Natural Product (NP) Details

General Information of the NP (ID: NP6514)
Name
Demethoxycurcumin
Synonyms
Demethoxycurcumin; 22608-11-3; monodemethoxycurcumin; BHCFM; 24939-17-1; 4-Hydroxycinnamoyl(feroyl)methane; desmethoxycurcumin; Feruloyl-P-hydroxycinnnamoylmethane; curcuminII; (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; UNII-W2F8059T80; 1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-; 33171-16-3; p-Hydroxycinnamoylferuloylmethane; CHEBI:65737; 4-hydroxycinnamoyl(feruloyl)methane; MFCD03427310; NSC687841; W2F8059T80; (E/Z)-Demethoxycurcumin; 1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione; 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; demethoxy-curcumin; (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione; (1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione; (2E)-Demethoxy Curcumin; feruloyl-p-coumaroylmethane; (1E,6E)-Demethoxycurcumin; SCHEMBL431246; CHEMBL105360; SCHEMBL2553051; SCHEMBL13521973; cid_5324476; HY-N0006A; DTXSID00873751; (1E,6E)-1-(4-HYDROXY-3-METHOXY-PHENYL)-7-(4-HYDROXYPHENYL)HEPTA-1,6-DI ENE-3,5-DIONE; ZINC5115722; Demethoxycurcumin, >=98% (HPLC); 9331AF; BDBM50163744; s9280; Demethoxycurcumin, analytical standard; AKOS015903509; CCG-267896; NSC-687841; (E,E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione; LS-14764; CS-0009120; N1720; X1121; A14545; 6-Bromo-2-pyridin-4-yl-quinoline-4-carboxylicacid; Q-100287; Q5264607; 1-(4-Hydroxystyryl)-3-(3-methoxy-4-hydroxystyryl)propanedial; (1E,6E)-1-(4-Hydroxy-3-methoxy-phenyl)-7-(4-hydroxy-phenyl)-hepta-1,6-diene-3,5-dione; 1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)- (VAN); 1,6-Heptadiene-3,5-dione, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-, (1E,6E)-; 1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9CI; 5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one; (1E,4Z,6E)-5-Hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-7-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one; (1E,6E)-1-(4-HYDROXY-3-METHOXY-PHENYL)-7-(4-HYDROXYPHENYL)HEPTA-1,6-DIENE-3,5-DIONE; 297160-27-1
    Click to Show/Hide
Species Origin Curcumin ...     Click to Show/Hide
Curcumin
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Cucurbitales
Family: Cucurbitaceae
Genus: Curcumin
Disease Staphylococcus infection [ICD-11: 1C41] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.297
 
MDCK Permeability
 -4.932
 
PAMPA
 - -
 
HIA
 - - -
 
Distribution
VDss
 -0.627
 
PPB
 97.2%
 
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
 9.365
 
T1/2
 1.006
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.
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C20H18O5
PubChem CID
5469424
Canonical SMILES
COC1=C(C=CC(=C1)C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
InChI
1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+
InChIKey
HJTVQHVGMGKONQ-LUZURFALSA-N
CAS Number
CAS 22608-11-3
ChEBI ID
CHEBI:65737
Herb ID
HBIN023227
SymMap ID
SMIT00432
TCMSP ID
MOL000946
TTD Drug ID
D03EDF
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Resistance can be Reversed by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     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		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
                    In-vivo Model For a xenograft model, A549/DDP cells were injected into the inguinal mammary fat pad of Balb/c congenic athymic nude mice.
                    Experimental
                    Result(s)		 DMC in combination with DDP may be considered as a novel combination regimen for restoring DDP sensitivity in DDP-resistant NSCLC cells.
          AT101      Prostate cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     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 Phosphorylation AKT1  Molecule Info 
Pathway MAP
                    In-vitro Model Cells derived from glioblastoma multiforme patients Glioblastoma multiforme Homo sapiens
                    Experimental
                    Result(s)		 Phosphorylation and thereby activation of the kinases p44/42 and Akt, which are involved in proliferation and survival processes, were inhibited, the mitochondrial membrane potential of the GBM cells was altered, and genes involved in dormancy-associated processes were regulated by the combined treatment strategy.
Target and Pathway
Target(s) Prostaglandin G/H synthase 1 (COX-1)  Molecule Info  [4]
BioCyc C20 prostanoid biosynthesis Click to Show/Hide
KEGG Pathway Arachidonic acid metabolism Click to Show/Hide
2 Metabolic pathways
3 Platelet activation
4 Serotonergic synapse
NetPath Pathway TGF_beta_Receptor Signaling Pathway Click to Show/Hide
Panther Pathway Inflammation mediated by chemokine and cytokine signaling pathway Click to Show/Hide
Pathwhiz Pathway Arachidonic Acid Metabolism Click to Show/Hide
WikiPathways Prostaglandin Synthesis and Regulation Click to Show/Hide
2 Arachidonic acid metabolism
3 Phase 1 - Functionalization of compounds
4 Eicosanoid Synthesis
5 Selenium Micronutrient Network
References
Reference 1 Study on Demethoxycurcumin as a Promising Approach to Reverse Methicillin-Resistance of Staphylococcus aureus. Int J Mol Sci. 2021 Apr 6;22(7):3778.
Reference 2 Demethoxycurcumin increases the sensitivity of cisplatin-resistant non-small lung cancer cells to cisplatin and induces apoptosis by activating the caspase signaling pathway. Oncol Lett. 2020 Nov;20(5):209.
Reference 3 Combined treatment of AT101 and demethoxycurcumin yields an enhanced anti-proliferative effect in human primary glioblastoma cells. J Cancer Res Clin Oncol. 2020 Jan;146(1):117-126.
Reference 4 Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammator... Bioorg Med Chem Lett. 2005 Apr 1;15(7):1793-7.
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link