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Showing metabocard for PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)) (HMDB0265290)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (61) Show 61 proteinsXML
enzymes (61) Show 61 proteins
Record Information
Version5.0
StatusPredicted
Creation Date2021-09-12 09:27:24 UTC
Update Date2022-11-30 19:55:47 UTC
HMDB IDHMDB0265290
Secondary Accession NumbersNone
Metabolite Identification
Common NamePA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z))
DescriptionPA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)) 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(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of one 9-oxo-octadecadienoyl at the C-1 position and one chain of 8Z,11Z,14Z,17Z-eicosapentaenoyl 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
MOLSDFPDBSMILESInChI

MOL for HMDB0265290 (PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)))

Not Available

3D MOL for HMDB0265290 (PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)))

Not Available

3D SDF for HMDB0265290 (PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)))

Not Available

3D-SDF for HMDB0265290 (PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)))

Not Available

PDB for HMDB0265290 (PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)))

Not Available

3D PDB for HMDB0265290 (PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)))

Not Available

SMILES for HMDB0265290 (PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)))

Not Available

INCHI for HMDB0265290 (PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)))

Not Available
View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC41H67O9P
Average Molecular Weight734.952
Monoisotopic Molecular Weight734.452270735
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILESNot Available
InChI Identifier
InChI=1S/C41H67O9P/c1-3-5-7-9-11-12-13-14-15-16-17-18-19-20-22-26-31-35-41(44)50-39(37-49-51(45,46)47)36-48-40(43)34-30-27-23-25-29-33-38(42)32-28-24-21-10-8-6-4-2/h5,7,11-12,14-15,17-18,21,24,28,32,39H,3-4,6,8-10,13,16,19-20,22-23,25-27,29-31,33-37H2,1-2H3,(H2,45,46,47)/b7-5-,12-11-,15-14-,18-17-,24-21-,32-28+/t39-/m1/s1
InChI KeyPFCVAZNWLDCIPK-CXZPVIMUSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot 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 Properties
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 9.04 minutes32390414
Predicted by Siyang on May 30, 202231.8012 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.02 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid4959.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid360.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid315.4 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid255.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid1081.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid1709.6 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid1010.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)233.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid3356.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid1159.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid2579.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid1206.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid705.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate252.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA714.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water11.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z))[H][C@@](COC(=O)CCCCCCCC(=O)\C=C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC5842.3Standard polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z))[H][C@@](COC(=O)CCCCCCCC(=O)\C=C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC4557.9Standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z))[H][C@@](COC(=O)CCCCCCCC(=O)\C=C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC5343.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC(=O)/C=C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C5390.2Semi standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC(=O)/C=C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C4753.5Standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC(=O)/C=C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C5963.2Standard polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=C(/C=C/C=C\CCCCC)O[Si](C)(C)C)COP(=O)(O)O5554.6Semi standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=C(/C=C/C=C\CCCCC)O[Si](C)(C)C)COP(=O)(O)O4742.6Standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=C(/C=C/C=C\CCCCC)O[Si](C)(C)C)COP(=O)(O)O6627.4Standard polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),2TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC(=O)/C=C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C5398.5Semi standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),2TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC(=O)/C=C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C4727.0Standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),2TMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC(=O)/C=C/C=C\CCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C5210.2Standard polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),2TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=C(/C=C/C=C\CCCCC)O[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C5480.6Semi standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),2TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=C(/C=C/C=C\CCCCC)O[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C4722.7Standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),2TMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=C(/C=C/C=C\CCCCC)O[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C5774.0Standard polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC(=O)/C=C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C5601.9Semi standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC(=O)/C=C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C4874.2Standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TBDMS,isomer #1CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC(=O)/C=C/C=C\CCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C5935.6Standard polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=C(/C=C/C=C\CCCCC)O[Si](C)(C)C(C)(C)C)COP(=O)(O)O5802.5Semi standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=C(/C=C/C=C\CCCCC)O[Si](C)(C)C(C)(C)C)COP(=O)(O)O4873.4Standard non polar33892256
PA(18:2(10E,12Z)+=O(9)/20:4(8Z,11Z,14Z,17Z)),1TBDMS,isomer #2CC/C=C\C/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COC(=O)CCCCCCC=C(/C=C/C=C\CCCCC)O[Si](C)(C)C(C)(C)C)COP(=O)(O)O6535.8Standard polar33892256
Spectra
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
External LinksNot 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.

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Enzymes

Enzyme Details
1. Phospholipase D2
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
Enzyme Details
2. 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
3. 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
4. Lipid phosphate phosphohydrolase 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 PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
Enzyme Details
5. Diacylglycerol kinase alpha
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
Enzyme Details
6. Diacylglycerol kinase delta
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
Enzyme Details
7. Lipid phosphate phosphohydrolase 1
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
Enzyme Details
8. Diacylglycerol kinase beta
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
Enzyme Details
9. Diacylglycerol kinase iota
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
Enzyme Details
10. Lipid phosphate phosphohydrolase 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 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.

Show all enzymes and transporters