IMPPAT Phytochemical information: 
6,14-dihydroxy-7-methoxy-13-[(2R,3R,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]oxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
6,14-dihydroxy-7-methoxy-13-[(2R,3R,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]oxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
Summary

SMILES: COc1c(O)cc2c3c1oc(=O)c1c3c(oc2=O)c(c(c1)O[C@@H]1O[C@@H]([C@@H]([C@H]1O)O)O)O
InChI: InChI=1S/C19H14O12/c1-27-13-6(20)2-4-9-8-5(17(25)30-15(9)13)3-7(10(21)14(8)29-16(4)24)28-19-12(23)11(22)18(26)31-19/h2-3,11-12,18-23,26H,1H3/t11-,12-,18+,19-/m1/s1
InChIKey: NKEMTKOCZMOURK-QLMQOPPUSA-N
DeepSMILES: COccO)cccc6oc=O)cc6coc%10=O)))ccc6)O[C@@H]O[C@@H][C@@H][C@H]5O))O))O))))))O
Scaffold Graph/Node/Bond level: O=c1oc2cc(OC3CCCO3)cc3c(=O)oc4cccc1c4c23
Scaffold Graph/Node level: OC1OC2CC(OC3CCCO3)CC3C(O)OC4CCCC1C4C23
Scaffold Graph level: CC1CC2CC(CC3CCCC3)CC3C(C)CC4CCCC1C4C23
Functional groups: cOC; cO; coc; c=O; cO[C@H]1CC[C@@H](O)O1; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Tannins
ClassyFire Subclass: Hydrolyzable tannins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
ducheside-b
External chemical identifiers:
CID:CID_5316974; ZINC:ZINC000033830866
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
6,14-dihydroxy-7-methoxy-13-[(2R,3R,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]oxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 434.31
Log P RDKit -0.31
Topological polar surface area (Å2) RDKit 189.26
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.26
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5
6,14-dihydroxy-7-methoxy-13-[(2R,3R,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]oxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.209084
6,14-dihydroxy-7-methoxy-13-[(2R,3R,4R,5S)-3,4,5-trihydroxyoxolan-2-yl]oxy-2,9-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
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 -9.10
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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