Record Information
Version1.0
Creation date2010-04-08 22:06:41 UTC
Update date2019-11-26 03:00:35 UTC
Primary IDFDB005456
Secondary Accession Numbers
  • FDB007538
Chemical Information
FooDB NameAnthocyanins
DescriptionAnthocyanins belongs to the class of organic compounds known as anthocyanidins. These are sugar-free counterparts of anthocyanins based on the flavylium ion or 2-phenylchromenylium ion. Anthocyanins is possibly neutral. Anthocyanins is found, on average, in the highest concentration within a few different foods, such as american pokeweeds, blackcurrants, and roselles. Anthocyanins has also been detected, but not quantified in, several different foods, such as american cranberries, bilberries, figs, soy beans, and common grapes. This could make anthocyanins a potential biomarker for the consumption of these foods.
CAS Number11029-12-2
Structure
Thumb
Synonyms
SynonymSource
2-PhenylchromenyliumChEBI
AnthocyanidinMeSH
AnthocyanidinsMeSH
LeucoanthocyanidinsMeSH
AnthocyaninMeSH
AnthocyaninsMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.0011 g/LALOGPS
logP5.02ALOGPS
logP4.47ChemAxon
logS-5.4ALOGPS
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.21 m³·mol⁻¹ChemAxon
Polarizability23.33 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H11O
IUPAC name2-phenyl-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C15H11O/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-11H/q+1
InChI KeyNWKFECICNXDNOQ-UHFFFAOYSA-N
Isomeric SMILESC1=CC=C(C=C1)C1=[O+]C2=CC=CC=C2C=C1
Average Molecular Weight207.2472
Monoisotopic Molecular Weight207.080989974
Classification
Description Belongs to the class of organic compounds known as anthocyanidins. These are sugar-free counterparts of anthocyanins based on the flavylium ion or 2-phenylchromenylium ion.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassAnthocyanidins
Direct ParentAnthocyanidins
Alternative Parents
Substituents
  • Anthocyanidin
  • 1-benzopyran
  • Benzopyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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 DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAnthocyanins, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pb9-1970000000-603db105c804c564f4e8Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-c23fff5e59428c734d362016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-c81ae21e4d9b1779daff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9720000000-8ef05b420f668c3a73262016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-f5e63df09506bd768f832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-89eaecd39ea180f1bb162016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3930000000-04c1ce77ba70dddb634c2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID38697
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID1540
Dr. Duke IDANTHOCYANINS|ANTHOCYANIN
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-apoptoticAn agent that inhibits programmed cell death, promoting cell survival. It plays a biological role in regulating cell growth and development. Therapeutically, it has applications in cancer treatment, neurodegenerative diseases, and tissue repair. Key medical uses include preventing cell loss in stroke, Alzheimer's, and Parkinson's diseases, as well as in cancer therapy to protect healthy cells from chemotherapy-induced damage.DUKE
Anti-arthritic52217 An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.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 carcinogenic35610 An agent that prevents or inhibits the formation of cancer, reducing tumor growth and proliferation. It plays a biological role in protecting cells from DNA damage and mutation. Therapeutically, it is used to prevent cancer development, with key medical applications in chemotherapy, radiation protection, and cancer prevention programs.DUKE
Anti-collagenase23924 An agent that inhibits collagenase activity, reducing tissue breakdown and inflammation. Therapeutically, it is used to manage conditions such as osteoarthritis, tendonitis, and periodontal disease, promoting tissue repair and wound healing.DUKE
Anti-diabetic52217 An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes.DUKE
Anti elastase23924 An agent that inhibits elastase activity, reducing tissue damage and inflammation. It plays a biological role in protecting tissues from enzymatic degradation. Therapeutically, it is used to manage conditions such as chronic obstructive pulmonary disease (COPD), cystic fibrosis, and acute respiratory distress syndrome (ARDS), where excessive elastase activity contributes to disease progression.DUKE
Anti hyperglycemicAn agent that lowers elevated blood glucose levels, playing a crucial biological role in regulating glucose metabolism. Therapeutically, it is used to manage hyperglycemia, with key medical applications in treating diabetes mellitus, reducing the risk of complications, and improving glycemic control.DUKE
Anti hyperinsulinemicAn agent that lowers elevated blood insulin levels, reducing insulin resistance and hyperinsulinemia. It plays a biological role in regulating glucose metabolism and has therapeutic applications in managing type 2 diabetes, polycystic ovary syndrome (PCOS), and metabolic syndrome. Key medical uses include improving insulin sensitivity and reducing the risk of cardiovascular disease.DUKE
Anti hyperleptinemicAn agent that reduces leptin levels in the bloodstream, regulating energy balance and metabolism. It has therapeutic applications in managing obesity, metabolic syndrome, and related disorders, and is used to treat conditions associated with high leptin levels, such as insulin resistance and type 2 diabetes.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-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 myopicAn agent that corrects nearsightedness (myopia), a refractive error of the eye, by slowing eye growth and improving vision. Its biological role is to regulate axial elongation, and its therapeutic applications include orthokeratology and pharmaceutical treatments. Key medical uses include preventing myopia progression in children and reducing the risk of myopia-related complications.DUKE
Anti nyctalopicAn agent that enhances sight in dim light or at night, countering nyctalopia (night blindness). Its biological role is to improve visual acuity in low-light conditions. Therapeutically, it has applications in treating night blindness and other visual impairments. Key medical uses include managing vitamin A deficiency, a common cause of night blindness, and improving visual function in individuals with impaired low-light vision.DUKE
Anti-obesity52217 An agent that reduces body weight, commonly used in managing obesity and related disorders, by regulating appetite, metabolism, and fat storage, with therapeutic applications in preventing chronic diseases such as diabetes and cardiovascular disease.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 proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.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
Anti-varicose52217 An agent that improves blood circulation and strengthens vein walls, reducing swelling and discomfort. Therapeutically, it is used to manage varicose veins, edema, and hemorrhoids, promoting overall vascular health.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Chemopreventive35610 An agent that prevents or delays the development of cancer, reducing the risk of tumor formation and progression. It plays a biological role in inhibiting carcinogenesis, and has therapeutic applications in cancer prevention, with key medical uses including reducing the risk of colorectal, breast, and prostate cancers.DUKE
Cyclooxygenase-1 inhibitor50630 An agent that blocks the activity of cyclooxygenase-1 (COX-1), reducing inflammation and pain. Therapeutically, it is used to manage conditions like arthritis, and as a nonsteroidal anti-inflammatory drug (NSAID) to relieve pain, fever, and inflammation, while minimizing gastrointestinal side effects.DUKE
Cyclooxygenase-2 inhibitor50629 An agent that blocks the activity of cyclooxygenase-2 (COX-2), reducing inflammation and pain. Therapeutically, it is used to manage conditions such as arthritis, menstrual cramps, and other inflammatory disorders, providing relief from symptoms with reduced gastrointestinal side effects compared to non-selective NSAIDs.DUKE
GoitrogenicA substance that interferes with thyroid hormone production by blocking iodine uptake, leading to increased TSH release and potential goiter formation, with therapeutic applications in managing hyperthyroidism and certain thyroid disorders.DUKE
HemostatAn agent that controls bleeding, playing a biological role in blood coagulation. Therapeutically, it promotes clot formation, and its key medical uses include treating wounds, surgical bleeding, and hemorrhages, helping to stabilize patients and prevent excessive blood loss.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
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
VasoactiveAn agent that affects blood vessel diameter, regulating blood pressure and flow. It plays a biological role in maintaining cardiovascular homeostasis. Therapeutically, vasoactive agents are used to treat conditions like hypertension, heart failure, and shock, and have applications in managing bleeding and perfusion during surgery.DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.DUKE
VasoprotectiveAn agent that protects and alleviates blood vessel conditions, such as hemorrhoids and varicose veins, by strengthening vessel walls and improving circulation, with therapeutic applications in managing vascular disorders, and key medical uses including hormone replacement therapy with estrogen.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).