IMPPAT Phytochemical information: 
Cheilanthatriol

Cheilanthatriol
Summary

SMILES: OC/C=C(\CC[C@@H]1[C@@](C)(O)CC[C@H]2[C@@]1(C)C[C@H](O)[C@@H]1[C@]2(C)CCCC1(C)C)/C
InChI: InChI=1S/C25H44O3/c1-17(11-15-26)8-9-20-24(5)16-18(27)21-22(2,3)12-7-13-23(21,4)19(24)10-14-25(20,6)28/h11,18-21,26-28H,7-10,12-16H2,1-6H3/b17-11-/t18-,19+,20-,21-,23+,24+,25-/m0/s1
InChIKey: QVSOUBMAPDSQTQ-DWYUODLQSA-N
DeepSMILES: OC/C=C\CC[C@@H][C@@]C)O)CC[C@H][C@@]6C)C[C@H]O)[C@@H][C@]6C)CCCC6C)C)))))))))))))))))/C
Scaffold Graph/Node/Bond level: C1CCC2C(C1)CCC1CCCCC12
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCCC12
Functional groups: CO; C/C=C(\C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesterterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesterterpenoids
NP Classifier Class: Cheilanthane sesterterpenoids
Synonymous chemical names:
Cheilanthatriol, cheilanthatriol
External chemical identifiers:
CID:CID_21629962
Chemical structure download


Cheilanthatriol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 392.62
Log P RDKit 5.09
Topological polar surface area (Å2) RDKit 60.69
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 25
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.28
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 23
Shape complexity RDKit 0.92
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Cheilanthatriol
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 1
Ghose filter RDKit Failed
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 0.584332


Cheilanthatriol
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 -4.77
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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