Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2014-04-11 22:00:51 UTC
Update Date2022-11-30 19:11:53 UTC
HMDB IDHMDB0061501
Secondary Accession Numbers
  • HMDB61501
Metabolite Identification
Common NamePE(DiMe(9,3)/DiMe(9,3))
DescriptionPE(DiMe(9,3)/DiMe(9,3)) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(DiMe(9,3)/DiMe(9,3)), in particular, consists of two chains of 10,13-epoxy-11-methylhexadeca-10,12-dienoic acid at the C-1 and C-2 positions. The 10,13-epoxy-11-methylhexadeca-10,12-dienoic acid moieties are derived from fish oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Structure
Data?1563866195
Synonyms
ValueSource
PE(DiMe(9,3)/DiMe(9,3))SMPDB
Phosphatidylethanolamine(9D3/9D3)SMPDB
Phosphatidylethanolamine(DiMe(9,3)/DiMe(9,3))SMPDB
PE(9D3/9D3)SMPDB
Chemical FormulaC41H70NO10P
Average Molecular Weight767.969
Monoisotopic Molecular Weight767.473733977
IUPAC Name(2-aminoethoxy)[(2R)-2,3-bis({[9-(3,4-dimethyl-5-propylfuran-2-yl)nonanoyl]oxy})propoxy]phosphinic acid
Traditional Name2-aminoethoxy((2R)-2,3-bis({[9-(3,4-dimethyl-5-propylfuran-2-yl)nonanoyl]oxy})propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O1
InChI Identifier
InChI=1S/C41H70NO10P/c1-7-21-36-31(3)33(5)38(51-36)23-17-13-9-11-15-19-25-40(43)47-29-35(30-49-53(45,46)48-28-27-42)50-41(44)26-20-16-12-10-14-18-24-39-34(6)32(4)37(52-39)22-8-2/h35H,7-30,42H2,1-6H3,(H,45,46)/t35-/m1/s1
InChI KeyJZTBVIMTIWLPNI-PGUFJCEWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphoethanolamine
  • Furanoid fatty acid
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Heteroaromatic compound
  • Furan
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Carbonyl group
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP6.31ALOGPS
logP9.58ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)1.87ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area160.66 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity209.79 m³·mol⁻¹ChemAxon
Polarizability89.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+277.28531661259
DarkChem[M-H]-277.6731661259
DeepCCS[M+H]+278.80130932474
DeepCCS[M-H]-276.6730932474
DeepCCS[M-2H]-309.90930932474
DeepCCS[M+Na]+284.67430932474
AllCCS[M+H]+263.732859911
AllCCS[M+H-H2O]+263.432859911
AllCCS[M+NH4]+263.832859911
AllCCS[M+Na]+263.932859911
AllCCS[M-H]-250.232859911
AllCCS[M+Na-2H]-256.832859911
AllCCS[M+HCOO]-264.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PE(DiMe(9,3)/DiMe(9,3))CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O15225.9Standard polar33892256
PE(DiMe(9,3)/DiMe(9,3))CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O14819.9Standard non polar33892256
PE(DiMe(9,3)/DiMe(9,3))CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O15188.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PE(DiMe(9,3)/DiMe(9,3)),1TMS,isomer #1CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O15443.2Semi standard non polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TMS,isomer #1CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O14416.7Standard non polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TMS,isomer #1CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O17457.3Standard polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TMS,isomer #2CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O15507.9Semi standard non polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TMS,isomer #2CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O14624.5Standard non polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TMS,isomer #2CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O17169.2Standard polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TBDMS,isomer #1CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O15648.6Semi standard non polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TBDMS,isomer #1CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O14485.4Standard non polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TBDMS,isomer #1CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(OCCN)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O17379.5Standard polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TBDMS,isomer #2CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O15726.4Semi standard non polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TBDMS,isomer #2CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O14710.7Standard non polar33892256
PE(DiMe(9,3)/DiMe(9,3)),1TBDMS,isomer #2CCCC1=C(C)C(C)=C(CCCCCCCCC(=O)OC[C@H](COP(=O)(O)OCCN[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCC2=C(C)C(C)=C(CCC)O2)O17070.1Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 10V, Positive-QTOFsplash10-0006-9020200200-d54a3571283c50e23f302017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 20V, Positive-QTOFsplash10-0006-9110100100-35559024c60d945f49792017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 40V, Positive-QTOFsplash10-0006-9113011000-1ce7ec0cb65f43f8264e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 10V, Negative-QTOFsplash10-0096-1290400600-93a2b7569ba901e5e16c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 20V, Negative-QTOFsplash10-002f-6590200100-b442b2cf542e4e72d5f12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 40V, Negative-QTOFsplash10-01t9-9210000000-1cb33946b8766e471b762017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 10V, Positive-QTOFsplash10-014i-0000001900-dfe0273d3613ff7d24ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 20V, Positive-QTOFsplash10-00or-0001309700-2fe1d89d6958211e8e372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 40V, Positive-QTOFsplash10-004i-0001309300-7c1fd56c88da44d0006f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 10V, Negative-QTOFsplash10-014i-0010000900-480ae9d19be4fe7fd6712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 20V, Negative-QTOFsplash10-014i-0010000900-480ae9d19be4fe7fd6712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 40V, Negative-QTOFsplash10-00kf-0390300600-c73a53fd52529e0aa2f82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 10V, Positive-QTOFsplash10-0006-0000001900-700b2e0b62f511ed025d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 20V, Positive-QTOFsplash10-0007-0000001900-c8e3c2c483dd7e1fc8bf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PE(DiMe(9,3)/DiMe(9,3)) 40V, Positive-QTOFsplash10-0002-0100101900-469d52f4ba16adbc9e8f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Spiteller G: Furan fatty acids: occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet? Lipids. 2005 Aug;40(8):755-71. [PubMed:16296395 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  7. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  9. Jean E. Vance (2008). Thematic Review Series: Glycerolipids. Phosphatidylserine and phosphatidylethanolamine in mammalian cells: two metabolically related aminophospholipids. The Journal of Lipid Research, 49, 1377-1387..
  10. The AOCS Lipid Library [Link]

Only showing the first 10 proteins. There are 43 proteins in total.

Enzymes

General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:
PLA2G5
Uniprot ID:
P39877
Molecular weight:
15674.065
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:
PLA2G2F
Uniprot ID:
Q9BZM2
Molecular weight:
23256.29
General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:
PLA2G4A
Uniprot ID:
P47712
Molecular weight:
85210.19
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G1B
Uniprot ID:
P04054
Molecular weight:
16359.535
General function:
Involved in phospholipase A2 activity
Specific function:
Not known; does not seem to have catalytic activity.
Gene Name:
PLA2G12B
Uniprot ID:
Q9BX93
Molecular weight:
Not Available
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:
PLA2G10
Uniprot ID:
O15496
Molecular weight:
18153.04
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:
PLA2G2E
Uniprot ID:
Q9NZK7
Molecular weight:
15988.525
General function:
Involved in metabolic process
Specific function:
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:
PLA2G6
Uniprot ID:
O60733
Molecular weight:
84092.635
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Molecular weight:
16546.1
General function:
Involved in protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
PLD2
Uniprot ID:
O14939
Molecular weight:
104656.485

Only showing the first 10 proteins. There are 43 proteins in total.