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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:13 UTC
Update Date2022-03-07 02:52:09 UTC
HMDB IDHMDB0029406
Secondary Accession Numbers
  • HMDB29406
Metabolite Identification
Common 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 has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, green vegetables, and spinaches (Spinacia oleracea). This could make amaranthin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Amaranthin.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC30H34N2O19
Average Molecular Weight726.593
Monoisotopic Molecular Weight726.175576916
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
Traditional 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-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene}-6-hydroxy-2,3-dihydro-1H-1λ⁵-indol-1-ylium-2-carboxylate
CAS Registry Number15167-84-7
SMILES
OCC1OC(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
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000495
KNApSAcK IDC00001581
Chemspider ID3678679
KEGG Compound IDC08537
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4480711
PDB IDNot Available
ChEBI ID2621
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kwon SY, An CS, Liu JR, Paek KH: A ribosome-inactivating protein from Amaranthus viridis. Biosci Biotechnol Biochem. 1997 Sep;61(9):1613-4. [PubMed:9339569 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215