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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2019-12-02 16:13:24 UTC
Update Date2022-11-30 19:53:42 UTC
HMDB IDHMDB0240601
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPG(16:0/0:0)
DescriptionLysoPG(16:0/0:0) is a lysophosphatidylglycerol. It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic. However, it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Lysophosphatidylglycerols 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. LysoPG(16:0/0:0), in particular, consists of one chain of palmitic acid at the C-1 position.
Structure
Data?1575303586
Synonyms
ValueSource
1-Palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol)ChEBI
LPG(16:0/0:0)ChEBI
PG(16:0/0:0)ChEBI
1-Palmitoyl-GPGHMDB
1-Palmitoyl-lysophosphatidylglycerolHMDB
1-Palmitoyl-sn-glycero-3-phospho-(1’-sn-glycerol)HMDB
1-Palmitoyl-sn-glycero-3-phosphoglycerolHMDB
GPG(16:0)HMDB
GPG(16:0/0:0)HMDB
LPG(16:0)HMDB
LysoPG(16:0)HMDB
Lysophosphatidylglycerol(16:0)HMDB
Lysophosphatidylglycerol(16:0/0:0)HMDB
LysoPG(16:0/0:0)HMDB
Chemical FormulaC22H45O9P
Average Molecular Weight484.567
Monoisotopic Molecular Weight484.280120027
IUPAC Name[(2S)-2,3-dihydroxypropoxy][(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphinic acid
Traditional Name(2S)-2,3-dihydroxypropoxy((2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy)phosphinic acid
CAS Registry Number116870-26-9
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OC[C@@H](O)CO
InChI Identifier
InChI=1S/C22H45O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-22(26)29-17-21(25)19-31-32(27,28)30-18-20(24)16-23/h20-21,23-25H,2-19H2,1H3,(H,27,28)/t20-,21+/m0/s1
InChI KeyBVJSKAUUFXBDOB-LEWJYISDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lysophosphatidylglycerols. These are glycerophosphoglycerols (molecules containing a glycerol moiety attached to the phosphate group linked to a glycerol) in which only one fatty acid is bonded to the 1-glycerol moiety (through an ester linkage).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct ParentLysophosphatidylglycerols
Alternative Parents
Substituents
  • Monoacylglycerophosphoglycerol
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
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 IDC00059317
Chemspider ID24823104
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound42607483
PDB IDNot Available
ChEBI ID75376
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. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]