Showing metabocard for PIP2(18:0/18:1(9Z)) (BMDB0010063)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 17:58:14 UTC
Update Date2020-05-11 19:49:38 UTC
BMDB IDBMDB0010063
Secondary Accession Numbers
  • BMDB10063
Metabolite Identification
Common NamePIP2(18:0/18:1(9Z))
DescriptionPIP2(18:0/18:1(9Z)) belongs to the class of organic compounds known as phosphatidylinositol-4,5-bisphosphates. These are phosphatidylinositol bisphosphates in which the two phosphate groups are at C-4 and C-5 of the inositol moiety. PIP2(18:0/18:1(9Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
{[(1S,2S,3S)-2,4,5-trihydroxy-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)-6-(phosphonooxy)cyclohexyl]oxy}phosphonateGenerator
Chemical FormulaC45H87O19P3
Average Molecular Weight1025.093
Monoisotopic Molecular Weight1024.505441575
IUPAC Name{[(1S,2S,3S)-2,4,5-trihydroxy-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphoryl}oxy)-6-(phosphonooxy)cyclohexyl]oxy}phosphonic acid
Traditional Name[(1S,2S,3S)-2,4,5-trihydroxy-3-{[hydroxy((2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy)phosphoryl]oxy}-6-(phosphonooxy)cyclohexyl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCCCCCCCCCCCC)COP(O)(=O)O[C@@]1([H])C([H])(O)C([H])(O)C([H])(OP(O)(O)=O)[C@@]([H])(OP(O)(O)=O)[C@@]1([H])O
InChI Identifier
InChI=1S/C45H87O19P3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(46)59-35-37(61-39(47)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)36-60-67(57,58)64-43-40(48)41(49)44(62-65(51,52)53)45(42(43)50)63-66(54,55)56/h18,20,37,40-45,48-50H,3-17,19,21-36H2,1-2H3,(H,57,58)(H2,51,52,53)(H2,54,55,56)/b20-18-/t37-,40?,41?,42+,43+,44?,45+/m1/s1
InChI KeyBWAQTKMFCCUVOJ-QDZBYNPGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylinositol-4,5-bisphosphates. These are phosphatidylinositol bisphosphates in which the two phosphate groups are at C-4 and C-5 of the inositol moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositol phosphates
Direct ParentPhosphatidylinositol-4,5-bisphosphates
Alternative Parents
Substituents
  • Diacylglycerophosphoinositol-4,5-bisphosphate
  • 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.48ALOGPS
logP10.16ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)0.63ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area302.57 ŲChemAxon
Rotatable Bond Count45ChemAxon
Refractivity251.83 m³·mol⁻¹ChemAxon
Polarizability111.31 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ar3-9072102502-7e43d61c814b35b9728aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066u-3093502300-15c77a05486763189b11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2093103101-4659ea106fcb375860d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05iu-9060200500-984f851389bffcb23df0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9021200201-da22efcac932719dfbddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010100000-9f44b48dd1de41a4e16aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Brain
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Profilin-1
General function:
Involved in actin binding
Specific function:
Binds to actin and affects the structure of the cytoskeleton. At high concentrations, profilin prevents the polymerization of actin, whereas it enhances it at low concentrations. By binding to PIP2, it inhibits the formation of IP3 and DG. Inhibits androgen receptor (AR) and HTT aggregation and binding of G-actin is essential for its inhibition of AR (By similarity).
Gene Name:
PFN1
Uniprot ID:
P02584
Molecular weight:
15057.0
Enzyme Details
2. Profilin-2
General function:
Involved in actin binding
Specific function:
Binds to actin and affects the structure of the cytoskeleton. At high concentrations, profilin prevents the polymerization of actin, whereas it enhances it at low concentrations. By binding to PIP2, it inhibits the formation of IP3 and DG.
Gene Name:
PFN2
Uniprot ID:
Q09430
Molecular weight:
15032.0
Enzyme Details
3. Unconventional myosin-Ic
General function:
Involved in actin binding
Specific function:
Myosins are actin-based motor molecules with ATPase activity. Unconventional myosins serve in intracellular movements. Their highly divergent tails are presumed to bind to membranous compartments, which would be moved relative to actin filaments. Involved in glucose transporter recycling in response to insulin by regulating movement of intracellular GLUT4-containing vesicles to the plasma membrane. Component of the hair cell's (the sensory cells of the inner ear) adaptation-motor complex. Acts as a mediator of adaptation of mechanoelectrical transduction in stereocilia of vestibular hair cells. Binds phosphoinositides and links the actin cytoskeleton to cellular membranes (By similarity).
Gene Name:
MYO1C
Uniprot ID:
Q27966
Molecular weight:
121936.0
Enzyme Details
4. Arf-GAP with coiled-coil, ANK repeat and PH domain-containing protein 1
General function:
Involved in ARF GTPase activator activity
Specific function:
GTPase-activating protein (GAP) for ADP ribosylation factor 6 (ARF6) required for clathrin-dependent export of proteins from recycling endosomes to trans-Golgi network and cell surface. Required for regulated export of ITGB1 from recycling endosomes to the cell surface and ITGB1-dependent cell migration (By similarity).
Gene Name:
ACAP1
Uniprot ID:
A5PK26
Molecular weight:
82129.0
Enzyme Details
5. Arf-GAP with SH3 domain, ANK repeat and PH domain-containing protein 1
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Possesses phosphatidylinositol 4,5-bisphosphate-dependent GTPase-activating protein activity for ARF1 (ADP ribosylation factor 1) and ARF5 and a lesser activity towards ARF6. May coordinate membrane trafficking with cell growth or actin cytoskeleton remodeling by binding to both SRC and PIP2. Plays a role in ciliogenesis (By similarity). May function as a signal transduction protein involved in the differentiation of fibroblasts into adipocytes and possibly other cell types.
Gene Name:
ASAP1
Uniprot ID:
O97902
Molecular weight:
125382.0