Secondary metabolite: 2,3,4,5-Tetrahydro-2,7-dihydroxy-5,8,10,10-tetramethyl-2,5-methano-1-benzoxepin



2,3,4,5-Tetrahydro-2,7-dihydroxy-5,8,10,10-tetramethyl-2,5-methano-1-benzoxepin
Summary
Molecular formula: C15H20O3
SMILES: Oc1cc2c(cc1C)O[C@]1(C([C@]2(C)CC1)(C)C)O
InChI: InChI=1S/C15H20O3/c1-9-7-12-10(8-11(9)16)14(4)5-6-15(17,18-12)13(14,2)3/h7-8,16-17H,5-6H2,1-4H3/t14-,15-/m1/s1
InChIKey: KANVQRLDTGOSBL-HUUCEWRRSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Benzopyrans
Sub class: 1-benzopyrans
Synonymous chemical names:
2,3,4,5-tetrahydro-2,7-dihydroxy-5,8,10,10-tetramethyl-2,5-methano-1-benzoxepin, enokipodin a
Chemical structure download



2,3,4,5-Tetrahydro-2,7-dihydroxy-5,8,10,10-tetramethyl-2,5-methano-1-benzoxepin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 248.32
Log P RDKit 2.86
Topological polar surface area (Å2) RDKit 49.69
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 9
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.6
Shape complexity RDKit 0.6
Number of rotatable bonds SwissADME 0
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3



2,3,4,5-Tetrahydro-2,7-dihydroxy-5,8,10,10-tetramethyl-2,5-methano-1-benzoxepin
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’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.74



2,3,4,5-Tetrahydro-2,7-dihydroxy-5,8,10,10-tetramethyl-2,5-methano-1-benzoxepin
ADMET 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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.51
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes




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