IMPPAT Phytochemical information: 
20-Deoxocarnosol

20-Deoxocarnosol
Summary

SMILES: Oc1c(O)c(cc2c1[C@]13CCCC([C@@H]3C[C@@H]2OC1)(C)C)C(C)C
InChI: InChI=1S/C20H28O3/c1-11(2)12-8-13-14-9-15-19(3,4)6-5-7-20(15,10-23-14)16(13)18(22)17(12)21/h8,11,14-15,21-22H,5-7,9-10H2,1-4H3/t14-,15-,20+/m0/s1
InChIKey: XCVWKCGUFCXDHN-AUSJPIAWSA-N
DeepSMILES: OccO)cccc6[C@@]CCCC[C@@H]6C[C@@H]%10OC%10)))))C)C)))))))))CC)C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)C1CC3CCCCC23CO1
Scaffold Graph/Node level: C1CCC2C(C1)C1CC3CCCCC32CO1
Scaffold Graph level: C1CCC2C(C1)C1CCC23CCCCC3C1
Functional groups: cO; COC
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: Abietane diterpenoids|Icetexane diterpenoids
Synonymous chemical names:
20-deoxocarnosol
External chemical identifiers:
CID:CID_13855851; ChEMBL:CHEMBL491879; ZINC:ZINC000013383630; SureChEMBL:SCHEMBL9923663; MolPort-039-338-881
Chemical structure download


20-Deoxocarnosol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 316.44
Log P RDKit 4.76
Topological polar surface area (Å2) RDKit 49.69
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.15
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 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


20-Deoxocarnosol
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 0.734389


20-Deoxocarnosol
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 -4.93
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes