Natural Product (NP) Details

General Information of the NP (ID: NP0956)
Name
Bisdemethoxycurcumin
Synonyms
Bisdemethoxycurcumin; 33171-05-0; Curcumin III; Didemethoxycurcumin; (1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; Bis(4-hydroxycinnamoyl)methane; 24939-16-0; Bis-demethoxycurcumin; Bis(p-hydroxycinnamoyl)methane; UNII-2EFO1BP34R; 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-; NSC687839; 2EFO1BP34R; 1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione; CHEMBL105350; CHEBI:71045; bisdesmethoxycurcumin; (1E,6E)-1,7-Bis(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione; BHCMT; 1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione; Curcumin Lll; Curcuminoid A; Curcumin III,; Bisdemethoxy Curcumin; di-p-coumaroylmethane; Dide Methoxycurcu Min; SCHEMBL428638; SCHEMBL13521971; cid_5324473; DTXSID00872663; ZINC1651126; 1,3-Di(4-hydroxystyryl)propanedial; BDBM50059989; MFCD03419284; AKOS015902102; CCG-207959; CCG-208635; NSC-687839; Bisdemethoxycurcumin, analytical standard; AC-24239; ADAMANTAN-1-YL-ACETICACIDHYDRAZIDE; AS-57295; AS-68737; B3347; Bisdemethoxycurcumin, >=98% (HPLC), solid; N1712; S3938; V2229; A14544; Q-100322; Q4917168; BRD-K37445107-001-01-9; 1,7-bis(4-hydroxyphenyl)-1,6-Heptadiene-3,5-dione(E,E); 1,7-bis(4-hydroxyphenyl)-3-hydroxy-1,3,6-heptatrien-5-one; (1E,6E)-1,7-Bis-(4-hydroxy-phenyl)-hepta-1,6-diene-3,5-dione; 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (1E,6E)-; 1,6-Heptadiene-3,5-dione, 1,7-bis(4-hydroxyphenyl)-, (E,E)-; 5-Hydroxy-1,7-bis-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one; (1E,4Z,6E)-5-Hydroxy-1,7-bis-(4-hydroxy-phenyl)-hepta-1,4,6-trien-3-one; 22608-12-4
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Species Origin Curcumin ...     Click to Show/Hide
Curcumin
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Cucurbitales
Family: Cucurbitaceae
Genus: Curcumin
Disease Ovarian cancer [ICD-11: 2C73] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C19H16O4
PubChem CID
5315472
Canonical SMILES
C1=CC(=CC=C1C=CC(=O)CC(=O)C=CC2=CC=C(C=C2)O)O
InChI
1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
InChIKey
PREBVFJICNPEKM-YDWXAUTNSA-N
CAS Number
CAS 33171-05-0
ChEBI ID
CHEBI:71045
Herb ID
HBIN018620
SymMap ID
SMIT00431
TCMSP ID
MOL000940
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Ampicillin      Bacterial infection     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 UL54  Molecule Info 
Pathway MAP
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Antimicrobial effect of BDMC combined with antibiotics was superior to treatment with that of a single agent alone.
          Gentamicin      Bacterial infection     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 UL54  Molecule Info 
Pathway MAP
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Antimicrobial effect of BDMC combined with antibiotics was superior to treatment with that of a single agent alone.
          Oxacillin      Bacterial infection     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 UL54  Molecule Info 
Pathway MAP
                    In-vitro Model Staphylococcus aureus strains Microorganism model Staphylococcus aureus
                    Experimental
                    Result(s)		 Antimicrobial effect of BDMC combined with antibiotics was superior to treatment with that of a single agent alone.
          X-ray irradiation      Scaphoid Fracture     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		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
                    In-vitro Model MOLT-4 CVCL_0013 Adult T acute lymphoblastic leukemia Homo sapiens
                    Experimental
                    Result(s)		 BDMC stimulates the dephosphorylation and p53-binding activity of Bcl-2 and suggest that BDMC may induce a neutralization of Bcl-2's anti-apoptotic function, thereby enhancing X-ray-induced apoptosis.
          Lcotinib      Pulmonary hypertension     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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
NCI-H1781 CVCL_1494 Lung adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Co-treatment with NAC attenuated the two drug combination-induced autophagy, apoptosis, DNA damage and decrease of cell migration and invasion ability.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Cisplatin      Bladder 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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model HK2 CVCL_0302 Healthy Homo sapiens
HKC CVCL_WZ51 Healthy Homo sapiens
HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
                    In-vivo Model Male Institute of Cancer Research (ICR) mice were used in this study.
                    Experimental
                    Result(s)		 Bisdemethoxycurcumin attenuates cisplatin-induced renal injury through anti-apoptosis, anti-oxidant and anti-inflammatory.
          Alpha PD-L1 antibody      Osteosarcoma     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 [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression IFNG  Molecule Info 
Pathway MAP
                    In-vitro Model MB49 CVCL_7076 Bladder transitional cell carcinoma Mus musculus
                    In-vivo Model To establish s.c. bladder cancer models, 1*106 MB49 cells in 100 uL PBS were injected in the right shaved flank of female C57BL/6 mice.
                    Experimental
                    Result(s)		 Bisdemethoxycurcumin in combination with Alpha-PD-L1 antibody boosts immune response against bladder cancer.
References
Reference 1 Bisdemethoxycurcumin inhibits ovarian cancer via reducing oxidative stress mediated MMPs expressions. Sci Rep. 2016 Jun 28;6:28773.
Reference 2 The Mechanism of Bisdemethoxycurcumin Enhances Conventional Antibiotics against Methicillin-Resistant Staphylococcus aureus. Int J Mol Sci. 2020 Oct 26;21(21):7945.
Reference 3 Bisdemethoxycurcumin enhances X-ray-induced apoptosis possibly through p53/Bcl-2 pathway. Mutat Res. 2017 Mar;815:1-5.
Reference 4 Bisdemethoxycurcumin Enhances the Sensitivity of Non-small Cell Lung Cancer Cells to Icotinib via Dual Induction of Autophagy and Apoptosis. Int J Biol Sci. 2020 Mar 5;16(9):1536-1550.
Reference 5 Bisdemethoxycurcumin attenuates cisplatin-induced renal injury through anti-apoptosis, anti-oxidant and anti-inflammatory. Eur J Pharmacol. 2020 May 5;874:173026.
Reference 6 Bisdemethoxycurcumin in combination with Alpha-PD-L1 antibody boosts immune response against bladder cancer. Onco Targets Ther. 2017 May 22;10:2675-2683.
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