Showing metabocard for LysoPC(26:1(5Z)) (BMDB0063650)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-01-31 17:06:54 UTC
Update Date2020-06-04 19:13:32 UTC
BMDB IDBMDB0063650
Secondary Accession Numbers
  • BMDB63650
Metabolite Identification
Common NameLysoPC(26:1(5Z))
DescriptionLysoPC(26:1(5Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(26:1(5Z)/0:0), in particular, consists of one 5Z-hexacosenoyl chain. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LysoPC a C26:1HMDB
Chemical FormulaC34H68NO7P
Average Molecular Weight633.88
Monoisotopic Molecular Weight633.473340047
IUPAC Name(2-{[(2R)-3-[(5E)-hexacos-5-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
Traditional Name(2-{[(2R)-3-[(5E)-hexacos-5-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCCC\C=C\CCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C
InChI Identifier
InChI=1S/C34H68NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-34(37)40-31-33(36)32-42-43(38,39)41-30-29-35(2,3)4/h24-25,33,36H,5-23,26-32H2,1-4H3/b25-24+/t33-/m1/s1
InChI KeyHHNUOPXCCKOIPL-VTFFUMFSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-acyl-sn-glycero-3-phosphocholines
Alternative Parents
Substituents
  • 1-acyl-sn-glycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic salt
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.67ALOGPS
logP5.28ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity189.4 m³·mol⁻¹ChemAxon
Polarizability78.51 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("LysoPC(26:1(5Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000019000-0edeb428caef03240dbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001o-0000299000-db891b68f24dca95401cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0300940000-332d1d90f877058f4d6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000009000-783de816747a9d9c06cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-0009007000-1e2ac78ba83f1d0a9320View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0039003000-43707775e3257dcc276bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0000009000-7a1134097b83ef8e917bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900006000-00a5e4dc9f4a2d45137cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsi-0910004000-ed0e52742641f76a9dfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0002009000-cb722ac02fc6c2885eedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1009001000-bd8d04af871020f8293eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0009000000-ee0ada34d8043a65fdbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000019000-14405b14f8b1a14d6bfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-0000196000-3bd895a17ee3a705fdeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fdk-1600971000-b3f9c50d70cb136254b3View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • Blood
  • Liver
  • Longissimus Thoracis Muscle
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.1 +/- 0.04 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
LiverDetected and Quantified0.04 +/- 0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Longissimus Thoracis MuscleDetected and Quantified0.05 +/- 0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Semimembranosus MuscleDetected and Quantified0.06 +/- 0.02 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
TestisDetected and Quantified0.04 +/- 0.01 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0029220
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031405
KNApSAcK IDNot Available
Chemspider ID35032839
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131750814
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available