NP-MRD: Showing NP-Card for (2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid (NP0164325)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 23:11:15 UTC

Updated at

2022-09-02 23:11:15 UTC

NP-MRD ID

NP0164325

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid

Description

Asn-Trp-Cys-His, also known as N-W-C-H or NWCH, 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. Asn-Trp-Cys-His is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid is found in Trypanosoma brucei. Based on a literature review very few articles have been published on Asn-Trp-Cys-His.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201112D          

 39 41  0  0  1  0            999 V2000
   -3.1089   -5.1900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020   -5.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7499   -5.6315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723   -0.3107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5174    0.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    1.0870    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -0.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.2669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    0.1308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9383   -0.0407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4903    0.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2354    1.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7203    2.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2354    2.6919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4508    2.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4508    1.6120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -0.9968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412   -1.4384    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  4  0  0  0
  7  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  4  0  0  0
 21 23  2  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  4  0  0  0
 27 29  2  0  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 32 36  1  0  0  0  0
 30 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END

     RDKit          3D

 69 71  0  0  0  0  0  0  0  0999 V2000
   -2.6712   -2.7093   -2.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7615   -3.1283   -2.1344 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8334   -3.7931   -1.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3220   -5.1125   -1.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4224   -3.3101    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7498   -1.8329    0.0972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6971   -1.5069   -0.9331 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5205   -1.0264   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3663   -1.2690    0.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393   -0.1104   -1.0089 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5133    0.7740   -1.3931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2569    1.9797   -0.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4206    2.8676   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6116    3.9619   -1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7845    4.5282   -0.9767 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3523    3.8206    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5233    3.9351    0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8782    3.0631    1.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0136    2.0230    2.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8391    1.8698    1.3711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5024    2.7668    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2290    0.0310   -1.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2852   -0.8678   -2.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7683    0.2835   -0.9657 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0935   -0.2521   -1.0071 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1456   -1.4983   -1.8246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0514   -2.7358   -1.0983 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0993    0.7500   -1.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8402    1.5952   -2.5119 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087    0.9179   -0.8421 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5948    0.1006    0.3007 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1110    0.0619    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242   -0.7656    1.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0691   -0.7345    1.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2666   -1.6612    2.5437 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1149   -2.2599    2.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673   -1.6999    2.0342 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057    0.7469    1.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3950    0.3563    2.6962 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2695    1.8613    1.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9454   -5.8320   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940   -3.4980    1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3838   -3.8477    0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1895   -1.4798    1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3722   -0.6740   -1.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6285   -1.2345   -0.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888   -1.7737    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    1.1306   -2.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4072    2.5401   -1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294    1.6547    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9347    4.3403   -2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2238    5.3647   -1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1891    4.7577    0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7974    3.1406    2.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2451    1.3061    2.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1466    1.0685    1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6910   -0.6457   -3.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2907   -0.5877    0.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -1.3335   -2.9076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1831   -1.9515   -1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -2.6464    0.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9181    1.5431   -2.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2301   -0.9014    0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5460    1.0871    0.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3426   -0.4030   -0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7947   -0.0707    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9794   -3.0432    3.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1744   -2.0567    2.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167    2.0261    2.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 11 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 31 38  1  0
 38 40  1  0
 38 39  2  0
 21 13  1  0
 37 33  1  0
 21 16  1  0
  7 45  1  0
  7 46  1  0
  6 44  1  1
  5 42  1  0
  5 43  1  0
  4 41  1  0
  2  1  1  0
  9 47  1  0
 11 48  1  6
 12 49  1  0
 12 50  1  0
 14 51  1  0
 15 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 20 56  1  0
 23 57  1  0
 25 58  1  1
 26 59  1  0
 26 60  1  0
 27 61  1  0
 29 62  1  0
 31 63  1  6
 32 64  1  0
 32 65  1  0
 34 66  1  0
 36 67  1  0
 37 68  1  0
 40 69  1  0
M  END


  Mrv1652309032201112D          

 39 41  0  0  1  0            999 V2000
   -3.1089   -5.1900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020   -5.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7499   -5.6315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723   -0.3107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5174    0.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    1.0870    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5793   -0.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.2669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1313    0.1308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9383   -0.0407    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4903    0.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2354    1.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7203    2.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2354    2.6919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4508    2.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4508    1.6120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -0.9968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6412   -1.4384    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  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  4  0  0  0
  7  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
 10 21  1  0  0  0  0
 21 22  1  4  0  0  0
 21 23  2  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  4  0  0  0
 27 29  2  0  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 32 36  1  0  0  0  0
 30 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164325

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC(O)=N)C(O)=N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=N[C@@H](CS)C(O)=N[C@@H](CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30N8O6S/c25-15(7-20(26)33)21(34)30-17(5-12-8-28-16-4-2-1-3-14(12)16)22(35)32-19(10-39)23(36)31-18(24(37)38)6-13-9-27-11-29-13/h1-4,8-9,11,15,17-19,28,39H,5-7,10,25H2,(H2,26,33)(H,27,29)(H,30,34)(H,31,36)(H,32,35)(H,37,38)/t15-,17-,18-,19-/m0/s1

> <INCHI_KEY>
OKWDNPXELOHZLD-WNHJNPCNSA-N

> <FORMULA>
C24H30N8O6S

> <MOLECULAR_WEIGHT>
558.61

> <EXACT_MASS>
558.200901892

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.957080454210406

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2R)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-0.59

> <JCHEM_LOGP>
-5.920124694454713

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
2.940741572252579

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.064441004048871

> <JCHEM_PKA_STRONGEST_BASIC>
12.871624660117684

> <JCHEM_POLAR_SURFACE_AREA>
249.63999999999993

> <JCHEM_REFRACTIVITY>
153.74230000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2R)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3H-imidazol-4-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  N   UNK     0      -5.803  -9.688   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -4.297  -9.368   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.267 -10.512   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.821  -7.903   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.284  -8.727   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.869  -4.974   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.393  -3.509   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      -0.411  -1.724   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -1.442  -0.580   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.966   0.885   0.000  0.00  0.00           C+0
HETATM   26  S   UNK     0      -1.996   2.029   0.000  0.00  0.00           S+0
HETATM   27  C   UNK     0      -2.948  -0.900   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.424  -2.365   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0      -3.978   0.244   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -5.485  -0.076   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.515   1.069   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.039   2.533   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -6.945   3.779   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -6.039   5.025   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      -4.575   4.549   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      -4.575   3.009   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      -5.961  -1.541   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -7.467  -1.861   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -4.930  -2.685   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   12   15                                                  
CONECT   21   10   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   32                                                       
CONECT   37   30   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
L-Asn-L-TRP-L-cys-L-his	ChEBI
N-W-C-H	ChEBI
NWCH	ChEBI

Chemical Formula

C₂₄H₃₀N₈O₆S

Average Mass

558.6100 Da

Monoisotopic Mass

558.20090 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

N[C@@H](CC(O)=N)C(O)=N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=N[C@@H](CS)C(O)=N[C@@H](CC1=CN=CN1)C(O)=O

InChI Identifier

InChI=1S/C24H30N8O6S/c25-15(7-20(26)33)21(34)30-17(5-12-8-28-16-4-2-1-3-14(12)16)22(35)32-19(10-39)23(36)31-18(24(37)38)6-13-9-27-11-29-13/h1-4,8-9,11,15,17-19,28,39H,5-7,10,25H2,(H2,26,33)(H,27,29)(H,30,34)(H,31,36)(H,32,35)(H,37,38)/t15-,17-,18-,19-/m0/s1

InChI Key

OKWDNPXELOHZLD-WNHJNPCNSA-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
Trypanosoma brucei	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
Histidine or derivatives
Asparagine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
Triptan
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole or derivatives
Indole
Imidazolyl carboxylic acid derivative
N-acyl-amine
Substituted pyrrole
Fatty acyl
Fatty amide
Benzenoid
Pyrrole
Imidazole
Azole
Heteroaromatic compound
Primary carboxylic acid amide
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Alkylthiol
Azacycle
Carboxylic acid
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrapeptide (CHEBI:73415 )

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	-0.59	ALOGPS
logS	-4	ALOGPS

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

28639304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464618

PDB ID

Not Available

ChEBI ID

73415

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid (NP0164325)

MOL for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D MOL for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D SDF for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D-SDF for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

PDB for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D PDB for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

SMILES for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

INCHI for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

Structure for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D Structure for NP0164325 ((2s)-2-{[(2r)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-(c-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-1-hydroxy-3-sulfanylpropylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)