IMPPAT Phytochemical information: 
3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid

3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid
Summary

SMILES: O=C1c2cccc(c2C(=O)c2c1cc(O)c(c2C)C(=O)O)O
InChI: InChI=1S/C16H10O6/c1-6-11-8(5-10(18)12(6)16(21)22)14(19)7-3-2-4-9(17)13(7)15(11)20/h2-5,17-18H,1H3,(H,21,22)
InChIKey: MHABMANUFPZXEB-UHFFFAOYSA-N
DeepSMILES: O=Ccccccc6C=O)cc%10ccO)cc6C))C=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: cC(=O)c; cO; cC(=O)O
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:
3,8-dihydroxy-1-methylanthraquinone-2-carboxylic-acid
External chemical identifiers:
CID:CID_14379528; ChEMBL:CHEMBL235387; ChEBI:CHEBI:174833; ZINC:ZINC000013334444; SureChEMBL:SCHEMBL5142787
Chemical structure download


3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 298.25
Log P RDKit 1.88
Topological polar surface area (Å2) RDKit 111.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 3
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 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


3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.63


3,8-Dihydroxy-1-methylanthraquinone-2-carboxylic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.88
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