IMPPAT Phytochemical information: 
Labd-14-ene, 8,13-epoxy-, (13S)-

Labd-14-ene, 8,13-epoxy-, (13S)-
Summary

SMILES: C=C[C@@]1(C)CC[C@H]2[C@@](O1)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C
InChI: InChI=1S/C20H34O/c1-7-18(4)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)21-18/h7,15-16H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1
InChIKey: IGGWKHQYMAJOHK-HHUCQEJWSA-N
DeepSMILES: C=C[C@@]C)CC[C@H][C@@]O6)C)CC[C@@H][C@]6C)CCCC6C)C
Scaffold Graph/Node/Bond level: C1CCC2C(C1)CCC1OCCCC12
Scaffold Graph/Node level: C1CCC2C(C1)CCC1OCCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCCC12
Functional groups: COC; C=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Triterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Labdane diterpenoids|Norlabdane diterpenoids
Synonymous chemical names:
manoyl oxide, Manoyl oxide, Labd-14-ene, 8,13-epoxy-, (13S)-, mannoyl oxide, 13-epi-manoyl oxide
External chemical identifiers:
CID:CID_6432025; ZINC:ZINC000003153996; SureChEMBL:SCHEMBL3967644
Chemical structure download


Labd-14-ene, 8,13-epoxy-, (13S)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 290.49
Log P RDKit 5.74
Topological polar surface area (Å2) RDKit 9.23
Number of hydrogen bond acceptors RDKit 1
Number of hydrogen bond donors RDKit 0
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 5
Stereochemical complexity RDKit 0.25
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 2
Number of aliphatic heterocycles RDKit 1
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 2
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


Labd-14-ene, 8,13-epoxy-, (13S)-
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 0.559234


Labd-14-ene, 8,13-epoxy-, (13S)-
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 No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -3.86
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No