IMPPAT Phytochemical information: 
Ammiol glucoside

Ammiol glucoside
Summary

SMILES: OC[C@H]1O[C@@H](OCc2cc(=O)c3c(o2)c(OC)c2c(c3OC)cco2)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C20H22O11/c1-26-16-9-3-4-28-17(9)19(27-2)18-12(16)10(22)5-8(30-18)7-29-20-15(25)14(24)13(23)11(6-21)31-20/h3-5,11,13-15,20-21,23-25H,6-7H2,1-2H3/t11-,13-,14+,15-,20-/m1/s1
InChIKey: CLABIQPMDJOSBJ-ZHQGELOASA-N
DeepSMILES: OC[C@H]O[C@@H]OCccc=O)cco6)cOC))ccc6OC)))cco5)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1cc(COC2CCCCO2)oc2cc3occc3cc12
Scaffold Graph/Node level: OC1CC(COC2CCCCO2)OC2CC3OCCC3CC12
Scaffold Graph level: CC1CC(CCC2CCCCC2)CC2CC3CCCC3CC12
Functional groups: CO; CO[C@@H](C)OC; c=O; coc; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzopyrans
ClassyFire Subclass: 1-benzopyrans
NP Classifier Biosynthetic pathway: Polyketides
NP Classifier Superclass: Chromanes
NP Classifier Class: Chromones
Synonymous chemical names:
ammiol glucoside
External chemical identifiers:
CID:CID_14377805; ZINC:ZINC000031156000; FDASRS:L7QP4Q03Y2
Chemical structure download


Ammiol glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 438.39
Log P RDKit -0.13
Topological polar surface area (Å2) RDKit 161.19
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.45
Number of rotatable bonds RDKit 6
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 2
Number of aromatic rings RDKit 3
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


Ammiol glucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
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 0.41


Ammiol glucoside
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 -9.39
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