Secondary metabolite: Hypocrellin D



Hypocrellin D
Summary
Molecular formula: C30H26O12
SMILES: COc1c(O)c2C(=O)C=C(C(=O)c2c2c1C[C@](C)(O)[C@@H](c1c2c2C(=O)C(=CC(=O)c2c(c1OC)O)OC)C(=O)C)OC
InChI: InChI=1S/C30H26O12/c1-10(31)23-22-19(21-18(27(37)29(22)42-6)13(33)8-15(40-4)25(21)35)16-11(9-30(23,2)38)28(41-5)26(36)17-12(32)7-14(39-3)24(34)20(16)17/h7-8,23,36-38H,9H2,1-6H3/t23-,30+/m1/s1
InChIKey: UVHNWRDTZAYVST-DJUQAAIZSA-N
Chemical classification
Kingdom: Organic compounds
Super class: Benzenoids
Class: Naphthalenes
Sub class: Naphthoquinones
Synonymous chemical names:
hypocrellin d
Chemical structure download



Hypocrellin D
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 578.53
Log P RDKit 2.58
Topological polar surface area (Å2) RDKit 182.96
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 21
Number of sp3 hybridized carbon atoms RDKit 9
Fraction of sp3 hybridized carbon atoms (Fsp3) RDKit 0.3
Shape complexity RDKit 0.3
Number of rotatable bonds SwissADME 5
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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



Hypocrellin D
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Egan filter RDKit Bad
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 0.47



Hypocrellin D
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -7.62
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
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