You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2008-09-11 00:41:42 UTC
Update Date2013-02-09 00:15:33 UTC
HMDB IDHMDB06953
Secondary Accession NumbersNone
Metabolite Identification
Common Name1-Phosphatidyl-D-myo-inositol
Description1-Phosphatidyl-D-myo-inositol is an intermediate in inositol phosphate metabolism (KEGG ID C04637). It is generated from 1-phosphatidyl-1D-myo-inositol-5P via the enzyme 1-phosphatidylinositol-5-phosphate 4-kinase [EC:2.7.1.149] and then converted to 1D-myo-inositol-1,4,5P3 via the enzyme 1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase [EC:3.1.4.11].
Structure
Thumb
Synonyms
  1. (3-Phosphatidyl)-1-D-inositol
  2. 1,2-Diacyl-sn-glycero-3-phosphoinositol
  3. 1-Phosphatidyl-1D-myo-inositol
  4. 1-Phosphatidyl-myo-inositol
  5. Phosphatidyl-1D-myo-inositol
  6. Phosphatidylinositol
Chemical FormulaC11H19O13P
Average Molecular Weight390.2345
Monoisotopic Molecular Weight390.056327206
IUPAC Name[2,3-bis(formyloxy)propoxy]({[(2R,3S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
Traditional IUPAC Name2,3-bis(formyloxy)propoxy[(2R,3S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid
CAS Registry NumberNot Available
SMILES
OC1C(O)[C@H](O)C(OP(O)(=O)OCC(COC=O)OC=O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C11H19O13P/c12-3-21-1-5(22-4-13)2-23-25(19,20)24-11-9(17)7(15)6(14)8(16)10(11)18/h3-11,14-18H,1-2H2,(H,19,20)/t5?,6?,7-,8?,9+,10-,11?/m0/s1
InChI KeyGUBXYMKIJFOYOA-WSRCIYAPSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositols
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
Substituents
  • 1,2 Diol
  • Carboxylic Acid Ester
  • Cyclic Alcohol
  • Cyclitol Derivative
  • Cyclohexane
  • Inositol Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct ParentPhosphatidylinositols
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
water solubility27 g/LALOGPS
logP-1.7ALOGPS
logP-4.1ChemAxon
logS-1.2ALOGPS
pKa (strongest acidic)1.83ChemAxon
pKa (strongest basic)-3.6ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count9ChemAxon
hydrogen donor count6ChemAxon
polar surface area209.51ChemAxon
rotatable bond count10ChemAxon
refractivity72.71ChemAxon
polarizability32.85ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Inositol MetabolismSMP00011map00562
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024159
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01194
BioCyc ID1-PHOSPHATIDYL-MYO-INOSITOL
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06953
Metagene LinkHMDB06953
METLIN IDNot Available
PubChem Compound53477912
PDB IDNot Available
ChEBI ID16749
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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 binding
Specific function:
ATP + 1-phosphatidyl-1D-myo-inositol 4,5- bisphosphate = ADP + 1-phosphatidyl-1D-myo-inositol 3,4,5- trisphosphate
Gene Name:
PIK3CD
Uniprot ID:
O00329
Molecular weight:
119478.1
General function:
Involved in phosphatidylinositol phosphate kinase activity
Specific function:
Catalyzes the phosphorylation of phosphatidylinositol-5- phosphate on the fourth hydroxyl of the myo-inositol ring, to form phosphatidylinositol-4,5-biphosphate
Gene Name:
PIP4K2A
Uniprot ID:
P48426
Molecular weight:
46224.3
General function:
Involved in binding
Specific function:
Phosphorylates PtdIns, PtdIns4P and PtdIns(4,5)P2 with a preference for PtdIns(4,5)P2
Gene Name:
PIK3CB
Uniprot ID:
P42338
Molecular weight:
122761.2
General function:
Involved in binding
Specific function:
Phosphorylates PtdIns, PtdIns4P and PtdIns(4,5)P2 with a preference for PtdIns(4,5)P2
Gene Name:
PIK3CA
Uniprot ID:
P42336
Molecular weight:
124283.0
General function:
Involved in protein binding
Specific function:
The PI(3,5)P2 regulatory complex regulates both the synthesis and turnover of phosphatidylinositol-3,5-bisphosphate (PtdIns(3,5)P2). Catalyzes the phosphorylation of phosphatidylinositol-3-phosphate on the fifth hydroxyl of the myo- inositol ring, to form phosphatidylinositol-3,5-bisphosphate. Required for endocytic-vacuolar pathway and nuclear migration. Plays a role in the biogenesis of endosome carrier vesicles (ECV)/ multivesicular bodies (MVB) transport intermediates from early endosomes
Gene Name:
PIKFYVE
Uniprot ID:
Q9Y2I7
Molecular weight:
237134.1
General function:
Involved in phosphatidylinositol phosphate kinase activity
Specific function:
Participates in the biosynthesis of phosphatidylinositol-4,5-bisphosphate
Gene Name:
PIP4K2B
Uniprot ID:
P78356
Molecular weight:
47377.6
General function:
Involved in binding
Specific function:
3-phosphorylates the cellular phosphoinositide PtdIns- 4,5-biphosphate (PtdIns(4,5)P2) to produce PtdIns-3, 4,5- triiphosphate (PtdIns(3,4,5)P3). Links G-protein coupled receptor activation to the secondary messenger PtdIns(3,4,5)P3 production
Gene Name:
PIK3CG
Uniprot ID:
P48736
Molecular weight:
126452.6
General function:
Involved in binding
Specific function:
Acts on phosphatidylinositol (PtdIns) in the first committed step in the production of the second messenger inositol- 1,4,5,-trisphosphate
Gene Name:
PI4KA
Uniprot ID:
P42356
Molecular weight:
231316.9
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Converts phosphatidylinositol 4,5-bisphosphate to phosphatidylinositol 4-phosphate. Also converts inositol 1,4,5-trisphosphate to inositol 1,4-bisphosphate and inositol 1,3,4,5-tetrakisphosphate to inositol 1,3,4-trisphosphate. May function in lysosomal membrane trafficking by regulating the specific pool of phosphatidylinositol 4,5-bisphosphate that is associated with lysosomes. Involved in primary cilia assembly.
Gene Name:
OCRL
Uniprot ID:
Q01968
Molecular weight:
104203.78
General function:
Involved in magnesium ion binding
Specific function:
Tumor suppressor. Acts as a dual-specificity protein phosphatase, dephosphorylating tyrosine-, serine- and threonine-phosphorylated proteins. Also acts as a lipid phosphatase, removing the phosphate in the D3 position of the inositol ring from phosphatidylinositol 3,4,5-trisphosphate, phosphatidylinositol 3,4-diphosphate, phosphatidylinositol 3-phosphate and inositol 1,3,4,5-tetrakisphosphate with order of substrate preference in vitro PtdIns(3,4,5)P3 > PtdIns(3,4)P2 > PtdIns3P > Ins(1,3,4,5)P4. The lipid phosphatase activity is critical for its tumor suppressor function. Antagonizes the PI3K-AKT/PKB signaling pathway by dephosphorylating phosphoinositides and thereby modulating cell cycle progression and cell survival. The unphosphorylated form cooperates with AIP1 to suppress AKT1 activation. Dephosphorylates tyrosine-phosphorylated focal adhesion kinase and inhibits cell migration and integrin-mediated cell spreading and focal adhesion formation. Plays a role as a key modulator of the AKT-mTOR signaling pathway controlling the tempo of the process of newborn neurons integration during adult neurogenesis, including correct neuron positioning, dendritic development and synapse formation. May be a negative regulator of insulin signaling and glucose metabolism in adipose tissue. The nuclear monoubiquitinated form possesses greater apoptotic potential, whereas the cytoplasmic nonubiquitinated form induces less tumor suppressive ability.
Gene Name:
PTEN
Uniprot ID:
P60484
Molecular weight:
47165.92
General function:
Involved in nucleotide binding
Specific function:
Inositol 5-phosphatase which may be involved in distinct membrane trafficking and signal transduction pathways. May mediate the inhibitory effect of Rac1 on endocytosis.
Gene Name:
SYNJ2
Uniprot ID:
O15056
Molecular weight:
165536.575
General function:
Involved in inositol-polyphosphate 5-phosphatase activity
Specific function:
Converts phosphatidylinositol 3,4,5-trisphosphate (PtdIns 3,4,5-P3) to PtdIns-P2. Specific for lipid substrates, inactive towards water soluble inositol phosphates.
Gene Name:
INPP5E
Uniprot ID:
Q9NRR6
Molecular weight:
70204.435
General function:
Cell cycle control, cell division, chromosome partitioning
Specific function:
Inositol 5-phosphatase which has a role in clathrin-mediated endocytosis.
Gene Name:
SYNJ1
Uniprot ID:
O43426
Molecular weight:
143252.18
General function:
Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:
Hydrolyzes phosphatidylinositol 4,5-bisphosphate (PtIns(4,5)P2) and the signaling molecule phosphatidylinositol 1,4,5-trisphosphate (PtIns(1,4,5)P3), and thereby modulates cellular signaling events.
Gene Name:
INPP5B
Uniprot ID:
P32019
Molecular weight:
103986.41
General function:
Involved in phosphatidylinositol phosphate kinase activity
Specific function:
Plays a role in membrane ruffling and assembly of clathrin-coated pits at the synapse. Mediates RAC1-dependent reorganization of actin filaments. Participates in the biosynthesis of phosphatidylinositol-4,5-bisphosphate
Gene Name:
PIP5K1C
Uniprot ID:
O60331
Molecular weight:
73259.3
General function:
Involved in binding
Specific function:
Catalytic subunit of the PI3K complex. Involved in the transport of lysosomal enzyme precursors to lysosomes
Gene Name:
PIK3C3
Uniprot ID:
Q8NEB9
Molecular weight:
101548.6
General function:
Involved in phosphatidylinositol phosphate kinase activity
Specific function:
May play an important role in the production of Phosphatidylinositol bisphosphate (PIP2), in the endoplasmic reticulum
Gene Name:
PIP4K2C
Uniprot ID:
Q8TBX8
Molecular weight:
47285.5
General function:
Involved in calcium ion binding
Specific function:
Hydrolyzes the phosphatidylinositol 4,5-bisphosphate (PIP2) to generate 2 second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). DAG mediates the activation of protein kinase C (PKC), while IP3 releases Ca(2+) from intracellular stores. Required for acrosome reaction in sperm during fertilization, probably by acting as an important enzyme for intracellular Ca(2+) mobilization in the zona pellucida-induced acrosome reaction. May play a role in cell growth. Modulates the liver regeneration in cooperation with nuclear PKC. Overexpression up-regulates the Erk signaling pathway and proliferation.
Gene Name:
PLCD4
Uniprot ID:
Q9BRC7
Molecular weight:
87584.515
General function:
Involved in calcium ion binding
Specific function:
Hydrolyzes the phosphatidylinositol 4,5-bisphosphate (PIP2) to generate 2 second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). DAG mediates the activation of protein kinase C (PKC), while IP3 releases Ca(2+) from intracellular stores. Essential for trophoblast and placental development. May participate in cytokinesis by hydrolyzing PIP2 at the cleavage furrow.
Gene Name:
PLCD3
Uniprot ID:
Q8N3E9
Molecular weight:
89257.54
General function:
Involved in phosphatase activity
Specific function:
Lipid phosphatase which dephosphorylates phosphatidylglycerophosphate (PGP) to phosphatidylglycerol (PG). PGP is an essential intermediate in the biosynthetic pathway of cardiolipin, a mitochondrial-specific phospholipid regulating the membrane integrity and activities of the organelle. Has also been shown to display phosphatase activity toward phosphoprotein substrates, specifically mediates dephosphorylation of mitochondrial proteins, thereby playing an essential role in ATP production. Has probably a preference for proteins phosphorylated on Ser and/or Thr residues compared to proteins phosphorylated on Tyr residues. Probably involved in regulation of insulin secretion in pancreatic beta cells (By similarity).
Gene Name:
PTPMT1
Uniprot ID:
Q8WUK0
Molecular weight:
16458.74