IMPPAT Phytochemical information: 
9-Hydroxy-3-(hydroxymethyl)furo[3,2-b]naphtho[2,3-d]furan-5,10-dione
9-Hydroxy-3-(hydroxymethyl)furo[3,2-b]naphtho[2,3-d]furan-5,10-dione
Summary

SMILES: OCc1coc2c1oc1c2C(=O)c2c(C1=O)cccc2O
InChI: InChI=1S/C15H8O6/c16-4-6-5-20-15-10-12(19)9-7(2-1-3-8(9)17)11(18)14(10)21-13(6)15/h1-3,5,16-17H,4H2
InChIKey: ZPHYXTATIAWVPS-UHFFFAOYSA-N
DeepSMILES: OCccocc5occ5C=O)ccC6=O))cccc6O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2c1oc1ccoc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2C3OCCC3OC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2C3CCCC3CC12
Functional groups: CO; coc; cC(=O)c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthofurans
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthoquinones
Synonymous chemical names:
9-hydroxy-3-hydroxymethylfuro[3,2-b]naphtho[2,3-d]-furan-5,10-dione
External chemical identifiers:
CID:CID_641262; ZINC:ZINC000012153368
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
9-Hydroxy-3-(hydroxymethyl)furo[3,2-b]naphtho[2,3-d]furan-5,10-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 284.22
Log P RDKit 2
Topological polar surface area (Å2) RDKit 100.88
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 21
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 14
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.07
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4
9-Hydroxy-3-(hydroxymethyl)furo[3,2-b]naphtho[2,3-d]furan-5,10-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 0.55
9-Hydroxy-3-(hydroxymethyl)furo[3,2-b]naphtho[2,3-d]furan-5,10-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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.56
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No