Survey with prize
Back to Compounds

Showing Compound PIP(18:1(11Z)/20:3(8Z,11Z,14Z)) (FDB027153)

Record Information
Version1.0
Creation date2011-09-21 01:20:27 UTC
Update date2015-07-21 06:59:01 UTC
Primary IDFDB027153
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePIP(18:1(11Z)/20:3(8Z,11Z,14Z))
DescriptionPIP(18:1(11Z)/20:3(8Z,11Z,14Z)) is a phosphatidylinositol phosphate. 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. Phosphatidylinositols phosphates can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 18 and 20 carbons are the most common. PIP(18:1(11Z)/20:3(8Z,11Z,14Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of homo-g-linolenic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the homo-g-linolenic acid moiety is derived from fish oils, liver and kidney. 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. Phosphatidylinositols phosphates are usually present at low levels only in tissues, typically at about 1 to 3% of the concentration of phosphatidylinositol. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-(11Z-Octadecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-O-(1'-myo-inositol-3'-ate)HMDB
1-(11Z-octadecenoyl)-2-(8Z,11Z,14Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3'-phosphate)hmdb
1-Vaccenoyl-2-homo-g-linolenoyl-sn-glycero-3-oinositol-ateHMDB
1-vaccenoyl-2-homo-g-linolenoyl-sn-glycero-3-phosphoinositol-phosphatehmdb
1-Vaccenoyl-2-homo-gamma-linolenoyl-sn-glycero-3-oinositol-ateHMDB
1-vaccenoyl-2-homo-gamma-linolenoyl-sn-glycero-3-phosphoinositol-phosphatehmdb
Atidylinositol ate(18:1N7/20:3N6)HMDB
Atidylinositol ate(18:1W7/20:3W6)HMDB
Phosphatidylinositol Phosphate(18:1n7/20:3n6)hmdb
Phosphatidylinositol Phosphate(18:1w7/20:3w6)hmdb
PIP(18:1n7/20:3n6)hmdb
PIP(18:1w7/20:3w6)hmdb
PIP[3'](18:1(11Z)/20:3(8Z,11Z,14Z))hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0048 g/LALOGPS
logP6.73ALOGPS
logP10.09ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)1.08ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area256.04 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity253.51 m³·mol⁻¹ChemAxon
Polarizability107.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC47H84O16P2
IUPAC name{[(1R,5S)-2,3,4,6-tetrahydroxy-5-({hydroxy[(2R)-2-(icosa-8,11,14-trienoyloxy)-3-(octadec-11-enoyloxy)propoxy]phosphoryl}oxy)cyclohexyl]oxy}phosphonic acid
InChI IdentifierInChI=1S/C47H84O16P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(49)61-39(37-59-40(48)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)38-60-65(57,58)63-47-44(52)42(50)43(51)46(45(47)53)62-64(54,55)56/h11,13-14,16-17,19,22,24,39,42-47,50-53H,3-10,12,15,18,20-21,23,25-38H2,1-2H3,(H,57,58)(H2,54,55,56)/t39-,42?,43?,44?,45?,46-,47+/m1/s1
InChI KeyFNRVZZIQRKZPPZ-CSDMGBHBSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(COP(O)(=O)O[C@@]1([H])C(O)C(O)C(O)[C@@]([H])(OP(O)(O)=O)C1O)OC(=O)CCCCCCC=CCC=CCC=CCCCCC
Average Molecular Weight967.1078
Monoisotopic Molecular Weight966.523459664
Classification
Description Belongs to the class of organic compounds known as glycerophosphoinositol phosphates. These are lipids containing a common glycerophosphate skeleton linked to at least one fatty acyl chain and an inositol-5-phosphate moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositol phosphates
Direct ParentGlycerophosphoinositol phosphates
Alternative Parents
Substituents
  • Glycerophosphoinositol phosphate
  • Diacylglycerophosphoinositol
  • Glycerophosphoinositol
  • Inositol phosphate
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Fatty acid ester
  • Cyclohexanol
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Cyclitol or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID24767847
ChEMBL IDNot Available
KEGG Compound IDC00626
Pubchem Compound ID53480161
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB09966
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLecithin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Phosphatidylserine synthase 1PTDSS1P48651
Phosphatidylserine synthase 2PTDSS2Q9BVG9
N-acetylglucosaminyl-phosphatidylinositol de-N-acetylasePIGLQ9Y2B2
Phosphatidylinositol N-acetylglucosaminyltransferase subunit QPIGQQ9BRB3
Phosphatidylinositol N-acetylglucosaminyltransferase subunit APIGAP37287
Phosphatidylinositol N-acetylglucosaminyltransferase subunit HPIGHQ14442
Phosphatidylinositol N-acetylglucosaminyltransferase subunit CPIGCQ92535
GPI mannosyltransferase 1PIGMQ9H3S5
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Phosphatidylinositol-glycan biosynthesis class X proteinPIGXQ8TBF5
GPI mannosyltransferase 4PIGZQ86VD9
GPI mannosyltransferase 3PIGBQ92521
Phosphatidylinositol-glycan biosynthesis class F proteinPIGFQ07326
GPI ethanolamine phosphate transferase 2PIGGQ5H8A4
GPI ethanolamine phosphate transferase 1PIGNO95427
GPI ethanolamine phosphate transferase 3PIGOQ8TEQ8
GPI transamidase component PIG-SPIGSQ96S52
GPI transamidase component PIG-TPIGTQ969N2
Phosphatidylinositol glycan anchor biosynthesis class U proteinPIGUQ9H490
GPI mannosyltransferase 2PIGVQ9NUD9
Phosphatidylinositol N-acetylglucosaminyltransferase subunit YPIGYQ3MUY2
Phosphatidylserine decarboxylase proenzymePISDQ9UG56
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2INPPL1O15357
Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 1INPP5DQ92835
Phosphatidylinositol 3,4,5-trisphosphate 3-phosphatase TPTE2TPTE2Q6XPS3
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit delta isoformPIK3CDO00329
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit beta isoformPIK3CBP42338
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha isoformPIK3CAP42336
Phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit gamma isoformPIK3CGP48736
Phospholipase A1 member APLA1AQ53H76
PI-PLC X domain-containing protein 2PLCXD2Q0VAA5
PI-PLC X domain-containing protein 1PLCXD1Q9NUJ7
PI-PLC X domain-containing protein 3PLCXD3Q63HM9
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference