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
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
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
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.753438
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
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000168ENSG00000176444CLK21196ChEMBL, NPASS
TAR_EXP_000027ENSG00000123374CDK21017ChEMBL, NPASS
TAR_EXP_000034ENSG00000105810CDK61021ChEMBL, NPASS
TAR_EXP_000042ENSG00000130669PAK410298ChEMBL, NPASS
TAR_EXP_000055ENSG00000115694STK2510494ChEMBL, NPASS
TAR_EXP_000064ENSG00000110931CAMKK210645ChEMBL, NPASS
TAR_EXP_000067BUB1B-PAK6106821730ChEMBL
TAR_EXP_000072ENSG00000142731PLK410733ChEMBL, NPASS
TAR_EXP_000078ENSG00000119408NEK610783ChEMBL, NPASS
TAR_EXP_000101ENSG00000102096PIM211040ChEMBL, NPASS
TAR_EXP_000118ENSG00000183765CHEK211200ChEMBL, NPASS
TAR_EXP_000136ENSG00000112079STK3811329ChEMBL, NPASS
TAR_EXP_000167ENSG00000013441CLK11195ChEMBL, NPASS
TAR_EXP_000169ENSG00000179335CLK31198ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001938ENSG00000172939OXSR19943ChEMBL, NPASS
TAR_EXP_001208ENSG00000058729RIOK255781ChEMBL, NPASS
TAR_EXP_001244ENSG00000108984MAP2K65608ChEMBL, NPASS
TAR_EXP_001241ENSG00000126934MAP2K25605ChEMBL, NPASS
TAR_EXP_000229ENSG00000133275CSNK1G21455ChEMBL, NPASS
TAR_EXP_000230ENSG00000151292CSNK1G31456ChEMBL, NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557NPASS
TAR_EXP_001240ENSG00000169032MAP2K15604BindingDB, ChEMBL, NPASS
TAR_EXP_001236ENSG00000185386MAPK115600ChEMBL, NPASS
TAR_EXP_001233ENSG00000069956MAPK65597ChEMBL, NPASS
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL, NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_001043ENSG00000105053VRK351231ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000291ENSG00000167657DAPK31613ChEMBL, NPASS
TAR_EXP_000316ENSG00000104936DMPK1760ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_000959ENSG00000117650NEK24751ChEMBL, NPASS
TAR_EXP_000872ENSG00000197442MAP3K54217ChEMBL, NPASS
TAR_EXP_000858ENSG00000198355PIM3415116ChEMBL, NPASS
TAR_EXP_001087ENSG00000140992PDPK15170ChEMBL, NPASS
TAR_EXP_000783ENSG00000162434JAK13716ChEMBL, NPASS
TAR_EXP_001094ENSG00000134602STK2651765ChEMBL, NPASS
TAR_EXP_001272ENSG00000137843PAK656924NPASS
TAR_EXP_000752ENSG00000142192APP351ChEMBL, NPASS
TAR_EXP_000451ENSG00000154310TNIK23043ChEMBL, NPASS
TAR_EXP_001119ENSG00000137193PIM15292ChEMBL, NPASS
TAR_EXP_001139ENSG00000166851PLK15347ChEMBL, NPASS
TAR_EXP_001144ENSG00000169118CSNK1G153944ChEMBL, NPASS
TAR_EXP_001195ENSG00000162409PRKAA25563ChEMBL, NPASS
TAR_EXP_001198ENSG00000288516PRKACA5566ChEMBL, NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932ChEMBL, NPASS
TAR_EXP_001283ENSG00000183049CAMK1D57118ChEMBL, NPASS
TAR_EXP_001224ENSG00000168078PBK55872ChEMBL, NPASS
TAR_EXP_001287ENSG00000008118CAMK1G57172ChEMBL, NPASS
TAR_EXP_001927ENSG00000065613SLK9748ChEMBL, NPASS
TAR_EXP_001891ENSG00000164543STK17A9263ChEMBL, NPASS
TAR_EXP_001827ENSG00000100490CDKL18814ChEMBL, NPASS
TAR_EXP_001802ENSG00000115661STK168576ChEMBL, NPASS
TAR_EXP_001746ENSG00000148660CAMK2G818ChEMBL, NPASS
TAR_EXP_001744ENSG00000145349CAMK2D817ChEMBL, NPASS
TAR_EXP_001743ENSG00000058404CAMK2B816ChEMBL, NPASS
TAR_EXP_001742ENSG00000070808CAMK2A815ChEMBL, NPASS
TAR_EXP_001740ENSG00000152495CAMK4814ChEMBL, NPASS
TAR_EXP_001672ENSG00000028116VRK27444ChEMBL, NPASS
TAR_EXP_001286ENSG00000101349PAK557144ChEMBL, NPASS
TAR_EXP_001671ENSG00000100749VRK17443ChEMBL, NPASS
TAR_EXP_001045ENSG00000102225CDK165127ChEMBL, NPASS
TAR_EXP_001431ENSG00000177189RPS6KA36197ChEMBL, NPASS
TAR_EXP_001573ENSG00000101109STK46789ChEMBL, NPASS
TAR_EXP_001576ENSG00000072786STK106793ChEMBL, NPASS