Secondary metabolite: 7,13,14-Trihydroxy-4-cadinen-15-oic acid methyl ester



7,13,14-Trihydroxy-4-cadinen-15-oic acid methyl ester
Summary
Molecular formula: C16H26O5
SMILES: OC[C@H]([C@@H]1CC[C@@](C2C1C=C(CC2)C(=O)OC)(O)CO)C
InChI: InChI=1S/C16H26O5/c1-10(8-17)12-5-6-16(20,9-18)14-4-3-11(7-13(12)14)15(19)21-2/h7,10,12-14,17-18,20H,3-6,8-9H2,1-2H3/t10-,12+,13?,14?,16-/m1/s1
InChIKey: QUILJUJWEWGRMX-SBRPMQCUSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Sesquiterpenoids
Synonymous chemical names:
7,13,14-trihydroxy-4-cadinen-15-oic acid methyl ester
Chemical structure download



7,13,14-Trihydroxy-4-cadinen-15-oic acid methyl ester
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 298.38
Log P RDKit 0.87
Topological polar surface area (Å2) RDKit 86.99
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 13
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.81
Shape complexity RDKit 0.81
Number of rotatable bonds SwissADME 5
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
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 2



7,13,14-Trihydroxy-4-cadinen-15-oic acid methyl ester
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
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 0.67



7,13,14-Trihydroxy-4-cadinen-15-oic acid methyl ester
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 -7.6
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




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