IMPPAT Phytochemical information: 
Hyperforin
Hyperforin
Summary

SMILES: CC(=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]2(C(=O)[C@]1(C(=O)C(C)C)C(=O)C(=C2O)CC=C(C)C)CC=C(C)C)C
InChI: InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1
InChIKey: KGSZHKRKHXOAMG-HQKKAZOISA-N
DeepSMILES: CC=CCC[C@]C)[C@@H]CC=CC)C))))C[C@]C=O)[C@]6C=O)CC)C)))C=O)C=C6O))CC=CC)C))))))))CC=CC)C)))))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC2CCCC1C2=O
Scaffold Graph/Node level: OC1CCC2CCCC1C2O
Scaffold Graph level: CC1CCC2CCCC1C2C
Functional groups: CC(C(C)=O)=C(C)O; CC(C)=O; CC=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Monoterpenoids
NP Classifier Biosynthetic pathway: Polyketides|Terpenoids
NP Classifier Superclass: Meroterpenoids
NP Classifier Class: Polyprenylated cyclic polyketides (Hop meroterpenoids)
Synonymous chemical names:
hyperforin
External chemical identifiers:
CID:441298; ChEMBL:CHEMBL501711; ZINC:ZINC000100076763; SureChEMBL:SCHEMBL15557965
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Hyperforin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 536.8
Log P RDKit 8.99
Topological polar surface area (Å2) RDKit 71.44
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 22
Shape complexity RDKit 0.63
Number of rotatable bonds RDKit 11
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Hyperforin
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 4
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 0.2112
Hyperforin
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -2.74
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 2.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
Hyperforin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000215832MAPK1700
ENSP00000263025MAPK3700
ENSP00000270202AKT1786
ENSP00000306512IL8938
ENSP00000336528NR1I2986
ENSP00000337915CYP3A4843
ENSP00000340913TRPC6870
ENSP00000354612PTGS1800
ENSP00000361125VEGFA800
ENSP00000361405MMP9800
ENSP00000363512ALOX5800
ENSP00000369050CYP1A1722
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.