IMPPAT Phytochemical information: 
(S)-7-(((2-O-6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
(S)-7-(((2-O-6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc3O[C@@H](CC(=O)c3c(c2)O)c2ccc(c(c2)O)OC)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI: InChI=1S/C28H34O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-7,10,17,19,21-31,33-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
InChIKey: ARGKVCXINMKCAZ-UZRWAPQLSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccO[C@@H]CC=O)c6cc%10)O)))))cccccc6)O))OC))))))))))))[C@@H][C@H][C@@H]6O))O))O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)Oc2cc(OC3OCCCC3OC3CCCCO3)ccc21
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CC(OC3OCCCC3OC3CCCCO3)CCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CC(CC3CCCCC3CC3CCCCC3)CCC12
Functional groups: CO; CO[C@@H](C)OC; cO[C@@H](C)OC; cOC; cC(=O)C; cO
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: Flavanones
Synonymous chemical names:
Neohesperidin, neohesperidin, hesperetin-7-neohesperidoside
External chemical identifiers:
CID:CID_442439; ChEMBL:CHEMBL506398; ChEBI:CHEBI:59016; ZINC:ZINC000008234302; FDASRS:OA5C88H3L0; SureChEMBL:SCHEMBL121675; MolPort-003-938-738
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(S)-7-(((2-O-6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 610.57
Log P RDKit -1.16
Topological polar surface area (Å2) RDKit 234.29
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.39
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
(S)-7-(((2-O-6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
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 0.18
(S)-7-(((2-O-6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one
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 -10.36
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 Yes