D-myo-Inositol 1,4,5-trisphosphate

Basic Info

Common NameD-myo-Inositol 1,4,5-trisphosphate(F01702)
2D Structure
FRCD IDF01702
CAS Number85166-31-0
PubChem CID439456
FormulaC6H15O15P3
IUPAC Name

[(1R,2S,3R,4R,5S,6R)-2,3,5-trihydroxy-4,6-diphosphonooxycyclohexyl] dihydrogen phosphate

InChI Key

MMWCIQZXVOZEGG-XJTPDSDZSA-N

InChI

InChI=1S/C6H15O15P3/c7-1-2(8)5(20-23(13,14)15)6(21-24(16,17)18)3(9)4(1)19-22(10,11)12/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1-,2+,3+,4-,5-,6-/m1/s1

Canonical SMILES

C1(C(C(C(C(C1OP(=O)(O)O)O)OP(=O)(O)O)OP(=O)(O)O)O)O

Isomeric SMILES

[C@H]1([C@@H]([C@H]([C@@H]([C@H]([C@@H]1OP(=O)(O)O)O)OP(=O)(O)O)OP(=O)(O)O)O)O

Synonyms
        
            inositol 1,4,5-trisphosphate
        
            1,4,5-Insp3
        
            InsP3
        
            1D-myo-Inositol 1,4,5-trisphosphate
        
            d-myo-inositol-1,4,5-triphosphate
        
            D-myo-Inositol 1,4,5-trisphosphate
        
            IP3
        
            Ins(1,4,5)P3
        
            85166-31-0
        
            CHEMBL279107
Classifies
                

                  
                    Predicted: Pesticide
Update DateNov 13, 2018 16:49

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassAlcohols and polyols
Intermediate Tree NodesCyclic alcohols and derivatives - Cyclitols and derivatives
Direct ParentInositol phosphates
Alternative Parents
Molecular FrameworkAliphatic homomonocyclic compounds
SubstituentsInositol phosphate - Monoalkyl phosphate - Cyclohexanol - Alkyl phosphate - Phosphoric acid ester - Organic phosphoric acid derivative - Secondary alcohol - Polyol - Organic oxide - Hydrocarbon derivative - Aliphatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as inositol phosphates. These are compounds containing a phosphate group attached to an inositol (or cyclohexanehexol) moiety.

Properties

Property NameProperty Value
Molecular Weight420.092
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count15
Rotatable Bond Count6
Complexity574
Monoisotopic Mass419.962
Exact Mass419.962
XLogP-7
Formal Charge0
Heavy Atom Count24
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8479
Human Intestinal AbsorptionHIA-0.8832
Caco-2 PermeabilityCaco2-0.7234
P-glycoprotein SubstrateNon-substrate0.7441
P-glycoprotein InhibitorNon-inhibitor0.8584
Non-inhibitor0.9895
Renal Organic Cation TransporterNon-inhibitor0.9412
Distribution
Subcellular localizationMitochondria0.7880
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8138
CYP450 2D6 SubstrateNon-substrate0.8465
CYP450 3A4 SubstrateNon-substrate0.6386
CYP450 1A2 InhibitorNon-inhibitor0.9175
CYP450 2C9 InhibitorNon-inhibitor0.9120
CYP450 2D6 InhibitorNon-inhibitor0.9193
CYP450 2C19 InhibitorNon-inhibitor0.9051
CYP450 3A4 InhibitorNon-inhibitor0.9633
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9736
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9094
Non-inhibitor0.9157
AMES ToxicityNon AMES toxic0.8541
CarcinogensNon-carcinogens0.7577
Fish ToxicityHigh FHMT0.7148
Tetrahymena Pyriformis ToxicityHigh TPT0.6526
Honey Bee ToxicityHigh HBT0.7915
BiodegradationNot ready biodegradable0.7532
Acute Oral ToxicityIII0.7170
Carcinogenicity (Three-class)Non-required0.6017
Model Value Unit
Absorption
Aqueous solubility-1.9459LogS
Caco-2 Permeability-1.0814LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1296LD50, mol/kg
Fish Toxicity1.5406pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.0100pIGC50, ug/L

References

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The thiol reagent, thimerosal, evokes Ca2+ spikes in HeLa cells by sensitizingthe inositol 1,4,5-trisphosphate receptor.J Biol Chem1992 Dec 151334081
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