IMPPAT Phytochemical information: 
Squamone
Squamone
Summary

SMILES: CCCCCCCCCCCCC(C1CCC(O1)C(CCCCCC(=O)CCCCC1CC(C(=O)O1)CC(=O)C)O)O
InChI: InChI=1S/C35H62O7/c1-3-4-5-6-7-8-9-10-11-14-21-31(38)33-23-24-34(42-33)32(39)22-15-12-13-18-29(37)19-16-17-20-30-26-28(25-27(2)36)35(40)41-30/h28,30-34,38-39H,3-26H2,1-2H3
InChIKey: PAFMHAFYJMTISR-UHFFFAOYSA-N
DeepSMILES: CCCCCCCCCCCCCCCCCO5)CCCCCCC=O)CCCCCCCC=O)O5))CC=O)C))))))))))))))))O))))))O
Scaffold Graph/Node/Bond level: O=C(CCCCCCC1CCCO1)CCCCC1CCC(=O)O1
Scaffold Graph/Node level: OC(CCCCCCC1CCCO1)CCCCC1CCC(O)O1
Scaffold Graph level: CC(CCCCCCC1CCCC1)CCCCC1CCC(C)C1
Functional groups: COC(=O)C; CC(C)=O; CO; COC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Fatty Acyls
ClassyFire Subclass: Fatty alcohols
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Linear polyketides
NP Classifier Class: Acetogenins
Synonymous chemical names:
Squamone, squamone
External chemical identifiers:
CID:CID_130901; ChEBI:CHEBI:171852
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Squamone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 594.87
Log P RDKit 7.56
Topological polar surface area (Å2) RDKit 110.13
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 35
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 32
Shape complexity RDKit 0.91
Number of rotatable bonds RDKit 26
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
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 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Squamone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.08
Squamone
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 -4.55
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes