IMPPAT Phytochemical information: 
8-[[(2S)-3,3-Dimethyloxiran-2-yl]methyl]-5,7-dimethoxychromen-2-one
8-[[(2S)-3,3-Dimethyloxiran-2-yl]methyl]-5,7-dimethoxychromen-2-one
Summary

SMILES: COc1cc(OC)c2c(c1C[C@@H]1OC1(C)C)oc(=O)cc2
InChI: InChI=1S/C16H18O5/c1-16(2)13(21-16)7-10-12(19-4)8-11(18-3)9-5-6-14(17)20-15(9)10/h5-6,8,13H,7H2,1-4H3/t13-/m0/s1
InChIKey: UOEQXGRDVIMHFZ-ZDUSSCGKSA-N
DeepSMILES: COcccOC))ccc6C[C@@H]OC3C)C))))))oc=O)cc6
Scaffold Graph/Node/Bond level: O=c1ccc2cccc(CC3CO3)c2o1
Scaffold Graph/Node level: OC1CCC2CCCC(CC3CO3)C2O1
Scaffold Graph level: CC1CCC2CCCC(CC3CC3)C2C1
Functional groups: cOC; C[C@@H]1OC1(C)C; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
sibiricin, Sibiricin
External chemical identifiers:
CID:CID_12315527; ZINC:ZINC000014708565; MolPort-035-705-775
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
8-[[(2S)-3,3-Dimethyloxiran-2-yl]methyl]-5,7-dimethoxychromen-2-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 290.32
Log P RDKit 2.53
Topological polar surface area (Å2) RDKit 61.2
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3
8-[[(2S)-3,3-Dimethyloxiran-2-yl]methyl]-5,7-dimethoxychromen-2-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.64
8-[[(2S)-3,3-Dimethyloxiran-2-yl]methyl]-5,7-dimethoxychromen-2-one
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.35
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No