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Details

Stereochemistry ACHIRAL
Molecular Formula C19H16O4
Molecular Weight 308.3279
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BISDEMETHOXYCURCUMIN

SMILES

OC1=CC=C(C=C1)\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2

InChI

InChIKey=PREBVFJICNPEKM-YDWXAUTNSA-N
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+

HIDE SMILES / InChI

Molecular Formula C19H16O4
Molecular Weight 308.3279
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23873854 | https://www.ncbi.nlm.nih.gov/pubmed/26546528 | https://www.ncbi.nlm.nih.gov/pubmed/26546528 | https://www.ncbi.nlm.nih.gov/pubmed/26777574

Bisdemethoxycurcumin (BDMC) is a minor constituent (approximately 3%) of curcuminoids that has been shown to be more stable than the other two main curcuminoids, that is, curcumin and desmethoxycurcumin. Bisdemethoxycurcumin inhibits the proliferation and survival of several types of tumor cells including colon cancer cells, breast cancer cells, leukemia cells, and glioma cells. In addition, Bisdemethoxycurcumin suppresses cancer invasion and has the highest anti-metastatic potency in HT1080 human fibrosarcoma cells among the three curcuminoids. Bisdemethoxycurcumin has been reported to possess anti-oxidant and anti-inflammatory activities. However, the underlying molecular mechanisms responsible for the inhibitory action of Bisdemethoxycurcumin on tumor invasion and migration have remained largely unknown. More interestingly, the anti-cancer effects of Bisdemethoxycurcumin are comparable to and sometimes more potent than those of curcumin in different conditions.

Originator

Sources: Pharmaceutica Acta Helvetiae (1959), 34, 181-8.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action.
1997 Sep 12
Curcuminoids and sesquiterpenoids in turmeric (Curcuma longa L.) suppress an increase in blood glucose level in type 2 diabetic KK-Ay mice.
2005 Feb 23
Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds.
2005 Jun 15
Curcuminoids purified from turmeric powder modulate the function of human multidrug resistance protein 1 (ABCC1).
2006 Feb
Regulation of heme oxygenase-1 expression by demethoxy curcuminoids through Nrf2 by a PI3-kinase/Akt-mediated pathway in mouse beta-cells.
2007 Sep
Comparison of suppressive effects of demethoxycurcumin and bisdemethoxycurcumin on expressions of inflammatory mediators in vitro and in vivo.
2008 Apr
Immune defects in Alzheimer's disease: new medications development.
2008 Dec 3
Comparison of inhibitory potency of three different curcuminoid pigments on nitric oxide and tumor necrosis factor production of rat primary microglia induced by lipopolysaccharide.
2008 Dec 5
Dimethoxycurcumin, a synthetic curcumin analogue with higher metabolic stability, inhibits NO production, inducible NO synthase expression and NF-kappaB activation in RAW264.7 macrophages activated with LPS.
2008 Sep
Effect of pure curcumin, demethoxycurcumin, and bisdemethoxycurcumin on WT1 gene expression in leukemic cell lines.
2008 Sep
Comparative antiulcer effect of bisdemethoxycurcumin and curcumin in a gastric ulcer model system.
2009 Apr
Optimized turmeric extracts have potent anti-amyloidogenic effects.
2009 Dec
Inhibitory effect of curcuminoids on acetylcholinesterase activity and attenuation of scopolamine-induced amnesia may explain medicinal use of turmeric in Alzheimer's disease.
2009 Feb
Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the down-regulation of MMPs and uPA.
2009 Feb
Induction of antioxidant enzymes by curcumin and its analogues in human islets: implications in transplantation.
2009 May
Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity.
2010 Oct
Evaluation in vitro of synthetic curcumins as agents promoting monocytic gene expression related to β-amyloid clearance.
2012 Jan 13
Curcuminoids distinctly exhibit antioxidant activities and regulate expression of scavenger receptors and heme oxygenase-1.
2013 Sep
Patents

Patents

Sample Use Guides

Mice were treated with Bisdemethoxycurcumin as a dose of either 1 or 5 g/kg diet for 15 weeks.
Route of Administration: Oral
NCI-H460 cells at a density of 5Ч105 cells/ml were maintained on 12-well plates with RPMI-1640 medium for 24 h and then incubated with or without 35 μM of Bisdemethoxycurcumin for 24 h. At the end of incubation, cells were collected from each treatment and total RNA was extracted by using the Qiagen RNeasy Mini Kit (Qiagen, Inc, Valencia, CA, USA)
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:42:25 GMT 2023
Edited
by admin
on Fri Dec 15 15:42:25 GMT 2023
Record UNII
2EFO1BP34R
Record Status Validated (UNII)
Record Version
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Name Type Language
BISDEMETHOXYCURCUMIN
Common Name English
BISDESMETHOXYCURCUMIN
Common Name English
BISDESMETHOXYCURCUMIN (CONSTITUENT OF TURMERIC) [DSC]
Common Name English
BIS-DEMETHOXYCURCUMIN [INCI]
Common Name English
1,6-HEPTADIENE-3,5-DIONE, 1,7-BIS(4-HYDROXYPHENYL)-, (1E,6E)-
Systematic Name English
BIS-DEMETHOXYCURCUMIN
INCI  
INCI  
Official Name English
INS NO.100(III)
Common Name English
1,7-BIS-(4-HYDROXYPHENYL)-HEPTA-1,6-DIENE-3,5-DIONE
Systematic Name English
DIDEMETHOXYCURCUMIN
Common Name English
BISDESMETHOXYCURCUMIN [USP-RS]
Common Name English
CURCUMIN III
Common Name English
E-100(III)
Common Name English
INS-100(III)
Common Name English
Classification Tree Code System Code
DSLD 3710 (Number of products:81)
Created by admin on Fri Dec 15 15:42:25 GMT 2023 , Edited by admin on Fri Dec 15 15:42:25 GMT 2023
Code System Code Type Description
SMS_ID
300000009705
Created by admin on Fri Dec 15 15:42:25 GMT 2023 , Edited by admin on Fri Dec 15 15:42:25 GMT 2023
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FDA UNII
2EFO1BP34R
Created by admin on Fri Dec 15 15:42:25 GMT 2023 , Edited by admin on Fri Dec 15 15:42:25 GMT 2023
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EPA CompTox
DTXSID00872663
Created by admin on Fri Dec 15 15:42:25 GMT 2023 , Edited by admin on Fri Dec 15 15:42:25 GMT 2023
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CHEBI
71045
Created by admin on Fri Dec 15 15:42:25 GMT 2023 , Edited by admin on Fri Dec 15 15:42:25 GMT 2023
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CAS
33171-05-0
Created by admin on Fri Dec 15 15:42:25 GMT 2023 , Edited by admin on Fri Dec 15 15:42:25 GMT 2023
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PUBCHEM
5315472
Created by admin on Fri Dec 15 15:42:25 GMT 2023 , Edited by admin on Fri Dec 15 15:42:25 GMT 2023
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WIKIPEDIA
Curcumin III
Created by admin on Fri Dec 15 15:42:25 GMT 2023 , Edited by admin on Fri Dec 15 15:42:25 GMT 2023
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RS_ITEM_NUM
1075305
Created by admin on Fri Dec 15 15:42:25 GMT 2023 , Edited by admin on Fri Dec 15 15:42:25 GMT 2023
PRIMARY