U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H18O5
Molecular Weight 338.3539
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of DEMETHOXYCURCUMIN

SMILES

COC1=C(O)C=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=C1

InChI

InChIKey=HJTVQHVGMGKONQ-LUZURFALSA-N
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+

HIDE SMILES / InChI

Molecular Formula C20H18O5
Molecular Weight 338.3539
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/27503249 | https://www.ncbi.nlm.nih.gov/pubmed/22546674 | https://www.ncbi.nlm.nih.gov/pubmed/9301668 | https://clinicaltrials.gov/ct2/show/NCT02724202

Demethoxycurcumin is a derivative or curcumin and represents one of the major active components of curcumin products isolated from Curcumae sp. In preclinical models, Demethoxycurcumin inhibits LPS-induced nitric oxide (NO) production, and expression of iNOS and COX2 in RAW264.7 cells by blocking NF-kB activation. Demethoxycurcumin also inhibits NF-kB dependent iNOS, TNFα and IL-1β expression in LPS-treated rat microglial cells. Demethoxycurcumin suppresses the expression of MMPs and ICAM-1 in MDA-MB-231 human breast cancer cells by inhibition of NF-kB. Demethoxycurcumin is currently in Phase I clinical trials.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
24.0 µM [IC50]
21.36 µM [IC50]
120.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
85.8 ng/mL
44.25 mg/kg single, oral
dose: 44.25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEMETHOXYCURCUMIN tumor
Mus musculus
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
506.6 ng × h/mL
44.25 mg/kg single, oral
dose: 44.25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEMETHOXYCURCUMIN tumor
Mus musculus
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
39.7 h
44.25 mg/kg single, oral
dose: 44.25 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
DEMETHOXYCURCUMIN tumor
Mus musculus
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
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
Effect of pure curcumin, demethoxycurcumin, and bisdemethoxycurcumin on WT1 gene expression in leukemic cell lines.
2008 Sep
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
Curcuminoids distinctly exhibit antioxidant activities and regulate expression of scavenger receptors and heme oxygenase-1.
2013 Sep
Patents

Sample Use Guides

500 mg (95% curcumin, 5% desmethoxycurcumin) twice per day for 2 weeks.
Route of Administration: Oral
Cytotoxicity of compound 7 (Demethoxycurcumin) were evaluated against a panel of 8 cancer cell lines; lung (A549), prostate (DU-145), skin (SK-MEL-5), pancreatic (BxPC-3), liver (Hep G2), colon (HT-29), breast (MCF-7) and (MDA-MB-231). Cell lines were cultured in DMEM media supplemented with 2 mM L-glutamine, 10% fetal bovine serum, 50 mkg/ml gentamycin and 2.5 mkg/ml amphotericin B, maintained in a 37 C humid atmosphere of 5% CO2 cell incubator. Samples and drug standards (cisplatin and vinblastine sulfate) were dissolved in DMSO and immediately diluted with DMEM media to yield a final DMSO concentration of less than 0.5% v/v. Cells were plated into 96-well microplates at 5,000–10,000 cells per well and maintained in the cell incubator for 24 h. Then, 100 mkL of samples were introduced in triplicates to a final concentration of 15–150 mkM. Drug standards were also introduced to a final concentration of 0.03–2000 mkM (cisplatin) and 0.002–100 mkM (vinblastine sulfate). Cells were further incubated for 48 h and then, cell viability was determined according to the manufacturer protocol of a commercial MTS assay kit
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:59:08 GMT 2023
Edited
by admin
on Fri Dec 15 15:59:08 GMT 2023
Record UNII
W2F8059T80
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEMETHOXYCURCUMIN
INCI  
INCI  
Official Name English
1-(4-HYDROXYPHENYL)-7-(4-HYDROXY-3-METHOXYPHENYL)-HEPTA-1,6-DIENE-3,5-DIONE
Systematic Name English
DEMETHOXYCURCUMIN [INCI]
Common Name English
DEMETHOXY CURCUMIN
Common Name English
DESMETHOXYCURCUMIN (CONSTITUENT OF TURMERIC) [DSC]
Common Name English
DESMETHOXYCURCUMIN
Common Name English
CURCUMIN II
Common Name English
DESMETHOXYCURCUMIN [USP-RS]
Common Name English
INS NO.100(II)
Common Name English
MONODEMETHOXYCURCUMIN
Common Name English
1,6-HEPTADIENE-3,5-DIONE, 1-(4-HYDROXY-3-METHOXYPHENYL)-7-(4-HYDROXYPHENYL)-, (1E,6E)-
Systematic Name English
E-100(II)
Common Name English
INS-100(II)
Common Name English
Classification Tree Code System Code
DSLD 3710 (Number of products:81)
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
Code System Code Type Description
CAS
22608-11-3
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
PRIMARY
CAS
33171-16-3
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
SUPERSEDED
FDA UNII
W2F8059T80
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID00873751
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
PRIMARY
CHEBI
65737
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
PRIMARY
PUBCHEM
5469424
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
PRIMARY
RS_ITEM_NUM
1173100
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
PRIMARY
WIKIPEDIA
DESMETHOXYCURCUMIN
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
PRIMARY
SMS_ID
300000009706
Created by admin on Fri Dec 15 15:59:08 GMT 2023 , Edited by admin on Fri Dec 15 15:59:08 GMT 2023
PRIMARY