IMPPAT Phytochemical information: 
1,3,5-trihydroxy-2,7-dimethyl-8-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
1,3,5-trihydroxy-2,7-dimethyl-8-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
Summary

SMILES: OC[C@H]1OC(Oc2c(C)cc(c3c2C(=O)c2c(C3=O)cc(c(c2O)C)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C22H22O11/c1-6-3-10(25)13-14(18(29)12-8(16(13)27)4-9(24)7(2)15(12)26)21(6)33-22-20(31)19(30)17(28)11(5-23)32-22/h3-4,11,17,19-20,22-26,28,30-31H,5H2,1-2H3/t11-,17-,19+,20-,22?/m1/s1
InChIKey: SNLCLOKRJWQPAX-CEKMPUIXSA-N
DeepSMILES: OC[C@H]OCOccC)cccc6C=O)ccC6=O))cccc6O))C))O))))))))O))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2c(OC3CCCCO3)cccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2C(OC3CCCCO3)CCCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2C(CC3CCCCC3)CCCC12
Functional groups: CO; cOC(C)OC; cC(=O)c; cO
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:
1,3,5,trihydroxy-2,7-dimethylanthraquinone 8-o-alpha-d-glucopyranoside, Nodososide, nodososide
External chemical identifiers:
CID:CID_3084554
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
1,3,5-trihydroxy-2,7-dimethyl-8-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 462.41
Log P RDKit -0.63
Topological polar surface area (Å2) RDKit 194.21
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.23
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
1,3,5-trihydroxy-2,7-dimethyl-8-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.261964
1,3,5-trihydroxy-2,7-dimethyl-8-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.08
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 Yes