Secondary metabolite: Meshimakobnol A



Meshimakobnol A
Summary
Molecular formula: C20H12O8
SMILES: Oc1ccc(cc1O)/C=C/c1oc(=O)c2c(c1)oc(=O)c1c2cc(O)c(c1)O
InChI: InChI=1S/C20H12O8/c21-13-4-2-9(5-14(13)22)1-3-10-6-17-18(20(26)27-10)11-7-15(23)16(24)8-12(11)19(25)28-17/h1-8,21-24H/b3-1+
InChIKey: KKEIHFGUYDHUBS-HNQUOIGGSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Phenylpropanoids and polyketides
Class: Isocoumarins and derivatives
Synonymous chemical names:
meshimakobnol a, phelligridin d
Chemical structure download



Meshimakobnol A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 380.31
Log P RDKit 2.89
Topological polar surface area (Å2) RDKit 141.34
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 0
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds SwissADME 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



Meshimakobnol A
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 Bad
Pfizer’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.31



Meshimakobnol A
ADMET 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 -6.86
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No




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