IMPPAT Phytochemical information: 
Lettucenin A

Lettucenin A
Summary

SMILES: O=Cc1c(=O)oc2-c1ccc(c1c2C(=C)CC1)C
InChI: InChI=1S/C15H12O3/c1-8-3-6-11-12(7-16)15(17)18-14(11)13-9(2)4-5-10(8)13/h3,6-7H,2,4-5H2,1H3
InChIKey: PATCUDSVUMFCMB-UHFFFAOYSA-N
DeepSMILES: O=Ccc=O)oc-c5ccccc7C=C)CC5)))))C
Scaffold Graph/Node/Bond level: C=C1CCc2cccc3cc(=O)oc-3c21
Scaffold Graph/Node level: CC1CCC2CCCC3CC(O)OC3C12
Scaffold Graph level: CC1CC2CCCC3CCC(C)C3C2C1
Functional groups: cC=O; c=O; coc; cC(=C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Cycloheptafurans
Synonymous chemical names:
13-oxo-1(10),4(15),5,7(11),8-guaiapentaen-12,6-olide, lettucenin a
External chemical identifiers:
CID:CID_178999; ChEBI:CHEBI:174240
Chemical structure download


Lettucenin A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 240.26
Log P RDKit 2.82
Topological polar surface area (Å2) RDKit 47.28
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 3
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 12
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
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


Lettucenin A
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.719937


Lettucenin A
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.05
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No