IMPPAT Phytochemical information: 
Verminoside
Verminoside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3OC(=O)/C=C/c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C24H28O13/c25-8-14-17(30)18(31)19(32)23(34-14)36-22-16-11(5-6-33-22)20(21-24(16,9-26)37-21)35-15(29)4-2-10-1-3-12(27)13(28)7-10/h1-7,11,14,16-23,25-28,30-32H,8-9H2/b4-2+/t11-,14-,16-,17-,18+,19-,20+,21+,22+,23+,24-/m1/s1
InChIKey: MZQXNUBTVLKMLP-QOEJBJAYSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@H]OC=C[C@@H][C@H]6[C@@]CO))O[C@H]3[C@H]6OC=O)/C=C/cccccc6)O))O))))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1C2C=COC(OC3CCCCO3)C2C2OC12
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1C2CCOC(OC3CCCCO3)C2C2OC12
Scaffold Graph level: CC(CCC1CCCCC1)CC1C2CC2C2C(CC3CCCCC3)CCCC12
Functional groups: CO; CO[C@@H](O[C@H]1CCC=CO1)C; C[C@]1(C)O[C@H]1C; c/C=C/C(=O)OC; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Cinnamic acids and derivatives
ClassyFire Subclass: Hydroxycinnamic acids and derivatives
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Monoterpenoids
NP Classifier Class: Iridoids monoterpenoids
Synonymous chemical names:
Verminoside, verminoside
External chemical identifiers:
CID:CID_12000883; ChEBI:CHEBI:69799; ZINC:ZINC000067912123; MolPort-005-945-817
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Verminoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 524.48
Log P RDKit -1.91
Topological polar surface area (Å2) RDKit 208.13
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.46
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Verminoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
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 0.0899754
Verminoside
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 -10.40
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 3
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