IMPPAT Phytochemical information: 
(1R,2S,4R,7R,10S,13R)-6-(hydroxymethyl)-2,6,12-trimethyltetracyclo[11.2.1.01,10.02,7]hexadec-11-en-4-ol
(1R,2S,4R,7R,10S,13R)-6-(hydroxymethyl)-2,6,12-trimethyltetracyclo[11.2.1.01,10.02,7]hexadec-11-en-4-ol
Summary

SMILES: OCC1(C)C[C@H](O)C[C@]2([C@H]1CC[C@@H]1[C@@]32CC[C@H](C3)C(=C1)C)C
InChI: InChI=1S/C20H32O2/c1-13-8-15-4-5-17-18(2,12-21)10-16(22)11-19(17,3)20(15)7-6-14(13)9-20/h8,14-17,21-22H,4-7,9-12H2,1-3H3/t14-,15+,16+,17+,18?,19+,20-/m1/s1
InChIKey: OXKYBEZXRLIPKC-LMMYPSSLSA-N
DeepSMILES: OCCC)C[C@H]O)C[C@][C@H]6CC[C@@H][C@]6CC[C@H]C5)C=C7)C))))))))))C
Scaffold Graph/Node/Bond level: C1=CC2CCC3CCCCC3C23CCC1C3
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCC3CCC12C3
Scaffold Graph level: C1CCC2C(C1)CCC1CCC3CCC12C3
Functional groups: CO; CC(=CC)C
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: Aphidicolane diterpenoids
Synonymous chemical names:
oryzalexin s
External chemical identifiers:
CID:CID_90658877
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(1R,2S,4R,7R,10S,13R)-6-(hydroxymethyl)-2,6,12-trimethyltetracyclo[11.2.1.01,10.02,7]hexadec-11-en-4-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 304.47
Log P RDKit 3.92
Topological polar surface area (Å2) RDKit 40.46
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.9
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
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 4
(1R,2S,4R,7R,10S,13R)-6-(hydroxymethyl)-2,6,12-trimethyltetracyclo[11.2.1.01,10.02,7]hexadec-11-en-4-ol
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.72
(1R,2S,4R,7R,10S,13R)-6-(hydroxymethyl)-2,6,12-trimethyltetracyclo[11.2.1.01,10.02,7]hexadec-11-en-4-ol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.32
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes