IMPPAT Phytochemical information: 
Undulatoside A
Undulatoside A
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C16H18O9/c1-6-2-8(18)12-9(19)3-7(4-10(12)23-6)24-16-15(22)14(21)13(20)11(5-17)25-16/h2-4,11,13-17,19-22H,5H2,1H3/t11-,13-,14+,15-,16-/m1/s1
InChIKey: BYYDEEAJCDGLER-YMILTQATSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccO)ccc6)occc6=O)))C)))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1ccoc2cc(OC3CCCCO3)ccc12
Scaffold Graph/Node level: OC1CCOC2CC(OC3CCCCO3)CCC12
Scaffold Graph level: CC1CCCC2CC(CC3CCCCC3)CCC12
Functional groups: CO; cO[C@@H](C)OC; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Chromanes
NP Classifier Class: Chromones
Synonymous chemical names:
undulatoside a, Undulatoside A, undulatosides a, staphylin
External chemical identifiers:
CID:CID_5321494; ChEMBL:CHEMBL2087913; ZINC:ZINC000031156069; SureChEMBL:SCHEMBL20678163; MolPort-001-740-521
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Undulatoside A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.31
Log P RDKit -1.01
Topological polar surface area (Å2) RDKit 149.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.31
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3
Undulatoside A
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 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.47
Undulatoside A
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 -7.82
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 No