Bovine Metabolome Database: Showing metabocard for DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) (BMDB0007048)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:29:27 UTC

Update Date

2020-05-21 16:27:27 UTC

BMDB ID

BMDB0007048

Secondary Accession Numbers

BMDB07048

Metabolite Identification

Common Name

DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0)

Description

DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0), also known as dg(14:1(9z)/18:4(6z,9z,12z,15z)/0:0) or DAG(14:1/18:4), belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)); which is mediated by the enzyme phosphatidate phosphatase. Furthermore, DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and stearidonoyl-CoA can be converted into TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)); which is catalyzed by the enzyme dg(14:1(9z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. Furthermore, DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and gondoyl-CoA can be converted into TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)) through the action of the enzyme dg(14:1(9z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. Furthermore, DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)) through the action of the enzyme phosphatidate phosphatase. Finally, DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) and eicosatetraenoyl-CoA can be converted into TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) through its interaction with the enzyme dg(14:1(9z)/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. In cattle, DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) is involved in several metabolic pathways, some of which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(8Z,11Z,14Z,17Z)) pathway, and de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Myristoleoyl-2-stearidonoyl-sn-glycerol	HMDB
DAG(14:1/18:4)	HMDB
DAG(14:1N5/18:4N3)	HMDB
DAG(14:1W5/18:4W3)	HMDB
DAG(32:5)	HMDB
DG(14:1/18:4)	HMDB
DG(14:1N5/18:4N3)	HMDB
DG(14:1W5/18:4W3)	HMDB
DG(32:5)	HMDB
Diacylglycerol	HMDB
Diacylglycerol(14:1/18:4)	HMDB
Diacylglycerol(14:1n5/18:4n3)	HMDB
Diacylglycerol(14:1W5/18:4W3)	HMDB
Diacylglycerol(32:5)	HMDB
Diglyceride	HMDB
1-(9Z-Tetradecenoyl)-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-sn-glycerol	HMDB
DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0)	Lipid Annotator

Chemical Formula

C₃₅H₅₈O₅

Average Molecular Weight

558.832

Monoisotopic Molecular Weight

558.428424966

IUPAC Name

(2S)-1-hydroxy-3-[(9Z)-tetradec-9-enoyloxy]propan-2-yl (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoate

Traditional Name

diacylglycerol

CAS Registry Number

Not Available

SMILES

[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C35H58O5/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(38)40-33(31-36)32-39-34(37)29-27-25-23-21-19-14-12-10-8-6-4-2/h5,7,10-13,16-17,20,22,33,36H,3-4,6,8-9,14-15,18-19,21,23-32H2,1-2H3/b7-5-,12-10-,13-11-,17-16-,22-20-/t33-/m0/s1

InChI Key

XQJDPVVGWRYPNC-HWYSFVLZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
1,2-acyl-sn-glycerol
Diacylglycerol
Diradylglycerol
Fatty acid ester
Glycerolipid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
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	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	8.11	ALOGPS
logP	10.19	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	173.28 m³·mol⁻¹	ChemAxon
Polarizability	69.42 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00lr-6963113000-1c6aa1b19b430879b541	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000090000-b4c820bb9405ae3df9ed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0099090000-286a7610395e03007aa4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0099090000-4aad466c14221b28e3e1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000090000-76b6c73837e5022cc240	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0088090000-696df71820f9ee8ea0ea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0088090000-ef85d916dc5d469a3426	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0575590000-e55a557e1a5bb1a5c8ce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-2595010000-3d4baa786a73b5d250b9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a7i-3894100000-94af13f5a3f4171295c6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000090000-8d5fafc4f56495b8878a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000090000-8d5fafc4f56495b8878a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0019000000-051c0a836ea82888c57f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1091080000-fe9381de53a144de5b96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0adi-3091000000-fd788cedda2b35470b73	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-3290000000-098bf0b4210678391f24	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:2(11Z,14Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:3(5Z,8Z,11Z))		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007048

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024242

KNApSAcK ID

Not Available

Chemspider ID

24765882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477983

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Ethanolaminephosphotransferase 1

General function:: Involved in ethanolaminephosphotransferase activity
Specific function:: Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the foramtion of phosphatidylethanolamine via 'Kennedy' pathway (By similarity).
Gene Name:: SELENOI
Uniprot ID:: Q17QM4
Molecular weight:: 45214.0

Reactions

CDP-Ethanolamine + DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(14:1(9Z)/18:4(6Z,9Z,12Z,15Z))	details

Enzyme Details

2. 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(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:0)[iso6] + Coenzyme A	details
DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Gondoyl-CoA → TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)) + Coenzyme A	details
DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme A	details
DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Docosanoyl-CoA → TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:0)[iso6] + Coenzyme A	details
DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Erucoyl-CoA → TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:1(13Z)) + Coenzyme A	details
DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme A	details

Showing metabocard for DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0) (BMDB0007048)

Structure for BMDB0007048 (DG(14:1(9Z)/18:4(6Z,9Z,12Z,15Z)/0:0))

Enzymes

Reactions

Reactions