IMPPAT Phytochemical information: 
Arctiin
Arctiin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2OC)C[C@H]2C(=O)OC[C@@H]2Cc2ccc(c(c2)OC)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1
InChIKey: XOJVHLIYNSOZOO-SWOBOCGESA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6OC))))C[C@H]C=O)OC[C@@H]5Ccccccc6)OC)))OC))))))))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1OCC(Cc2ccccc2)C1Cc1ccc(OC2CCCCO2)cc1
Scaffold Graph/Node level: OC1OCC(CC2CCCCC2)C1CC1CCC(OC2CCCCO2)CC1
Scaffold Graph level: CC1CCC(CC2CCCCC2)C1CC1CCC(CC2CCCCC2)CC1
Functional groups: CO; COC(C)=O; cOC; cO[C@@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Dibenzylbutyrolactone lignans
Synonymous chemical names:
arctigenin-4'-glucoside(arctiin), arctiin
External chemical identifiers:
CID:100528; ChEMBL:CHEMBL388452; ChEBI:80793; ZINC:ZINC000028820378; FDASRS:TM5RQ949K7; SureChEMBL:SCHEMBL381867; MolPort-001-740-689
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Arctiin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 534.56
Log P RDKit 0.47
Topological polar surface area (Å2) RDKit 153.37
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 38
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 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 10
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 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Arctiin
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 3
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 0.3146
Arctiin
ADMET 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 -8.3
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes
Arctiin
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000227507CCND1800
ENSP00000337459NOS1786
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.