Secondary metabolite: Erinacine I



Erinacine I
Summary
Molecular formula: C22H32O4
SMILES: CC(=O)OCC1=C[C@]2(O[C@@H]1C[C@H]1[C@@]2(C)CC[C@@]2(C1=C(CC2)C(C)C)C)O
InChI: InChI=1S/C22H32O4/c1-13(2)16-6-7-20(4)8-9-21(5)17(19(16)20)10-18-15(12-25-14(3)23)11-22(21,24)26-18/h11,13,17-18,24H,6-10,12H2,1-5H3/t17-,18-,20-,21-,22-/m1/s1
InChIKey: WOKVOSAADLEXDD-ISMARYCFSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Diterpenoids
Synonymous chemical names:
erinacine i
Chemical structure download



Erinacine I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 360.49
Log P RDKit 4.14
Topological polar surface area (Å2) RDKit 55.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 17
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.77
Shape complexity RDKit 0.77
Number of rotatable bonds SwissADME 4
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4



Erinacine I
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer’s 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Number of Leadlikeness violations SwissADME 1
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61



Erinacine I
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.64
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 Yes
P-glycoprotein substrate SwissADME Yes




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