IMPPAT Phytochemical information: 
(2S)-2-[4-[(2S,3R,4S,5S,6R)-3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-hydroxy-2,3-dihydrochromen-4-one
(2S)-2-[4-[(2S,3R,4S,5S,6R)-3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-hydroxy-2,3-dihydrochromen-4-one
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)[C@@H]2CC(=O)c3c(O2)cc(cc3)O)[C@@H]([C@H]([C@@H]1O)O)O[C@H]1OC[C@@]([C@@H]1O)(O)CO
InChI: InChI=1S/C26H30O13/c27-9-19-20(31)21(32)22(39-25-23(33)26(34,10-28)11-35-25)24(38-19)36-14-4-1-12(2-5-14)17-8-16(30)15-6-3-13(29)7-18(15)37-17/h1-7,17,19-25,27-29,31-34H,8-11H2/t17-,19+,20+,21-,22+,23+,24+,25+,26-/m0/s1
InChIKey: FTVKHUHJWDMWIR-FRFGAYJHSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6))[C@@H]CC=O)ccO6)cccc6))O)))))))))))))[C@@H][C@H][C@@H]6O))O))O[C@H]OC[C@@][C@@H]5O))O)CO
Scaffold Graph/Node/Bond level: O=C1CC(c2ccc(OC3OCCCC3OC3CCCO3)cc2)Oc2ccccc21
Scaffold Graph/Node level: OC1CC(C2CCC(OC3OCCCC3OC3CCCO3)CC2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCC(CC3CCCCC3CC3CCCC3)CC2)CC2CCCCC12
Functional groups: CO; cO[C@@H](C)OC; cC(=O)C; cOC; cO; CO[C@H](OC)C
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:
liquiritin apioside
External chemical identifiers:
CID:CID_46232263; ChEMBL:CHEMBL600792; ZINC:ZINC000049762874
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
(2S)-2-[4-[(2S,3R,4S,5S,6R)-3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-hydroxy-2,3-dihydrochromen-4-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 550.51
Log P RDKit -1.26
Topological polar surface area (Å2) RDKit 204.83
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.5
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
(2S)-2-[4-[(2S,3R,4S,5S,6R)-3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-hydroxy-2,3-dihydrochromen-4-one
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 2
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 0.215344
(2S)-2-[4-[(2S,3R,4S,5S,6R)-3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-hydroxy-2,3-dihydrochromen-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 -10.25
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