Secondary metabolite: Hypholomine B



Hypholomine B
Summary
Molecular formula: C26H18O10
SMILES: Oc1cc(=O)oc(c1)[C@@H]1[C@H](Oc2c1c(=O)oc(c2)/C=C/c1ccc(c(c1)O)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C26H18O10/c27-14-9-20(35-22(32)10-14)23-24-21(36-25(23)13-3-6-17(29)19(31)8-13)11-15(34-26(24)33)4-1-12-2-5-16(28)18(30)7-12/h1-11,23,25,27-31H/b4-1+/t23-,25+/m0/s1
InChIKey: CGMQDMKDINCGOB-NJYVMNEESA-N
Chemical classification
Kingdom: Organic compounds
Super class: Benzenoids
Class: Phenols
Sub class: Benzenediols
Synonymous chemical names:
hypholomine b
Chemical structure download



Hypholomine B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 490.42
Log P RDKit 3.56
Topological polar surface area (Å2) RDKit 170.8
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 2
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.08
Shape complexity RDKit 0.08
Number of rotatable bonds SwissADME 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5



Hypholomine B
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 Bad
Egan filter RDKit Bad
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 0.27



Hypholomine B
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.45
Number of PAINS structural alerts SwissADME 1
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 No




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