IMPPAT Phytochemical information: 
Protohypericin
Protohypericin
Summary

SMILES: CC1=CC(=O)c2c(=C1)c1c3c(c2O)c(O)cc(c3c2c3c1c1=CC(=CC(=O)c1c(c3c(cc2O)O)O)C)O
InChI: InChI=1S/C30H18O8/c1-9-3-11-19(13(31)5-9)29(37)25-17(35)7-15(33)23-24-16(34)8-18(36)26-28(24)22(21(11)27(23)25)12-4-10(2)6-14(32)20(12)30(26)38/h3-8,33-38H,1-2H3
InChIKey: DPKVSJZTYNGFAW-UHFFFAOYSA-N
DeepSMILES: CC=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; 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
NP Classifier Class: Naphthoquinones
Synonymous chemical names:
protohypericin, Protohypericin, hypericin,proto
External chemical identifiers:
CID:CID_164660
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Protohypericin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 506.47
Log P RDKit 5.05
Topological polar surface area (Å2) RDKit 155.52
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 8
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 0
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
Protohypericin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
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 0.123268
Protohypericin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
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 -6.70
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