IMPPAT Phytochemical information: 
8-(3-Oxo-1-butenyl)-5,7-dimethoxy-2H-1-benzopyran-2-one

8-(3-Oxo-1-butenyl)-5,7-dimethoxy-2H-1-benzopyran-2-one
Summary

SMILES: COc1cc(OC)c2c(c1/C=C/C(=O)C)oc(=O)cc2
InChI: InChI=1S/C15H14O5/c1-9(16)4-5-10-12(18-2)8-13(19-3)11-6-7-14(17)20-15(10)11/h4-8H,1-3H3/b5-4+
InChIKey: MNCJDGPGSIIWJA-SNAWJCMRSA-N
DeepSMILES: COcccOC))ccc6/C=C/C=O)C)))))oc=O)cc6
Scaffold Graph/Node/Bond level: O=c1ccc2ccccc2o1
Scaffold Graph/Node level: OC1CCC2CCCCC2O1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: cOC; c/C=C/C(C)=O; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
Toddalenone, toddalenone
External chemical identifiers:
CID:CID_101893838; ChEMBL:CHEMBL3426685; ZINC:ZINC000014767821
Chemical structure download


8-(3-Oxo-1-butenyl)-5,7-dimethoxy-2H-1-benzopyran-2-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 274.27
Log P RDKit 2.41
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 15
Number of heavy atoms RDKit 20
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 12
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
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 2


8-(3-Oxo-1-butenyl)-5,7-dimethoxy-2H-1-benzopyran-2-one
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 Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.63


8-(3-Oxo-1-butenyl)-5,7-dimethoxy-2H-1-benzopyran-2-one
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 -6.58
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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