IMPPAT Phytochemical information: 
Pseudohypericin
Pseudohypericin
Summary

SMILES: OCC1=CC(=O)c2c3c1c1C(=CC(=O)c4c1c1c3c3c(c2O)c(O)cc(c3c2c1c(c4O)c(O)cc2O)O)C
InChI: InChI=1S/C30H16O9/c1-7-2-9(32)19-23-15(7)16-8(6-31)3-10(33)20-24(16)28-26-18(12(35)5-14(37)22(26)30(20)39)17-11(34)4-13(36)21(29(19)38)25(17)27(23)28/h2-5,31,34-39H,6H2,1H3
InChIKey: NODGUBIGZKATOM-UHFFFAOYSA-N
DeepSMILES: OCC=CC=O)ccc6cC=CC=O)cc6cc%10ccc%14O))cO)ccc6cc%10cc%14O))cO)cc6O))))))))O))))))))))))C
Scaffold Graph/Node/Bond level: O=c1ccc2c3ccc(=O)c4cc5cccc6c7cccc8cc1c2c(c87)c(c56)c43
Scaffold Graph/Node level: OC1CCC2C3CCC(O)C4CC5CCCC6C7CCCC8CC1C2C(C87)C(C56)C43
Scaffold Graph level: CC1CCC2C3CCC(C)C4CC5CCCC6C7CCCC8CC1C2C(C87)C(C56)C43
Functional groups: CO; cO; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Pyrenes
ClassyFire Subclass: Benzopyrenes
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
pseudohypericin, Pseudohypericin, hypericin, pseudo
External chemical identifiers:
CID:CID_4978
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Pseudohypericin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 520.45
Log P RDKit 4.26
Topological polar surface area (Å2) RDKit 175.75
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 28
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.07
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 8
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 8
Total number of rings RDKit 8
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 8
Pseudohypericin
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
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.123094
Pseudohypericin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly 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 -6.31
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No