IMPPAT Phytochemical information: 
2-Hydroxy-5-(4-hydroxyphenyl)phenalen-1-one

2-Hydroxy-5-(4-hydroxyphenyl)phenalen-1-one
Summary

SMILES: Oc1ccc(cc1)c1cc2C=C(O)C(=O)c3c2c(c1)ccc3
InChI: InChI=1S/C19H12O3/c20-15-6-4-11(5-7-15)13-8-12-2-1-3-16-18(12)14(9-13)10-17(21)19(16)22/h1-10,20-21H
InChIKey: OWLCEBLKTSXXFA-UHFFFAOYSA-N
DeepSMILES: Occcccc6))cccC=CO)C=O)cc6cc%10)ccc6
Scaffold Graph/Node/Bond level: O=C1C=Cc2cc(-c3ccccc3)cc3cccc1c23
Scaffold Graph/Node level: OC1CCC2CC(C3CCCCC3)CC3CCCC1C32
Scaffold Graph level: CC1CCC2CC(C3CCCCC3)CC3CCCC1C32
Functional groups: cO; cC=C(O)C(=O)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Naphthalenes
ClassyFire Subclass: Phenylnaphthalenes
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
Synonymous chemical names:
emenolone
External chemical identifiers:
CID:CID_101651627; ZINC:ZINC000238744224
Chemical structure download


2-Hydroxy-5-(4-hydroxyphenyl)phenalen-1-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 288.3
Log P RDKit 4.31
Topological polar surface area (Å2) RDKit 57.53
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 3
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 0
Shape complexity RDKit 0
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 3
Number of aromatic heterocycles RDKit 0
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


2-Hydroxy-5-(4-hydroxyphenyl)phenalen-1-one
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.7


2-Hydroxy-5-(4-hydroxyphenyl)phenalen-1-one
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately 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 -5.00
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 No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No