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)C; CC(=O)C; CC(C)=O; CC(=C(O)C)C(=O)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: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
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Drug-likeness
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 0.211192
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ADME 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
Number of Brenk structural alerts SwissADME 2
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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000182ENSG00000023839ABCC21244ChEMBL
TAR_EXP_000018ENSG00000282301CYP3A7-CYP3A51P100861540ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_001520ENSG00000108576SLC6A46532BindingDB, ChEMBL
TAR_EXP_001665ENSG00000111424VDR7421NPASS
TAR_EXP_001629ENSG00000137672TRPC67225ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001519ENSG00000142319SLC6A36531BindingDB, ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530BindingDB, ChEMBL
TAR_EXP_001500ENSG00000021461CYP3A4364816ChEMBL
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL, NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000473ENSG00000096717SIRT123411BindingDB, ChEMBL
TAR_EXP_000281ENSG00000106258CYP3A51577ChEMBL
TAR_EXP_000445ENSG00000068903SIRT222933BindingDB, ChEMBL
TAR_EXP_000313ENSG00000150768DLAT1737ChEMBL
TAR_EXP_000572ENSG00000108773KAT2A2648ChEMBL, NPASS
TAR_EXP_001914ENSG00000148344PTGES9536BindingDB, ChEMBL