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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

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
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
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
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
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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
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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
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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
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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
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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