Secondary metabolite: Phellinstatin



Phellinstatin
Summary
Molecular formula: C39H26O15
SMILES: Oc1cc(=O)oc(c1)[C@@H]1[C@H](Oc2c1c(=O)oc(c2)/C=C/c1cc(O)c(cc1c1c(O)cc(oc1=O)/C=C/c1ccc(c(c1)O)O)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C39H26O15/c40-20-12-31(53-33(48)13-20)35-36-32(54-37(35)19-4-8-25(42)27(44)11-19)15-22(52-39(36)50)6-3-18-10-28(45)29(46)16-23(18)34-30(47)14-21(51-38(34)49)5-1-17-2-7-24(41)26(43)9-17/h1-16,35,37,40-47H/b5-1+,6-3+/t35-,37+/m0/s1
InChIKey: KAEWYNFUJFCGQA-UPSVAIHWSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Benzenoids
Class: Phenols
Sub class: Benzenediols
Synonymous chemical names:
phellinstatin
Chemical structure download



Phellinstatin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 734.62
Log P RDKit 5.46
Topological polar surface area (Å2) RDKit 261.7
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 39
Number of heavy atoms RDKit 54
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 37
Number of sp3 hybridized carbon atoms RDKit 2
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.05
Shape complexity RDKit 0.05
Number of rotatable bonds SwissADME 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 3
Number of aromatic rings RDKit 6
Total number of rings RDKit 7
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 7



Phellinstatin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 4
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Egan filter RDKit Bad
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 2
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.09



Phellinstatin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.93
Number of PAINS structural alerts SwissADME 1
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