NP-MRD: Showing NP-Card for (2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid (NP0151661)

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Record Information

Version

2.0

Created at

2022-09-02 08:00:35 UTC

Updated at

2022-09-02 08:00:35 UTC

NP-MRD ID

NP0151661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid

Description

S-sinapylglutathione belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. (2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid is found in Ananas comosus. (2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid was first documented in 2017 (PMID: 28964359). Based on a literature review very few articles have been published on S-sinapylglutathione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210002D          

 34 34  0  0  1  0            999 V2000
  -13.5749    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    7.0125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    8.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

 63 63  0  0  0  0  0  0  0  0999 V2000
    5.9562    2.6717    2.1154 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4300    1.6133    1.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6129    0.8986    0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823    1.2387    0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4653    0.5490   -0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0504    0.7980   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4354    1.7439   -0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373    2.0267   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099    1.8030    1.4056 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6557    0.0344    1.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5038   -0.7272    0.8334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8519   -0.2774    0.9656 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036    0.1150   -0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8969    0.0979   -1.3147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8891    0.5648    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0263    2.0228   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6669    2.4064   -1.4963 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8518    3.8753   -1.5526 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5270    1.7653   -2.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2940    2.5116   -3.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5638    0.4192   -2.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400   -2.1928    1.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331   -3.0817    0.2708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271   -2.6404    2.0344 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6372   -4.0459    2.2972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9547   -4.6536    2.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772   -5.8730    2.8586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854   -3.8581    2.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148   -0.4984   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -0.8458   -1.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8556   -1.9097   -1.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9573   -2.6060   -2.7727 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1489   -0.1392   -0.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4854   -0.4898   -0.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7656    3.6008    1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7183    2.9243    2.8762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0163    2.4081    2.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8733    2.0472    0.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4766    0.1919   -1.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9468    2.3607    0.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4767    1.3832   -0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1098    3.0727   -0.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4142   -0.2879    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0554   -0.0713    2.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0873   -0.5047   -0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1130   -0.6029   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2584    0.2889    1.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5260   -0.0411   -0.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0431    2.3900    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3374    2.6123    0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833    2.2097   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0969    4.2633   -0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7561    4.0412   -1.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3749   -0.1437   -2.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7646   -3.2132   -0.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2091   -4.6115    1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748   -4.1670    3.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9393   -4.1134    2.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3884   -1.0802   -1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4357   -1.8872   -3.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797   -3.3955   -3.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1701   -3.0330   -2.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0692    0.0421    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 21  1  0
 19 20  2  0
 11 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 28  1  0
 26 27  2  0
  5 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  2  0
 33 34  1  0
 33  3  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  6 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  6
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  6
 18 52  1  0
 18 53  1  0
 21 54  1  0
 23 55  1  0
 25 56  1  0
 25 57  1  0
 28 58  1  0
 29 59  1  0
 32 60  1  0
 32 61  1  0
 32 62  1  0
 34 63  1  0
M  END


  Mrv1652309022210002D          

 34 34  0  0  1  0            999 V2000
  -13.5749    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0026    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8592    7.0125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    7.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579    8.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7171    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4315    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8605    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  5 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0151661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\CSC[C@H](N=C(O)CC[C@H](N)C(O)=O)C(O)=NCC(O)=O)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H29N3O9S/c1-32-15-8-12(9-16(33-2)19(15)28)4-3-7-34-11-14(20(29)23-10-18(26)27)24-17(25)6-5-13(22)21(30)31/h3-4,8-9,13-14,28H,5-7,10-11,22H2,1-2H3,(H,23,29)(H,24,25)(H,26,27)(H,30,31)/b4-3+/t13-,14-/m0/s1

> <INCHI_KEY>
HLZFIHFPAUUHBI-NVFZZLLCSA-N

> <FORMULA>
C21H29N3O9S

> <MOLECULAR_WEIGHT>
499.54

> <EXACT_MASS>
499.1624507

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.37752546721764

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-1.3442103281319444

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.37250263779813

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8634099837049072

> <JCHEM_PKA_STRONGEST_BASIC>
9.783462209860593

> <JCHEM_POLAR_SURFACE_AREA>
204.48999999999998

> <JCHEM_REFRACTIVITY>
124.69699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0     -25.340  13.090   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -24.006  13.860   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -22.673  13.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -21.339  13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -20.005  13.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.672  13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -17.338  13.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -16.004  13.860   0.000  0.00  0.00           C+0
HETATM    9  S   UNK     0     -14.670  13.090   0.000  0.00  0.00           S+0
HETATM   10  C   UNK     0     -13.337  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.003  13.090   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0     -10.669  13.860   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -9.336  13.090   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.336  11.550   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  13.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -5.335  15.400   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667  13.860   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.001  11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -12.003  11.550   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -13.337  10.780   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0     -10.669  10.780   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.002   9.240   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -20.005  11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -21.339  10.780   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -21.339   9.240   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -22.673   8.470   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -22.673  11.550   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -24.006  10.780   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   11   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    5   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₉N₃O₉S

Average Mass

499.5400 Da

Monoisotopic Mass

499.16245 Da

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional Name

(2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\CSC[C@H](N=C(O)CC[C@H](N)C(O)=O)C(O)=NCC(O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C21H29N3O9S/c1-32-15-8-12(9-16(33-2)19(15)28)4-3-7-34-11-14(20(29)23-10-18(26)27)24-17(25)6-5-13(22)21(30)31/h3-4,8-9,13-14,28H,5-7,10-11,22H2,1-2H3,(H,23,29)(H,24,25)(H,26,27)(H,30,31)/b4-3+/t13-,14-/m0/s1

InChI Key

HLZFIHFPAUUHBI-NVFZZLLCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ananas comosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
N-substituted-alpha-amino acid
Methoxyphenol
Alpha-amino acid or derivatives
L-alpha-amino acid
Alpha-amino acid
M-dimethoxybenzene
Dimethoxybenzene
Methoxybenzene
Phenol ether
Phenoxy compound
Styrene
Anisole
Alkyl aryl ether
Phenol
Fatty amide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Dialkylthioether
Sulfenyl compound
Thioether
Carboxylic acid
Ether
Organic oxide
Primary amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organosulfur compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-1	ALOGPS
logP	-1.3	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	204.49 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	124.7 m³·mol⁻¹	ChemAxon
Polarizability	50.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00058022

Chemspider ID

67156115

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72720606

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Steingass CB, Glock MP, Lieb VM, Carle R: Light-induced alterations of pineapple (Ananas comosus [L.] Merr.) juice volatiles during accelerated ageing and mass spectrometric studies into their precursors. Food Res Int. 2017 Oct;100(Pt 3):366-374. doi: 10.1016/j.foodres.2017.06.030. Epub 2017 Jun 19. [PubMed:28964359 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid (NP0151661)

MOL for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D MOL for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D SDF for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D-SDF for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

PDB for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D PDB for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

SMILES for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

INCHI for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

Structure for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D Structure for NP0151661 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)