IMPPAT Phytochemical information: 
alpha-Toxicarol
alpha-Toxicarol
Summary

SMILES: COc1cc2OC[C@@H]3[C@H](c2cc1OC)C(=O)c1c(O3)c2C=CC(Oc2cc1O)(C)C
InChI: InChI=1S/C23H22O7/c1-23(2)6-5-11-15(30-23)8-13(24)20-21(25)19-12-7-16(26-3)17(27-4)9-14(12)28-10-18(19)29-22(11)20/h5-9,18-19,24H,10H2,1-4H3/t18-,19+/m1/s1
InChIKey: JLTNCZQNGBLBGO-MOPGFXCFSA-N
DeepSMILES: COcccOC[C@@H][C@H]c6cc%10OC)))))C=O)ccO6)cC=CCOc6cc%10O)))))C)C
Scaffold Graph/Node/Bond level: O=C1c2ccc3c(c2OC2COc4ccccc4C12)C=CCO3
Scaffold Graph/Node level: OC1C2CCC3OCCCC3C2OC2COC3CCCCC3C21
Scaffold Graph level: CC1C2CCC3CCCCC3C2CC2CCC3CCCCC3C21
Functional groups: cOC; cC(=O)C; cC=CC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Rotenoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavanones|Rotenoids
Synonymous chemical names:
Toxicarol, alpha-toxicarol, toxicarol
External chemical identifiers:
CID:CID_442826; ChEMBL:CHEMBL508992; ChEBI:CHEBI:9643; ZINC:ZINC000001684799; SureChEMBL:SCHEMBL4742046
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
alpha-Toxicarol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 410.42
Log P RDKit 3.71
Topological polar surface area (Å2) RDKit 83.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
alpha-Toxicarol
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 Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.807951
alpha-Toxicarol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -6.03
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No