IMPPAT Phytochemical information: 
Protopseudohypericin
Protopseudohypericin
Summary

SMILES: OCC1=CC(=O)c2c(=C1)c1c3c(c2O)c(O)cc(c3c2c3c1c1=CC(=CC(=O)c1c(c3c(cc2O)O)O)C)O
InChI: InChI=1S/C30H18O9/c1-9-2-11-19(13(32)3-9)29(38)25-17(36)6-15(34)23-24-16(35)7-18(37)26-28(24)22(21(11)27(23)25)12-4-10(8-31)5-14(33)20(12)30(26)39/h2-7,31,34-39H,8H2,1H3
InChIKey: KBECZWWSHDRKOW-UHFFFAOYSA-N
DeepSMILES: OCC=CC=O)cc=C6)cccc6O))cO)ccc6ccc%10c=CC=CC=O)c6cc%10ccc%14O)))O)))O)))))C))))))))O
Scaffold Graph/Node/Bond level: O=c1cccc2c1cc1cccc3c4cccc5cc6c(=O)cccc6c(c54)c2c13
Scaffold Graph/Node level: OC1CCCC2C1CC1CCCC3C4CCCC5CC6C(O)CCCC6C(C54)C2C13
Scaffold Graph level: CC1CCCC2C1CC1CCCC3C4CCCC5CC6C(C)CCCC6C(C54)C2C13
Functional groups: CO; cO; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
ClassyFire Subclass: Phenanthrols
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
Synonymous chemical names:
hypericin,proto-pseudo, protopseudohypericin, Protopseudohypericin
External chemical identifiers:
CID:CID_171335
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Protopseudohypericin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 522.47
Log P RDKit 4.24
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 7
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 7
Total number of rings RDKit 7
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 7
Protopseudohypericin
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 0.122802
Protopseudohypericin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -7.68
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