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Details

Stereochemistry ACHIRAL
Molecular Formula C21H20O6
Molecular Weight 368.3799
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CURCUMIN

SMILES

COC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC=C1O

InChI

InChIKey=VFLDPWHFBUODDF-FCXRPNKRSA-N
InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+

HIDE SMILES / InChI
Curcumin is a bright yellow chemical produced by some plants, for example, it is the principal curcuminoid of turmeric. It is sold as a food flavoring, food colorant, herbal supplement, and cosmetic ingredient. Although curcumin has been widely studied it has not been officially endorsed for any pharmaceutical use due to issues of stability and bioavailability; although it continues to b marketed as a health supplement. Curcumin has been investigated for the treatment of a number of cancers, asthma, mucositis, schizophrenia, mild cognitive impairment, and depression.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11473
Gene ID: 7421.0
Gene Symbol: VDR
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Oral administration of a turmeric extract inhibits LDL oxidation and has hypocholesterolemic effects in rabbits with experimental atherosclerosis.
1999 Dec
The effect of curcumin on glutathione-linked enzymes in K562 human leukemia cells.
1999 Sep 20
Pulmonary protective effects of curcumin against paraquat toxicity.
2000
Therapeutic potential of curcumin in human prostate cancer-I. curcumin induces apoptosis in both androgen-dependent and androgen-independent prostate cancer cells.
2000 Aug
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.
2004 Jan 9
Evidence against the rescue of defective DeltaF508-CFTR cellular processing by curcumin in cell culture and mouse models.
2004 Sep 24
Gene expression profiling identifies activating transcription factor 3 as a novel contributor to the proapoptotic effect of curcumin.
2005 Feb
Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds.
2005 Jun 15
Preventive and therapeutic effects of NF-kappaB inhibitor curcumin in rats colitis induced by trinitrobenzene sulfonic acid.
2005 Mar 28
Expression profiles of apoptotic genes induced by curcumin in human breast cancer and mammary epithelial cell lines.
2005 Sep-Oct
Curcumin inhibits trinitrobenzene sulphonic acid-induced colitis in rats by activation of peroxisome proliferator-activated receptor gamma.
2006 Aug
Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways.
2006 Feb
Curcumin protects against radiation-induced acute and chronic cutaneous toxicity in mice and decreases mRNA expression of inflammatory and fibrogenic cytokines.
2006 Jul 1
Regulation of LDL receptor expression by the effect of curcumin on sterol regulatory element pathway.
2006 Jul-Aug
Silencing of the human microsomal glucose-6-phosphate translocase induces glioma cell death: potential new anticancer target for curcumin.
2006 Jun 26
Inhibition of homodimerization of Toll-like receptor 4 by curcumin.
2006 Jun 28
Immediate and delayed treatments with curcumin prevents forebrain ischemia-induced neuronal damage and oxidative insult in the rat hippocampus.
2006 May
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines.
2007 Feb
Curcumin induces changes in expression of genes involved in cholesterol homeostasis.
2007 Feb
Disruption of transforming growth factor-beta signaling by curcumin induces gene expression of peroxisome proliferator-activated receptor-gamma in rat hepatic stellate cells.
2007 Jan
Patents

Sample Use Guides

Patients with a history of stable persistent asthma and allergic sensitivities received oral supplementation of 2000 mg of curcumin.
Route of Administration: Oral
Human colorectal adenocarcinoma cells (Caco-2) were grown at 37 deg-C under a 5% CO2 were plated at a density of 40,000 cells per well in minimum essential medium, supplemented with 20% fetal bovine serum, 1 mM sodium pyruvate, 0.1 mM nonessential amino acids, 100 units/mL penicillin and 100 micro-g/mL streptomycin. Transfection was conducted with each well receiving 1 μL of Lipofectamine Reagent, 2 μL of Plus Reagent, 500 ng of pTZ18U carrier DNA plasmid, and 20 ng of pRL-null. Each well also received 250 ng of pLuc-MCS plasmid containing an oligonucleotide with two copies of a nuclear receptor responsive element upstream of the firefly luciferase gene. In addition to the responsive element reporter constructs, cells were also cotransfected with 50 ng of a pSG5-based expression plasmid containing the appropriate nuclear receptor. The cells received both 50 ng of pSG5-VDR (vitamin D receptor), and 20 ng of pSG5-RXRα when the VDRE-containing reporter was employed. The cells were treated with known nuclear receptor ligands or curcumin (6.7 and 10 microM), 18 hours after completion of transfection; treatment times ranged from 24 to 30 hours. After incubation with ligands, cells were collected and the amount of reporter gene product (luciferase) produced in the cells was measured using the Dual-Luciferase® Reporter Assay System. Cells treated with 6.7 and 10 microM curcumin demonstrated a dose-dependent increase in the level of transcription of the VDRE-reporter plasmid of 2.1 and 5.0 fold respectively.
Name Type Language
CURCUMIN
HSDB   INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
CURCUMIN [MI]
Common Name English
CURCUMIN [USP-RS]
Common Name English
(1E,6E)-1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)-1,6-HEPTADIENE-3,5-DIONE
Systematic Name English
C.I. NATURAL YELLOW 3
Common Name English
E-100
Code English
MERITA EARTH
Common Name English
C.I. 75300
Common Name English
E 100
Code English
TURMERIC YELLOW
Common Name English
HALDAR
Common Name English
JIANGHUANGSU
Common Name English
INS-100(I)
Code English
Curcumin [WHO-DD]
Common Name English
CURCUMIN [HSDB]
Common Name English
CI 75300 [INCI]
Common Name English
KURKUM
Common Name English
E100
Code English
CURCUMIN [INCI]
Common Name English
NANOCURC
Common Name English
NSC-687842
Code English
CI 75300
INCI  
INCI  
Official Name English
LIPOCURC
Common Name English
KACHA HALDI
Common Name English
CURCUMIN (CONSTITUENT OF TURMERIC) [DSC]
Common Name English
INS NO. 100(I)
Code English
1,7-BIS-(4-HYDROXY-3-METHOXYPHENYL)-HEPTA-1,6-DIENE-3,5-DIONE
Systematic Name English
CURCUMIN E100
Common Name English
CURCUMIN [MART.]
Common Name English
DIFERULOYLMETHANE
Common Name English
NSC-32982
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 167603
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
CODEX ALIMENTARIUS (GSFA) INS-100(I)
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
JECFA EVALUATION INS-100(I)
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
DSLD 2377 (Number of products:310)
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
NCI_THESAURUS C1967
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
Code System Code Type Description
WIKIPEDIA
CURCUMIN
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
CAS
458-37-7
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
EU FOOD ADDITIVES
E100(I)
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
MESH
D003474
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EPA CompTox
DTXSID8031077
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
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NCI_THESAURUS
C401
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DRUG BANK
DB11672
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GRAS Notification (GRN No.)
822
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DAILYMED
IT942ZTH98
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-280-5
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PRIMARY
SMS_ID
100000093154
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PRIMARY
RXCUI
2955
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY RxNorm
GRAS Notification (GRN No.)
686
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
CHEBI
3962
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
EU FOOD ADDITIVES
E 100
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
MERCK INDEX
m3933
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY Merck Index
NSC
687842
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
NSC
32982
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
PUBCHEM
969516
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
FDA UNII
IT942ZTH98
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
RS_ITEM_NUM
1151855
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
EVMPD
SUB29071
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY
HSDB
4334
Created by admin on Fri Dec 15 15:10:05 GMT 2023 , Edited by admin on Fri Dec 15 15:10:05 GMT 2023
PRIMARY