IMPPAT Phytochemical information: 
Taxiphyllin

Taxiphyllin
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H](c2ccc(cc2)O)C#N)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C14H17NO7/c15-5-9(7-1-3-8(17)4-2-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2/t9-,10+,11+,12-,13+,14+/m0/s1
InChIKey: NVLTYOJHPBMILU-GMDXDWKASA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H]cccccc6))O)))))C#N))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc(COC2CCCCO2)cc1
Scaffold Graph/Node level: C1CCC(COC2CCCCO2)CC1
Scaffold Graph level: C1CCC(CCC2CCCCC2)CC1
Functional groups: CO; CO[C@@H](C)OC; cO; CC#N
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
(s)-2-(glucopyranosyloxy)-2-(4-hydroxyphenyl)acetonitrile, Taxiphyllin, taxiphyllin
External chemical identifiers:
CID:CID_107721; ChEMBL:CHEMBL469825; ChEBI:CHEBI:16267; ZINC:ZINC000004095731; SureChEMBL:SCHEMBL1332701; MolPort-035-706-129
Chemical structure download


Taxiphyllin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 311.29
Log P RDKit -1.23
Topological polar surface area (Å2) RDKit 143.4
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 22
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


Taxiphyllin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.47


Taxiphyllin
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 Low
Log Kp (Skin permeation, cm/s) SwissADME -8.85
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


Taxiphyllin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000471024827
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.