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Showing Compound Bisdemethoxycurcumin (FDB011961)

Record Information
Version1.0
Creation date2010-04-08 22:09:55 UTC
Update date2019-11-26 03:05:50 UTC
Primary IDFDB011961
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBisdemethoxycurcumin
DescriptionIsolated from Curcuma zedoaria (zedoary) and Curcuma longa (turmeric) Bisdemethoxycurcumin is a curcuminoid, a component of tumeric. Tumeric is a spice that comes from the root Curcuma longa, a member of the ginger family, Zingaberaceae. It is bright yellow and has been used as a coloring agent in food in the United States. In India, it has been used for centuries as a spice and a food preservative, and also for its various medicinal properties. In Ayurveda (Indian traditional medicine), tumeric has been used for its medicinal properties for various indications and through different routes of administration. It has been used topically on the skin for wounds, blistering diseases such as pemphigus and herpes zoster, for parasitic skin infections, and for acne. It has been used via oral administration for the common cold, liver diseases, urinary tract diseases, and as a blood purifier. For chronic rhinitis and coryza, it has been used via inhalation. The average intake of tumeric in the diet in India is approximately 2 to 2.5 g in a 60 kg individual. This corresponds to an intake of approximately 60 to 100 mg of curcumin daily. The Food and Drug Administration has classified tumeric among substances Generally Recognized as Safe (GRAS). A large number of in vitro and animal studies have been conducted to evaluate the effect of curcumin on inflammation. It has been found to act at various different levels of the arachadonic acid inflammatory cascade and through effects on various enzymes and cytokines. (PMID: 12676044) [HMDB]. Bisdemethoxycurcumin is found in turmeric and herbs and spices.
CAS Number24939-16-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dioneChEBI
1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9CIdb_source
1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione(e,e)HMDB
Bis-demethoxycurcuminhmdb
Bis(4-hydroxycinnamoyl)methanehmdb
Bis(p-hydroxycinnamoyl)methanehmdb
Bisdemethoxycurcumindb_source
Bisdesmethoxycurcuminmanual
Curcumin IIIChEBI
DidemethoxycurcuminChEBI
p,p'-Dihydroxydicinnamoylmethanedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.5ALOGPS
logP4.07ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.64ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.2 m³·mol⁻¹ChemAxon
Polarizability33.98 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H16O4
IUPAC name(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
InChI IdentifierInChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-13,20-22H/b11-5+,12-6+,18-13-
InChI KeyYXAKCQIIROBKOP-HSSGTREWSA-N
Isomeric SMILESO\C(\C=C\C1=CC=C(O)C=C1)=C/C(=O)/C=C/C1=CC=C(O)C=C1
Average Molecular Weight308.3279
Monoisotopic Molecular Weight308.104859
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentCurcuminoids
Alternative Parents
Substituents
  • Bis-desmethoxycurcumin
  • Hydroxycinnamic acid or derivatives
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Enol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 74.01%; H 5.23%; O 20.76%DFC
Melting PointMp 224°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0619000000-04c5e653489d11d272bc2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0911000000-45b276752a6ac22386a22016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066v-3900000000-6fb504b278c1fe28ae9d2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0509000000-d7d0265e261b4033bbda2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0905000000-99988579561e10c6b6032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-1910000000-0dbe79994d1f7acb89472016-08-03View Spectrum
NMRNot Available
ChemSpider ID4474770
ChEMBL IDCHEMBL105350
KEGG Compound IDNot Available
Pubchem Compound ID5315472
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID715
DrugBank IDNot Available
HMDB IDHMDB02114
CRC / DFC (Dictionary of Food Compounds) IDHFR53-E:HCC43-J
EAFUS IDNot Available
Dr. Duke IDBIS-DEMETHOXYCURCUMIN|BIS-DESMETHOXYCURCUMIN|DIDESMETHOXYCURCUMIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti aflatoxin35222 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-Alzheimeran52217 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-betaAn 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-angiogenic48422 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-cholereticAn agent that inhibits excessive bile production in the liver, reducing bile flow into the intestine. It has therapeutic applications in managing biliary colic, cholecystitis, and other liver disorders, and is used to treat conditions characterized by excessive bile secretion.DUKE
Anti-inflammatory35472 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 leishmanic33281 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 lipoperoxidantAn 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-mutagenicAn 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-nitrosatingAn 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-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-papillomic22587 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 promoter35610 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-protectiveAn 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
Nematicide25491 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 scavengerAn 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
PlasmodicideAn 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 inducerAn 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 inhibitor23924 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 inhibitor50750 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 inhibitor50276 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).