Secondary metabolite: Erinacine R



Erinacine R
Summary
Molecular formula: C27H38O9
SMILES: O=CC1=C[C@H](O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)[C@]2([C@H](C[C@H]1OC(=O)C)C1=C(CC[C@@]1(C(=O)C2)C)C(C)C)C
InChI: InChI=1S/C27H38O9/c1-13(2)16-6-7-26(4)20(31)10-27(5)17(22(16)26)9-19(35-14(3)29)15(11-28)8-21(27)36-25-24(33)23(32)18(30)12-34-25/h8,11,13,17-19,21,23-25,30,32-33H,6-7,9-10,12H2,1-5H3/t17-,18-,19-,21+,23+,24-,25+,26-,27-/m1/s1
InChIKey: SRARCXKPZDYZMB-GYGNKXPFSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Lipids and lipid-like molecules
Class: Prenol lipids
Sub class: Diterpenoids
Synonymous chemical names:
erinacine r
Chemical structure download



Erinacine R
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 506.59
Log P RDKit 1.62
Topological polar surface area (Å2) RDKit 139.59
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 20
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.74
Shape complexity RDKit 0.74
Number of rotatable bonds SwissADME 6
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 1
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 R
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
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 0.29



Erinacine R
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -9.57
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 No
P-glycoprotein substrate SwissADME No




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