IMPPAT Phytochemical information: 
1-Hydroxy-2-carboxy-3-methoxyanthraquinone
1-Hydroxy-2-carboxy-3-methoxyanthraquinone
Summary

SMILES: COc1cc2C(=O)c3ccccc3C(=O)c2c(c1C(=O)O)O
InChI: InChI=1S/C16H10O6/c1-22-10-6-9-11(15(19)12(10)16(20)21)14(18)8-5-3-2-4-7(8)13(9)17/h2-6,19H,1H3,(H,20,21)
InChIKey: VVXSWOYLOUBWNW-UHFFFAOYSA-N
DeepSMILES: COcccC=O)cccccc6C=O)c%10cc%14C=O)O)))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2ccccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CCCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CCCCC12
Functional groups: cOC; cC(=O)c; cC(=O)O; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthracenecarboxylic acids and derivatives
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
1-hydroxy-2-carboxy-3-methoxyanthraquinone, 1-hydroxy-2-carboxy-3-methoxy anthraquinone
External chemical identifiers:
CID:CID_129670276; ZINC:ZINC000095911983
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1-Hydroxy-2-carboxy-3-methoxyanthraquinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 298.25
Log P RDKit 1.87
Topological polar surface area (Å2) RDKit 100.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 22
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 1
Shape complexity RDKit 0.06
Number of rotatable bonds RDKit 2
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
1-Hydroxy-2-carboxy-3-methoxyanthraquinone
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.748732
1-Hydroxy-2-carboxy-3-methoxyanthraquinone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME 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 -6.30
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No