IMPPAT Phytochemical information: 
Tomentolide B
Tomentolide B
Summary

SMILES: CCCc1cc(=O)oc2c1c1OC(C)C(C(=O)c1c1c2C=CC(O1)(C)C)C
InChI: InChI=1S/C22H24O5/c1-6-7-13-10-15(23)26-19-14-8-9-22(4,5)27-20(14)17-18(24)11(2)12(3)25-21(17)16(13)19/h8-12H,6-7H2,1-5H3
InChIKey: QOFDITUHNAYYJC-UHFFFAOYSA-N
DeepSMILES: CCCccc=O)occ6cOCC)CC=O)c6cc%10C=CCO6)C)C))))))))C
Scaffold Graph/Node/Bond level: O=C1CCOc2c1c1c(c3oc(=O)ccc23)C=CCO1
Scaffold Graph/Node level: OC1CCC2C(O1)C1CCCOC1C1C(O)CCOC21
Scaffold Graph level: CC1CCC2C(C1)C1CCCCC1C1C(C)CCCC21
Functional groups: c=O; coc; cOC; cC(=O)C; cC=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Pyranocoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Pyranocoumarins|Simple coumarins
Synonymous chemical names:
Tomentolide B, tomentolide b
External chemical identifiers:
CID:CID_5321974
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Tomentolide B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 368.43
Log P RDKit 4.53
Topological polar surface area (Å2) RDKit 65.74
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4
Tomentolide B
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.73
Tomentolide B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.58
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No