IMPPAT Phytochemical information: 
Naphthoherniarin
Naphthoherniarin
Summary

SMILES: COC1=CC(=O)c2c(C1=O)c(cc(c2)C)c1cc2ccc(=O)oc2cc1OC
InChI: InChI=1S/C22H16O6/c1-11-6-14(21-15(7-11)16(23)9-19(27-3)22(21)25)13-8-12-4-5-20(24)28-17(12)10-18(13)26-2/h4-10H,1-3H3
InChIKey: MSDIEAZOLJWCBV-UHFFFAOYSA-N
DeepSMILES: COC=CC=O)ccC6=O))cccc6)C)))cccccc=O)oc6cc%10OC
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2c1cccc2-c1ccc2oc(=O)ccc2c1
Scaffold Graph/Node level: OC1CCC2CC(C3CCCC4C(O)CCC(O)C43)CCC2O1
Scaffold Graph level: CC1CCC2CC(C3CCCC4C(C)CCC(C)C43)CCC2C1
Functional groups: COC1=CC(=O)ccC1=O; c=O; coc; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Naphthoquinones
NP Classifier Biosynthetic pathway: Polyketides|Shikimates and Phenylpropanoids
NP Classifier Superclass: Naphthalenes|Coumarins
NP Classifier Class: Naphthoquinones|Simple coumarins
Synonymous chemical names:
naphthoherniarin
External chemical identifiers:
CID:CID_363452; ChEBI:CHEBI:169827; ZINC:ZINC000001619934
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Naphthoherniarin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 376.36
Log P RDKit 3.69
Topological polar surface area (Å2) RDKit 82.81
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
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 19
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.14
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
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
Naphthoherniarin
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 0.65
Naphthoherniarin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.05
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No