Secondary metabolite: Laetirobin



Laetirobin
Summary
Molecular formula: C44H32O12
SMILES: CC(=O)c1cc2c(cc1O)OC1=C(CCC(C21)(c1cc2c(o1)cc(c(c2)C(=O)C)O)c1cc2c(o1)cc(c(c2)C(=O)C)O)c1cc2c(o1)cc(c(c2)C(=O)C)O
InChI: InChI=1S/C44H32O12/c1-18(45)26-7-22-10-38(53-35(22)14-31(26)49)25-5-6-44(40-11-23-8-27(19(2)46)32(50)15-36(23)54-40,41-12-24-9-28(20(3)47)33(51)16-37(24)55-41)42-30-13-29(21(4)48)34(52)17-39(30)56-43(25)42/h7-17,42,49-52H,5-6H2,1-4H3
InChIKey: SGSHORQVHJQLLG-UHFFFAOYSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Benzofurans
Synonymous chemical names:
laetirobin
Chemical structure download



Laetirobin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 752.73
Log P RDKit 9.23
Topological polar surface area (Å2) RDKit 197.85
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 44
Number of heavy atoms RDKit 56
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.02
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 36
Number of sp3 hybridized carbon atoms RDKit 8
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.18
Shape complexity RDKit 0.18
Number of rotatable bonds SwissADME 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 3
Number of aromatic rings RDKit 7
Total number of rings RDKit 9
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 9



Laetirobin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
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 0.11



Laetirobin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Insoluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -5.25
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