IMPPAT Phytochemical information: 
1,3-Dimethoxy-2-hydroxy-9,10-anthraquinone

1,3-Dimethoxy-2-hydroxy-9,10-anthraquinone
Summary

SMILES: COc1c(O)c(OC)cc2c1C(=O)c1ccccc1C2=O
InChI: InChI=1S/C16H12O5/c1-20-11-7-10-12(16(21-2)15(11)19)14(18)9-6-4-3-5-8(9)13(10)17/h3-7,19H,1-2H3
InChIKey: VVVZBZBYGDTROV-UHFFFAOYSA-N
DeepSMILES: COccO)cOC))ccc6C=O)cccccc6C%10=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; cO; cC(=O)c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthraquinones
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones
Synonymous chemical names:
1,3-dimethoxy-2-hydroxyanthraquinone
External chemical identifiers:
CID:CID_15118825; ZINC:ZINC000014775071; SureChEMBL:SCHEMBL18601894; MolPort-039-338-633
Chemical structure download


1,3-Dimethoxy-2-hydroxy-9,10-anthraquinone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 284.27
Log P RDKit 2.18
Topological polar surface area (Å2) RDKit 72.83
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 5
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 2
Shape complexity RDKit 0.12
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


1,3-Dimethoxy-2-hydroxy-9,10-anthraquinone
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 0.78053


1,3-Dimethoxy-2-hydroxy-9,10-anthraquinone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -6.29
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No