IMPPAT Phytochemical information: 
Lophirone A
Lophirone A
Summary

SMILES: Oc1ccc(cc1)C(C(c1coc2c(c1=O)ccc(c2)O)C(=O)c1ccc(cc1O)O)c1ccc(cc1)O
InChI: InChI=1S/C30H22O8/c31-18-5-1-16(2-6-18)27(17-3-7-19(32)8-4-17)28(30(37)22-11-9-20(33)13-25(22)35)24-15-38-26-14-21(34)10-12-23(26)29(24)36/h1-15,27-28,31-35H
InChIKey: ZPIXFZZVVJUNDO-UHFFFAOYSA-N
DeepSMILES: Occcccc6))CCccoccc6=O))cccc6)O)))))))))C=O)cccccc6O)))O)))))))cccccc6))O
Scaffold Graph/Node/Bond level: O=C(c1ccccc1)C(c1coc2ccccc2c1=O)C(c1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC1C2CCCCC2OCC1C(C(O)C1CCCCC1)C(C1CCCCC1)C1CCCCC1
Scaffold Graph level: CC1C2CCCCC2CCC1C(C(C)C1CCCCC1)C(C1CCCCC1)C1CCCCC1
Functional groups: cO; coc; c=O; cC(C)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Linear 1,3-diarylpropanoids
ClassyFire Subclass: Chalcones and dihydrochalcones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Chromanes
NP Classifier Class: Chromones
Synonymous chemical names:
lophirone a
External chemical identifiers:
CID:CID_5488805
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Lophirone A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 510.5
Log P RDKit 5.12
Topological polar surface area (Å2) RDKit 148.43
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
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 1
Stereochemical complexity RDKit 0.03
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 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 4
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 5
Total number of rings RDKit 5
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 5
Lophirone A
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 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 0.197737
Lophirone A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -5.83
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No