Secondary metabolite: Palustrisolide B



Palustrisolide B
Summary
Molecular formula: C37H56O8
SMILES: O=C(C[C@](CC(=O)O)(O)C)O[C@@H]1CC[C@]2([C@H](C1(C)C)CCC1=C2C[C@H](O)[C@]2([C@@]1(C)CC[C@@H]2[C@@H](C[C@@H]1OC(=O)C(=C1C)C)C)C)C
InChI: InChI=1S/C37H56O8/c1-20(16-26-21(2)22(3)32(42)44-26)23-12-15-36(8)24-10-11-27-33(4,5)29(45-31(41)19-34(6,43)18-30(39)40)13-14-35(27,7)25(24)17-28(38)37(23,36)9/h20,23,26-29,38,43H,10-19H2,1-9H3,(H,39,40)/t20-,23-,26+,27+,28+,29-,34+,35-,36+,37+/m1/s1
InChIKey: LBKWQFFXMHXISP-URPUTOFOSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub class: Steroid lactones
Synonymous chemical names:
palustrisolide b
Chemical structure download



Palustrisolide B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 628.85
Log P RDKit 6.52
Topological polar surface area (Å2) RDKit 130.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 37
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 30
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.81
Shape complexity RDKit 0.81
Number of rotatable bonds SwissADME 9
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5



Palustrisolide B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Egan filter RDKit Bad
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 3
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.2



Palustrisolide B
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
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 -6.23
Number of PAINS structural alerts SwissADME 0
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 Yes
P-glycoprotein substrate SwissADME Yes




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