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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-09 05:46:26 UTC
Update Date2021-10-28 10:42:25 UTC
HMDB IDHMDB0115767
Secondary Accession NumbersNone
Metabolite Identification
Common NamePA(a-25:0/i-16:0)
DescriptionPA(a-25:0/i-16:0) 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(a-25:0/i-16:0), in particular, consists of one chain of anteisopentacosanoic acid at the C-1 position and one chain of isohexadecanoic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.
Structure
Data?1563873633
Synonyms
ValueSource
1-anteisopentacosanoyl-2-isohexadecanoyl-sn-glycero-3-phosphateSMPDB, HMDB
1-anteisopentacosanoyl-2-isohexadecanoyl-sn-phosphatidic acidSMPDB, HMDB
PA(a-25:0/i-16:0)SMPDB
PA(41:0)SMPDB, HMDB
Phosphatidic acid(a-25:0/i-16:0)SMPDB, HMDB
Phosphatidic acid(41:0)SMPDB, HMDB
Phosphatidate(a-25:0/i-16:0)SMPDB, HMDB
Phosphatidate(41:0)SMPDB, HMDB
[(2R)-2-[(14-Methylpentadecanoyl)oxy]-3-[(22-methyltetracosanoyl)oxy]propoxy]phosphonateGenerator, HMDB
Chemical FormulaC44H87O8P
Average Molecular Weight775.146
Monoisotopic Molecular Weight774.613856759
IUPAC Name[(2R)-2-[(14-methylpentadecanoyl)oxy]-3-[(22-methyltetracosanoyl)oxy]propoxy]phosphonic acid
Traditional Name(2R)-2-[(14-methylpentadecanoyl)oxy]-3-[(22-methyltetracosanoyl)oxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC(C)CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCC(C)C
InChI Identifier
InChI=1S/C44H87O8P/c1-5-41(4)35-31-27-23-19-14-12-10-8-6-7-9-11-13-15-20-24-28-32-36-43(45)50-38-42(39-51-53(47,48)49)52-44(46)37-33-29-25-21-17-16-18-22-26-30-34-40(2)3/h40-42H,5-39H2,1-4H3,(H2,47,48,49)/t41?,42-/m1/s1
InChI KeyRZLXHFNPJXJJPM-FBUHDGFBSA-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 DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

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
logP10(9.76) g/LALOGPS
logP10(15.57) g/LChemAxon
logS10(-7.3) g/LALOGPS
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 Count43ChemAxon
Refractivity219.88 m³·mol⁻¹ChemAxon
Polarizability99.32 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]+293.91831661259
DarkChem[M-H]-283.57231661259
DeepCCS[M+H]+289.29230932474
DeepCCS[M-H]-286.03330932474
DeepCCS[M-2H]-320.28930932474
DeepCCS[M+Na]+296.7930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PA(a-25:0/i-16:0)[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC(C)CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCC(C)C4705.7Standard polar33892256
PA(a-25:0/i-16:0)[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC(C)CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCC(C)C4665.0Standard non polar33892256
PA(a-25:0/i-16:0)[H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC(C)CC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCC(C)C5383.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
PA(a-25:0/i-16:0),1TMS,isomer #1CCC(C)CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC(C)C5358.5Semi standard non polar33892256
PA(a-25:0/i-16:0),1TMS,isomer #1CCC(C)CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC(C)C4612.1Standard non polar33892256
PA(a-25:0/i-16:0),1TMS,isomer #1CCC(C)CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC(C)C6172.2Standard polar33892256
PA(a-25:0/i-16:0),1TBDMS,isomer #1CCC(C)CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC(C)C5577.4Semi standard non polar33892256
PA(a-25:0/i-16:0),1TBDMS,isomer #1CCC(C)CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC(C)C4731.9Standard non polar33892256
PA(a-25:0/i-16:0),1TBDMS,isomer #1CCC(C)CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC(C)C6132.4Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 10V, Positive-QTOFsplash10-0699-2279052700-e16206a8f73ce3b0c85a2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 20V, Positive-QTOFsplash10-01bj-5579221300-82d4581426c9cd2502e52019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 40V, Positive-QTOFsplash10-007a-5935401100-e403394446c05d5e5fa32019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 10V, Negative-QTOFsplash10-071i-4039030300-574c52bd1b429e04270e2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 20V, Negative-QTOFsplash10-004i-9005000000-bcfd8823ce8de0ff95772019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 40V, Negative-QTOFsplash10-004i-9000000000-5f7bfc462b9170d56e632019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 10V, Positive-QTOFsplash10-0a6r-0000000900-9bdd887dca6037bdc4032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 20V, Positive-QTOFsplash10-004i-0000005900-4e3066a659b7b8e910ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 40V, Positive-QTOFsplash10-00ou-0006069300-59704e7cc0c41eb8dc5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 10V, Negative-QTOFsplash10-00di-0000000900-02dc5b3cf396b5aa7b142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 20V, Negative-QTOFsplash10-06l3-1149170600-17122d26d1b5ac7212e52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 40V, Negative-QTOFsplash10-053r-1159120100-c5df32cf810a2ea9c9772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 10V, Positive-QTOFsplash10-0002-0000000900-59b73e7131dd061f227c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 20V, Positive-QTOFsplash10-0002-0000009900-101a6d0d1696f8bd79052021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - PA(a-25:0/i-16:0) 40V, Positive-QTOFsplash10-00ke-0000994600-4df8d72a40656790584a2021-09-25Wishart 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 Compound131822423
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 ReferencesNot Available

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.