IMPPAT Phytochemical information: 
Loquatoside
Loquatoside
Summary

SMILES: Oc1cc(O)c2c(c1)OC(C(C2O)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)c1ccc(c(c1)O)O
InChI: InChI=1S/C20H22O11/c21-8-4-11(24)14-13(5-8)30-18(7-1-2-9(22)10(23)3-7)19(16(14)27)31-20-17(28)15(26)12(25)6-29-20/h1-5,12,15-28H,6H2/t12-,15-,16?,17+,18?,19?,20-/m0/s1
InChIKey: YISJRMFABYGQSX-NUVGQASKSA-N
DeepSMILES: OcccO)ccc6)OCCC6O))O[C@@H]OC[C@@H][C@@H][C@H]6O))O))O)))))))cccccc6)O))O
Scaffold Graph/Node/Bond level: c1ccc(C2Oc3ccccc3CC2OC2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(C2OC3CCCCC3CC2OC2CCCCO2)CC1
Scaffold Graph level: C1CCC(CC2CC3CCCCC3CC2C2CCCCC2)CC1
Functional groups: cO; cOC; CO; CO[C@@H](C)OC
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: Flavan-3-ols|Flavandiols (Leucoanthocyanidins)
Synonymous chemical names:
loquatoside, Loquatoside
External chemical identifiers:
CID:CID_156269; ChEBI:CHEBI:176124
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Loquatoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 438.39
Log P RDKit -0.5
Topological polar surface area (Å2) RDKit 189.53
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 8
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 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 3
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
Loquatoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
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 0.288403
Loquatoside
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 -9.84
Number of PAINS structural alerts SwissADME 1
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 No
P-glycoprotein substrate SwissADME No