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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:13 UTC

Update Date

2022-03-07 02:52:09 UTC

HMDB ID

HMDB0029406

Secondary Accession Numbers

HMDB29406

Metabolite Identification

Common 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 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241215082D          

 51 55  0  0  0  0            999 V2000
    3.0605   -1.0200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896   -0.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8857   -0.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -0.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162   -1.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9581   -0.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7002   -1.0818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0605   -1.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0605   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5041   -2.8133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2460    0.4016    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.7002    0.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9581    0.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162    0.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253    0.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292    0.5253    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
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    2.4421    1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513    2.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552    2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8644    3.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6683    3.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2867    2.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6171   -1.5765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7302   -1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4421    3.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2460    3.9881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331    5.2867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1736   -2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6171   -2.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6171   -3.4316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 16  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 25  1  0  0  0  0
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 23 35  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 49  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 33  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 42  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 43  1  0  0  0  0
 40 46  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
M  CHG  2  12  -1  17   1
M  END

HMDB0029406
     RDKit          3D
Amaranthin
 85 89  0  0  0  0  0  0  0  0999 V2000
    8.7483   -5.4099    1.0163 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1381   -4.3336    0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4788   -4.1884    0.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
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  6 46  1  0
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  5 53  1  0
  7 54  1  0
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 11 56  1  0
 13 57  1  0
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 41 78  1  0
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 42 80  1  0
 46 81  1  0
 46 82  1  0
 47 83  1  0
 50 84  1  0
 51 85  1  0
M  CHG  2   9   1  45  -1
M  END


  Mrv0541 02241215082D          

 51 55  0  0  0  0            999 V2000
    3.0605   -1.0200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896   -0.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2162   -1.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7513    2.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552    2.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8644    3.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6683    3.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2867    2.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4421    3.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
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  5 16  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 25  1  0  0  0  0
 10 11  1  0  0  0  0
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 11 38  1  0  0  0  0
 13 14  1  0  0  0  0
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 20 21  1  0  0  0  0
 20 29  1  0  0  0  0
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 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 33  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 42  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
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 40 46  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
M  CHG  2  12  -1  17   1
M  END
> <DATABASE_ID>
HMDB0029406

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C30H34N2O19

> <MOLECULAR_WEIGHT>
726.593

> <EXACT_MASS>
726.175576916

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
68.53776015054362

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(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

> <ALOGPS_LOGP>
-0.38

> <JCHEM_LOGP>
-6.829223572138412

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.7168905413358195

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4401824643530539

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9485410703715607

> <JCHEM_POLAR_SURFACE_AREA>
345.6

> <JCHEM_REFRACTIVITY>
181.9865000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029406
     RDKit          3D
Amaranthin
 85 89  0  0  0  0  0  0  0  0999 V2000
    8.7483   -5.4099    1.0163 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8400   -2.2449    0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2222    0.2498    1.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
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 25 67  1  0
 27 68  1  0
 29 69  1  0
 32 70  1  0
 33 71  1  0
 34 72  1  0
 35 73  1  0
 36 74  1  0
 37 75  1  0
 38 76  1  0
 39 77  1  0
 41 78  1  0
 41 79  1  0
 42 80  1  0
 46 81  1  0
 46 82  1  0
 47 83  1  0
 50 84  1  0
 51 85  1  0
M  CHG  2   9   1  45  -1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       5.713  -1.904   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.021  -0.405   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.520  -0.289   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.481  -1.673   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.981  -1.211   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.404  -2.019   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.788  -1.211   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.174  -2.019   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.713  -3.520   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.713  -4.674   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.674  -5.251   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.059   0.750   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0      -3.174   1.327   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.788   0.404   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.404   1.327   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.981   0.404   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.481   0.981   0.000  0.00  0.00           N+1
HETATM   18  C   UNK     0       3.058   2.481   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.559   2.827   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.136   4.328   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.636   4.674   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.214   6.175   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.714   6.521   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.869   5.367   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -6.752  -2.943   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -7.791  -3.520   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.830  -2.827   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -9.869  -3.520   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.982   5.598   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.559   7.098   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       6.059   7.444   0.000  0.00  0.00           N+0
HETATM   32  O   UNK     0       3.982   9.869   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.405   8.253   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.904   8.022   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.291   8.137   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -1.904  -4.443   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.904  -5.713   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.943  -6.290   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.943  -7.444   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.904  -8.022   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.172  -5.713   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.865  -6.290   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.865  -7.444   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.172  -8.137   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -2.943  -9.869   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -1.904  -9.291   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -0.865  -9.869   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -8.830  -5.251   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -7.791  -4.674   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -6.752  -5.251   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -6.752  -6.406   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11   50                                                  
CONECT   11   10   38                                                       
CONECT   12    2                                                            
CONECT   13   14                                                            
CONECT   14    7   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    5   15   17                                                  
CONECT   17    3   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   35                                                  
CONECT   24   23                                                            
CONECT   25    9   26                                                       
CONECT   26   25   27   49                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   20   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   22   30                                                       
CONECT   32   33                                                            
CONECT   33   30   32   34                                                  
CONECT   34   33                                                            
CONECT   35   23                                                            
CONECT   36   37                                                            
CONECT   37   36   38   42                                                  
CONECT   38   11   37   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   43   46                                                  
CONECT   41   42                                                            
CONECT   42   37   41   43                                                  
CONECT   43   40   42   44                                                  
CONECT   44   43                                                            
CONECT   45   46                                                            
CONECT   46   40   45   47                                                  
CONECT   47   46                                                            
CONECT   48   49                                                            
CONECT   49   26   48   50                                                  
CONECT   50   10   49   51                                                  
CONECT   51   50                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

COMPND    HMDB0029406
HETATM    1  O1  UNL     1       8.748  -5.410   1.016  1.00  0.00           O  
HETATM    2  C1  UNL     1       9.138  -4.334   0.518  1.00  0.00           C  
HETATM    3  O2  UNL     1      10.479  -4.188   0.237  1.00  0.00           O  
HETATM    4  C2  UNL     1       8.242  -3.220   0.219  1.00  0.00           C  
HETATM    5  C3  UNL     1       6.957  -3.346   0.487  1.00  0.00           C  
HETATM    6  C4  UNL     1       5.972  -2.265   0.217  1.00  0.00           C  
HETATM    7  C5  UNL     1       4.840  -2.245   0.796  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.687  -1.481   0.823  1.00  0.00           C  
HETATM    9  N1  UNL     1       3.122  -0.518   0.240  1.00  0.00           N1+
HETATM   10  C7  UNL     1       1.818   0.052   0.589  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.222   0.250   1.785  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.021   0.839   1.871  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.583   1.017   3.119  1.00  0.00           O  
HETATM   14  C10 UNL     1      -0.725   1.261   0.724  1.00  0.00           C  
HETATM   15  O4  UNL     1      -1.961   1.844   0.868  1.00  0.00           O  
HETATM   16  C11 UNL     1      -2.702   2.349  -0.175  1.00  0.00           C  
HETATM   17  O5  UNL     1      -3.241   3.590   0.244  1.00  0.00           O  
HETATM   18  C12 UNL     1      -3.623   4.341  -0.850  1.00  0.00           C  
HETATM   19  C13 UNL     1      -4.329   5.591  -0.364  1.00  0.00           C  
HETATM   20  O6  UNL     1      -4.686   6.342  -1.479  1.00  0.00           O  
HETATM   21  C14 UNL     1      -4.533   3.553  -1.772  1.00  0.00           C  
HETATM   22  O7  UNL     1      -3.917   3.193  -2.960  1.00  0.00           O  
HETATM   23  C15 UNL     1      -5.023   2.351  -1.001  1.00  0.00           C  
HETATM   24  O8  UNL     1      -5.766   2.735   0.097  1.00  0.00           O  
HETATM   25  C16 UNL     1      -3.853   1.450  -0.583  1.00  0.00           C  
HETATM   26  O9  UNL     1      -4.302   0.608   0.407  1.00  0.00           O  
HETATM   27  C17 UNL     1      -4.335  -0.697  -0.046  1.00  0.00           C  
HETATM   28  O10 UNL     1      -5.627  -1.192  -0.156  1.00  0.00           O  
HETATM   29  C18 UNL     1      -6.273  -1.433   1.027  1.00  0.00           C  
HETATM   30  C19 UNL     1      -7.523  -2.229   0.776  1.00  0.00           C  
HETATM   31  O11 UNL     1      -8.232  -2.566   1.729  1.00  0.00           O  
HETATM   32  O12 UNL     1      -7.889  -2.586  -0.494  1.00  0.00           O  
HETATM   33  C20 UNL     1      -5.443  -2.149   2.044  1.00  0.00           C  
HETATM   34  O13 UNL     1      -6.217  -3.131   2.650  1.00  0.00           O  
HETATM   35  C21 UNL     1      -4.265  -2.793   1.345  1.00  0.00           C  
HETATM   36  O14 UNL     1      -4.674  -3.736   0.414  1.00  0.00           O  
HETATM   37  C22 UNL     1      -3.480  -1.657   0.707  1.00  0.00           C  
HETATM   38  O15 UNL     1      -2.732  -1.047   1.721  1.00  0.00           O  
HETATM   39  C23 UNL     1      -0.072   1.034  -0.466  1.00  0.00           C  
HETATM   40  C24 UNL     1       1.172   0.445  -0.588  1.00  0.00           C  
HETATM   41  C25 UNL     1       2.070   0.037  -1.684  1.00  0.00           C  
HETATM   42  C26 UNL     1       3.470   0.192  -0.933  1.00  0.00           C  
HETATM   43  C27 UNL     1       3.675   1.629  -0.747  1.00  0.00           C  
HETATM   44  O16 UNL     1       4.776   2.153  -0.621  1.00  0.00           O  
HETATM   45  O17 UNL     1       2.573   2.522  -0.703  1.00  0.00           O1-
HETATM   46  C28 UNL     1       6.405  -1.162  -0.622  1.00  0.00           C  
HETATM   47  C29 UNL     1       7.897  -0.871  -0.331  1.00  0.00           C  
HETATM   48  C30 UNL     1       8.365   0.209  -1.219  1.00  0.00           C  
HETATM   49  O18 UNL     1       9.415   0.109  -1.903  1.00  0.00           O  
HETATM   50  O19 UNL     1       7.670   1.397  -1.347  1.00  0.00           O  
HETATM   51  N2  UNL     1       8.723  -2.020  -0.351  1.00  0.00           N  
HETATM   52  H1  UNL     1      11.091  -4.965   0.184  1.00  0.00           H  
HETATM   53  H2  UNL     1       6.556  -4.265   0.911  1.00  0.00           H  
HETATM   54  H3  UNL     1       4.746  -3.161   1.522  1.00  0.00           H  
HETATM   55  H4  UNL     1       2.995  -1.826   1.714  1.00  0.00           H  
HETATM   56  H5  UNL     1       1.734  -0.072   2.712  1.00  0.00           H  
HETATM   57  H6  UNL     1      -1.507   1.447   3.247  1.00  0.00           H  
HETATM   58  H7  UNL     1      -2.067   2.468  -1.075  1.00  0.00           H  
HETATM   59  H8  UNL     1      -2.726   4.612  -1.424  1.00  0.00           H  
HETATM   60  H9  UNL     1      -3.716   6.148   0.360  1.00  0.00           H  
HETATM   61  H10 UNL     1      -5.292   5.237   0.091  1.00  0.00           H  
HETATM   62  H11 UNL     1      -4.435   7.295  -1.324  1.00  0.00           H  
HETATM   63  H12 UNL     1      -5.425   4.152  -2.010  1.00  0.00           H  
HETATM   64  H13 UNL     1      -4.478   3.401  -3.768  1.00  0.00           H  
HETATM   65  H14 UNL     1      -5.705   1.792  -1.671  1.00  0.00           H  
HETATM   66  H15 UNL     1      -5.336   2.473   0.948  1.00  0.00           H  
HETATM   67  H16 UNL     1      -3.598   0.897  -1.529  1.00  0.00           H  
HETATM   68  H17 UNL     1      -3.962  -0.677  -1.118  1.00  0.00           H  
HETATM   69  H18 UNL     1      -6.614  -0.476   1.497  1.00  0.00           H  
HETATM   70  H19 UNL     1      -7.293  -2.511  -1.312  1.00  0.00           H  
HETATM   71  H20 UNL     1      -5.005  -1.437   2.779  1.00  0.00           H  
HETATM   72  H21 UNL     1      -5.797  -3.378   3.512  1.00  0.00           H  
HETATM   73  H22 UNL     1      -3.672  -3.293   2.136  1.00  0.00           H  
HETATM   74  H23 UNL     1      -5.584  -4.015   0.602  1.00  0.00           H  
HETATM   75  H24 UNL     1      -2.767  -2.137   0.012  1.00  0.00           H  
HETATM   76  H25 UNL     1      -1.850  -1.490   1.731  1.00  0.00           H  
HETATM   77  H26 UNL     1      -0.533   1.319  -1.401  1.00  0.00           H  
HETATM   78  H27 UNL     1       1.961  -1.009  -1.953  1.00  0.00           H  
HETATM   79  H28 UNL     1       2.103   0.775  -2.489  1.00  0.00           H  
HETATM   80  H29 UNL     1       4.115  -0.322  -1.639  1.00  0.00           H  
HETATM   81  H30 UNL     1       6.314  -1.299  -1.710  1.00  0.00           H  
HETATM   82  H31 UNL     1       5.952  -0.184  -0.279  1.00  0.00           H  
HETATM   83  H32 UNL     1       7.914  -0.434   0.709  1.00  0.00           H  
HETATM   84  H33 UNL     1       7.777   2.164  -0.713  1.00  0.00           H  
HETATM   85  H34 UNL     1       9.696  -2.046  -0.770  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   52
CONECT    4    5    5   51
CONECT    5    6   53
CONECT    6    7    7   46
CONECT    7    8   54
CONECT    8    9    9   55
CONECT    9   10   42
CONECT   10   11   11   40
CONECT   11   12   56
CONECT   12   13   14   14
CONECT   13   57
CONECT   14   15   39
CONECT   15   16
CONECT   16   17   25   58
CONECT   17   18
CONECT   18   19   21   59
CONECT   19   20   60   61
CONECT   20   62
CONECT   21   22   23   63
CONECT   22   64
CONECT   23   24   25   65
CONECT   24   66
CONECT   25   26   67
CONECT   26   27
CONECT   27   28   37   68
CONECT   28   29
CONECT   29   30   33   69
CONECT   30   31   31   32
CONECT   32   70
CONECT   33   34   35   71
CONECT   34   72
CONECT   35   36   37   73
CONECT   36   74
CONECT   37   38   75
CONECT   38   76
CONECT   39   40   40   77
CONECT   40   41
CONECT   41   42   78   79
CONECT   42   43   80
CONECT   43   44   44   45
CONECT   46   47   81   82
CONECT   47   48   51   83
CONECT   48   49   49   50
CONECT   50   84
CONECT   51   85
END

HMDB0029406
     RDKit          3D
Amaranthin
 85 89  0  0  0  0  0  0  0  0999 V2000
    8.7483   -5.4099    1.0163 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1381   -4.3336    0.5182 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4788   -4.1884    0.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2421   -3.2202    0.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9573   -3.3462    0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9723   -2.2651    0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8400   -2.2449    0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6866   -1.4809    0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1224   -0.5179    0.2396 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.8184    0.0519    0.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2222    0.2498    1.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    0.8393    1.8707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830    1.0168    3.1192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7255    1.2614    0.7243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9607    1.8438    0.8677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7022    2.3489   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2408    3.5901    0.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6228    4.3408   -0.8495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291    5.5914   -0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6863    6.3415   -1.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5333    3.5529   -1.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9174    3.1927   -2.9600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0227    2.3507   -1.0009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7655    2.7346    0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    1.4495   -0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3022    0.6079    0.4072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3346   -0.6973   -0.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6270   -1.1925   -0.1560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2731   -1.4326    1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5233   -2.2288    0.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2318   -2.5657    1.7294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8893   -2.5864   -0.4941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4425   -2.1494    2.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2168   -3.1307    2.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649   -2.7928    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6738   -3.7358    0.4143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4802   -1.6569    0.7070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7323   -1.0469    1.7215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719    1.0343   -0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    0.4453   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0700    0.0375   -1.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4697    0.1919   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6753    1.6290   -0.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7764    2.1531   -0.6207 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5729    2.5219   -0.7028 O   0  0  0  0  0  1  0  0  0  0  0  0
    6.4048   -1.1625   -0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8968   -0.8706   -0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3653    0.2094   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4145    0.1085   -1.9025 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6698    1.3970   -1.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7229   -2.0202   -0.3513 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0907   -4.9655    0.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5558   -4.2655    0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7460   -3.1607    1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -1.8261    1.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7342   -0.0716    2.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5072    1.4473    3.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0674    2.4683   -1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256    4.6125   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7165    6.1482    0.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2916    5.2369    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4352    7.2948   -1.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4251    4.1524   -2.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4779    3.4009   -3.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7051    1.7924   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3363    2.4732    0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5979    0.8974   -1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9618   -0.6772   -1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6139   -0.4762    1.4969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2933   -2.5112   -1.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0050   -1.4366    2.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7966   -3.3783    3.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723   -3.2934    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5844   -4.0153    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7673   -2.1373    0.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501   -1.4899    1.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5329    1.3187   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614   -1.0089   -1.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028    0.7754   -2.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1146   -0.3221   -1.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3140   -1.2988   -1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9515   -0.1840   -0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9144   -0.4339    0.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7767    2.1639   -0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6961   -2.0459   -0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 29 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 14 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  2  0
 43 45  1  0
  6 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  2  0
 48 50  1  0
 47 51  1  0
 51  4  1  0
 42  9  1  0
 40 10  1  0
 25 16  1  0
 37 27  1  0
  3 52  1  0
  5 53  1  0
  7 54  1  0
  8 55  1  0
 11 56  1  0
 13 57  1  0
 16 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  0
 21 63  1  0
 22 64  1  0
 23 65  1  0
 24 66  1  0
 25 67  1  0
 27 68  1  0
 29 69  1  0
 32 70  1  0
 33 71  1  0
 34 72  1  0
 35 73  1  0
 36 74  1  0
 37 75  1  0
 38 76  1  0
 39 77  1  0
 41 78  1  0
 41 79  1  0
 42 80  1  0
 46 81  1  0
 46 82  1  0
 47 83  1  0
 50 84  1  0
 51 85  1  0
M  CHG  2   9   1  45  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

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 Weight

726.593

Monoisotopic Molecular Weight

726.175576916

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 Number

15167-84-7

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 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

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029406)
Cytoplasm (HMDB: HMDB0029406)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029406)

Source

Endogenous

Endogenous (HMDB: HMDB0029406)

Plant

Plant (HMDB: HMDB0029406)
Poaceae (HMDB: HMDB0029406)

Exogenous

Food

Food (HMDB: HMDB0029406)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Leaf vegetable

Spinach (FooDB: FOOD00178)
Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0029406)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antiviral

Antiviral (HMDB: HMDB0029406)

Manufacturing industry

Material processing agent

Coloring agent

Pigment (HMDB: HMDB0029406)
Pigment (HMDB: HMDB0029406)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	241.19	30932474
DeepCCS	[M-H]-	239.365	30932474
DeepCCS	[M-2H]-	273.192	30932474
DeepCCS	[M+Na]+	246.967	30932474
AllCCS	[M+H]+	244.9	32859911
AllCCS	[M+H-H2O]+	244.6	32859911
AllCCS	[M+NH4]+	245.1	32859911
AllCCS	[M+Na]+	245.1	32859911
AllCCS	[M-H]-	237.7	32859911
AllCCS	[M+Na-2H]-	239.9	32859911
AllCCS	[M+HCOO]-	242.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.94 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3351 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.85 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	429.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1360.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	222.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	62.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	88.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	350.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	412.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	921.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	772.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	218.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1443.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	533.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	408.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	539.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amaranthin	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	7903.3	Standard polar	33892256
Amaranthin	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	3907.2	Standard non polar	33892256
Amaranthin	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	6344.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_1_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amaranthin GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

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

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4480711

PDB ID

Not Available

ChEBI ID

2621

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B4

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

Enzyme Details

2. UDP-glucuronosyltransferase 1-4

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

Enzyme Details

3. UDP-glucuronosyltransferase 2B7

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

Enzyme Details

4. UDP-glucuronosyltransferase 1-1

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

Enzyme Details

5. UDP-glucuronosyltransferase 1-9

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

Enzyme Details

6. UDP-glucuronosyltransferase 1-6

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

Showing metabocard for Amaranthin (HMDB0029406)

MOL for HMDB0029406 (Amaranthin)

3D MOL for HMDB0029406 (Amaranthin)

3D SDF for HMDB0029406 (Amaranthin)

3D-SDF for HMDB0029406 (Amaranthin)

PDB for HMDB0029406 (Amaranthin)

3D PDB for HMDB0029406 (Amaranthin)

SMILES for HMDB0029406 (Amaranthin)

INCHI for HMDB0029406 (Amaranthin)

Structure for HMDB0029406 (Amaranthin)

3D Structure for HMDB0029406 (Amaranthin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes