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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

Molecular Formula C21H20O6
Molecular Weight 368.3799
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

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
The effect of curcumin on glutathione-linked enzymes in K562 human leukemia cells.
1999 Sep 20
Modulation of apoptotic and inflammatory genes by bioflavonoids and angiotensin II inhibition in ureteral obstruction.
2000 Aug 1
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
Spontaneous shift in transcriptional profile of explanted glomeruli via activation of the MAP kinase family.
2000 Nov
Inhibitors of human immunodeficiency virus type 1 reverse transcriptase target distinct phases of early reverse transcription.
2001 Apr
Quercetin and curcumin up-regulate antioxidant gene expression in rat kidney after ureteral obstruction or ischemia/reperfusion injury.
2001 Sep
Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.
2003 Dec
Hepatobiliary clearance of labelled mebrofenin in normal and D-galactosamine HCl-induced hepatitis rats and the protective effect of turmeric extract.
2003 Jul
Age-related difference in susceptibility of Apc(Min/+) mice towards the chemopreventive efficacy of dietary aspirin and curcumin.
2003 May 6
Hepatoprotective effect of sesquiterpenes in turmeric.
2004
Curcumin, a major constituent of turmeric, corrects cystic fibrosis defects.
2004 Apr 23
[Modulation of intestinal mucosal inflammatory factors by curcumin in rats with colitis].
2004 Dec
Curcumin protects mitochondria from oxidative damage and attenuates apoptosis in cortical neurons.
2004 Dec
Curcumin-induced apoptosis in scleroderma lung fibroblasts: role of protein kinase cepsilon.
2004 Jul
Induction of manganese-superoxide dismutase by YS 51, a synthetic 1-(beta-naphtylmethyl)6,7-dihydroxy- 1,2,3,4-tetrahydroisoquinoline alkaloid: implication for anti-inflammatory actions.
2004 Jun
Therapeutic potential of curcumin in prostate cancer--V: Interference with the osteomimetic properties of hormone refractory C4-2B prostate cancer cells.
2004 Jun 15
Anti-apoptotic effects of curcumin on photosensitized human epidermal carcinoma A431 cells.
2004 May 1
CSN5/Jab1 is involved in ligand-dependent degradation of estrogen receptor {alpha} by the proteasome.
2005 Jun
Curcumin selectively induces apoptosis in deregulated cyclin D1-expressed cells at G2 phase of cell cycle in a p53-dependent manner.
2005 May 20
Effect of artemisinin/artesunate as inhibitors of hepatitis B virus production in an "in vitro" replicative system.
2005 Nov
Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression, by curcumin and its analog, alpha-diisoeugenol.
2005 Nov-Dec
Effects of nuclear factor-kappaB inhibitors and its implication on natural killer T-cell lymphoma cells.
2005 Oct
Curcumin suppresses the paclitaxel-induced nuclear factor-kappaB pathway in breast cancer cells and inhibits lung metastasis of human breast cancer in nude mice.
2005 Oct 15
The antioxidants curcumin and quercetin inhibit inflammatory processes associated with arthritis.
2006 Apr
Selective protection of curcumin against carbon tetrachloride-induced inactivation of hepatic cytochrome P450 isozymes in rats.
2006 Apr 4
Curcumin inhibits trinitrobenzene sulphonic acid-induced colitis in rats by activation of peroxisome proliferator-activated receptor gamma.
2006 Aug
A specific method for measurement of equine active myeloperoxidase in biological samples and in in vitro tests.
2006 Jul
Curcumin protects against radiation-induced acute and chronic cutaneous toxicity in mice and decreases mRNA expression of inflammatory and fibrogenic cytokines.
2006 Jul 1
Curcumin-attenuated trinitrobenzene sulphonic acid induces chronic colitis by inhibiting expression of cyclooxygenase-2.
2006 Jun 28
Immediate and delayed treatments with curcumin prevents forebrain ischemia-induced neuronal damage and oxidative insult in the rat hippocampus.
2006 May
Curcumin inhibits hypoxia-inducible factor-1 by degrading aryl hydrocarbon receptor nuclear translocator: a mechanism of tumor growth inhibition.
2006 Nov
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Jak3- and JNK-dependent vascular endothelial growth factor expression in cutaneous T-cell lymphoma.
2006 Oct
Curcumin sensitizes tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-mediated apoptosis through CHOP-independent DR5 upregulation.
2006 Oct
TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin.
2006 Oct 16
Inhibitory effect of curcumin on nitric oxide production from lipopolysaccharide-activated primary microglia.
2006 Oct 19
Modification by curcumin of mutagenic activation of carcinogenic N-nitrosamines by extrahepatic cytochromes P-450 2B1 and 2E1 in rats.
2006 Sep
Curcumin inhibits neurotensin-mediated interleukin-8 production and migration of HCT116 human colon cancer cells.
2006 Sep 15
Hydrogen peroxide-mediated downregulation of matrix metalloprotease-2 in indomethacin-induced acute gastric ulceration is blocked by melatonin and other antioxidants.
2006 Sep 15
Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines.
2007 Feb
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:10:05 GMT 2023
Edited
by admin
on Fri Dec 15 15:10:05 GMT 2023
Record UNII
IT942ZTH98
Record Status Validated (UNII)
Record Version
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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
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
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
PRIMARY
NCI_THESAURUS
C401
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
DRUG BANK
DB11672
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
GRAS Notification (GRN No.)
822
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
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
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
SMS_ID
100000093154
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
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
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
IN-VIVO
PLASMA
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE -> PARENT
Significant Metabolite
METABOLITE -> PARENT
IN-VIVO
PLASMA
METABOLITE -> PARENT
Significant Metabolite
METABOLITE -> PARENT
Significant Metabolite
METABOLITE -> PARENT
IN-VIVO
METABOLITE -> PARENT
Significant Metabolite
METABOLITE -> PARENT
Unit: mcg/mL; Fraction of curcumin glucuronide in plasma at Cmax after administration of 10g curcumin (n=6); Total curcumin: 3.10 +/- 0.60 mcg/mL
IN-VIVO
PLASMA
METABOLITE -> PARENT
IN-VIVO
METABOLITE -> PARENT
Unit: mcg/mL; Fraction of curcumin sulfate in plasma at Cmax after administration of 12 g curcumin; Total curcumin: 2.27 +/- 1.17 mcg/mL
IN-VIVO
PLASMA
Related Record Type Details
ACTIVE MOIETY