ContaminantDB: Amaranthin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 20:51:15 UTC

Update Date

2016-11-09 01:17:38 UTC

Accession Number

CHEM023129

Identification

Common Name

Amaranthin

Class

Small Molecule

Description

Pigment from Amaranthus caudatus (love-lies-bleeding) and Amaranthus tricolor (Chinese spinach). Amaranthin is found in cereals and cereal products, green vegetables, and spinach.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Amaranthin betacyanin	HMDB
Amaranthin pigment	HMDB
Amarantin	HMDB
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 acid	Generator

Chemical Formula

C₃₀H₃₄N₂O₁₉

Average Molecular Mass

726.593 g/mol

Monoisotopic Mass

726.176 g/mol

CAS Registry Number

15167-84-7

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

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 Key

ATSKDYKYMQVTGH-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.

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

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	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	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0100000900-46bc8e7882121882aa67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-0100001900-bc26b445f185f27f97b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03g3-8902110100-0923027a01bd8b2a1ffe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2601000900-94b92375bb079fa31d47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004m-2900000200-b70bb86099c182e957a9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-5900000000-bb3f3ada8952fb605945	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0560-0005009700-0b46d25db413704c8c3d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01si-0203029100-44e910f9eb3385435db1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-5819007100-492d6fc05502e938edd9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-0102129800-c025ebf26be9e2d44fc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-1708019100-533b23540d2bd00412a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0109003000-07844da90b8f910c2609	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0029406

FooDB ID

FDB000495

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001581

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

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.

2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Amaranthin (CHEM023129)

Structure for CHEM023129: Amaranthin