PIP3   Click here for help

GtoPdb Ligand ID: 2353

Synonyms: phosphatidylinositol-3,4,5-trisphosphate
Compound class: Metabolite
Comment: There is some ambiguity in the literature and on online resources as to the exact structure and stereochemistry of this compound. Other representations include CID 24755492, and CID 53477782.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 22
Hydrogen bond donors 9
Rotatable bonds 15
Topological polar surface area 388.34
Molecular weight 643.97
XLogP -8.19
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(=O)OC(OC(=O)C)COP(=O)(OC1C(O)C(OP(=O)(O)O)C(C(C1O)OP(=O)(O)O)OP(=O)(O)O)O
Isomeric SMILES CC(=O)OC(OC(=O)C)COP(=O)(O[C@@H]1[C@H](O)[C@H](OP(=O)(O)O)[C@H]([C@@H]([C@H]1O)OP(=O)(O)O)OP(=O)(O)O)O
InChI InChI=1S/C12H24O22P4/c1-4(13)29-6(30-5(2)14)3-28-38(26,27)34-9-7(15)10(31-35(17,18)19)12(33-37(23,24)25)11(8(9)16)32-36(20,21)22/h6-12,15-16H,3H2,1-2H3,(H,26,27)(H2,17,18,19)(H2,20,21,22)(H2,23,24,25)/t7-,8-,9-,10+,11-,12-/m0/s1
InChI Key RQQIRMLGKSPXSE-UQPICLANSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Bae YS, Cantley LG, Chen CS, Kim SR, Kwon KS, Rhee SG. (1998)
Activation of phospholipase C-gamma by phosphatidylinositol 3,4,5-trisphosphate.
J Biol Chem, 273 (8): 4465-9. [PMID:9468499]
2. Brady JD, Rich ED, Martens JR, Karpen JW, Varnum MD, Brown RL. (2006)
Interplay between PIP3 and calmodulin regulation of olfactory cyclic nucleotide-gated channels.
Proc Natl Acad Sci USA, 103 (42): 15635-40. [PMID:17032767]
3. Dong LQ, Landa LR, Wick MJ, Zhu L, Mukai H, Ono Y, Liu F. (2000)
Phosphorylation of protein kinase N by phosphoinositide-dependent protein kinase-1 mediates insulin signals to the actin cytoskeleton.
Proc Natl Acad Sci USA, 97 (10): 5089-94. [PMID:10792047]
4. Piechulek T, Rehlen T, Walliser C, Vatter P, Moepps B, Gierschik P. (2005)
Isozyme-specific stimulation of phospholipase C-gamma2 by Rac GTPases.
J Biol Chem, 280 (47): 38923-31. [PMID:16172125]
5. Walliser C, Retlich M, Harris R, Everett KL, Josephs MB, Vatter P, Esposito D, Driscoll PC, Katan M, Gierschik P et al.. (2008)
rac regulates its effector phospholipase Cgamma2 through interaction with a split pleckstrin homology domain.
J Biol Chem, 283 (44): 30351-62. [PMID:18728011]