Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2008-09-12 01:27:08 UTC
Update Date2021-09-14 15:00:03 UTC
HMDB IDHMDB0007849
Secondary Accession Numbers
  • HMDB07849
Metabolite Identification
Common NameLysoPA(0:0/16:0)
DescriptionLysoPA(0:0/16:0) 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. 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. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers (PMID 11585410 ). LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233 ). In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. (PMID 15271293 ).
Structure
Data?1582752506
Synonyms
ValueSource
2-Palmitoyl-glycero-3-phosphateHMDB
LPA(0:0/16:0)HMDB
Lysophosphatidic acid(0:0/16:0)HMDB
LPA(16:0)HMDB
2-Hexadecanoyl-phosphatidic acidHMDB
2-Hexadecanoyl-glycero-3-phosphateHMDB
Lysophosphatidic acid(16:0)HMDB
[2-(Hexadecanoyloxy)-3-hydroxypropoxy]phosphonateHMDB
2-Hexadecanoyl-sn-glycerol 3-phosphoric acidHMDB
Chemical FormulaC19H39O7P
Average Molecular Weight410.4825
Monoisotopic Molecular Weight410.243340114
IUPAC Name[2-(hexadecanoyloxy)-3-hydroxypropoxy]phosphonic acid
Traditional Name2-(hexadecanoyloxy)-3-hydroxypropoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC(CO)COP(O)(O)=O
InChI Identifier
InChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)26-18(16-20)17-25-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)
InChI KeyLPQBQFLKBCPNAV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-2 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent2-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 2-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

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
Water Solubility0.0027 g/LALOGPS
logP10(3.96) g/LALOGPS
logP10(4.96) g/LChemAxon
logS10(-5.2) g/LALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity104.98 m³·mol⁻¹ChemAxon
Polarizability46.84 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LysoPA(0:0/16:0)CCCCCCCCCCCCCCCC(=O)OC(CO)COP(O)(O)=O3322.0Standard polar33892256
LysoPA(0:0/16:0)CCCCCCCCCCCCCCCC(=O)OC(CO)COP(O)(O)=O2715.3Standard non polar33892256
LysoPA(0:0/16:0)CCCCCCCCCCCCCCCC(=O)OC(CO)COP(O)(O)=O3050.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
LysoPA(0:0/16:0),1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O3046.3Semi standard non polar33892256
LysoPA(0:0/16:0),1TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O)O[Si](C)(C)C3041.7Semi standard non polar33892256
LysoPA(0:0/16:0),2TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C3054.4Semi standard non polar33892256
LysoPA(0:0/16:0),2TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C2871.8Standard non polar33892256
LysoPA(0:0/16:0),2TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C3706.5Standard polar33892256
LysoPA(0:0/16:0),2TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3064.1Semi standard non polar33892256
LysoPA(0:0/16:0),2TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2900.2Standard non polar33892256
LysoPA(0:0/16:0),2TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3436.0Standard polar33892256
LysoPA(0:0/16:0),3TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3070.0Semi standard non polar33892256
LysoPA(0:0/16:0),3TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2927.9Standard non polar33892256
LysoPA(0:0/16:0),3TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3229.3Standard polar33892256
LysoPA(0:0/16:0),1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O3317.6Semi standard non polar33892256
LysoPA(0:0/16:0),1TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O)O[Si](C)(C)C(C)(C)C3282.3Semi standard non polar33892256
LysoPA(0:0/16:0),2TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C3548.9Semi standard non polar33892256
LysoPA(0:0/16:0),2TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C3188.5Standard non polar33892256
LysoPA(0:0/16:0),2TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C3811.5Standard polar33892256
LysoPA(0:0/16:0),2TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3519.3Semi standard non polar33892256
LysoPA(0:0/16:0),2TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3170.9Standard non polar33892256
LysoPA(0:0/16:0),2TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3602.2Standard polar33892256
LysoPA(0:0/16:0),3TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3780.0Semi standard non polar33892256
LysoPA(0:0/16:0),3TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3337.5Standard non polar33892256
LysoPA(0:0/16:0),3TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3452.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - LysoPA(0:0/16:0) GC-MS (1 TMS) - 70eV, Positivesplash10-01ot-9440000000-bf1d1f237edf728eb2c52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - LysoPA(0:0/16:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - LysoPA(0:0/16:0) 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(0:0/16:0) 10V, Positive-QTOFsplash10-08g0-3975600000-8a269b545c4d24da9aad2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 20V, Positive-QTOFsplash10-0btj-6952000000-be4d81f8aa90afc599052015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 40V, Positive-QTOFsplash10-054k-9720000000-2af12860245e1cdaf48f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 10V, Negative-QTOFsplash10-0a4i-9871700000-49682f37e6e51ea574e72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 20V, Negative-QTOFsplash10-004i-9110000000-ad3918383a58c2aba3982015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 40V, Negative-QTOFsplash10-004i-9000000000-4a8a491ed626534005d72015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 10V, Positive-QTOFsplash10-03di-2039500000-ff5001fecfa0d240ff692021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 20V, Positive-QTOFsplash10-01p9-2695000000-cc51ff937b2c609be46f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 40V, Positive-QTOFsplash10-052b-9100000000-832946b2e9b8f954e29c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 10V, Negative-QTOFsplash10-0a4i-4000900000-0d0d9baf6df77f542e342021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 20V, Negative-QTOFsplash10-004j-9100000000-0954a22e4e318311db162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(0:0/16:0) 40V, Negative-QTOFsplash10-004i-9000000000-a195e098f58b4f2bb72e2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
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 Compound56960317
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. Shen Z, Wu M, Elson P, Kennedy AW, Belinson J, Casey G, Xu Y: Fatty acid composition of lysophosphatidic acid and lysophosphatidylinositol in plasma from patients with ovarian cancer and other gynecological diseases. Gynecol Oncol. 2001 Oct;83(1):25-30. [PubMed:11585410 ]
  2. Gerrard JM, Clawson CC, White JG: Lysophosphatidic acids: III. Enhancement of neutrophil chemotaxis. Am J Pathol. 1980 Sep;100(3):609-18. [PubMed:7416233 ]
  3. Aoki J: Mechanisms of lysophosphatidic acid production. Semin Cell Dev Biol. 2004 Oct;15(5):477-89. [PubMed:15271293 ]

Only showing the first 10 proteins. There are 46 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 catalytic activity
Specific function:
Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor.
Gene Name:
ENPP2
Uniprot ID:
Q13822
Molecular weight:
98992.78
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 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 46 proteins in total.