Showing Compound Curcumin (FDB012292)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:05 UTC

Update date

2019-11-26 03:06:32 UTC

Primary ID

FDB012292

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Curcumin

Description

Curcumin, also known as diferuloylmethane or turmeric yellow, belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. Curcumin is found, on average, in the highest concentration within turmerics (Curcuma longa) and curry powder. Curcumin has also been detected, but not quantified in, several different foods, such as atlantic herrings (Clupea harengus harengus), saskatoon berries (Amelanchier alnifolia), peanuts (Arachis hypogaea), lettuces (Lactuca sativa), and green bell peppers (Capsicum annuum). This could make curcumin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Curcumin.

CAS Number

458-37-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Show entries

Search:

Synonym	Source
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione	HMDB
1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione, 9CI	db_source
1,7-Bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione	HMDB
1,9-Bis(4-hydroxy-3-methoxyphenyl)-2,7-nonadiene-4,6-dione	HMDB
C.I. 75300	ChEBI
C.I. natural yellow 3	ChEBI
C.I. Natural Yellow 3	db_source
CI natural yellow 3	HMDB
Cucurmin	HMDB
Curcuma	HMDB

Showing 1 to 10 of 42 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0058 g/L	ALOGPS
logP	3.62	ALOGPS
logP	4.12	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	103.81 m³·mol⁻¹	ChemAxon
Polarizability	38.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H20O6

IUPAC name

(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

InChI Identifier

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+

InChI Key

VFLDPWHFBUODDF-FCXRPNKRSA-N

Isomeric SMILES

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

Average Molecular Weight

368.3799

Monoisotopic Molecular Weight

368.125988372

Classification

Description

Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Curcumin
Hydroxycinnamic acid or derivatives
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
1,3-diketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
1,3-dicarbonyl compound
Monocyclic benzene moiety
Acryloyl-group
Alpha,beta-unsaturated ketone
Enone
Ketone
Ether
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:3962 )
enone (CHEBI:3962 )
polyphenol (CHEBI:3962 )
beta-diketone (CHEBI:3962 )
diarylheptanoid (CHEBI:3962 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Animal

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 68.47%; H 5.47%; O 26.06%	DFC
Melting Point	Mp 183°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Curcumin, non-derivatized, GC-MS Spectrum	splash10-0fbc-0923000000-107f42bbc825be91449b	Spectrum
GC-MS	Curcumin, non-derivatized, GC-MS Spectrum	splash10-0fbc-0923000000-107f42bbc825be91449b	Spectrum
Predicted GC-MS	Curcumin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-0902000000-a583c69443735ecee34d	Spectrum
Predicted GC-MS	Curcumin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006t-3090600000-d97f58b9779a3d4c58d5	Spectrum
Predicted GC-MS	Curcumin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Curcumin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF , negative	splash10-0600-0920000000-c006d38848959c621ec5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0982000000-2c508f0e4a39ae290728	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-0950000000-af821cd7589af1e24d16	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0fk9-0981000000-e4da18f81a545b08874b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-002b-2920000000-3c3aa8613bf16651cdf5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000t-0911000000-abf0df68155c943697d1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0900000000-0a0213a836a78f6e54cd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03k9-0169000000-ba031996da79b96e1951	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004r-0960000000-f8dd0033b656ce57faaa	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0291000000-2396d815134514f2f735	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014j-0982000000-9cbccf58679bdd2133ef	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0209000000-f995da101a08357914b0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0913000000-6bece31c8c8078c2fda4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-1900000000-6706d488783638730883	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0109000000-3cbd5e4d9320bc54c318	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0729000000-ae0fe93ebdfbeed7cc4f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004v-0914000000-72385474a47d42818f05	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0419000000-9ca31d2513afa0489fab	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ls-0924000000-a7bc7daf4e9622a19a4b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-008j-0922000000-5ce00b7393b9b7b00d5b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-016r-0609000000-79fd92244350d542a9f0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0171-0955000000-d16b5d995679749aff17	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002k-1943000000-404ab5fc28a3d651940e	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

713

DrugBank ID

Not Available

HMDB ID

HMDB02269

CRC / DFC (Dictionary of Food Compounds) ID

HFR53-E:HFR53-E

EAFUS ID

Not Available

Dr. Duke ID

DIFERULOYL-METHANE|CURCUMIN

BIGG ID

Not Available

KNApSAcK ID

C00002731

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Show entries

Search:

Descriptor	ID	Definition	Reference
12-lipoxygenase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
5-hydroxyeicosatetraenoic-acid inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
5-lipoxygenase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
5alpha-reductase inhibitor	50781	An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.	DUKE
8-hydroxyeicosatetraenoic-acid inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti adenoma carcinogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti aflatoxin	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti aggregant			DUKE
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti amyloid-beta			DUKE