IMPPAT Phytochemical information: 
Isomonospermoside
Isomonospermoside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(ccc2O)C2CC(=O)c3c(O2)cc(cc3)O)[C@@H]([C@@H]([C@@H]1O)O)O
InChI: InChI=1S/C21H22O10/c22-8-17-18(26)19(27)20(28)21(31-17)30-16-5-9(1-4-12(16)24)14-7-13(25)11-3-2-10(23)6-15(11)29-14/h1-6,14,17-24,26-28H,7-8H2/t14?,17-,18-,19-,20-,21-/m1/s1
InChIKey: DYRDBDVHLCRXAE-GCDPEQLBSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6O))))CCC=O)ccO6)cccc6))O))))))))))))[C@@H][C@@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC(c2cccc(OC3CCCCO3)c2)Oc2ccccc21
Scaffold Graph/Node level: OC1CC(C2CCCC(OC3CCCCO3)C2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCC(CC3CCCCC3)C2)CC2CCCCC12
Functional groups: CO; cO[C@@H](C)OC; cO; cC(=O)C; cOC
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:
Isomonospermoside, isomonospermoside
External chemical identifiers:
CID:CID_42607822
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isomonospermoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 434.4
Log P RDKit -0.02
Topological polar surface area (Å2) RDKit 166.14
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 4
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
Isomonospermoside
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 0.385026
Isomonospermoside
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 -8.85
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