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Showing Compound Rhamnetin (FDB002829)

Record Information
Version1.0
Creation date2010-04-08 22:05:32 UTC
Update date2020-02-24 19:11:09 UTC
Primary IDFDB002829
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRhamnetin
Description2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one, also known as 7-methoxyquercetin or quercetin 7-methyl ether, is a member of the class of compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one can be found in a number of food items such as tea, apple, sweet orange, and parsley, which makes 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one a potential biomarker for the consumption of these food products.
CAS Number90-19-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3,3',4',5-Tetrahydroxy-7-methoxyflavoneChEBI
3,5,3',4'-Tetrahydroxy-7-methoxyflavoneChEBI
7-MethoxyquercetinChEBI
7-MethylquercetinChEBI
7-O-MethylquercetinChEBI
beta-RhamnocitrinChEBI
Quercetin 7-methyl etherChEBI
b-RhamnocitrinGenerator
Β-rhamnocitrinGenerator
2-(3,4-Dihydroxy-phenyl)-3,5-dihydroxy-7-methoxy-chromen-4-oneHMDB
7-Methoxy-quercetinHMDB
2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4H-1-benzopyran-4-one, 9CIdb_source
3',4',5-Trihydroxy-7-methoxyflavonoldb_source
Rhamnetindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP1.97ALOGPS
logP2.3ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.13ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.34 m³·mol⁻¹ChemAxon
Polarizability30.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H12O7
IUPAC name2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C16H12O7/c1-22-8-5-11(19)13-12(6-8)23-16(15(21)14(13)20)7-2-3-9(17)10(18)4-7/h2-6,17-19,21H,1H3
InChI KeyJGUZGNYPMHHYRK-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C1=CC(O)=C(O)C=C1
Average Molecular Weight316.2623
Monoisotopic Molecular Weight316.058302738
Classification
Description Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • 3-hydroxyflavone
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.76%; H 3.82%; O 35.41%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data371 (e 43500) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRhamnetin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0080-0052090000-8926787915c495727846Spectrum
Predicted GC-MSRhamnetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-0891000000-59deef854b61dae91d10Spectrum
Predicted GC-MSRhamnetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0029000000-1d946c0ef8ee8179fce42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0289000000-89d98f81b4fad73860f22016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldr-5960000000-700b5c56b65843c6063c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-6d44c67213250435bf3f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0179000000-dc41ca9114ec2bc3ded12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-5970000000-4ab273910487b2ae5af62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-d4d9bcf99cd318117dc62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-2f9aa69d63fed47fa3a92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2912000000-6a9144cbb1d8c0686dc72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-6ca2cca4fa059e6970072021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0619000000-7b5be2250e588a7e9a872021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1930000000-0c2db176c8e2fd05d2962021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID325
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCNW46-E:CNW46-E
EAFUS IDNot Available
Dr. Duke IDRHAMNETIN
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
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Allergenic50904 A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
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 bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-cancer35610 An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.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-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 radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.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
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Dye37958 A coloring agent with various biological roles, therapeutic applications, and medical uses, including diagnostic imaging, photodynamic therapy, and wound healing, while also serving as a contrast agent to enhance visualization in medical imaging procedures.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— 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.