IMPPAT Phytochemical information: 
Apiosylskimmin
Apiosylskimmin
Summary

SMILES: OC[C@@]1(O)CO[C@H]([C@@H]1O)OC[C@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C20H24O12/c21-7-20(27)8-29-19(17(20)26)28-6-12-14(23)15(24)16(25)18(32-12)30-10-3-1-9-2-4-13(22)31-11(9)5-10/h1-5,12,14-19,21,23-27H,6-8H2/t12-,14-,15+,16-,17+,18-,19-,20-/m1/s1
InChIKey: SXPBJYHKMRWZNA-ZITSYKRSSA-N
DeepSMILES: OC[C@@]O)CO[C@H][C@@H]5O))OC[C@H]O[C@@H]Occcccc6)oc=O)cc6))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1ccc2ccc(OC3CCCC(COC4CCCO4)O3)cc2o1
Scaffold Graph/Node level: OC1CCC2CCC(OC3CCCC(COC4CCCO4)O3)CC2O1
Scaffold Graph level: CC1CCC2CCC(CC3CCCC(CCC4CCCC4)C3)CC2C1
Functional groups: CO; CO[C@@H](C)OC; cO[C@@H](C)OC; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Coumarin glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
adicardin
External chemical identifiers:
CID:CID_14236613; ChEMBL:CHEMBL1719219; ZINC:ZINC000031157867; MolPort-006-668-333
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Apiosylskimmin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 456.4
Log P RDKit -2.56
Topological polar surface area (Å2) RDKit 188.51
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Apiosylskimmin
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 0.249853
Apiosylskimmin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.53
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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