IMPPAT Phytochemical information: 
Arctigenin

Arctigenin
Summary

SMILES: COc1cc(ccc1OC)C[C@H]1COC(=O)[C@@H]1Cc1ccc(c(c1)OC)O
InChI: InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1
InChIKey: NQWVSMVXKMHKTF-JKSUJKDBSA-N
DeepSMILES: COcccccc6OC)))))C[C@H]COC=O)[C@@H]5Ccccccc6)OC)))O
Scaffold Graph/Node/Bond level: O=C1OCC(Cc2ccccc2)C1Cc1ccccc1
Scaffold Graph/Node level: OC1OCC(CC2CCCCC2)C1CC1CCCCC1
Scaffold Graph level: CC1CCC(CC2CCCCC2)C1CC1CCCCC1
Functional groups: cOC; COC(=O)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Furanoid lignans
ClassyFire Subclass: Tetrahydrofuran lignans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Dibenzylbutyrolactone lignans
Synonymous chemical names:
(-)-arctigenin, arctigenin
External chemical identifiers:
CID:CID_64981; ChEMBL:CHEMBL435734; ChEBI:CHEBI:79; ZINC:ZINC000001615344; FDASRS:U76MR9VS6M; SureChEMBL:SCHEMBL381820; MolPort-001-742-543
Chemical structure download


Arctigenin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 372.42
Log P RDKit 2.99
Topological polar surface area (Å2) RDKit 74.22
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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


Arctigenin
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 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.75


Arctigenin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.02
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No


Arctigenin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000327850NFATC1784
ENSP00000216117HMOX1800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.