IMPPAT Phytochemical information: 
2-(1-Hydroxyethyl)naphtho(2,3-b)furan-4,9-dione
2-(1-Hydroxyethyl)naphtho(2,3-b)furan-4,9-dione
Summary

SMILES: CC(c1cc2c(o1)C(=O)c1c(C2=O)cccc1)O
InChI: InChI=1S/C14H10O4/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-7,15H,1H3
InChIKey: SAXKEWRSGLPYPB-UHFFFAOYSA-N
DeepSMILES: CCcccco5)C=O)ccC6=O))cccc6)))))))))))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2occc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2OCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CCCC12
Functional groups: 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:
2-(1-hydroxyethyl)naphtho[2,3-b]-furan-4,9-dione, 2-(1-hydroxyethyl)naphthol[2,3-b]furan-4,9-dione, 2-(1-hydroxyethylnaphtho[2,3-b]furan-4,9-dione, 2-(1-hydroxyethyl)-naphtho[2,3-b] furan-4,9-dione
External chemical identifiers:
CID:CID_150068; ChEMBL:CHEMBL294323; SureChEMBL:SCHEMBL1887185
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-(1-Hydroxyethyl)naphtho(2,3-b)furan-4,9-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 242.23
Log P RDKit 2.11
Topological polar surface area (Å2) RDKit 67.51
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.14
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 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
2-(1-Hydroxyethyl)naphtho(2,3-b)furan-4,9-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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.71
2-(1-Hydroxyethyl)naphtho(2,3-b)furan-4,9-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 -6.49
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No