Natural Product (NP) Details

General Information of the NP (ID: NP6882)
Name
Arctigenin
Synonyms
Arctigenin; (-)-Arctigenin; 7770-78-7; UNII-U76MR9VS6M; C21H24O6; CHEBI:79; U76MR9VS6M; (3R,4R)-4-(3,4-dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one; 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R-trans)-; (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one; (3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone; 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R,4R)-; (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3- [(4-hydroxy-3-methoxyphenyl)methyl]-2-tetrahydrofuranone; (+/-)-Arctigenin; Arctigenin, (+/-)-; Arctigenen; Arctigenin, trans-((+/-)-; 2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-; Tocris-1777; SCHEMBL381820; CHEMBL435734; MEGxp0_001799; ACon1_000416; DTXSID60998919; HMS3268E18; HMS3412H04; HMS3676H04; HY-N0035; ZINC1615344; BDBM50375656; MFCD00870597; s3897; STL565840; AKOS015897121; CCG-268327; MCULE-1275881531; MCULE-5621583813; NCGC00025291-01; NCGC00025291-02; NCGC00025291-04; 144901-91-7; 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R,4R)-rel-; 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, trans-; AS-56162; AB0019692; (-)-Arctigenin, >=95% (LC/MS-ELSD); N2399; C10545; 770A787; SR-01000597504; Q-100825; Q4787603; SR-01000597504-1; BRD-K53523901-001-01-0; UNII-2FD8L150E7 component NQWVSMVXKMHKTF-JKSUJKDBSA-N; 4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one; (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-oxidanyl-phenyl)methyl]oxolan-2-one; (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran-2-one; (3R-trans)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy- 3-methoxyphenyl)methyl]-4,5-dihydrofuran-2(3H)-one; 4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-Furanone; 4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-Furanone; EQC
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Species Origin Arctium lappa ...     Click to Show/Hide
Arctium lappa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Arctium
Species: Arctium lappa
Disease Depression [ICD-11: 6A70-6A71] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.022
 
MDCK Permeability
 -4.715
 
PAMPA
 - - -
 
HIA
 - - -
 
Distribution
VDss
 -0.365
 
PPB
 95.8%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - -
CYP2C19 inhibitor
 ++
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 +++
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 +++
CYP2B6 inhibitor
 +++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 +++
 
Excretion
CLplasma
 5.071
 
T1/2
 2.222
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 - -
 
FDAMDD
 +
 
Respiratory
 -
 
Human Hepatotoxicity
 +++
 
Ototoxicity
 +
 
Drug-induced Nephrotoxicity
 ++
 
Drug-induced Neurotoxicity
 ++
 
Hematotoxicity
 +
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C21H24O6
PubChem CID
64981
Canonical SMILES
COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC
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
CAS Number
CAS 7770-78-7
ChEBI ID
CHEBI:79
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
                    In-vitro Model NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Arctigenin has a therapeutic potential in combination with chemotherapeutic agents for NSLC.
          Ultraviolet A irradiation      Systemic sclerosis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression PRKAA2  Molecule Info 
Pathway MAP
                    In-vitro Model Human mesenchymal stem cells derived from adipose tissue Healthy Homo sapiens
                    Experimental
                    Result(s)		 Arctigenin protects against ultraviolet-A-induced damage to stemness through inhibition of the NF-KappaB/MAPK pathway.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression STAT3  Molecule Info 
Pathway MAP
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 ATG might alleviate the side effects and improve the therapeutic efficacy of DOX.
References
Reference 1 Arctigenin protects against depression by inhibiting microglial activation and neuroinflammation via HMGB1/TLR4/NF-KappaB and TNF-Alpha/TNFR1/NF-KappaB pathways. Br J Pharmacol. 2020 Nov;177(22):5224-5245.
Reference 2 Arctigenin enhances chemosensitivity to cisplatin in human nonsmall lung cancer H460 cells through downregulation of survivin expression. J Biochem Mol Toxicol. 2014 Jan;28(1):39-45.
Reference 3 Arctigenin protects against ultraviolet-A-induced damage to stemness through inhibition of the NF-KappaB/MAPK pathway. Chem Biol Interact. 2018 Feb 25;282:63-68.
Reference 4 Arctigenin Enhances the Cytotoxic Effect of Doxorubicin in MDA-MB-231 Breast Cancer Cells. Int J Mol Sci. 2020 Apr 23;21(8):2997.
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