IMPPAT Phytochemical information: 
Sikkimotoxin

Sikkimotoxin
Summary

SMILES: COc1cc2[C@H](O)[C@H]3COC(=O)[C@@H]3[C@@H](c2cc1OC)c1cc(OC)c(c(c1)OC)OC
InChI: InChI=1S/C23H26O8/c1-26-15-8-12-13(9-16(15)27-2)21(24)14-10-31-23(25)20(14)19(12)11-6-17(28-3)22(30-5)18(7-11)29-4/h6-9,14,19-21,24H,10H2,1-5H3/t14-,19+,20-,21-/m0/s1
InChIKey: JQNGRAVMNACCCG-MGNXDGSBSA-N
DeepSMILES: COccc[C@H]O)[C@H]COC=O)[C@@H]5[C@@H]c9cc%13OC)))))cccOC))ccc6)OC)))OC
Scaffold Graph/Node/Bond level: O=C1OCC2Cc3ccccc3C(c3ccccc3)C12
Scaffold Graph/Node level: OC1OCC2CC3CCCCC3C(C3CCCCC3)C21
Scaffold Graph level: CC1CCC2CC3CCCCC3C(C3CCCCC3)C12
Functional groups: cOC; CO; COC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan lactones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
sikkimotoxin
External chemical identifiers:
CID:CID_3010626; ChEMBL:CHEMBL2288931; ZINC:ZINC000033503715; FDASRS:P32T3N2QMR
Chemical structure download


Sikkimotoxin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 430.45
Log P RDKit 2.7
Topological polar surface area (Å2) RDKit 92.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Sikkimotoxin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.699695


Sikkimotoxin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.41
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No