| Common Name |
Betanin
| Description |
Isobetanin is found in red beetroot. Minor congener of Betanin, e.g. from beetroot and Amaranthus speciesBetanin belongs to the family of Betacyanins and Derivatives. These are organic compounds containing a glycoside of indolium-2-carboxylic acid attached, with the nitrogen ring of the indolium ring attached to an ethylpyridine-2,6-dicarboxylic acid derivative. Betacyanins are red nitrogenous pigments found in certain plants, such as beetroots[1]. (Reference: [1] Betalains: properties, sources, applications, and stability – a review Azeredo (2006)).
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29408 (Betanin)
| Synonyms |
| Value |
Source |
BetanineHMDB
e162HMDB
PhytolaccaninHMDB
Betalain pigmentsMeSH
| Chemical Formlia |
C24H26N2O13
| Average Molecliar Weight |
550.4688
| Monoisotopic Molecliar Weight |
550.143488928
| IUPAC Name |
(1E)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate
| Traditional Name |
(1E)-1-{2-[(4E)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate
| CAS Registry Number |
7659-95-2
| SMILES |
OCC1OC(OC2=C(O)C=C3C(CC(C([O-])=O)[N+]3=C/C=C3CC(NC(=C3)C(O)=O)C(O)=O)=C2)C(O)C(O)C1O
| InChI Identifier |
InChI=1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)
| InChI Key |
DHHFDKNIEVKVKS-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as betacyanins and derivatives. These are organic compounds containing a glycoside of indolium-2-carboxylic acid attached, with the nitrogen ring of the indolium ring attached to an ethylpyridine-2,6-dicarboxylic acid derivative. Betacyanins are red nitrogenous pigments found in certain plants, such as beetroots.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Alkaloids and derivatives
| Sub Class |
Betalains
| Direct Parent |
Betacyanins and derivatives
| Alternative Parents |
Phenolic glycosides
Hexoses
Indolecarboxylic acids
O-glycosyl compounds
Alpha amino acids
Tricarboxylic acids and derivatives
Tetrahydropyridines
1-hydroxy-2-unsubstituted benzenoids
Oxanes
Shiff bases
Secondary alcohols
Amino acids
Carboxylic acid salts
Propargyl-type 1,3-dipolar organic compounds
Acetals
Polyols
Azacyclic compounds
Oxacyclic compounds
Carboxylic acids
Dialkylamines
Enamines
Primary alcohols
Carbonyl compounds
Organopnictogen compounds
Hydrocarbon derivatives
Organic zwitterions
Organic salts
Organic oxides
| Substituents |
Betacyanin
Phenolic glycoside
Hexose monosaccharide
Indolecarboxylic acid
Indolecarboxylic acid derivative
O-glycosyl compound
Glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Tetrahydropyridine
Oxane
Monosaccharide
Benzenoid
Hydropyridine
Amino acid
Carboxylic acid salt
Secondary alcohol
Amino acid or derivatives
Shiff base
Acetal
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Enamine
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Polyol
Amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organic salt
Carbonyl group
Alcohol
Organic zwitterion
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Primary alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.5 mg/mLALOGPS
logP0.21ALOGPS
logP-5.4ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area249.38 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity149.71 m3·mol-1ChemAxon
Polarizability52.97 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
709
| FoodDB ID |
FDB000786
| KNApSAcK ID |
C00001593
| Chemspider ID |
3678684
| KEGG Compound ID |
C08540
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Betanin
| NuGOwiki Link |
HMDB29408
| Metagene Link |
HMDB29408
| METLIN ID |
Not Available
| PubChem Compound |
4480716
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Scopoletin
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 9720804
