Human Metabolome Database: Showing metabocard for DG(O-18:0/2:0/0:0) (HMDB0011147)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (130) Show 130 proteins XML

enzymes (130) Show 130 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2008-10-29 14:21:43 UTC

Update Date

2020-02-26 21:34:33 UTC

HMDB ID

HMDB0011147

Secondary Accession Numbers

HMDB11147

Metabolite Identification

Common Name

DG(O-18:0/2:0/0:0)

Description

2-Acetyl-1-octadecyl-sn-glycerol, or DG(O-18:0/2:0/0:0), is an intermediate in ether lipid metabolism. 2-Acetyl-1-octadecyl-sn-glycerol is converted from 1-octadecyl-glycerone-3-phosphate. This is an ether lipid with a structure similar to platelet-activating factor which has an acetyl group instead of an acyl chain at the second position (SN-2). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Acetyl-1-octadecyl-sn-glycerol	HMDB
DG(O-18:0/2:0/0:0)	HMDB
(2S)-1-Hydroxy-3-(octadecyloxy)propan-2-yl acetic acid	Generator

Chemical Formula

C₂₃H₄₆O₄

Average Molecular Weight

386.6089

Monoisotopic Molecular Weight

386.33960996

IUPAC Name

(2S)-1-hydroxy-3-(octadecyloxy)propan-2-yl acetate

Traditional Name

(2S)-1-hydroxy-3-(octadecyloxy)propan-2-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@](CO)(COCCCCCCCCCCCCCCCCCC)OC(C)=O

InChI Identifier

InChI=1S/C23H46O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26-21-23(20-24)27-22(2)25/h23-24H,3-21H2,1-2H3/t23-/m0/s1

InChI Key

HUQABGDIJUXLRG-QHCPKHFHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-alkyl,2-acylglycerols. These are glycerides consisting of two fatty acyl chains covalently bonded to a glycerol molecule at the 1- and 2-positions through an ether and an ester linkage, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Diradylglycerols

Direct Parent

1-alkyl,2-acylglycerols

Alternative Parents

Substituents

1-alkyl,2-acylglycerol
Glycerol ether
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
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

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Biological role:

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
Water Solubility	9.8e-05 g/L	ALOGPS
logP	7.98	ALOGPS
logP	6.79	ChemAxon
logS	-6.6	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	55.76 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	112.71 m³·mol⁻¹	ChemAxon
Polarizability	50.7 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	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	splash10-0udl-8941000000-8cb2d7a88d725caf4f5d	Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027922

KNApSAcK ID

Not Available

Chemspider ID

18558312

KEGG Compound ID

C03820

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13341683

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 130 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Diacylglycerol kinase theta

General function:: Involved in diacylglycerol kinase activity
Specific function:: Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:: DGKQ
Uniprot ID:: P52824
Molecular weight:: 101154.0

Enzyme Details

2. Pancreatic triacylglycerol lipase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: PNLIP
Uniprot ID:: P16233
Molecular weight:: 51156.48

Enzyme Details

3. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:: PLCB1
Uniprot ID:: Q9NQ66
Molecular weight:: 138565.805

Enzyme Details

4. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. This form has a role in retina signal transduction.
Gene Name:: PLCB4
Uniprot ID:: Q15147
Molecular weight:: 136105.065

Enzyme Details

5. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:: PLCB2
Uniprot ID:: Q00722
Molecular weight:: 134023.21

Enzyme Details

6. Diacylglycerol kinase gamma

General function:: Involved in diacylglycerol kinase activity
Specific function:: Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:: DGKG
Uniprot ID:: P49619
Molecular weight:: 89095.3

Enzyme Details

7. Hepatic triacylglycerol lipase

General function:: Involved in catalytic activity
Specific function:: Hepatic lipase has the capacity to catalyze hydrolysis of phospholipids, mono-, di-, and triglycerides, and acyl-CoA thioesters. It is an important enzyme in HDL metabolism. Hepatic lipase binds heparin.
Gene Name:: LIPC
Uniprot ID:: P11150
Molecular weight:: 55914.1

Enzyme Details

8. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3

General function:: Involved in calcium ion binding
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:: PLCB3
Uniprot ID:: Q01970
Molecular weight:: 138797.725

Enzyme Details

9. Inactive pancreatic lipase-related protein 1

General function:: Involved in catalytic activity
Specific function:: May function as inhibitor of dietary triglyceride digestion. Lacks detectable lipase activity towards triglycerides, diglycerides, phosphatidylcholine, galactolipids or cholesterol esters (in vitro) (By similarity).
Gene Name:: PNLIPRP1
Uniprot ID:: P54315
Molecular weight:: Not Available

Enzyme Details

10. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2

General function:: Involved in phosphoinositide phospholipase C activity
Specific function:: The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. It is a crucial enzyme in transmembrane signaling.
Gene Name:: PLCG2
Uniprot ID:: P16885
Molecular weight:: 147868.67

Only showing the first 10 proteins. There are 130 proteins in total.

Show all enzymes and transporters

Showing metabocard for DG(O-18:0/2:0/0:0) (HMDB0011147)

Structure for HMDB0011147 (DG(O-18:0/2:0/0:0))

Enzymes