NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid (NP0161338)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 19:29:07 UTC

Updated at

2022-09-02 19:29:07 UTC

NP-MRD ID

NP0161338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid

Description

Phe-Trp-Trp, also known as F-W-W or L-phe-L-TRP-L-TRP, 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. Phe-Trp-Trp 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-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid is found in Trypanosoma brucei. (2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid was first documented in 2006 (PMID: 16316619). Based on a literature review very few articles have been published on Phe-Trp-Trp (PMID: 24007263).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022221292D          

 40 44  0  0  1  0            999 V2000
   -3.6610   -4.5769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -3.7923    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9580   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7650   -3.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200   -4.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8269   -4.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3790   -3.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1240   -2.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3171   -2.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545   -3.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -3.8364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4465   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610   -5.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610   -5.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4465   -6.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -5.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -5.0559    0.0000 C   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
   -0.2203   -0.9238    0.0000 O   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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  6  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  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 23  1  0  0  0  0
 18 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  4  0  0  0
 24 26  2  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  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
 36 37  2  0  0  0  0
 29 37  1  0  0  0  0
 32 37  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END

     RDKit          3D

 71 75  0  0  0  0  0  0  0  0999 V2000
   -2.8152   -2.3050   -3.0156 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8017   -2.0999   -1.9211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8026   -3.2982   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6845   -3.3398    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2091   -2.9600    1.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0826   -3.0109    2.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3917   -3.4203    2.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8452   -3.7979    1.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9863   -3.7498   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2959   -0.9116   -1.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1478   -0.2244   -0.2922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0813   -0.5524   -1.2287 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468    0.4973   -0.6191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9553    1.1768    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1467    2.2930    1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648    2.3507    2.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0995    3.5632    2.4468 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1845    4.3222    1.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1384    5.6273    1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3252    6.1250   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0996    5.3649   -1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4204    4.0566   -0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9587    3.5547    0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0026   -0.0843   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1017   -1.2367    0.5498 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    0.4918   -0.5587 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951    0.0902   -0.2709 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3948    1.2126   -0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7423    0.7032   -0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5213    1.0321    0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6945    0.3826    0.8316 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7006   -0.3615   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6565   -1.2013   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4421   -1.8725   -1.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2506   -1.6915   -2.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -0.8548   -2.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4902   -0.1725   -0.9529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5746   -0.2928    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.8408    1.5197 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650   -0.0617    2.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974   -3.2799   -3.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562   -2.1338   -2.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509   -1.8768   -2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7402   -3.4527   -0.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9542   -4.2189   -1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036   -2.6312    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7524   -2.7225    3.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0770   -3.4640    3.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8607   -4.1267    0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3389   -4.0389   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2729   -0.2448    0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1392    1.2496   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1337    0.4418    1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9349    1.6638    0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4200    1.5112    3.0239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738    3.8647    3.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7459    6.2365    1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0972    7.1423   -0.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4881    5.6976   -1.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0310    3.4494   -1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417   -1.4062    1.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434   -0.7722   -0.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2889    1.5002   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1065    2.0511    0.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2480    1.7028    1.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4612    0.4581    1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5814   -1.3312   -0.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2037   -2.5396   -2.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1044   -2.2372   -3.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3637   -0.7144   -2.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124   -0.2816    3.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 13 24  1  0
 24 25  1  0
 24 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 27 38  1  0
 38 40  1  0
 38 39  2  0
  9  4  1  0
 23 15  1  0
 37 29  1  0
 23 18  1  0
 37 32  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  6
  3 44  1  0
  3 45  1  0
  5 46  1  0
  6 47  1  0
  7 48  1  0
  8 49  1  0
  9 50  1  0
 11 51  1  0
 13 52  1  6
 14 53  1  0
 14 54  1  0
 16 55  1  0
 17 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 22 60  1  0
 25 61  1  0
 27 62  1  6
 28 63  1  0
 28 64  1  0
 30 65  1  0
 31 66  1  0
 33 67  1  0
 34 68  1  0
 35 69  1  0
 36 70  1  0
 40 71  1  0
M  END


  Mrv1652309022221292D          

 40 44  0  0  1  0            999 V2000
   -3.6610   -4.5769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -3.7923    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9580   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7650   -3.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200   -4.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8269   -4.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3790   -3.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1240   -2.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3171   -2.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441   -2.8361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -4.2338    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -4.0623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6880   -4.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -4.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545   -3.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -3.8364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4465   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610   -5.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610   -5.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4465   -6.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -5.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -5.0559    0.0000 C   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
   -0.2203   -0.9238    0.0000 O   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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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  2  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  6  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  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 15 23  1  0  0  0  0
 18 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  4  0  0  0
 24 26  2  0  0  0  0
 27 26  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  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
 36 37  2  0  0  0  0
 29 37  1  0  0  0  0
 32 37  1  0  0  0  0
 27 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161338

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=CC=CC=C1)C(O)=N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H31N5O4/c32-24(14-19-8-2-1-3-9-19)29(37)35-27(15-20-17-33-25-12-6-4-10-22(20)25)30(38)36-28(31(39)40)16-21-18-34-26-13-7-5-11-23(21)26/h1-13,17-18,24,27-28,33-34H,14-16,32H2,(H,35,37)(H,36,38)(H,39,40)/t24-,27-,28-/m0/s1

> <INCHI_KEY>
MJOJSHOTYWABPR-WIRXVTQYSA-N

> <FORMULA>
C31H31N5O4

> <MOLECULAR_WEIGHT>
537.62

> <EXACT_MASS>
537.237604498

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
57.60338392281094

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
2.506262911251461

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.9860007145160012

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3484519606491805

> <JCHEM_PKA_STRONGEST_BASIC>
9.534665763210453

> <JCHEM_POLAR_SURFACE_AREA>
160.07999999999998

> <JCHEM_REFRACTIVITY>
152.16550000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-3-(1H-indol-3-yl)propanoic 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  N   UNK     0      -6.834  -8.544   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -6.358  -7.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.388  -5.934   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.895  -6.255   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.371  -7.719   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.877  -8.039   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.907  -6.895   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -11.432  -5.430   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.925  -5.110   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.852  -6.759   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.376  -5.294   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      -3.821  -7.903   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.284  -8.727   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.848  -7.000   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.380  -7.161   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.700  -8.668   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.034  -9.438   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.034 -10.978   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.700 -11.748   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.367 -10.978   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.367  -9.438   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.869  -4.974   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.411  -1.724   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.393  -3.509   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   18                                                  
CONECT   24   13   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   38                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   29   32                                                  
CONECT   38   27   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
F-W-W	ChEBI
FWW	ChEBI
L-Phe-L-TRP-L-TRP	ChEBI

Chemical Formula

C₃₁H₃₁N₅O₄

Average Mass

537.6200 Da

Monoisotopic Mass

537.23760 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

N[C@@H](CC1=CC=CC=C1)C(O)=N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=N[C@@H](CC1=CNC2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C31H31N5O4/c32-24(14-19-8-2-1-3-9-19)29(37)35-27(15-20-17-33-25-12-6-4-10-22(20)25)30(38)36-28(31(39)40)16-21-18-34-26-13-7-5-11-23(21)26/h1-13,17-18,24,27-28,33-34H,14-16,32H2,(H,35,37)(H,36,38)(H,39,40)/t24-,27-,28-/m0/s1

InChI Key

MJOJSHOTYWABPR-WIRXVTQYSA-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
Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
Triptan
Alpha-amino acid amide
Indolyl carboxylic acid derivative
N-substituted-alpha-amino acid
3-alkylindole
Amphetamine or derivatives
Alpha-amino acid or derivatives
Indole
Indole or derivatives
Aralkylamine
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Fatty amide
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Primary amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tripeptide (CHEBI:73642 )

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	1.25	ALOGPS
logS	-5.4	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

29368058

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44611955

PDB ID

Not Available

ChEBI ID

73642

Good Scents ID

Not Available

References

General References

de Almeida NE, Lund MN, Andersen ML, Cardoso DR: Beer thiol-containing compounds and redox stability: kinetic study of 1-hydroxyethyl radical scavenging ability. J Agric Food Chem. 2013 Oct 2;61(39):9444-52. doi: 10.1021/jf402159a. Epub 2013 Sep 23. [PubMed:24007263 ]
Chekmeneva E, Diaz-Cruz JM, Arino C, Esteban M: Identification of heavy metal complexes of a hexapeptide inhibitor of the human immunodeficiency virus integrase protein by using a voltammetric approach. Anal Biochem. 2006 Jan 15;348(2):252-8. doi: 10.1016/j.ab.2005.10.031. Epub 2005 Nov 7. [PubMed:16316619 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid (NP0161338)

MOL for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D MOL for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D SDF for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D-SDF for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

PDB for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D PDB for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

SMILES for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

INCHI for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

Structure for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)

3D Structure for NP0161338 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-3-(1h-indol-3-yl)propanoic acid)