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.
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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)
InChI Key OEKHZIJBKVQWQC-UHFFFAOYSA-N
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
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