IMPPAT Phytochemical information: 
Humulone

Humulone
Summary

SMILES: CC(=CCC1=C(O)[C@](C(=O)C(=C1O)C(=O)CC(C)C)(O)CC=C(C)C)C
InChI: InChI=1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/t21-/m1/s1
InChIKey: VMSLCPKYRPDHLN-OAQYLSRUSA-N
DeepSMILES: CC=CCC=CO)[C@]C=O)C=C6O))C=O)CCC)C))))))O)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; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbonyl compounds
NP Classifier Biosynthetic pathway: Polyketides|Terpenoids
NP Classifier Superclass: Meroterpenoids
NP Classifier Class: Polyprenylated cyclic polyketides (Hop meroterpenoids)
Synonymous chemical names:
humulon, humulone
External chemical identifiers:
CID:CID_442911; ChEMBL:CHEMBL3814665; ChEBI:CHEBI:5769; ZINC:ZINC000100071914; SureChEMBL:SCHEMBL144835
Chemical structure download


Humulone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 362.47
Log P RDKit 4.25
Topological polar surface area (Å2) RDKit 94.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 7
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


Humulone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.464702


Humulone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.54
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes


Humulone
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000356438PTGS2816
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.