Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2020-02-24 19:10:08 UTC
Primary IDFDB000495
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAmaranthin
DescriptionAmaranthin 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. Amaranthin is an extremely weak basic (essentially neutral) compound (based on its pKa). Amaranthin has been detected, but not quantified in, a few different foods, such as cereals and cereal products, green vegetables, and spinachs. This could make amaranthin a potential biomarker for the consumption of these foods.
CAS Number15167-84-7
Structure
Thumb
Synonyms
SynonymSource
Amaranthin betacyaninHMDB
Amaranthin pigmentHMDB
AmarantinHMDB
2-Carboxy-5-({3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl}oxy)-1-[2-(2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene)ethylidene]-2,3-dihydro-1H-1λ⁵-indol-1-ylium-6-olic acidGenerator
Amaranthindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.57 g/LALOGPS
logP-0.38ALOGPS
logP-6.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)1.44ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area345.6 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity181.99 m³·mol⁻¹ChemAxon
Polarizability68.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H34N2O19
IUPAC name(1E)-5-({3-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl}oxy)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-6-hydroxy-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate
InChI IdentifierInChI=1S/C30H34N2O19/c33-8-17-18(35)20(37)24(51-29-22(39)19(36)21(38)23(50-29)28(46)47)30(49-17)48-16-6-10-5-14(27(44)45)32(13(10)7-15(16)34)2-1-9-3-11(25(40)41)31-12(4-9)26(42)43/h1-3,6-7,12,14,17-24,29-30,33,35-39H,4-5,8H2,(H5,34,40,41,42,43,44,45,46,47)
InChI KeyATSKDYKYMQVTGH-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=C(O)C=C3C(CC(C([O-])=O)\[N+]3=C/C=C3\CC(NC(=C3)C(O)=O)C(O)=O)=C2)C(OC2OC(C(O)C(O)C2O)C(O)=O)C(O)C1O
Average Molecular Weight726.593
Monoisotopic Molecular Weight726.175576916
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
  • O-glucuronide
  • 1-o-glucuronide
  • Tetracarboxylic acid or derivatives
  • Glucuronic acid or derivatives
  • Indolecarboxylic acid
  • Indolecarboxylic acid derivative
  • O-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • Beta-hydroxy acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Tetrahydropyridine
  • Oxane
  • Hydropyridine
  • Pyran
  • Hydroxy acid
  • Benzenoid
  • Amino acid or derivatives
  • Secondary alcohol
  • Carboxylic acid salt
  • Shiff base
  • Amino acid
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Carboxylic acid
  • Secondary aliphatic amine
  • Azacycle
  • Enamine
  • 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
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic zwitterion
  • Alcohol
  • Primary alcohol
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 49.59%; H 4.72%; N 3.86%; O 41.84%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
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0100000900-46bc8e7882121882aa67JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-0100001900-bc26b445f185f27f97b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03g3-8902110100-0923027a01bd8b2a1ffeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2601000900-94b92375bb079fa31d47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004m-2900000200-b70bb86099c182e957a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-5900000000-bb3f3ada8952fb605945JSpectraViewer
ChemSpider ID3678679
ChEMBL IDNot Available
KEGG Compound IDC08537
Pubchem Compound ID4480711
Pubchem Substance IDNot Available
ChEBI ID2621
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29406
CRC / DFC (Dictionary of Food Compounds) IDBCX92-K:BCX86-L
EAFUS IDNot Available
Dr. Duke IDAMARANTHIN
BIGG IDNot Available
KNApSAcK IDC00001581
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
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.DUKE
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-6UGT1A6P19224
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).