Secondary metabolite: 1,2,6,10-Tetrahydroxy-3,9-epoxy-14-nor-5(15)-eudesmane



1,2,6,10-Tetrahydroxy-3,9-epoxy-14-nor-5(15)-eudesmane
Summary
Molecular formula: C14H22O5
SMILES: CC([C@@H]1C[C@H]2O[C@H]3C(=C)[C@@H]([C@@H]1O)[C@]2(O)[C@@H]([C@H]3O)O)C
InChI: InChI=1S/C14H22O5/c1-5(2)7-4-8-14(18)9(10(7)15)6(3)12(19-8)11(16)13(14)17/h5,7-13,15-18H,3-4H2,1-2H3/t7-,8+,9-,10+,11-,12-,13+,14-/m0/s1
InChIKey: GUOWYTGCMUSCDT-DOTWCUCFSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organic oxygen compounds
Class: Organooxygen compounds
Sub class: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
1,2,6,10-tetrahydroxy-3,9-epoxy-14-nor-5(15)-eudesmane
Chemical structure download



1,2,6,10-Tetrahydroxy-3,9-epoxy-14-nor-5(15)-eudesmane
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 270.32
Log P RDKit -0.57
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 14
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.57
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 12
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.86
Shape complexity RDKit 0.86
Number of rotatable bonds SwissADME 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
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 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



1,2,6,10-Tetrahydroxy-3,9-epoxy-14-nor-5(15)-eudesmane
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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Egan filter RDKit Good
Pfizer’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 0
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.48



1,2,6,10-Tetrahydroxy-3,9-epoxy-14-nor-5(15)-eudesmane
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.58
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 Yes




Designed by R.P. Vivek-Ananth, M Karthikeyan and Ajaya Kumar Sahoo