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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-09-12 02:05:57 UTC
Update Date2019-01-11 19:27:28 UTC
HMDB IDHMDB0010151
Secondary Accession Numbers
  • HMDB10151
Metabolite Identification
Common NamePIP3(18:0/16:1(9Z))
DescriptionPIP3(18:0/16:1(9Z)) is a phosphatidylinositol trisphosphate. Phosphatidylinositol trisphosphates are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to a trisphosphorylated inositol (hexahydroxycyclohexane). Phosphatidylinositol trisphosphates 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 trisphosphates 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. PIP3(18:0/16:1(9Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. The most important phosphatidylinositol trisphosphate in both quantitative and biological terms is phosphatidylinositol 3,4,5-triphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signalling 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.
Structure
Data?1547234848
Synonyms
ValueSource
1-Octadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-myo-inositol-3',4',5'-trisphosphate)HMDB
1-Stearoyl-2-palmitoleoyl-sn-glycero-3-phosphoinositol-trisphosphateHMDB
Phosphatidylinositol triphosphate(18:0/16:1)HMDB
Phosphatidylinositol triphosphate(18:0/16:1n7)HMDB
Phosphatidylinositol triphosphate(18:0/16:1W7)HMDB
Phosphatidylinositol triphosphate(34:1)HMDB
PIP3(18:0/16:1)HMDB
PIP3(18:0/16:1n7)HMDB
PIP3(18:0/16:1W7)HMDB
PIP3(34:1)HMDB
PIP3[3',4',5'](18:0/16:1(9Z))HMDB
Chemical FormulaC43H84O22P4
Average Molecular Weight1077.0089
Monoisotopic Molecular Weight1076.44047042
IUPAC Name{[(3s,5S)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2,4-dihydroxy-5,6-bis(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(3s,5S)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2,4-dihydroxy-5,6-bis(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O[C@H]1C(O)C(OP(=O)(O)O)C(OP(=O)(O)O)[C@@H](OP(=O)(O)O)C1O)OC(=O)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C43H84O22P4/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-36(44)59-33-35(61-37(45)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)34-60-69(57,58)65-40-38(46)41(62-66(48,49)50)43(64-68(54,55)56)42(39(40)47)63-67(51,52)53/h14,16,35,38-43,46-47H,3-13,15,17-34H2,1-2H3,(H,57,58)(H2,48,49,50)(H2,51,52,53)(H2,54,55,56)/b16-14-/t35-,38?,39?,40-,41+,42?,43?/m1/s1
InChI KeyLNEUQXPUYSJZFM-XNAFLRJISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phosphatidylinositol-3,4,5-trisphosphates. These are phosphatidylinositol bisphosphates in which the inositol moiety is substituted by a phosphate group at the C-3, C-4, and C-5 positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositol phosphates
Direct ParentPhosphatidylinositol-3,4,5-trisphosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoinositol-3,4,5-trisphosphate
  • Diacylglycerophosphoinositol
  • Glycerophosphoinositol
  • Inositol phosphate
  • Cyclohexanol
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Fatty acid ester
  • Cyclitol or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP4.4ALOGPS
logP9.15ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)0.38ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area349.1 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity253.51 m³·mol⁻¹ChemAxon
Polarizability110.78 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • All Tissues
  • Brain
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
FoodDB IDFDB027334
KNApSAcK IDNot Available
Chemspider ID24768028
KEGG Compound IDC00626
BioCyc IDPhosphatidylinositols
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 81 proteins in total.

Enzymes

General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:
PLCB1
Uniprot ID:
Q9NQ66
Molecular weight:
138565.805
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. This form has a role in retina signal transduction.
Gene Name:
PLCB4
Uniprot ID:
Q15147
Molecular weight:
136105.065
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:
PLCB2
Uniprot ID:
Q00722
Molecular weight:
134023.21
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes.
Gene Name:
PLCB3
Uniprot ID:
Q01970
Molecular weight:
138797.725
General function:
Involved in phosphoinositide phospholipase C activity
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. It is a crucial enzyme in transmembrane signaling.
Gene Name:
PLCG2
Uniprot ID:
P16885
Molecular weight:
147868.67
General function:
Involved in calcium ion binding
Specific function:
Mediates the production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). Plays an important role in the regulation of intracellular signaling cascades. Becomes activated in response to ligand-mediated activation of receptor-type tyrosine kinases, such as PDGFRA, PDGFRB, FGFR1, FGFR2, FGFR3 and FGFR4. Plays a role in actin reorganization and cell migration.
Gene Name:
PLCG1
Uniprot ID:
P19174
Molecular weight:
148658.92
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. Essential for trophoblast and placental development.
Gene Name:
PLCD1
Uniprot ID:
P51178
Molecular weight:
88134.23
General function:
Involved in N-acetylglucosaminylphosphatidylinositol de
Specific function:
Involved in the second step of GPI biosynthesis. De-N-acetylation of N-acetylglucosaminyl-phosphatidylinositol.
Gene Name:
PIGL
Uniprot ID:
Q9Y2B2
Molecular weight:
28530.965
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis.
Gene Name:
PIGQ
Uniprot ID:
Q9BRB3
Molecular weight:
65343.25
General function:
Involved in biosynthetic process
Specific function:
Necessary for the synthesis of N-acetylglucosaminyl-phosphatidylinositol, the very early intermediate in GPI-anchor biosynthesis.
Gene Name:
PIGA
Uniprot ID:
P37287
Molecular weight:
54126.065

Only showing the first 10 proteins. There are 81 proteins in total.