IMPPAT Phytochemical information: 
5-Hydroxy-3-methoxyphenanthrene-1,4-dione

5-Hydroxy-3-methoxyphenanthrene-1,4-dione
Summary

SMILES: COC1=CC(=O)c2c(C1=O)c1c(O)cccc1cc2
InChI: InChI=1S/C15H10O4/c1-19-12-7-11(17)9-6-5-8-3-2-4-10(16)13(8)14(9)15(12)18/h2-7,16H,1H3
InChIKey: DDEQWQREGNUPCT-UHFFFAOYSA-N
DeepSMILES: COC=CC=O)ccC6=O))ccO)cccc6cc%10
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2c1ccc1ccccc21
Scaffold Graph/Node level: OC1CCC(O)C2C1CCC1CCCCC12
Scaffold Graph level: CC1CCC(C)C2C1CCC1CCCCC12
Functional groups: COC1=CC(=O)ccC1=O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
ClassyFire Subclass: Phenanthrols
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Naphthalenes
NP Classifier Class: Naphthoquinones
Synonymous chemical names:
Cymbinodin A, cymbinodin a
External chemical identifiers:
CID:CID_3086629
Chemical structure download


5-Hydroxy-3-methoxyphenanthrene-1,4-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 254.24
Log P RDKit 2.45
Topological polar surface area (Å2) RDKit 63.6
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
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 2
Number of aromatic heterocycles RDKit 0
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-3-methoxyphenanthrene-1,4-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 0.85


5-Hydroxy-3-methoxyphenanthrene-1,4-dione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.85
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 -6.05
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No