IMPPAT Phytochemical information: 
5-hydroxy-2,2-dimethyl-3H-pyrano[3,2-g]chromene-4,8-dione
5-hydroxy-2,2-dimethyl-3H-pyrano[3,2-g]chromene-4,8-dione
Summary

SMILES: O=c1ccc2c(o1)cc1c(c2O)C(=O)CC(O1)(C)C
InChI: InChI=1S/C14H12O5/c1-14(2)6-8(15)12-10(19-14)5-9-7(13(12)17)3-4-11(16)18-9/h3-5,17H,6H2,1-2H3
InChIKey: XFSINVCSJTYZGH-UHFFFAOYSA-N
DeepSMILES: O=ccccco6)cccc6O))C=O)CCO6)C)C
Scaffold Graph/Node/Bond level: O=C1CCOc2cc3oc(=O)ccc3cc21
Scaffold Graph/Node level: OC1CCC2CC3C(O)CCOC3CC2O1
Scaffold Graph level: CC1CCC2CC3C(C)CCCC3CC2C1
Functional groups: c=O; coc; cO; cC(=O)C; cOC
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:
clausenin
External chemical identifiers:
CID:CID_5315948; ZINC:ZINC000005734433
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
5-hydroxy-2,2-dimethyl-3H-pyrano[3,2-g]chromene-4,8-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 260.25
Log P RDKit 2.24
Topological polar surface area (Å2) RDKit 76.74
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 19
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 10
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 0
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-hydroxy-2,2-dimethyl-3H-pyrano[3,2-g]chromene-4,8-dione
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.73
5-hydroxy-2,2-dimethyl-3H-pyrano[3,2-g]chromene-4,8-dione
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 -6.34
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No