IMPPAT Phytochemical information: 
2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-
2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)[C@@H]2CC=CC(=O)O2)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C17H20O8/c18-8-12-14(20)15(21)16(22)17(25-12)23-10-6-4-9(5-7-10)11-2-1-3-13(19)24-11/h1,3-7,11-12,14-18,20-22H,2,8H2/t11-,12+,14+,15-,16+,17+/m0/s1
InChIKey: NHQCBCFHSBCPOB-HJIDVSFMSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6))[C@@H]CC=CC=O)O6)))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1C=CCC(c2ccc(OC3CCCCO3)cc2)O1
Scaffold Graph/Node level: OC1CCCC(C2CCC(OC3CCCCO3)CC2)O1
Scaffold Graph level: CC1CCCC(C2CCC(CC3CCCCC3)CC2)C1
Functional groups: CO; cO[C@@H](C)OC; O=C1C=CCCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavanones
Synonymous chemical names:
psilotin, Psilotin
External chemical identifiers:
CID:CID_6452048; ZINC:ZINC000033833416
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.34
Log P RDKit -0.59
Topological polar surface area (Å2) RDKit 125.68
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.529968
2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.62
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