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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-12 11:25:55 UTC
Update Date2021-10-28 10:05:07 UTC
HMDB IDHMDB0266541
Secondary Accession NumbersNone
Metabolite Identification
Common NamePA(2:0/18:1(12Z)-O(9S,10R))
DescriptionPA(2:0/18:1(12Z)-O(9S,10R)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(2:0/18:1(12Z)-O(9S,10R)), in particular, consists of one chain of one acetyl at the C-1 position and one chain of 9,10-epoxy-octadecenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396 ).
Structure
Thumb
Synonyms
ValueSource
[(2R)-3-(Acetyloxy)-2-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy]phosphonateGenerator
Chemical FormulaC23H41O9P
Average Molecular Weight492.546
Monoisotopic Molecular Weight492.248819898
IUPAC Name[(2R)-3-(acetyloxy)-2-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy]phosphonic acid
Traditional Name(2R)-3-(acetyloxy)-2-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(C)=O)(COP(O)(O)=O)OC(=O)CCCCCCCC1OC1C\C=C/CCCCC
InChI Identifier
InChI=1S/C23H41O9P/c1-3-4-5-6-8-11-14-21-22(32-21)15-12-9-7-10-13-16-23(25)31-20(17-29-19(2)24)18-30-33(26,27)28/h8,11,20-22H,3-7,9-10,12-18H2,1-2H3,(H2,26,27,28)/b11-8-/t20-,21?,22?/m1/s1
InChI KeyGVNMSKGKKMJKKB-WBOFDTGBSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Not Available
Physical Properties
StateNot Available
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
logP10(4.01) g/LALOGPS
logP10(4.63) g/LChemAxon
logS10(-5.6) g/LALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area131.89 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity123.97 m³·mol⁻¹ChemAxon
Polarizability54.13 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+223.20732859911
AllCCS[M+H-H2O]+221.53232859911
AllCCS[M+Na]+225.16832859911
AllCCS[M+NH4]+224.73432859911
AllCCS[M-H]-216.8232859911
AllCCS[M+Na-2H]-219.82232859911
AllCCS[M+HCOO]-223.2732859911
DeepCCS[M+H]+207.47530932474
DeepCCS[M-H]-205.11730932474
DeepCCS[M-2H]-238.23130932474
DeepCCS[M+Na]+213.56830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PA(2:0/18:1(12Z)-O(9S,10R))[H][C@@](COC(C)=O)(COP(O)(O)=O)OC(=O)CCCCCCCC1OC1C\C=C/CCCCC3845.6Standard polar33892256
PA(2:0/18:1(12Z)-O(9S,10R))[H][C@@](COC(C)=O)(COP(O)(O)=O)OC(=O)CCCCCCCC1OC1C\C=C/CCCCC2957.1Standard non polar33892256
PA(2:0/18:1(12Z)-O(9S,10R))[H][C@@](COC(C)=O)(COP(O)(O)=O)OC(=O)CCCCCCCC1OC1C\C=C/CCCCC3448.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PA(2:0/18:1(12Z)-O(9S,10R)),1TMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O)O[Si](C)(C)C3415.6Semi standard non polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),1TMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O)O[Si](C)(C)C3224.4Standard non polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),1TMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O)O[Si](C)(C)C4569.1Standard polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),2TMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3418.4Semi standard non polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),2TMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3264.5Standard non polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),2TMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3920.4Standard polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),1TBDMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3644.3Semi standard non polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),1TBDMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3392.3Standard non polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),1TBDMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C4607.8Standard polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),2TBDMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3884.3Semi standard non polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),2TBDMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3539.2Standard non polar33892256
PA(2:0/18:1(12Z)-O(9S,10R)),2TBDMS,isomer #1CCCCC/C=C\CC1OC1CCCCCCCC(=O)O[C@H](COC(C)=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4008.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9331200000-8261276c10d88e9457af2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) 10V, Positive-QTOFsplash10-014i-0000090000-0b1ee4f3a49207425c662021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) 20V, Positive-QTOFsplash10-014i-0000990000-91d785bee7554a3dfd0b2021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) 40V, Positive-QTOFsplash10-014i-0060940000-735802c0825922d6b56f2021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) 10V, Negative-QTOFsplash10-0006-0000900000-a805f14bb93e17bff3632021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) 20V, Negative-QTOFsplash10-0005-4540900000-beed3d4b25b0bdaae5252021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) 40V, Negative-QTOFsplash10-052b-9260300000-6b957e3aeac30fb8d3392021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) 10V, Positive-QTOFsplash10-004l-0000900000-92d86dc1e863df7fac082021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) 20V, Positive-QTOFsplash10-0007-0005900000-8d42f618edf532b58b892021-09-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(2:0/18:1(12Z)-O(9S,10R)) 40V, Positive-QTOFsplash10-0002-0508900000-2fad0d5dea83bb4fde6a2021-09-28Wishart 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. Hajeyah AA, Griffiths WJ, Wang Y, Finch AJ, O'Donnell VB: The Biosynthesis of Enzymatically Oxidized Lipids. Front Endocrinol (Lausanne). 2020 Nov 19;11:591819. doi: 10.3389/fendo.2020.591819. eCollection 2020. [PubMed:33329396 ]

Only showing the first 10 proteins. There are 61 proteins in total.

Enzymes

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
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
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
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
General function:
Involved in diacylglycerol kinase activity
Specific function:
Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:
DGKA
Uniprot ID:
P23743
Molecular weight:
82629.5
General function:
Involved in diacylglycerol kinase activity
Specific function:
Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:
DGKD
Uniprot ID:
Q16760
Molecular weight:
134524.2
General function:
Involved in catalytic activity
Specific function:
Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:
PPAP2A
Uniprot ID:
O14494
Molecular weight:
32155.715
General function:
Involved in diacylglycerol kinase activity
Specific function:
Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:
DGKB
Uniprot ID:
Q9Y6T7
Molecular weight:
90594.7
General function:
Involved in diacylglycerol kinase activity
Specific function:
ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:
DGKI
Uniprot ID:
O75912
Molecular weight:
116996.2
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:
PPAP2B
Uniprot ID:
O14495
Molecular weight:
35115.61

Only showing the first 10 proteins. There are 61 proteins in total.