Human Metabolome Database: Showing metabocard for DG(16:0e/18:0/0:0) (HMDB11146)

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

3.6

Creation Date

2008-10-29 14:21:14 UTC

Update Date

2013-02-09 00:25:46 UTC

HMDB ID

HMDB11146

Secondary Accession Numbers

HMDB11184

Metabolite Identification

Common Name

DG(16:0e/18:0/0:0)

Description

2-Octadecanoyl-1-hexadecyl-sn-glycerol is an intermediate in ether lipid metabolism. 2-Octadecanoyl-1-hexadecyl-sn-glycerol is converted from 2-octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate via phosphatidate phosphatase (EC: 3.1.3.4). 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. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'.

Structure

MOL SDF PDB SMILES InChI View Structure

Synonyms

2-Octadecanoyl-1-hexadecyl-sn-glycerol
DG(O-16:0/18:0/0:0)

Chemical Formula

C₃₇H₇₄O₄

Average Molecular Weight

582.9811

Monoisotopic Molecular Weight

582.558710856

IUPAC Name

(2S)-1-(hexadecyloxy)-3-hydroxypropan-2-yl octadecanoate

Traditional IUPAC Name

(2S)-1-(hexadecyloxy)-3-hydroxypropan-2-yl octadecanoate

CAS Registry Number

Not Available

SMILES

[H][C@](CO)(COCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C37H74O4/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(39)41-36(34-38)35-40-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h36,38H,3-35H2,1-2H3/t36-/m0/s1

InChI Key

ALBMTLREXAADKV-BHVANESWSA-N

Chemical Taxonomy

Kingdom

Organic Compounds

Super Class

Lipids

Class

Glycerolipids

Sub Class

Other Glycerolipids

Other Descriptors

Aliphatic Acyclic Compounds

Substituents

Carboxylic Acid Ester
Dialkyl Ether
Fatty Acid Ester
Primary Alcohol
Saccharide
Triose Monosaccharide

Direct Parent

Other Glycerolipids

Ontology

Status

Expected and Not Quantified

Origin

Endogenous

Food

Biofunction

Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability

Application

Nutrients
Stabilizers
Surfactants and Emulsifiers

Cellular locations

Extracellular
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
water solubility	1.570E-05 g/L	ALOGPS
logP	10.43	ALOGPS
logP	13.27	ChemAxon
logS	-7.6	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	ChemAxon
rotatable bond count	36	ChemAxon
refractivity	177.15	ChemAxon
polarizability	79.55	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Location

Not Available

Pathways

Not Available

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

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB027921

KNApSAcK ID

Not Available

Chemspider ID

18558308

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

NuGOwiki Link

HMDB11146

Metagene Link

HMDB11146

METLIN ID

Not Available

PubChem Compound

18603089

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 50 proteins. There are 130 proteins in total.

Show all enzymes and transporters

Enzymes

1. Diacylglycerol kinase theta

Gene Name:: DGKQ
Uniprot ID:: P52824

2. Pancreatic triacylglycerol lipase

Gene Name:: PNLIP
Uniprot ID:: P16233

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

Gene Name:: PLCB1
Uniprot ID:: Q9NQ66

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

Gene Name:: PLCB4
Uniprot ID:: Q15147

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

Gene Name:: PLCB2
Uniprot ID:: Q00722

6. Diacylglycerol kinase gamma

Gene Name:: DGKG
Uniprot ID:: P49619

7. Hepatic triacylglycerol lipase

Gene Name:: LIPC
Uniprot ID:: P11150

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

Gene Name:: PLCB3
Uniprot ID:: Q01970

9. Inactive pancreatic lipase-related protein 1

Gene Name:: PNLIPRP1
Uniprot ID:: P54315

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

Gene Name:: PLCG2
Uniprot ID:: P16885

11. Lipid phosphate phosphohydrolase 2

Gene Name:: PPAP2C
Uniprot ID:: O43688

12. Patatin-like phospholipase domain-containing protein 3

Gene Name:: PNPLA3
Uniprot ID:: Q9NST1

13. Diacylglycerol kinase alpha

Gene Name:: DGKA
Uniprot ID:: P23743

14. Diacylglycerol kinase delta

Gene Name:: DGKD
Uniprot ID:: Q16760

15. Diacylglycerol kinase epsilon

Gene Name:: DGKE
Uniprot ID:: P52429

16. Gastric triacylglycerol lipase

Gene Name:: LIPF
Uniprot ID:: P07098

17. Lipid phosphate phosphohydrolase 1

Gene Name:: PPAP2A
Uniprot ID:: O14494

18. Diacylglycerol kinase beta

Gene Name:: DGKB
Uniprot ID:: Q9Y6T7

19. Endothelial lipase

Gene Name:: LIPG
Uniprot ID:: Q9Y5X9

20. Diacylglycerol kinase iota

Gene Name:: DGKI
Uniprot ID:: O75912

21. Bile salt-activated lipase

Gene Name:: CEL
Uniprot ID:: P19835

22. Lipid phosphate phosphohydrolase 3

Gene Name:: PPAP2B
Uniprot ID:: O14495

23. Diacylglycerol O-acyltransferase 1

Gene Name:: DGAT1
Uniprot ID:: O75907

24. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1

Gene Name:: PLCG1
Uniprot ID:: P19174

25. Pancreatic lipase-related protein 2

Gene Name:: PNLIPRP2
Uniprot ID:: P54317

26. Diacylglycerol kinase zeta

Gene Name:: DGKZ
Uniprot ID:: Q13574

27. 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1

Gene Name:: PLCD1
Uniprot ID:: P51178

28. Lipoprotein lipase

Gene Name:: LPL
Uniprot ID:: P06858

29. Galactosylceramide sulfotransferase

Gene Name:: GAL3ST1
Uniprot ID:: Q99999

30. Hormone-sensitive lipase

Gene Name:: LIPE
Uniprot ID:: Q05469

31. Phosphatidate cytidylyltransferase 2

Gene Name:: CDS2
Uniprot ID:: O95674

32. Choline-phosphate cytidylyltransferase A

Gene Name:: PCYT1A
Uniprot ID:: P49585

33. Phosphatidate cytidylyltransferase 1

Gene Name:: CDS1
Uniprot ID:: Q92903

34. Phosphatidylcholine:ceramide cholinephosphotransferase 2

Gene Name:: SGMS2
Uniprot ID:: Q8NHU3

35. CDP-diacylglycerol--inositol 3-phosphatidyltransferase

Gene Name:: CDIPT
Uniprot ID:: O14735

36. Phosphatidylcholine:ceramide cholinephosphotransferase 1

Gene Name:: SGMS1
Uniprot ID:: Q86VZ5

37. Rap guanine nucleotide exchange factor 2

Gene Name:: RAPGEF2
Uniprot ID:: Q9Y4G8

38. RAF proto-oncogene serine/threonine-protein kinase

Gene Name:: RAF1
Uniprot ID:: P04049

39. Protein kinase C alpha type

Gene Name:: PRKCA
Uniprot ID:: P17252

40. Serine/threonine-protein kinase A-Raf

Gene Name:: ARAF
Uniprot ID:: P10398

41. Citron Rho-interacting kinase

Gene Name:: CIT
Uniprot ID:: O14578

42. Protein kinase C beta type

Gene Name:: PRKCB
Uniprot ID:: P05771

43. Protein kinase C zeta type

Gene Name:: PRKCZ
Uniprot ID:: Q05513

44. Protein kinase C iota type

Gene Name:: PRKCI
Uniprot ID:: P41743

45. Rho-associated protein kinase 1

Gene Name:: ROCK1
Uniprot ID:: Q13464

46. Serine/threonine-protein kinase D1

Gene Name:: PRKD1
Uniprot ID:: Q15139

47. Protein kinase C gamma type

Gene Name:: PRKCG
Uniprot ID:: P05129

48. Rho-associated protein kinase 2

Gene Name:: ROCK2
Uniprot ID:: O75116

49. Protein kinase C delta type

Gene Name:: PRKCD
Uniprot ID:: Q05655

50. Serine/threonine-protein kinase D3

Gene Name:: PRKD3
Uniprot ID:: O94806

Only showing the first 50 proteins. There are 130 proteins in total.

Show all enzymes and transporters