IMPPAT Phytochemical information: 
(+)-Totarol

(+)-Totarol
Summary

SMILES: CC(c1c(O)ccc2c1CCC1C2(C)CCCC1(C)C)C
InChI: InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3
InChIKey: ZRVDANDJSTYELM-UHFFFAOYSA-N
DeepSMILES: CCccO)cccc6CCCC6C)CCCC6C)C)))))))))))))))C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CCC1CCCCC21
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCCC12
Functional groups: cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Totarane diterpenoids
Synonymous chemical names:
trans-totarol
External chemical identifiers:
CID:CID_326995; ChEMBL:CHEMBL1999971; SureChEMBL:SCHEMBL1839596
Chemical structure download


(+)-Totarol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 286.46
Log P RDKit 5.55
Topological polar surface area (Å2) RDKit 20.23
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 1
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
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 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


(+)-Totarol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 0.717711


(+)-Totarol
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -3.28
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No