Showing Compound Demethoxycurcumin (FDB011964)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:55 UTC

Update date

2025-11-18 23:32:32 UTC

Primary ID

FDB011964

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Demethoxycurcumin

Description

Demethoxycurcumin, also known as curcuminii or BHCFM, 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. Demethoxycurcumin is found, on average, in the highest concentration within turmerics (Curcuma longa). Demethoxycurcumin has also been detected, but not quantified in, a few different foods, such as beverages, herbs and spices, and root vegetables. This could make demethoxycurcumin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Demethoxycurcumin.

CAS Number

22608-11-3

Structure

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

Synonyms

Synonym	Source
(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione	ChEBI
(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione	ChEBI
4-Hydroxycinnamoyl(feroyl)methane	ChEBI
4-Hydroxycinnamoyl(feruloyl)methane	ChEBI
BHCFM	ChEBI
CurcuminII	ChEBI
Feruloyl-p-hydroxycinnnamoylmethane	ChEBI
Monodemethoxycurcumin	MeSH
Curcumin II	MeSH
Demethoxy-curcumin	MeSH
1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9ci	HMDB
P-Hydroxycinnamoylferuloylmethane	HMDB
(1e,6e)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione	ChEBI
(1e,6e)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dione	ChEBI
1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9CI	db_source
4-hydroxycinnamoyl(feroyl)methane	biospider
Bhcfm	biospider
Demethoxycurcumin	db_source
p-Hydroxycinnamoylferuloylmethane	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.0067 g/L	ALOGPS
logP	3.54	ALOGPS
logP	4.28	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.35 m³·mol⁻¹	ChemAxon
Polarizability	35.35 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

C20H18O5

IUPAC name

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

InChI Identifier

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+

InChI Key

HJTVQHVGMGKONQ-LUZURFALSA-N

Isomeric SMILES

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

Average Molecular Weight

338.3539

Monoisotopic Molecular Weight

338.115423686

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

Desmethoxycurcumin
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

enone (CHEBI:65737 )
polyphenol (CHEBI:65737 )
beta-diketone (CHEBI:65737 )
diarylheptanoid (CHEBI:65737 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 71.00%; H 5.36%; O 23.64%	DFC
Melting Point	Mp 168°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Demethoxycurcumin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00r2-0901000000-654fca3f02d69e7560db	Spectrum
Predicted GC-MS	Demethoxycurcumin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-3071900000-50aab8ffd9b366fd14d7	Spectrum
Predicted GC-MS	Demethoxycurcumin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0002-0900000000-9517befe911ff515a392	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0239000000-696b9f742f1375d511b6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0910000000-9ba8139233df2e7399cd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0920000000-d6ec1db1bc78454ca02e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-002b-0910000000-2b60408614dbac128af7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0900000000-5fbd4f101ab8f66c229a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a6s-0961000000-682f6b15c69a852c5c25	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0219000000-e3bd2864892e4f6e2318	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0910000000-dc9c78751e44dd920a70	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-014i-0900000000-0a19a373bd22907fff2f	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0419000000-127d78c62fb7431896b5	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-0901000000-c40b24a8778d2fa9787d	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-1900000000-82aa8b73d450c54c4c30	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0309000000-1e9e9a7c9cdc0d078ad5	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-0914000000-656374264de68ab93dd6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-07xs-1911000000-d77a4b8103374473002f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0709000000-d28143d2357c12a71e64	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0901000000-071370f22d66d14d47d2	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-1910000000-dbecc05d29e924e0b535	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0952000000-238d293f45f85e124a77	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-0913000000-2bcebdb0a036193118c7	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014r-0912000000-46bf9193d3b8351d3505	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4579941

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5469424

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

714

DrugBank ID

Not Available

HMDB ID

HMDB33801

CRC / DFC (Dictionary of Food Compounds) ID

HFR53-E:HCC54-N

EAFUS ID

Not Available

Dr. Duke ID

MONODEMETHOXYCURCUMIN|MONODESMETHOXYCURCUMIN|DEMETHOXYCURCUMIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

Desmethoxycurcumin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti aflatoxin	35222	An agent that neutralizes or removes aflatoxins, toxic compounds produced by mold, reducing the risk of liver damage and cancer. Therapeutically, it is used to prevent aflatoxin poisoning, commonly in food safety and liver protection applications, and may have potential in cancer prevention and treatment.	DUKE
Anti-Alzheimeran	52217	An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.	DUKE
Anti amyloid-beta		An agent that targets and reduces amyloid-beta peptides, implicated in Alzheimer's disease, to slow cognitive decline and neurodegeneration, with potential therapeutic applications in Alzheimer's treatment and prevention.	DUKE
Anti-angiogenic	48422	An agent that inhibits the formation of new blood vessels, playing a crucial role in cancer treatment by starving tumors of oxygen and nutrients. Therapeutically, it is used to manage cancer, age-related macular degeneration, and other diseases characterized by excessive angiogenesis, reducing tumor growth and slowing disease progression.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti leishmanic	33281	An agent that treats Leishmaniasis, a parasitic disease caused by Leishmania parasites. It kills or inhibits the growth of these parasites, reducing symptoms and preventing disease progression. Therapeutically, anti-leishmanics are used to manage cutaneous, visceral, and mucocutaneous Leishmaniasis, often in combination with other treatments. Key medical uses include treating infected individuals, particularly in endemic regions.	DUKE
Anti lipoperoxidant		An agent that prevents peroxidation of lipids, reducing oxidative stress and cell damage. Its biological role involves protecting cell membranes from degradation. Therapeutically, it has applications in managing conditions related to oxidative stress, with key medical uses including neuroprotection, anti-inflammation, and antioxidant therapy.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Anti-nitrosating		An agent that prevents the formation of nitroso compounds, reducing oxidative stress and inflammation. It plays a biological role in protecting cells from damage. Therapeutically, it has applications in managing cancer, neurodegenerative diseases, and inflammatory disorders, with key medical uses in preventing nitrosative stress and promoting cellular health.	DUKE
Anti-papillomic	22587	An agent that targets and inhibits the formation of papillomas, reducing the growth of abnormal cells. Therapeutically, it is used to treat and prevent human papillomavirus (HPV) related diseases, such as cervical cancer and genital warts, by boosting the immune system to fight off the virus.	DUKE
Antitumor promoter	35610	An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.	DUKE
DNA-protective		An agent that prevents or repairs DNA damage, playing a crucial role in maintaining genomic stability. Therapeutically, it has applications in cancer prevention, neuroprotection, and anti-aging. Key medical uses include reducing chemotherapy-induced DNA damage and mitigating radiation exposure effects.	DUKE
Nematicide	25491	An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.	DUKE
Nitric-oxide scavenger		An agent that retains nitric oxide, reducing its bioavailability. It plays a role in regulating vascular tone and inflammation. Therapeutically, it's used to manage conditions like hypertension and septic shock, with key medical uses including cardiovascular and critical care applications.	DUKE
Plasmodicide		An agent that kills malaria parasites, playing a crucial role in treating and preventing malaria. Therapeutically, it targets Plasmodium species, and its key medical uses include prophylaxis and treatment of malaria, particularly in endemic areas, helping to reduce transmission and alleviate disease burden.	DUKE
Quinone-reductase inducer		An agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.	DUKE
Sortase-A inhibitor	23924	An agent that blocks the activity of sortase-A, an enzyme essential for bacterial cell wall assembly, reducing bacterial virulence and infection. Therapeutically, it has applications in treating Gram-positive bacterial infections, particularly those caused by methicillin-resistant Staphylococcus aureus (MRSA).	DUKE
Topoisomerase-II inhibitor	50750	An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.	DUKE
Topoisomerase-I inhibitor	50276	An agent that blocks the activity of topoisomerase I, an enzyme involved in DNA replication. It is used therapeutically in cancer treatment, particularly for solid tumors, by inducing DNA damage and inhibiting cancer cell growth, with key medical uses in colorectal, lung, and breast cancers.	DUKE