILES

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

Chemical Taxonomy

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	7.5e-06 g/L	ALOGPS
logP	10.58	ALOGPS
logP	17.31	ChemAxon
logS	-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	46	ChemAxon
Refractivity	234.32 m³·mol⁻¹	ChemAxon
Polarizability	101.52 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Triacylglycerol metabolism TG(10:0/16:1(9Z)/20:1(13Z))

PW007730

KEGG Pathways

Not Available

SMPDB Reactions

long-chain fatty acyl-CoA + DG(10:0/20:1(13Z)/0:0) → Coenzyme A + TG(10:0/16:1(9Z)/20:1(13Z))

TG(10:0/16:1(9Z)/20:1(13Z)) + water → hydron + Fatty Acid + DG(10:0/20:1(13Z)/0:0)

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ami-0000999000-30d4a451c25a464f7983	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Diacylglycerol O-acyltransferase 1

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for storage lipid synthesis. May be involved in lipid particle synthesis from the endoplasmic reticulum and ergosterol biosynthesis
Gene Name:: DGA1
Uniprot ID:: Q08650
Molecular weight:: 47710.89844

Reactions

Acyl-CoA + 1,2-diacylglycerol → CoA + triacylglycerol.

Protein Details

2. Sterol esterase TGL1

General function:: Involved in lipid metabolic process
Specific function:: Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism. May have weak lipase activity toward triglycerides upon some conditions, however, the relevance of such activity is unclear in vivo
Gene Name:: TGL1
Uniprot ID:: P34163
Molecular weight:: 62978.39844

Reactions

A steryl ester + H(2)O → a sterol + a fatty acid.

Protein Details

3. Lipase 2

General function:: Involved in hydrolase activity, acting on ester bonds
Specific function:: Lipolytic activity towards triacylglycerols and diacylglycerols with short-chain fatty acids
Gene Name:: TGL2
Uniprot ID:: P54857
Molecular weight:: 37499.89844

Reactions

Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.

Protein Details

4. Lipase 3

General function:: Involved in metabolic process
Specific function:: Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process
Gene Name:: TGL3
Uniprot ID:: P40308
Molecular weight:: 73611.79688

Reactions

Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.

Protein Details

5. Lipase 5

General function:: Involved in metabolic process
Specific function:: Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:: TGL5
Uniprot ID:: Q12043
Molecular weight:: 84715.10156

Reactions

Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.

Protein Details

6. Lipase 4

General function:: Involved in metabolic process
Specific function:: Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:: TGL4
Uniprot ID:: P36165
Molecular weight:: 102716.0

Reactions

Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.

Structure for #<Compound:0xaae9573c>

Enzymes

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