IMPPAT Phytochemical information: 
Tomentonone

Tomentonone
Summary

SMILES: CC(=CCC1(CC=C(C)C)C(=O)CCc2c1c(=O)c1c(o2)cc(cc1O)O)C
InChI: InChI=1S/C23H26O5/c1-13(2)7-9-23(10-8-14(3)4)19(26)6-5-17-21(23)22(27)20-16(25)11-15(24)12-18(20)28-17/h7-8,11-12,24-25H,5-6,9-10H2,1-4H3
InChIKey: RUATYZIIFOANLT-UHFFFAOYSA-N
DeepSMILES: CC=CCCCC=CC)C))))C=O)CCcc6c=O)cco6)cccc6O)))O))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1CCc2oc3ccccc3c(=O)c2C1
Scaffold Graph/Node level: OC1CCC2OC3CCCCC3C(O)C2C1
Scaffold Graph level: CC1CCC2CC3CCCCC3C(C)C2C1
Functional groups: CC=C(C)C; CC(=O)C; c=O; coc; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
Tomentonone, tomentonone
External chemical identifiers:
CID:CID_132821921; ZINC:ZINC000014768077
Chemical structure download


Tomentonone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 382.46
Log P RDKit 4.67
Topological polar surface area (Å2) RDKit 87.74
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 5
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 14
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.39
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Tomentonone
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 0.750429


Tomentonone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.18
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No