IMPPAT Phytochemical information: 
(1R,2R,3S,6S,10S,11S,13S,14S)-11-(1-Hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.02,6.07,13.010,14]pentadecane-3,9,14-triol
(1R,2R,3S,6S,10S,11S,13S,14S)-11-(1-Hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.02,6.07,13.010,14]pentadecane-3,9,14-triol
Summary

SMILES: OCC([C@@H]1C[C@@H]2[C@@]3([C@@]1(C)C1(O)O[C@@H]3[C@H]3[C@@H](C2(C1)C)CC[C@]3(C)O)O)C
InChI: InChI=1S/C20H32O5/c1-10(8-21)12-7-13-16(2)9-19(23)18(12,4)20(13,24)15(25-19)14-11(16)5-6-17(14,3)22/h10-15,21-24H,5-9H2,1-4H3/t10?,11-,12-,13-,14+,15+,16?,17-,18+,19?,20+/m0/s1
InChIKey: RZCWUZMNOGOMNA-BLACLICWSA-N
DeepSMILES: OCC[C@@H]C[C@@H][C@@][C@@]5C)CO)O[C@@H]5[C@H][C@@H]C9C7)C))CC[C@]5C)O))))))))))O)))))C
Scaffold Graph/Node/Bond level: C1CC2C3CC4OC(C2C1)C1C4CCC31
Scaffold Graph/Node level: C1CC2C3CC4OC(C2C1)C1C4CCC31
Scaffold Graph level: C1CC2C3CC4CC(C2C1)C1C4CCC31
Functional groups: CO; CC(O)(C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Sesquiterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
Synonymous chemical names:
cinncassiol d1
External chemical identifiers:
CID:CID_46173968
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2R,3S,6S,10S,11S,13S,14S)-11-(1-Hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.02,6.07,13.010,14]pentadecane-3,9,14-triol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.47
Log P RDKit 1.28
Topological polar surface area (Å2) RDKit 90.15
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.55
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 20
Shape complexity RDKit 1
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(1R,2R,3S,6S,10S,11S,13S,14S)-11-(1-Hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.02,6.07,13.010,14]pentadecane-3,9,14-triol
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.601019
(1R,2R,3S,6S,10S,11S,13S,14S)-11-(1-Hydroxypropan-2-yl)-3,7,10-trimethyl-15-oxapentacyclo[7.5.1.02,6.07,13.010,14]pentadecane-3,9,14-triol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.78
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 Yes