IMPPAT Phytochemical information: 
Obtusifolin 2-glucoside
Obtusifolin 2-glucoside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2c(C)cc3c(c2OC)C(=O)c2c(C3=O)cccc2O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C22H22O10/c1-8-6-10-14(17(27)13-9(15(10)25)4-3-5-11(13)24)21(30-2)20(8)32-22-19(29)18(28)16(26)12(7-23)31-22/h3-6,12,16,18-19,22-24,26,28-29H,7H2,1-2H3/t12-,16-,18+,19-,22+/m1/s1
InChIKey: JMDQOFZFOJHOMU-UJPYTVAASA-N
DeepSMILES: OC[C@H]O[C@@H]OccC)cccc6OC)))C=O)ccC6=O))cccc6O))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1c2ccccc2C(=O)c2cc(OC3CCCCO3)ccc21
Scaffold Graph/Node level: OC1C2CCCCC2C(O)C2CC(OC3CCCCO3)CCC12
Scaffold Graph level: CC1C2CCCCC2C(C)C2CC(CC3CCCCC3)CCC12
Functional groups: CO; cO[C@@H](C)OC; cOC; cC(=O)c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Benzenoids
ClassyFire Class: Anthracenes
ClassyFire Subclass: Anthraquinones
NP Classifier Biosynthetic pathway: Polyketides|Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins|Polycyclic aromatic polyketides
NP Classifier Class: Anthraquinones and anthrones|Simple coumarins
Synonymous chemical names:
glucoobtusifolin, gluco-obtusifolin
External chemical identifiers:
CID:CID_442761; ChEMBL:CHEMBL517625; ChEBI:CHEBI:7716; ZINC:ZINC000004098692
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Obtusifolin 2-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 446.41
Log P RDKit -0.34
Topological polar surface area (Å2) RDKit 162.98
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 10
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 4
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
Obtusifolin 2-glucoside
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 Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36
Obtusifolin 2-glucoside
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 -8.14
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