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

Details

Stereochemistry ACHIRAL
Molecular Formula C21H20O6
Molecular Weight 368.3807
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CURCUMIN

SMILES

COc1cc(/C(/[H])=C(\[H])/C(=O)CC(=O)/C(/[H])=C(\[H])/c2ccc(c(c2)OC)O)ccc1O

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 368.3807
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
Protective role of aqueous turmeric extract against mutagenicity of direct-acting carcinogens as well as benzo [alpha] pyrene-induced genotoxicity and carcinogenicity.
1992
Hepatoprotective effect of sesquiterpenes in turmeric.
2004
Gene expression profiling identifies activating transcription factor 3 as a novel contributor to the proapoptotic effect of curcumin.
2005 Feb
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
Combined effects of GSTP1 and MRP1 in melanoma drug resistance.
2005 Jul 25
CSN5/Jab1 is involved in ligand-dependent degradation of estrogen receptor {alpha} by the proteasome.
2005 Jun
Antioxidant and antigenotoxic effects of plant cell wall hydroxycinnamic acids in cultured HT-29 cells.
2005 Jun
Inhibition of multidrug resistance proteins MRP1 and MRP2 by a series of alpha,beta-unsaturated carbonyl compounds.
2005 Jun 15
Antitumor effects of curcumin, alone or in combination with cisplatin or doxorubicin, on human hepatic cancer cells. Analysis of their possible relationship to changes in NF-kB activation levels and in IAP gene expression.
2005 Jun 16
Preventive and therapeutic effects of NF-kappaB inhibitor curcumin in rats colitis induced by trinitrobenzene sulfonic acid.
2005 Mar 28
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
Inhibition of nuclear translocation of nuclear factor-kappaB despite lack of functional IkappaBalpha protein overcomes multiple defects in apoptosis signaling in human B-cell malignancies.
2005 Nov 15
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
Curcumin (diferuloylmethane) inhibits constitutive NF-kappaB activation, induces G1/S arrest, suppresses proliferation, and induces apoptosis in mantle cell lymphoma.
2005 Sep 1
Expression profiles of apoptotic genes induced by curcumin in human breast cancer and mammary epithelial cell lines.
2005 Sep-Oct
Synergistic inhibitory effects of curcumin and 5-fluorouracil on the growth of the human colon cancer cell line HT-29.
2006
The antioxidants curcumin and quercetin inhibit inflammatory processes associated with arthritis.
2006 Apr
Indomethacin inactivates gastric peroxidase to induce reactive-oxygen-mediated gastric mucosal injury and curcumin protects it by preventing peroxidase inactivation and scavenging reactive oxygen.
2006 Apr 15
Selective protection of curcumin against carbon tetrachloride-induced inactivation of hepatic cytochrome P450 isozymes in rats.
2006 Apr 4
Curcumin regulated shift from Th1 to Th2 in trinitrobenzene sulphonic acid-induced chronic colitis.
2006 Aug
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
Curcuminoids purified from turmeric powder modulate the function of human multidrug resistance protein 1 (ABCC1).
2006 Feb
Amyloid-beta peptide binds with heme to form a peroxidase: relationship to the cytopathologies of Alzheimer's disease.
2006 Feb 28
Curcumin (diferuloylmethane) down-regulates expression of cell proliferation and antiapoptotic and metastatic gene products through suppression of IkappaBalpha kinase and Akt activation.
2006 Jan
Turmeric and curcumin modulate the conjugation of 1-naphthol in Caco-2 cells.
2006 Jul
Curcumin decreases binding of Shiga-like toxin-1B on human intestinal epithelial cell line HT29 stimulated with TNF-alpha and IL-1beta: suppression of p38, JNK and NF-kappaB p65 as potential targets.
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
Silencing of the human microsomal glucose-6-phosphate translocase induces glioma cell death: potential new anticancer target for curcumin.
2006 Jun 26
Curcumin-attenuated trinitrobenzene sulphonic acid induces chronic colitis by inhibiting expression of cyclooxygenase-2.
2006 Jun 28
Inhibition of homodimerization of Toll-like receptor 4 by curcumin.
2006 Jun 28
Turmeric extracts containing curcuminoids prevent experimental rheumatoid arthritis.
2006 Mar
Interleukin-18 induces the production of vascular endothelial growth factor (VEGF) in rheumatoid arthritis synovial fibroblasts via AP-1-dependent pathways.
2006 Mar 15
Immediate and delayed treatments with curcumin prevents forebrain ischemia-induced neuronal damage and oxidative insult in the rat hippocampus.
2006 May
Curcumin attenuates thermal hyperalgesia in a diabetic mouse model of neuropathic pain.
2006 May 1
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
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:46:14 UTC 2021
Edited
by admin
on Sat Jun 26 01:46:14 UTC 2021
Record UNII
IT942ZTH98
Record Status Validated (UNII)
Record Version
  • Download
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 [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
CURCUMIN [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 167603
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
NCI_THESAURUS C1323
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
CODEX ALIMENTARIUS (GSFA) INS-100(I)
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
JECFA EVALUATION INS-100(I)
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
DSLD 2377 (Number of products:310)
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
NCI_THESAURUS C1967
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
Code System Code Type Description
WIKIPEDIA
CURCUMIN
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
CAS
458-37-7
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
EU FOOD ADDITIVES
E100(I)
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
MESH
D003474
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
EPA CompTox
458-37-7
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
NCI_THESAURUS
C401
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
DRUG BANK
DB11672
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-280-5
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
RXCUI
2955
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY RxNorm
EU FOOD ADDITIVES
E 100
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
MERCK INDEX
M3933
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY Merck Index
PUBCHEM
969516
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
FDA UNII
IT942ZTH98
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
USP_CATALOG
1151855
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY USP-RS
JECFA MONOGRAPH
INS-100(I)
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
EVMPD
SUB29071
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
HSDB
4334
Created by admin on Sat Jun 26 01:46:14 UTC 2021 , Edited by admin on Sat Jun 26 01:46:14 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
IN-VIVO
PLASMA
METABOLITE -> PARENT
3.6 g/day curcumin oral administration, 24-hour urine, n=6 (white Caucasians with histologically proven adenocarcinoma of the colon or rectum)
IN-VIVO
URINE
METABOLITE -> PARENT
Significant Metabolite
METABOLITE -> PARENT
Unit: mcg/mL; Fraction of curcumin sulfate in plasma at Cmax after administration of 10 g curcumin; Total curcumin: 3.10 +/- 0.60 mcg/mL
IN-VIVO
PLASMA
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
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