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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-09 02:38:02 UTC
Update Date2022-11-30 19:25:53 UTC
HMDB IDHMDB0114760
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPA(a-13:0/0:0)
DescriptionLysoPA(a-13:0/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common. LysoPA(a-13:0/0:0), in particular, consists of one chain of anteisotridecanoic acid at the C-1 position. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes.
Structure
Data?1563873518
Synonyms
ValueSource
{2-hydroxy-3-[(10-methyldodecanoyl)oxy]propoxy}phosphonateHMDB
1-Anteisotridecanoyl-glycero-3-phosphateHMDB
1-Anteisotridecanoyl-lysophosphatidic acidHMDB
LPA(a-13:0)HMDB
Lysophosphatidic acid(a-13:0/0:0)HMDB
Lysophosphatidic acid(a-13:0)HMDB
LPA(a-13:0/0:0)HMDB
1-Anteisotridecanoyl-phosphatidic acidHMDB
LPA(13:0)HMDB
Lysophosphatidic acid(13:0)HMDB
Chemical FormulaC16H33O7P
Average Molecular Weight368.407
Monoisotopic Molecular Weight368.196390401
IUPAC Name{2-hydroxy-3-[(10-methyldodecanoyl)oxy]propoxy}phosphonic acid
Traditional Name2-hydroxy-3-[(10-methyldodecanoyl)oxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCC(C)CCCCCCCCC(=O)OCC(O)COP(O)(O)=O
InChI Identifier
InChI=1S/C16H33O7P/c1-3-14(2)10-8-6-4-5-7-9-11-16(18)22-12-15(17)13-23-24(19,20)21/h14-15,17H,3-13H2,1-2H3,(H2,19,20,21)
InChI KeyJKRXHZXDGVADEJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
Process
Naturally occurring process
RoleNot 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
logP2.77ALOGPS
logP3.47ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity91.12 m³·mol⁻¹ChemAxon
Polarizability40.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.69431661259
DarkChem[M-H]-188.69731661259
DeepCCS[M+H]+178.65130932474
DeepCCS[M-H]-176.06330932474
DeepCCS[M-2H]-209.76930932474
DeepCCS[M+Na]+186.39830932474
AllCCS[M+H]+193.532859911
AllCCS[M+H-H2O]+191.132859911
AllCCS[M+NH4]+195.732859911
AllCCS[M+Na]+196.432859911
AllCCS[M-H]-188.232859911
AllCCS[M+Na-2H]-189.732859911
AllCCS[M+HCOO]-191.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LysoPA(a-13:0/0:0)CCC(C)CCCCCCCCC(=O)OCC(O)COP(O)(O)=O3647.3Standard polar33892256
LysoPA(a-13:0/0:0)CCC(C)CCCCCCCCC(=O)OCC(O)COP(O)(O)=O2339.4Standard non polar33892256
LysoPA(a-13:0/0:0)CCC(C)CCCCCCCCC(=O)OCC(O)COP(O)(O)=O2740.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
LysoPA(a-13:0/0:0),1TMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O)O)O[Si](C)(C)C2777.7Semi standard non polar33892256
LysoPA(a-13:0/0:0),1TMS,isomer #2CCC(C)CCCCCCCCC(=O)OCC(O)COP(=O)(O)O[Si](C)(C)C2759.2Semi standard non polar33892256
LysoPA(a-13:0/0:0),2TMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2778.1Semi standard non polar33892256
LysoPA(a-13:0/0:0),2TMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2568.7Standard non polar33892256
LysoPA(a-13:0/0:0),2TMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3333.3Standard polar33892256
LysoPA(a-13:0/0:0),2TMS,isomer #2CCC(C)CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2774.1Semi standard non polar33892256
LysoPA(a-13:0/0:0),2TMS,isomer #2CCC(C)CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2555.9Standard non polar33892256
LysoPA(a-13:0/0:0),2TMS,isomer #2CCC(C)CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3062.2Standard polar33892256
LysoPA(a-13:0/0:0),3TMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2774.8Semi standard non polar33892256
LysoPA(a-13:0/0:0),3TMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2610.9Standard non polar33892256
LysoPA(a-13:0/0:0),3TMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2907.1Standard polar33892256
LysoPA(a-13:0/0:0),1TBDMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3044.6Semi standard non polar33892256
LysoPA(a-13:0/0:0),1TBDMS,isomer #2CCC(C)CCCCCCCCC(=O)OCC(O)COP(=O)(O)O[Si](C)(C)C(C)(C)C2995.0Semi standard non polar33892256
LysoPA(a-13:0/0:0),2TBDMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3243.9Semi standard non polar33892256
LysoPA(a-13:0/0:0),2TBDMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2883.3Standard non polar33892256
LysoPA(a-13:0/0:0),2TBDMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3458.9Standard polar33892256
LysoPA(a-13:0/0:0),2TBDMS,isomer #2CCC(C)CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3212.6Semi standard non polar33892256
LysoPA(a-13:0/0:0),2TBDMS,isomer #2CCC(C)CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2847.5Standard non polar33892256
LysoPA(a-13:0/0:0),2TBDMS,isomer #2CCC(C)CCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3252.7Standard polar33892256
LysoPA(a-13:0/0:0),3TBDMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3461.0Semi standard non polar33892256
LysoPA(a-13:0/0:0),3TBDMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3037.9Standard non polar33892256
LysoPA(a-13:0/0:0),3TBDMS,isomer #1CCC(C)CCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3150.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - LysoPA(a-13:0/0:0) GC-MS (1 TMS) - 70eV, Positivesplash10-01ot-9510000000-518ee7f821faa46910fa2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - LysoPA(a-13:0/0:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - LysoPA(a-13:0/0:0) 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 - LysoPA(a-13:0/0:0) 10V, Positive-QTOFsplash10-014i-0009000000-ae3cb9d947a21a68fc222021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(a-13:0/0:0) 20V, Positive-QTOFsplash10-014i-0009000000-ae3cb9d947a21a68fc222021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(a-13:0/0:0) 40V, Positive-QTOFsplash10-0fka-0904000000-3861437af1a9373083492021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(a-13:0/0:0) 10V, Negative-QTOFsplash10-014i-0009000000-85b0352f5970344af9282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(a-13:0/0:0) 20V, Negative-QTOFsplash10-014i-0009000000-85b0352f5970344af9282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(a-13:0/0:0) 40V, Negative-QTOFsplash10-0wmi-2956000000-7402ba42a10ec3c4105f2021-09-24Wishart 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 Compound131821852
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