IMPPAT Phytochemical information: 
2,5-Dihydroxy-6,7-dimethoxyphenanthrene-4-carboxylic acid

2,5-Dihydroxy-6,7-dimethoxyphenanthrene-4-carboxylic acid
Summary

SMILES: COc1c(OC)cc2c(c1O)c1c(cc2)cc(cc1C(=O)O)O
InChI: InChI=1S/C17H14O6/c1-22-12-6-9-4-3-8-5-10(18)7-11(17(20)21)13(8)14(9)15(19)16(12)23-2/h3-7,18-19H,1-2H3,(H,20,21)
InChIKey: NIBUFVBDSYMAKU-UHFFFAOYSA-N
DeepSMILES: COccOC))cccc6O))cccc6))cccc6C=O)O))))O
Scaffold Graph/Node/Bond level: c1ccc2c(c1)ccc1ccccc12
Scaffold Graph/Node level: C1CCC2C(C1)CCC1CCCCC12
Scaffold Graph level: C1CCC2C(C1)CCC1CCCCC12
Functional groups: cOC; cO; cC(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Phenanthrenes and derivatives
ClassyFire Subclass: Phenanthrols
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Phenanthrenoids
NP Classifier Class: Phenanthrenes
Synonymous chemical names:
Ochrolic acid, ochrolic acid
External chemical identifiers:
CID:CID_71355915
Chemical structure download


2,5-Dihydroxy-6,7-dimethoxyphenanthrene-4-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 314.29
Log P RDKit 3.12
Topological polar surface area (Å2) RDKit 96.22
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 23
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 15
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.12
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
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


2,5-Dihydroxy-6,7-dimethoxyphenanthrene-4-carboxylic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.642788


2,5-Dihydroxy-6,7-dimethoxyphenanthrene-4-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately 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 -5.96
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No