Bovine Metabolome Database: Showing metabocard for DG(18:1(9Z)/18:1(9Z)/0:0) (BMDB0007218)

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 23:32:56 UTC

Update Date

2020-06-04 20:21:04 UTC

BMDB ID

BMDB0007218

Secondary Accession Numbers

BMDB07218

Metabolite Identification

Common Name

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

Description

DG(18:1(9Z)/18:1(9Z)/0:0), also known as sn-1,2-dioleoylglycerol or sn-1,2-diolein, 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(18:1(9Z)/18:1(9Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:1(9Z)/18:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:1(9Z)/18:1(9Z)/0:0) exists in all living organisms, ranging from bacteria to humans. DG(18:1(9Z)/18:1(9Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(18:1(9Z)/18:1(9Z)/0:0) can be converted into cytidine monophosphate and PE(18:1(9Z)/18:1(9Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(18:1(9Z)/18:1(9Z)/0:0) can be converted into cytidine monophosphate and PC(18:1(9Z)/18:1(9Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(18:1(9Z)/18:1(9Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(18:1(9Z)/18:1(9Z)) pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Di-(9Z-octadecenoyl)-sn-glycerol	ChEBI
DG(18:1/18:1/0:0)	ChEBI
sn-1,2-Diolein	ChEBI
sn-1,2-Dioleoylglycerol	ChEBI
1,2-Dioleoyl-rac-glycerol	HMDB
Di-oleoylglycerol	HMDB
Glycerol dioleate	HMDB
Diolein	HMDB
Dioleoylglycerol	HMDB
1,2-Dioleoylglycerol	HMDB
Diacylglycerol(36:2)	HMDB
DG(18:1/18:1)	HMDB
DG(36:2)	HMDB
DAG(36:2)	HMDB
Diglyceride	HMDB
Diacylglycerol(18:1/18:1)	HMDB
Diacylglycerol	HMDB
DAG(18:1/18:1)	HMDB
1,2-Di(9Z-octadecenoyl)-rac-glycerol	HMDB
(+--)-1,2-Dioleoylglycerol	HMDB
1,2-Diolein	HMDB
9-Octadecenoic acid (9Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester	HMDB
Glyceryl 1,2-dioleate	HMDB
9-Octadecenoic acid (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester	HMDB
1,2-Glyceryl dioleate	HMDB
(+--)-1,2-Diolein	HMDB
1,2-Dioleoyl-DL-glycerol	HMDB
9-Octadecenoic acid (9Z)-, 1,1'-(1-(hydroxymethyl)-1,2-ethanediyl) ester	HMDB
9-Octadecenoic acid (9Z)-, diester with 1,2,3-propanetriol	HMDB
Oleic acid diglyceride	HMDB
DG(18:1(9Z)/18:1(9Z)/0:0)	Lipid Annotator

Chemical Formula

C₃₉H₇₂O₅

Average Molecular Weight

620.986

Monoisotopic Molecular Weight

620.537975414

IUPAC Name

(2S)-1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate

Traditional Name

1,2-dioleoyl-sn-glycerol

CAS Registry Number

24529-88-2

SMILES

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

InChI Identifier

InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18-/t37-/m0/s1

InChI Key

AFSHUZFNMVJNKX-LLWMBOQKSA-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:52333 )
dioleoylglycerol (CHEBI:52333 )
Diacylglycerols (LMGL02010049 )

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	10.26	ALOGPS
logP	13.06	ChemAxon
logS	-7.7	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	36	ChemAxon
Refractivity	188.34 m³·mol⁻¹	ChemAxon
Polarizability	80.99 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	splash10-03dr-4351956000-02493870893e9eaf8021	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("DG(18:1(9Z)/18:1(9Z)/0:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - n/a 43V, positive	splash10-0ufr-0025089000-86867947e5d654a1367e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 43V, positive	splash10-014i-0092020000-48754474f83689f7da27	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 43V, positive	splash10-03dr-0009000000-38a71500caac14fe5e10	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-00di-0001009000-ad8aa7c4c14b2b4811f0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, positive	splash10-0079-0079007000-878059044a8b6bd25bbf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 29V, positive	splash10-00kr-1389001000-88d226dc029ad1418f08	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 38V, positive	splash10-00ks-6965000000-0b86ba8ef5ef1cff8b10	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 45V, positive	splash10-00lj-8931000000-8dca4ecba590c00ca67e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, positive	splash10-00l2-9600000000-310135ebf19be0cf22fc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 60V, positive	splash10-05o1-9500000000-c6cc9222e27414e1a8c3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 68V, positive	splash10-05o1-9300000000-fbca81be56d5e04c9706	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 76V, positive	splash10-015a-9200000000-19fd61863fddb281d45e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 91V, positive	splash10-067i-9100000000-d08d8fd7ca1191a0774f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 115V, positive	splash10-067i-9000000000-b9daf31db2718f97206b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 137V, positive	splash10-0690-9000000000-22a10438f123ad9c81c2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 168V, positive	splash10-0690-9000000000-78e32b4bdcdd00b25bd7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 199V, positive	splash10-0ar0-9000000000-6c348586c0b4d81be070	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 245V, positive	splash10-0ar0-9000000000-1e4a43dab5d1cc87b20a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 43V, positive	splash10-0udr-0026069000-1d883e799bc5f0d1e2e1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 43V, positive	splash10-014j-0970000000-3b55de48b23381fee738	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 43V, positive	splash10-00ds-0900000000-4e9641ccd9863ab49ac2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 43V, positive	splash10-0002-3940000000-f7ed9cc10bd7a4729a0f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000009000-9185b686832caa4f55c4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-0009009000-33724f4f211af0262245	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0009009000-36758b4e03b2a3c426ea	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

All Tissues
Milk

Pathways

Name	SMPDB/Pathwhiz	KEGG
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z))		Not Available
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/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	25 +/- 2 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	55 +/- 4 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	118 +/- 3 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	2.6 +/- 0.1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0007218

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB094043

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

9543716

PDB ID

Not Available

ChEBI ID

52333

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(18:1(9Z)/18:1(9Z)/0:0) → Cytidine monophosphate + PE(18:1(9Z)/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(18:1(9Z)/18:1(9Z)) + Water → DG(18:1(9Z)/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(18:1(9Z)/18:1(9Z)/0:0) + Oleoyl-CoA → TG(18:1(9Z)/18:1(9Z)/18:1(9Z))[iso] + Coenzyme A	details
DG(18:1(9Z)/18:1(9Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z))[iso3] + Coenzyme A	details
DG(18:1(9Z)/18:1(9Z)/0:0) + Eicosanoyl-CoA → TG(18:1(9Z)/18:1(9Z)/20:0) + Coenzyme A	details
DG(18:1(9Z)/18:1(9Z)/0:0) + Gondoyl-CoA → TG(18:1(9Z)/18:1(9Z)/20:1(11Z)) + Coenzyme A	details
DG(18:1(9Z)/18:1(9Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme A	details
DG(18:1(9Z)/18:1(9Z)/0:0) + Docosanoyl-CoA → TG(18:1(9Z)/18:1(9Z)/22:0) + Coenzyme A	details
DG(18:1(9Z)/18:1(9Z)/0:0) + Erucoyl-CoA → TG(18:1(9Z)/18:1(9Z)/22:1(13Z)) + Coenzyme A	details
DG(18:1(9Z)/18:1(9Z)/0:0) + Clupanodonyl CoA → TG(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme A	details

Showing metabocard for DG(18:1(9Z)/18:1(9Z)/0:0) (BMDB0007218)

Structure for BMDB0007218 (DG(18:1(9Z)/18:1(9Z)/0:0))

Enzymes

Reactions

Reactions

Reactions