Secondary metabolite: Epicorazine A



Epicorazine A
Summary
Molecular formula: C18H16N2O6S2
SMILES: O[C@@H]1C=CC(=O)[C@H]2[C@@H]1N1C(=O)[C@@]34SS[C@@]1(C2)C(=O)N4[C@H]1[C@@H](C3)C(=O)C=C[C@@H]1O
InChI: InChI=1S/C18H16N2O6S2/c21-9-1-3-11(23)13-7(9)5-17-15(25)20-14-8(10(22)2-4-12(14)24)6-18(20,28-27-17)16(26)19(13)17/h1-4,7-8,11-14,23-24H,5-6H2/t7-,8-,11-,12+,13-,14-,17-,18-/m0/s1
InChIKey: RCODXLGTKJXDNC-ZSWOQMQUSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Diazinanes
Sub class: Piperazines
Synonymous chemical names:
epicorazine a
Chemical structure download



Epicorazine A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 420.47
Log P RDKit -0.78
Topological polar surface area (Å2) RDKit 115.22
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.44
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.56
Shape complexity RDKit 0.56
Number of rotatable bonds SwissADME 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 7
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 5
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7



Epicorazine 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 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer’s 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.49



Epicorazine A
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -10.08
Number of PAINS structural alerts SwissADME 0
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