IMPPAT Phytochemical information: 
2-Acetyl-1,6,8-trihydroxy-3-methylanthracene-9,10-dione
2-Acetyl-1,6,8-trihydroxy-3-methylanthracene-9,10-dione
Summary

SMILES: Oc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)c(c(c1)C)C(=O)C
InChI: InChI=1S/C17H12O6/c1-6-3-9-14(16(22)12(6)7(2)18)17(23)13-10(15(9)21)4-8(19)5-11(13)20/h3-5,19-20,22H,1-2H3
InChIKey: OJBWMXFOIJKIJP-UHFFFAOYSA-N
DeepSMILES: OcccO)ccc6)C=O)ccC6=O))cO)ccc6)C))C=O)C
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2ccccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CCCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CCCCC12
Functional groups: cO; cC(=O)c; cC(C)=O
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:
Emodin, 2-acctyl, 2-acetylemodin
External chemical identifiers:
CID:CID_12742404; ZINC:ZINC000013307165; SureChEMBL:SCHEMBL16226740
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-Acetyl-1,6,8-trihydroxy-3-methylanthracene-9,10-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 312.28
Log P RDKit 2.09
Topological polar surface area (Å2) RDKit 111.9
Number of hydrogen bond acceptors RDKit 6
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 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
2-Acetyl-1,6,8-trihydroxy-3-methylanthracene-9,10-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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.59
2-Acetyl-1,6,8-trihydroxy-3-methylanthracene-9,10-dione
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.11
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No