compound 5 [Noble et al., 1992]   Click here for help

GtoPdb Ligand ID: 8844

Synonyms: myo-inositol 1-phosphate 4,5-bisphosphorothioate
Compound class: Synthetic organic
Comment: Compound 5 is a non-hydrolysable phosphorothioates analogue of inositol phosphate 3 (IP3) [1]. As such this compound would be expected to behave as a substrate for IP3 metabolising inositol polyphosphate-5-phosphatase enzymes, with a negative effect on enzyme activity, and effect sustained release of intracellular calcium.
Note that we show the sugar moiety without stereochemistry.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 13
Hydrogen bond donors 9
Rotatable bonds 6
Topological polar surface area 320.44
Molecular weight 451.92
XLogP -3.39
No. Lipinski's rules broken 2
Click here for help
Canonical SMILES OC1C(OP(=S)(O)O)C(OP(=S)(O)O)C(C(C1O)OP(=O)(O)O)O
Isomeric SMILES OC1C(OP(=S)(O)O)C(OP(=S)(O)O)C(C(C1O)OP(=O)(O)O)O
InChI InChI=1S/C6H15O13P3S2/c7-1-2(8)5(18-21(13,14)23)6(19-22(15,16)24)3(9)4(1)17-20(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,23)(H2,15,16,24)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
[3,4-bis(dihydroxyphosphinothioyloxy)-2,5,6-trihydroxycyclohexyl] dihydrogen phosphate
Synonyms Click here for help
myo-inositol 1-phosphate 4,5-bisphosphorothioate
Database Links Click here for help
ChEMBL Ligand CHEMBL1161242
GtoPdb PubChem SID 252827501
PubChem CID 15931446
Search Google for chemical match using the InChIKey OEKHZIJBKVQWQC-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OEKHZIJBKVQWQC
UniChem Compound Search for chemical match using the InChIKey OEKHZIJBKVQWQC-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OEKHZIJBKVQWQC-UHFFFAOYSA-N