IMPPAT Phytochemical information: 
Hirsutidin 3-glucoside

Hirsutidin 3-glucoside
Summary

SMILES: OCC1O[C@@H](Oc2cc3c(O)cc(cc3[o+]c2c2cc(OC)c(c(c2)OC)O)OC)C([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C24H26O12/c1-31-11-6-13(26)12-8-17(35-24-22(30)21(29)20(28)18(9-25)36-24)23(34-14(12)7-11)10-4-15(32-2)19(27)16(5-10)33-3/h4-8,18,20-22,24-25,28-30H,9H2,1-3H3,(H-,26,27)/p+1/t18?,20-,21+,22?,24-/m1/s1
InChIKey: HOQYXINLVDTZAR-WXWBQYTQSA-O
DeepSMILES: OCCO[C@@H]OccccO)cccc6[o+]c%10cccOC))ccc6)OC)))O)))))))))OC)))))))))C[C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc(-c2[o+]c3ccccc3cc2OC2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(C2OC3CCCCC3CC2OC2CCCCO2)CC1
Scaffold Graph level: C1CCC(CC2CC3CCCCC3CC2C2CCCCC2)CC1
Functional groups: CO; cO[C@@H](C)OC; cO; c[o+]c; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
Synonymous chemical names:
hirsutidin 3-o-glucoside
External chemical identifiers:
CID:CID_44257023; ChEBI:CHEBI:169797
Chemical structure download


Hirsutidin 3-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 507.47
Log P RDKit 1
Topological polar surface area (Å2) RDKit 178.83
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 24
Number of heavy atoms RDKit 36
Number of heteroatoms RDKit 12
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
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


Hirsutidin 3-glucoside
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 1
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 0.25029


Hirsutidin 3-glucoside
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 -8.86
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No