IMPPAT Phytochemical information: 
Viscumiside A
Viscumiside A
Summary

SMILES: OCC1OC(Oc2cc3OC(CC(=O)c3c(c2)O)c2ccc(c(c2)OC)O)C(C(C1O)O)O
InChI: InChI=1S/C22H24O11/c1-30-15-4-9(2-3-11(15)24)14-7-13(26)18-12(25)5-10(6-16(18)32-14)31-22-21(29)20(28)19(27)17(8-23)33-22/h2-6,14,17,19-25,27-29H,7-8H2,1H3
InChIKey: KZQCCKUDYVSOLC-UHFFFAOYSA-N
DeepSMILES: OCCOCOcccOCCC=O)c6cc%10)O)))))cccccc6)OC)))O)))))))))))CCC6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)Oc2cc(OC3CCCCO3)ccc21
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CC(OC3CCCCO3)CCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CC(CC3CCCCC3)CCC12
Functional groups: CO; cOC(C)OC; cOC; cC(=O)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavanones
Synonymous chemical names:
viscumside a
External chemical identifiers:
CID:CID_14035424
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Viscumiside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 464.42
Log P RDKit -0.01
Topological polar surface area (Å2) RDKit 175.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
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 6
Stereochemical complexity RDKit 0.27
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.41
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
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
Viscumiside A
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
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 0.35
Viscumiside A
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 -8.69
Number of PAINS structural alerts SwissADME 0
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