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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-12 01:27:18 UTC
Update Date2022-03-07 02:49:56 UTC
HMDB IDHMDB0007859
Secondary Accession Numbers
  • HMDB07859
Metabolite Identification
Common NamePA(16:0/18:1(9Z))
DescriptionPA(16:0/18:1(9Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids 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. PA(16:0/18:1(9Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of oleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-CoA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218 , 16185776 ).
Structure
Data?1582752507
Synonyms
ValueSource
(2R)-1-(Palmitoyloxy)-3-(phosphonooxy)propan-2-yl (9Z)-octadec-9-enoateChEBI
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphateChEBI
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol 3-phosphateChEBI
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidic acidChEBI
PA(16:0/18:1)ChEBI
PA(16:0/18:1OMEGA9)ChEBI
PA(34:1)ChEBI
Phosphatidic acid(16:0/18:1)ChEBI
Phosphatidic acid(16:0/18:1omega9)ChEBI
Phosphatidic acid(34:1)ChEBI
(2R)-1-(Palmitoyloxy)-3-(phosphonooxy)propan-2-yl (9Z)-octadec-9-enoic acidGenerator
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoric acidGenerator
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol 3-phosphoric acidGenerator
1-Hexadecanoyl-2-(9Z-octadecenoyl)-sn-phosphatidateGenerator
Phosphatidate(16:0/18:1)Generator
Phosphatidate(16:0/18:1OMEGA9)Generator
Phosphatidate(34:1)Generator
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphateHMDB
PA(16:0/18:1N9)HMDB
PA(16:0/18:1W9)HMDB
Phosphatidic acid(16:0/18:1n9)HMDB
Phosphatidic acid(16:0/18:1W9)HMDB
Chemical FormulaC37H71O8P
Average Molecular Weight674.941
Monoisotopic Molecular Weight674.488656244
IUPAC Name[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C37H71O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h17-18,35H,3-16,19-34H2,1-2H3,(H2,40,41,42)/b18-17-/t35-/m1/s1
InChI KeyOPVZUEPSMJNLOM-QEJMHMKOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1,2-diacylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1,2-diacylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
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 Solubility7.7e-05 g/LALOGPS
logP8.91ALOGPS
logP12.41ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count37ChemAxon
Refractivity188.89 m³·mol⁻¹ChemAxon
Polarizability82.83 ųChemAxon
Number of Rings0ChemAxon
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]+269.9931661259
DarkChem[M-H]-259.49631661259
DeepCCS[M+H]+259.2530932474
DeepCCS[M-H]-256.89230932474
DeepCCS[M-2H]-289.77730932474
DeepCCS[M+Na]+265.34330932474
AllCCS[M+H]+273.132859911
AllCCS[M+H-H2O]+272.832859911
AllCCS[M+NH4]+273.332859911
AllCCS[M+Na]+273.432859911
AllCCS[M-H]-259.732859911
AllCCS[M+Na-2H]-265.132859911
AllCCS[M+HCOO]-271.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PA(16:0/18:1(9Z))[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC4380.8Standard polar33892256
PA(16:0/18:1(9Z))[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC4069.7Standard non polar33892256
PA(16:0/18:1(9Z))[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC4786.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PA(16:0/18:1(9Z)),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C4726.6Semi standard non polar33892256
PA(16:0/18:1(9Z)),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C4227.8Standard non polar33892256
PA(16:0/18:1(9Z)),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C5654.8Standard polar33892256
PA(16:0/18:1(9Z)),2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C4698.9Semi standard non polar33892256
PA(16:0/18:1(9Z)),2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C4214.6Standard non polar33892256
PA(16:0/18:1(9Z)),2TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C4903.1Standard polar33892256
PA(16:0/18:1(9Z)),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C4973.3Semi standard non polar33892256
PA(16:0/18:1(9Z)),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C4333.6Standard non polar33892256
PA(16:0/18:1(9Z)),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)O[Si](C)(C)C(C)(C)C5634.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - PA(16:0/18:1(9Z)) GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9262442000-58ec10db7c3cd7166bf12017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 10V, Positive-QTOFsplash10-0170-0192214000-48444709754241a6e0522015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 20V, Positive-QTOFsplash10-014s-1291111000-35dd0ee15b75325e57052015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 40V, Positive-QTOFsplash10-03kj-0392031000-b4b181aab2a3615e865b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 10V, Negative-QTOFsplash10-0adr-3091102000-d23618251b0771ae31c22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 20V, Negative-QTOFsplash10-004i-9060000000-f2f2bfe59ad744e382f32015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 40V, Negative-QTOFsplash10-004i-9010000000-5654cd8818162e3931e22015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 10V, Positive-QTOFsplash10-0002-0000009000-7a8dcb57e8915dfdc01e2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 20V, Positive-QTOFsplash10-0002-0000099000-fb2766a2242558fc72ac2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 40V, Positive-QTOFsplash10-00ke-0000923000-a64a8c3524dd252650762021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 10V, Positive-QTOFsplash10-0a6r-0000009000-66f4613996404f72ecaf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 20V, Positive-QTOFsplash10-004i-0000059000-de4f4fa418ad3835fa412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 40V, Positive-QTOFsplash10-00ou-0006693000-8de33d468e2501791cb72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 10V, Negative-QTOFsplash10-00di-0000009000-3235748ae8b8289ada882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 20V, Negative-QTOFsplash10-060x-1196606000-3ccaca91c3e223ea3bd62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(16:0/18:1(9Z)) 40V, Negative-QTOFsplash10-0a59-0090200000-8fe8a07c1711b3b3044e2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.147 +/- 0.012 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025051
KNApSAcK IDNot Available
Chemspider ID4446637
KEGG Compound IDC00416
BioCyc IDPhosphatidates-34-1
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283523
PDB IDNot Available
ChEBI ID64844
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. Niedernberg A, Tunaru S, Blaukat A, Ardati A, Kostenis E: Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63. Cell Signal. 2003 Apr;15(4):435-46. [PubMed:12618218 ]
  2. Park KA, Vasko MR: Lipid mediators of sensitivity in sensory neurons. Trends Pharmacol Sci. 2005 Nov;26(11):571-7. Epub 2005 Sep 26. [PubMed:16185776 ]

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.