Secondary metabolite: Epicorazine C



Epicorazine C
Summary
Molecular formula: C18H18N2O7S2
SMILES: O[C@H]1CC(=O)[C@H]2[C@@H]([C@H]1O)N1C(=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/C18H18N2O7S2/c21-8-1-2-9(22)12-6(8)4-17-16(27)20-13-7(10(23)3-11(24)14(13)25)5-18(20,29-28-17)15(26)19(12)17/h1-2,6-7,9,11-14,22,24-25H,3-5H2/t6-,7+,9+,11+,12+,13+,14+,17-,18-/m1/s1
InChIKey: NCDIBOQDVNONGL-HISJFFBUSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Organoheterocyclic compounds
Class: Diazinanes
Sub class: Piperazines
Synonymous chemical names:
epicorazine c
Chemical structure download



Epicorazine C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 438.48
Log P RDKit -1.58
Topological polar surface area (Å2) RDKit 135.45
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 2
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.5
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 12
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.67
Shape complexity RDKit 0.67
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 1
Number of saturated heterocycles RDKit 5
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7



Epicorazine C
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 0.38



Epicorazine C
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 -10.89
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