IMPPAT Phytochemical information: 
Sibiricaphenone
Sibiricaphenone
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)C(=O)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI: InChI=1S/C20H28O11/c1-8(22)10-3-5-11(6-4-10)29-20-18(16(26)14(24)12(7-21)30-20)31-19-17(27)15(25)13(23)9(2)28-19/h3-6,9,12-21,23-27H,7H2,1-2H3/t9-,12+,13-,14+,15+,16-,17+,18+,19-,20+/m0/s1
InChIKey: FOOOHAFYCMYYBP-QLDOSHOCSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6))C=O)C)))))))[C@@H][C@H][C@@H]6O))O))O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc(OC2OCCCC2OC2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(OC2OCCCC2OC2CCCCO2)CC1
Scaffold Graph level: C1CCC(CC2CCCCC2CC2CCCCC2)CC1
Functional groups: CO; cO[C@@H](C)OC; cC(C)=O; CO[C@@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
sibiricaphenone
External chemical identifiers:
CID:CID_5321295; ZINC:ZINC000070457464
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Sibiricaphenone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 444.43
Log P RDKit -2.08
Topological polar surface area (Å2) RDKit 175.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.65
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Sibiricaphenone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.27
Sibiricaphenone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.35
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No