IMPPAT Phytochemical information: 
Tomentolide A
Tomentolide A
Summary

SMILES: C[C@@H]1Oc2c(C(=O)[C@@H]1C)c1OC(C)(C)C=Cc1c1c2c(cc(=O)o1)c1ccccc1
InChI: InChI=1S/C25H22O5/c1-13-14(2)28-24-19-17(15-8-6-5-7-9-15)12-18(26)29-22(19)16-10-11-25(3,4)30-23(16)20(24)21(13)27/h5-14H,1-4H3/t13-,14+/m1/s1
InChIKey: JCKXVEVCXNXGQW-KGLIPLIRSA-N
DeepSMILES: C[C@@H]OccC=O)[C@@H]6C)))cOCC)C)C=Cc6cc%10ccc=O)o6)))cccccc6
Scaffold Graph/Node/Bond level: O=C1CCOc2c1c1c(c3oc(=O)cc(-c4ccccc4)c23)C=CCO1
Scaffold Graph/Node level: OC1CC(C2CCCCC2)C2C(O1)C1CCCOC1C1C(O)CCOC12
Scaffold Graph level: CC1CC(C2CCCCC2)C2C(C1)C1CCCCC1C1C(C)CCCC12
Functional groups: cOC; cC(=O)C; cC=CC; c=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Neoflavonoids
ClassyFire Subclass: Prenylated neoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Pyranocoumarins
Synonymous chemical names:
tomentolide a, Tomentolide A
External chemical identifiers:
CID:CID_44257541; ZINC:ZINC000014768068
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Tomentolide A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 402.45
Log P RDKit 5.24
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 25
Number of heavy atoms RDKit 30
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 0.08
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.28
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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
Tomentolide A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 0.52
Tomentolide A
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