Bovine Metabolome Database: Showing metabocard for DG(16:0/18:1(9Z)/0:0) (BMDB0007102)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:30:37 UTC

Update Date

2020-06-04 20:13:54 UTC

BMDB ID

BMDB0007102

Secondary Accession Numbers

BMDB07102

Metabolite Identification

Common Name

DG(16:0/18:1(9Z)/0:0)

Description

DG(16:0/18:1(9Z)/0:0), also known as diacylglycerol or DAG(16:0/18:1), belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(16:0/18:1(9Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:0/18:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(16:0/18:1(9Z)/0:0) exists in all living organisms, ranging from bacteria to humans. DG(16:0/18:1(9Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(16:0/18:1(9Z)/0:0) can be converted into cytidine monophosphate and PE(16:0/18:1(9Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(16:0/18:1(9Z)/0:0) can be converted into cytidine monophosphate and PC(16:0/18:1(9Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(16:0/18:1(9Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:0/18:1(9Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol	ChEBI
DG (16:0/18:1(N-9)/0:0)	ChEBI
DG(16:0/18:1/0:0)	ChEBI
1-(1-14C)Palmitoyl-2-oleoyl-sn-glycerol	MeSH
1-Palmitoyl-2-(1-14C)oleoyl-sn-glycerol	MeSH
1-Palmitoyl-2-oleoyl-sn-glycerol, (S)-isomer	MeSH
1-(14C)POG	MeSH
1-Palmitoyl-2-oleoylglycerol	MeSH
2-(14C)POG	MeSH
DG(16:0/18:1)	Lipid Annotator, HMDB
1-palmitoyl-2-oleoyl-sn-glycerol	Lipid Annotator, HMDB
DG(16:0/18:1(9Z)/0:0)	Lipid Annotator
Diacylglycerol(16:0/18:1)	Lipid Annotator, HMDB
DAG(16:0/18:1)	Lipid Annotator, HMDB
Diglyceride	Lipid Annotator, HMDB
Diacylglycerol(34:1)	Lipid Annotator, HMDB
Diacylglycerol	Lipid Annotator, HMDB
DAG(34:1)	Lipid Annotator, HMDB
DG(34:1)	Lipid Annotator, HMDB
DAG(16:0/18:1N9)	HMDB
DAG(16:0/18:1W9)	HMDB
DG(16:0/18:1N9)	HMDB
DG(16:0/18:1W9)	HMDB
Diacylglycerol(16:0/18:1n9)	HMDB
Diacylglycerol(16:0/18:1W9)	HMDB
DAG(16:0/18:1(9Z)/0:0)	HMDB
Diacylglycerol(16:0/18:1(9Z)/0:0)	HMDB

Chemical Formula

C₃₇H₇₀O₅

Average Molecular Weight

594.9487

Monoisotopic Molecular Weight

594.52232535

IUPAC Name

(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl (9Z)-octadec-9-enoate

Traditional Name

diacylglycerol

CAS Registry Number

3123-73-7

SMILES

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

InChI Identifier

InChI=1S/C37H70O5/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(40)42-35(33-38)34-41-36(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,35,38H,3-16,19-34H2,1-2H3/b18-17-/t35-/m0/s1

InChI Key

YEJYLHKQOBOSCP-OZKTZCCCSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Diradylglycerols

Direct Parent

1,2-diacylglycerols

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1,2-diacyl-sn-glycerol (CHEBI:75466 )
1-palmitoyl-2-oleoylglycerol (CHEBI:75466 )
Diacylglycerols (C13861 )
Diacylglycerols (LMGL02010006 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

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	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	10.1	ALOGPS
logP	12.53	ChemAxon
logS	-7.5	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	35	ChemAxon
Refractivity	178.02 m³·mol⁻¹	ChemAxon
Polarizability	78.32 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	splash10-0wmr-3392244000-4ba56791bc2b2029e43e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("DG(16:0/18:1(9Z)/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	splash10-03di-0000009000-225d2aaf58bce54f763b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03g0-0009030000-0a8c4afd771fbc7c0236	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-0009013000-4548a9e62eeaa76f0e2b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000009000-665e2e7dfdb7932c6210	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03g0-0009030000-c4d90eec24d38a397f26	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-0009013000-61d3d6ba131e45169e17	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1084090000-6035b535b622a7fd9d47	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2092000000-d8dddb3e2b96be7e8934	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-1290000000-5da0f14e6c04c359e742	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kk-1396070000-f5f62124f0638f1412a9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-3593010000-f0284f38f323f611b781	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bi-6942000000-37cf186273caca1f5908	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000009000-d1dcc3e98924441c6a0d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0000009000-d1dcc3e98924441c6a0d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e0-0009000000-2644e1602218313af4fd	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

All Tissues
Milk
Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:1(9Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:2(9Z,12Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:3(9Z,12Z,15Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(16:0/18:1(9Z)/18:4(6Z,9Z,12Z,15Z))		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
Milk	Detected and Quantified	33 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	42 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	55 +/- 2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	10 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007102

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4445454

KEGG Compound ID

C13861

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282283

PDB ID

Not Available

ChEBI ID

75466

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

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(16:0/18:1(9Z)/0:0) → Cytidine monophosphate + PE(16:0/18:1(9Z))	details

Enzyme Details

2. Lipin 1

General function:: Not Available
Specific function:: Not Available
Gene Name:: LPIN1
Uniprot ID:: E1BPE8
Molecular weight:: 102857.0

Reactions

PA(16:0/18:1(9Z)) + Water → DG(16:0/18:1(9Z)/0:0) + Hydrogen phosphate	details

Enzyme Details

3. 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(16:0/18:1(9Z)/0:0) + Oleoyl-CoA → TG(16:0/18:1(9Z)/18:1(9Z)) + Coenzyme A	details
DG(16:0/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:0/18:1(9Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme A	details
DG(16:0/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(16:0/18:1(9Z)/20:0) + Coenzyme A	details
DG(16:0/18:1(9Z)/0:0) + Gondoyl-CoA → TG(16:0/18:1(9Z)/20:1(11Z)) + Coenzyme A	details
DG(16:0/18:1(9Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:0/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme A	details
DG(16:0/18:1(9Z)/0:0) + Docosanoyl-CoA → TG(16:0/18:1(9Z)/22:0) + Coenzyme A	details
DG(16:0/18:1(9Z)/0:0) + Erucoyl-CoA → TG(16:0/18:1(9Z)/22:1(13Z)) + Coenzyme A	details
DG(16:0/18:1(9Z)/0:0) + Clupanodonyl CoA → TG(16:0/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z))[iso6] + Coenzyme A	details
DG(16:0/18:1(9Z)/0:0) + Tetracosanoyl-CoA → TG(16:0/18:1(9Z)/24:0) + Coenzyme A	details

Showing metabocard for DG(16:0/18:1(9Z)/0:0) (BMDB0007102)

Structure for BMDB0007102 (DG(16:0/18:1(9Z)/0:0))

Enzymes

Reactions

Reactions

Reactions