ContaminantDB: Glycerol 1,2-di-(9Z-octadecenoate)

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 22:05:03 UTC

Update Date

2016-11-09 01:18:00 UTC

Accession Number

CHEM025020

Identification

Common Name

Glycerol 1,2-di-(9Z-octadecenoate)

Class

Small Molecule

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.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical 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 Mass

620.986 g/mol

Monoisotopic Mass

620.538 g/mol

CAS Registry Number

24529-88-2

IUPAC Name

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

Traditional Name

1,2-dioleoyl-sn-glycerol

SMILES

CCCCCCCC\C=C\CCCCCCCC(=O)OCC(CO)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+

InChI Key

AFSHUZFNMVJNKX-XPWSMXQVSA-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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.2e-05 g/L	ALOGPS
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	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

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

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0007218

FooDB ID

FDB094043

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

52333

PubChem Compound ID

9543716

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

ECMDB23311

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)

Glycerol 1,2-di-(9Z-octadecenoate) (CHEM025020)

Structure for CHEM025020: Glycerol 1,2-di-(9Z-octadecenoate)