AFCDB: Amaranthin (FDB000495)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:35 UTC

Update date

2020-02-24 19:10:08 UTC

Primary ID

FDB000495

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Amaranthin

Description

Amaranthin 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 Number

15167-84-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.57 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	-6.8	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.44	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	345.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	181.99 m³·mol⁻¹	ChemAxon
Polarizability	68.54 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C30H34N2O19

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 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 Key

ATSKDYKYMQVTGH-UHFFFAOYSA-N

Isomeric 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

Average Molecular Weight

726.593

Monoisotopic Molecular Weight

726.175576916

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Betalains

Sub Class

Betacyanins and derivatives

Direct Parent

Betacyanins 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Antiviral

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 49.59%; H 4.72%; N 3.86%; O 41.84%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Amaranthin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_1_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amaranthin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0100000900-46bc8e7882121882aa67	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-0100001900-bc26b445f185f27f97b2	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03g3-8902110100-0923027a01bd8b2a1ffe	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2601000900-94b92375bb079fa31d47	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004m-2900000200-b70bb86099c182e957a9	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-5900000000-bb3f3ada8952fb605945	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0560-0005009700-0b46d25db413704c8c3d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01si-0203029100-44e910f9eb3385435db1	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-5819007100-492d6fc05502e938edd9	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-0102129800-c025ebf26be9e2d44fc7	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-1708019100-533b23540d2bd00412a5	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0109003000-07844da90b8f910c2609	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

3678679

ChEMBL ID

Not Available

KEGG Compound ID

C08537

Pubchem Compound ID

4480711

Pubchem Substance ID

Not Available

ChEBI ID

2621

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29406

CRC / DFC (Dictionary of Food Compounds) ID

BCX92-K:BCX86-L

EAFUS ID

Not Available

Dr. Duke ID

AMARANTHIN

BIGG ID

Not Available

KNApSAcK ID

C00001581

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
pigment	26130	An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.	DUKE

Enzymes

Name	Gene Name	UniProt ID
UDP-glucuronosyltransferase 2B4	UGT2B4	P06133
UDP-glucuronosyltransferase 1-4	UGT1A4	P22310
UDP-glucuronosyltransferase 2B7	UGT2B7	P16662
UDP-glucuronosyltransferase 1-1	UGT1A1	P22309
UDP-glucuronosyltransferase 1-9	UGT1A9	O60656
UDP-glucuronosyltransferase 1-6	UGT1A6	P19224

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Amaranthin (FDB000495)

Structure for FDB000495 (Amaranthin)