NP-MRD: Showing NP-Card for (2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid (NP0245103)

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Record Information

Version

2.0

Created at

2022-09-07 06:03:52 UTC

Updated at

2022-09-07 06:03:52 UTC

NP-MRD ID

NP0245103

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Sinapyl-glutathione belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid is found in Ananas comosus. Based on a literature review very few articles have been published on sinapyl-glutathione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072208032D          

 34 34  0  0  1  0            999 V2000
   -4.2868    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    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
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.1250    0.0000 C   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
   -5.7158    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    5.3625    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
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  4  0  0  0
 13 15  2  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  4  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 10 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
    4.4944   -1.9778    3.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5996   -1.6640    2.7955 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4139   -0.8910    1.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1852   -0.4030    1.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0081    0.3732    0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710    0.8358   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268    1.5792   -1.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387    2.0150   -1.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    1.6118   -2.6833 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    0.2335   -2.8856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8846   -0.2433   -1.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1767    0.5579   -1.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1382    0.0630   -0.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3138    0.7606   -0.6805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -0.9645   -0.1955 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7260   -1.5222    0.8434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1639   -1.1622    2.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891   -1.8369    3.5065 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1178   -1.0770    0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7804   -1.4143   -0.5063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7172   -0.3965    1.5745 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0833    0.0733    1.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1708    1.5214    1.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1144    2.1432    2.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3699    2.1879    1.7808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5640   -0.0187   -4.2090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8192    0.9127   -5.0120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9037   -1.3135   -4.5735 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1032    0.6528   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3581    0.1652   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4778    0.4434   -0.9866 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4928    1.2051   -2.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5343   -0.6032    0.8956 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7687   -1.0919    1.2871 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356   -2.6614    3.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9154   -1.0530    3.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8018   -2.4437    4.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3200   -0.6317    1.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247    0.5657    0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1038    1.8802   -1.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626    1.8158   -0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9903    3.1472   -1.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    2.1796   -2.9860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0151   -0.4009   -2.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4877   -0.0513   -0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0881   -1.3349   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    0.4856   -2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454    1.6182   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2463    1.7290   -0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7410   -2.6405    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1540   -1.6261    2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0136   -0.0739    2.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2422   -2.5791    2.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7233   -1.7773   -0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7400   -0.4995    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4724   -0.0802    0.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0624    1.9919    1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1219   -2.0381   -3.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9912    1.2556   -1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5081    1.5157   -2.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8037    2.0497   -2.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1183    0.5560   -3.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9132   -1.6535    2.1088 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
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 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
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 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
 10 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
  9 43  1  0
 10 44  1  6
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 14 49  1  0
 16 50  1  6
 17 51  1  0
 17 52  1  0
 18 53  1  0
 20 54  1  0
 22 55  1  0
 22 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


  Mrv1652309072208032D          

 34 34  0  0  1  0            999 V2000
   -4.2868    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    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
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.1250    0.0000 C   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
   -5.7158    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    5.3625    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
 10  9  1  1  0  0  0
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 11 12  1  0  0  0  0
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 13 14  1  4  0  0  0
 13 15  2  0  0  0  0
 16 15  1  6  0  0  0
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 19 20  1  0  0  0  0
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 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 10 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>
NP0245103

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
FZAGTHNEJOUFRM-NVFZZLLCSA-N

> <FORMULA>
C21H29N3O9S

> <MOLECULAR_WEIGHT>
499.54

> <EXACT_MASS>
499.1624507

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.03110348456012

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.3859014645794396

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.3722010612062485

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6177321492611476

> <JCHEM_PKA_STRONGEST_BASIC>
9.21496804508855

> <JCHEM_POLAR_SURFACE_AREA>
190.49999999999997

> <JCHEM_REFRACTIVITY>
124.77139999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002  12.320   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668  11.550   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.334   5.390   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       5.335   4.620   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0       9.336   5.390   0.000  0.00  0.00           S+0
HETATM   19  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0       8.002   7.700   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  10.010   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336  11.550   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.669   9.240   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.002   7.700   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.336   6.930   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -10.669   7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -9.336  10.010   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   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   10   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)-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-sulfanylethyl]-C-hydroxycarbonimidoyl}-2-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

FZAGTHNEJOUFRM-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 peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
L-alpha-amino acid
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Alpha-amino acid or derivatives
Alpha-amino acid
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
Phenol
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Amino acid
Amino acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Ether
Secondary aliphatic amine
Carboxylic acid
Carboximidic acid derivative
Carboximidic acid
Alkylthiol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	-1.4	ChemAxon
pKa (Strongest Acidic)	1.62	ChemAxon
pKa (Strongest Basic)	9.21	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	190.5 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	124.77 m³·mol⁻¹	ChemAxon
Polarizability	50.03 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133083793

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid (NP0245103)

MOL for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)

3D MOL for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)

3D SDF for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)

3D-SDF for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)

PDB for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)

3D PDB for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)

SMILES for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)

INCHI for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)

Structure for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)

3D Structure for NP0245103 ((2s)-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-sulfanylethyl]-c-hydroxycarbonimidoyl}-2-{[(2e)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-yl]amino}butanoic acid)