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Prebetanin (FDB000500)

Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2020-02-24 19:10:08 UTC
Primary IDFDB000500
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePrebetanin
DescriptionPrebetanin 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. Prebetanin is an extremely weak basic (essentially neutral) compound (based on its pKa). Prebetanin has been detected, but not quantified in, a few different foods, such as common beets, red beetroots, and root vegetables. This could make prebetanin a potential biomarker for the consumption of these foods.
CAS Number13798-16-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.86 g/LALOGPS
logP-0.28ALOGPS
logP-3.3ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)-2.3ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area292.75 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity159.7 m³·mol⁻¹ChemAxon
Polarizability57.83 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H26N2O16S
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-[(sulfooxy)methyl]oxan-2-yl}oxy)-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate
InChI IdentifierInChI=1S/C24H26N2O16S/c27-15-7-13-10(6-16(15)41-24-20(30)19(29)18(28)17(42-24)8-40-43(37,38)39)5-14(23(35)36)26(13)2-1-9-3-11(21(31)32)25-12(4-9)22(33)34/h1-3,6-7,12,14,17-20,24,28-30H,4-5,8H2,(H5,27,31,32,33,34,35,36,37,38,39)
InChI KeyOZXPZOHWSFDUDY-UHFFFAOYSA-N
Isomeric SMILESOC1C(O)C(COS(O)(=O)=O)OC(OC2=C(O)C=C3C(CC(C([O-])=O)\[N+]3=C/C=C3\CC(NC(=C3)C(O)=O)C(O)=O)=C2)C1O
Average Molecular Weight630.532
Monoisotopic Molecular Weight630.100303484
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
  • O-glycosyl compound
  • Glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Monosaccharide sulfate
  • Tricarboxylic acid or derivatives
  • Indole or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Tetrahydropyridine
  • Oxane
  • Sulfuric acid monoester
  • Sulfate-ester
  • Hydropyridine
  • Benzenoid
  • Monosaccharide
  • Sulfuric acid ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Amino acid or derivatives
  • Shiff base
  • Secondary alcohol
  • Amino acid
  • 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
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organic zwitterion
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 45.72%; H 4.16%; N 4.44%; O 40.60%; S 5.09%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 DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPrebetanin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03du-3933052000-52865dfdf3c8c16e8d7fSpectrum
Predicted GC-MSPrebetanin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPrebetanin, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-f06ba74c872c3030317e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000029000-7a807385dfb142fc8bb02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001c-2945335000-b5dcbe62cbfcea8e4b1f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000009000-4608c2229b8f5d6fe9492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2100009000-0f99adf1275ccea292062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-9300000000-a82b8cf32073b05102a62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004u-1006049000-dc43c4f6b5eb112f5b8f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-3309052000-58baa4a90c3208639a4c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9606140000-22df8e1c94c0fa18450c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0009037000-47ee25c626fa5e8e690c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053i-0205390000-a8fe56edc295f8e2f0852021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000g-1509110000-bfa6cace5d8d6d9beea82021-09-22View Spectrum
NMRNot Available
ChemSpider ID3679022
ChEMBL IDNot Available
KEGG Compound IDC08567
Pubchem Compound ID4481056
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29411
CRC / DFC (Dictionary of Food Compounds) IDBCX92-K:BCZ02-T
EAFUS IDNot Available
Dr. Duke IDPREBETANIN
BIGG IDNot Available
KNApSAcK IDC00001606
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).