IMPPAT Phytochemical information: 
Lupulone
Lupulone
Summary

SMILES: CC(=CCC1=C(O)C(C(=O)C(=C1O)C(=O)CC(C)C)(CC=C(C)C)CC=C(C)C)C
InChI: InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28-29H,10,13-15H2,1-8H3
InChIKey: LSDULPZJLTZEFD-UHFFFAOYSA-N
DeepSMILES: CC=CCC=CO)CC=O)C=C6O))C=O)CCC)C))))))CC=CC)C))))CC=CC)C)))))))))C
Scaffold Graph/Node/Bond level: O=C1C=CC=CC1
Scaffold Graph/Node level: OC1CCCCC1
Scaffold Graph level: CC1CCCCC1
Functional groups: CC=C(C)C; CC(=O)C1=C(O)C(C)=C(O)CC1=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Vinylogous acids
NP Classifier Biosynthetic pathway: Polyketides|Terpenoids
NP Classifier Superclass: Meroterpenoids
NP Classifier Class: Polyprenylated cyclic polyketides (Hop meroterpenoids)
Synonymous chemical names:
Lupulone, lupulone, lupulon
External chemical identifiers:
CID:CID_68051; ChEBI:CHEBI:6574; SureChEMBL:SCHEMBL819253; MolPort-046-196-932
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lupulone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 414.59
Log P RDKit 6.86
Topological polar surface area (Å2) RDKit 74.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 30
Number of heteroatoms RDKit 4
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 12
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1
Lupulone
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.318972
Lupulone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
Solubility class [ESOL] SwissADME Poorly 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 -4.05
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes