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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-13 12:49:41 UTC
Update Date2022-11-30 20:02:20 UTC
HMDB IDHMDB0279694
Secondary Accession NumbersNone
Metabolite Identification
Common NamePIP(20:2(11Z,14Z)/LTE4)
DescriptionPIP(20:2(11Z,14Z)/LTE4) is an oxidized phosphatidylinositol phosphate (PIP). As other PIPs, oxidized phosphatidylinositol phosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a phosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol phosphates are generated from phosphatidylinositols, which are phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated. Phosphatidylinositol phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PIP(20:2(11Z,14Z)/LTE4), in particular, consists of one chain of 11Z,14Z-eicosadienoyl at the C-1 position and one chain of Leukotriene E4 at the C-2 position. The most important phosphatidylinositol phosphate in both quantitative and biological terms is phosphatidylinositol 4-phosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. Phosphatidylinositol phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol.
Structure
Thumb
Synonyms
ValueSource
(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-{[hydroxy({[(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)cyclohexyl]oxy})phosphoryl]oxy}-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propan-2-yl]oxy}-3-oxopropyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoateHMDB
(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-{[hydroxy({[(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)cyclohexyl]oxy})phosphoryl]oxy}-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propan-2-yl]oxy}-3-oxopropyl]sulphanyl}-5-hydroxyicosa-7,9,11,14-tetraenoateHMDB
(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-{[hydroxy({[(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)cyclohexyl]oxy})phosphoryl]oxy}-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propan-2-yl]oxy}-3-oxopropyl]sulphanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acidHMDB
Chemical FormulaC52H89NO19P2S
Average Molecular Weight1126.28
Monoisotopic Molecular Weight1125.52247482
IUPAC Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-{[hydroxy({[(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)cyclohexyl]oxy})phosphoryl]oxy}-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propan-2-yl]oxy}-3-oxopropyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
Traditional Name(5S,6R,7E,9E,11Z,14Z)-6-{[(2R)-2-amino-3-{[(2R)-1-{[hydroxy([(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(phosphonooxy)cyclohexyl]oxy)phosphoryl]oxy}-3-[(11Z,14Z)-icosa-11,14-dienoyloxy]propan-2-yl]oxy}-3-oxopropyl]sulfanyl}-5-hydroxyicosa-7,9,11,14-tetraenoic acid
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCC(=O)OC[C@H](COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1OP(O)(O)=O)OC(=O)[C@@H](N)CS[C@H](\C=C\C=C\C=C/C\C=C/CCCCC)[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C52H89NO19P2S/c1-3-5-7-9-11-13-15-17-18-19-20-21-23-25-27-29-31-36-45(57)68-37-40(38-69-74(66,67)72-51-49(61)47(59)46(58)48(60)50(51)71-73(63,64)65)70-52(62)41(53)39-75-43(42(54)33-32-35-44(55)56)34-30-28-26-24-22-16-14-12-10-8-6-4-2/h11-14,17-18,22,24,26,28,30,34,40-43,46-51,54,58-61H,3-10,15-16,19-21,23,25,27,29,31-33,35-39,53H2,1-2H3,(H,55,56)(H,66,67)(H2,63,64,65)/b13-11-,14-12-,18-17-,24-22-,28-26+,34-30+/t40-,41+,42+,43-,46+,47+,48-,49-,50-,51+/m1/s1
InChI KeyMAVGEDXPDRLVJQ-BHHFKODNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylinositol phosphates. These are phosphorylated derivatives of phosphatidylinositols, which are glycerophosphoinositols where the glycerol is esterified with two fatty acids.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositol phosphates
Direct ParentPhosphatidylinositol phosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoinositol phosphate
  • Leukotriene
  • Diacylglycerophosphoinositol
  • Hydroxyeicosatetraenoic acid
  • Glycerophosphoinositol
  • Eicosanoid
  • Inositol phosphate
  • Alpha-amino acid ester
  • Cysteine or derivatives
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Thia fatty acid
  • Hydroxy fatty acid
  • Fatty acid ester
  • Cyclohexanol
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Amino acid or derivatives
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
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 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 Compound156983046
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