IMPPAT Phytochemical information: 
5-Methoxy-8,8-dimethyl-4-oxopyrano[2,3-h]chromene-2-carboxylic acid
5-Methoxy-8,8-dimethyl-4-oxopyrano[2,3-h]chromene-2-carboxylic acid
Summary

SMILES: COc1cc2OC(C)(C)C=Cc2c2c1c(=O)cc(o2)C(=O)O
InChI: InChI=1S/C16H14O6/c1-16(2)5-4-8-10(22-16)7-11(20-3)13-9(17)6-12(15(18)19)21-14(8)13/h4-7H,1-3H3,(H,18,19)
InChIKey: CYENPHRRKQQAOP-UHFFFAOYSA-N
DeepSMILES: COcccOCC)C)C=Cc6cc%10c=O)cco6)C=O)O
Scaffold Graph/Node/Bond level: O=c1ccoc2c3c(ccc12)OCC=C3
Scaffold Graph/Node level: OC1CCOC2C1CCC1OCCCC12
Scaffold Graph level: CC1CCCC2C1CCC1CCCCC12
Functional groups: cOC; cC=CC; c=O; coc; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Chromanes
NP Classifier Class: Chromones
Synonymous chemical names:
Perforatic acid, perforatic acid
External chemical identifiers:
CID:CID_125232; ChEMBL:CHEMBL2164949
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5-Methoxy-8,8-dimethyl-4-oxopyrano[2,3-h]chromene-2-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 302.28
Log P RDKit 2.68
Topological polar surface area (Å2) RDKit 85.97
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 6
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 4
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
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
5-Methoxy-8,8-dimethyl-4-oxopyrano[2,3-h]chromene-2-carboxylic acid
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.917539
5-Methoxy-8,8-dimethyl-4-oxopyrano[2,3-h]chromene-2-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.60
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No