Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2019-11-26 02:54:53 UTC
Primary IDFDB000494
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNeobetanin
DescriptionNeobetanin belongs to the class of organic compounds 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. Neobetanin is an extremely weak basic (essentially neutral) compound (based on its pKa). Neobetanin has been detected, but not quantified in, a few different foods, such as fruits, red beetroots, and root vegetables. This could make neobetanin a potential biomarker for the consumption of these foods.
CAS Number71199-29-6
Structure
Thumb
Synonyms
SynonymSource
Neobetanindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP0.49ALOGPS
logP-5.6ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)1.43ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area249.38 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity151.27 m³·mol⁻¹ChemAxon
Polarizability52.43 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H24N2O13
IUPAC name(1E)-1-[2-(2,6-dicarboxy-1,4-dihydropyridin-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
InChI IdentifierInChI=1S/C24H24N2O13/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/h1-4,6-7,14,17-20,24,27,29-31H,5,8H2,(H4,28,32,33,34,35,36,37)
InChI KeyKRZLUOUGQYWELW-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=C(O)C=C3C(CC(C([O-])=O)\[N+]3=C/C=C3C=C(NC(=C3)C(O)=O)C(O)=O)=C2)C(O)C(O)C1O
Average Molecular Weight548.453
Monoisotopic Molecular Weight548.127838864
Classification
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassBetalains
Sub ClassBetacyanins and derivatives
Direct ParentBetacyanins and derivatives
Alternative Parents
Substituents
  • Betacyanin
  • Phenolic glycoside
  • Hexose monosaccharide
  • Indolecarboxylic acid
  • Indolecarboxylic acid derivative
  • Glycosyl compound
  • O-glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • Tricarboxylic acid or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dihydropyridine
  • Hydropyridine
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid salt
  • Secondary alcohol
  • Shiff base
  • Acetal
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Oxacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Enamine
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Secondary amine
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Organic zwitterion
  • Organic salt
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.56%; H 4.41%; N 5.11%; O 37.92%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 Data365 () (H2O)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29405
CRC / DFC (Dictionary of Food Compounds) IDBCX92-K:BCX77-J
EAFUS IDNot Available
Dr. Duke IDNEOBETANIN
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 / BioactivitiesNot Available
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).