NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid (NP0177149)

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Record Information

Version

2.0

Created at

2022-09-03 14:56:46 UTC

Updated at

2022-09-03 14:56:47 UTC

NP-MRD ID

NP0177149

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid

Description

Ala-Leu-Leu-His, also known as a-L-L-H or ALLH, 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. Ala-Leu-Leu-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-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]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 Ala-Leu-Leu-His.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032216562D          

 32 32  0  0  1  0            999 V2000
   -3.0046    5.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    4.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191    3.5893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4335    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1480    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1480    4.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8625    3.1768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5770    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8625    2.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    2.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    1.9393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2901    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    0.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757   -0.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  1  0  0  0
  5 12  1  0  0  0  0
 12 13  1  4  0  0  0
 12 14  2  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  4  0  0  0
 20 22  2  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END

     RDKit          3D

 68 68  0  0  0  0  0  0  0  0999 V2000
   -3.2837    1.1226    3.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5636   -0.0973    2.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2534   -1.1022    3.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3889   -0.7062    2.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058    0.2014    1.0340 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6017    0.6119   -0.0097 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0122    1.7900   -0.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6040    2.8511    0.5103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9370    2.0311   -1.3760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2477    0.7418   -2.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3756    3.0451   -2.2252 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4565   -0.4118    0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549    0.3200   -0.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504   -1.5576    0.8398 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -2.2363    0.3544 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9329   -2.5926   -1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9324   -3.3621   -1.8038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2612   -2.7331   -1.9365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204   -4.7763   -1.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441   -1.2804    0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499   -1.3169    1.9868 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7532   -0.4401   -0.1256 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058    0.4435    0.2841 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4174    1.1470   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066    1.9503   -1.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974    1.5377   -2.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8307    2.5779   -3.0591 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1485    3.6389   -2.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1172    3.2374   -1.4104 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3662    1.3968    1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646    2.2472    1.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0738    1.4205    1.8163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0455    0.8804    4.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5545    1.8285    3.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2451    1.7125    3.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3697    0.1716    1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417   -1.8911    3.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -1.4800    4.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0265   -0.5165    4.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6713   -1.0301    2.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292   -1.6332    1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    1.1156    1.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2918    3.4391    0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9197    2.3978   -0.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6753    0.9373   -3.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8861    0.1328   -1.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2678    0.2057   -2.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3799    2.9257   -2.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6293    4.0078   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021    0.6273   -1.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2603   -3.1140    1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7050   -1.6159   -1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -3.1336   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5489   -3.5603   -2.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2737   -1.7299   -2.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9026   -3.3378   -2.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8470   -2.7111   -1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8594   -5.2611   -1.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5382   -4.7449   -0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1851   -5.3567   -1.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1373   -1.1549    2.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6368   -0.1920    0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194    0.3236   -1.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2614    1.7357   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638    0.5577   -3.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    4.5969   -2.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5240    3.8932   -0.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8595    1.2747    2.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  5 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 23 30  1  0
 30 32  1  0
 30 31  2  0
 29 25  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  1
  8 43  1  0
  9 44  1  1
 10 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 13 50  1  0
 15 51  1  1
 16 52  1  0
 16 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 19 60  1  0
 21 61  1  0
 23 62  1  1
 24 63  1  0
 24 64  1  0
 26 65  1  0
 28 66  1  0
 29 67  1  0
 32 68  1  0
M  END


  Mrv1652309032216562D          

 32 32  0  0  1  0            999 V2000
   -3.0046    5.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    4.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191    4.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191    3.5893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4335    3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1480    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1480    4.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8625    3.1768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5770    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8625    2.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    2.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    1.9393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2901    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    0.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757   -0.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  1  0  0  0
  5 12  1  0  0  0  0
 12 13  1  4  0  0  0
 12 14  2  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
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 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  4  0  0  0
 20 22  2  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0177149

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H36N6O5/c1-11(2)6-15(25-18(28)13(5)22)19(29)26-16(7-12(3)4)20(30)27-17(21(31)32)8-14-9-23-10-24-14/h9-13,15-17H,6-8,22H2,1-5H3,(H,23,24)(H,25,28)(H,26,29)(H,27,30)(H,31,32)/t13-,15-,16-,17-/m0/s1

> <INCHI_KEY>
RGDKRCPIFODMHK-HJWJTTGWSA-N

> <FORMULA>
C21H36N6O5

> <MOLECULAR_WEIGHT>
452.556

> <EXACT_MASS>
452.274718283

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.21293764225121

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(1H-imidazol-5-yl)propanoic acid

> <JCHEM_LOGP>
-1.4994367315075439

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.711195561738801

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2086611824472135

> <JCHEM_PKA_STRONGEST_BASIC>
9.570114922527896

> <JCHEM_POLAR_SURFACE_AREA>
189.76999999999998

> <JCHEM_REFRACTIVITY>
118.86349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]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  C   UNK     0      -5.609  10.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.609   9.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.275   8.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.942   8.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.942   6.700   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -8.276   5.930   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -9.610   6.700   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -9.610   8.240   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -10.943   5.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -12.277   6.700   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0     -10.943   4.390   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -5.609   5.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.275   6.700   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      -5.609   4.390   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -4.275   3.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.275   2.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.941   1.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.608   2.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.941  -0.230   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.941   4.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.941   5.930   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      -1.608   3.620   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.060   6.700   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.608   6.700   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   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25                                                       
CONECT   30   23   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Value	Source
a-L-L-H	ChEBI
ALLH	ChEBI
L-Ala-L-leu-L-leu-L-his	ChEBI

Chemical Formula

C₂₁H₃₆N₆O₅

Average Mass

452.5560 Da

Monoisotopic Mass

452.27472 Da

IUPAC Name

(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(1H-imidazol-5-yl)propanoic acid

Traditional Name

(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3H-imidazol-4-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H36N6O5/c1-11(2)6-15(25-18(28)13(5)22)19(29)26-16(7-12(3)4)20(30)27-17(21(31)32)8-14-9-23-10-24-14/h9-13,15-17H,6-8,22H2,1-5H3,(H,23,24)(H,25,28)(H,26,29)(H,27,30)(H,31,32)/t13-,15-,16-,17-/m0/s1

InChI Key

RGDKRCPIFODMHK-HJWJTTGWSA-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
Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alanine or derivatives
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Imidazolyl carboxylic acid derivative
N-acyl-amine
Fatty amide
Fatty acyl
Imidazole
Azole
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Amino acid or derivatives
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tetrapeptide (CHEBI:73365 )

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	-1.5	ChemAxon
pKa (Strongest Acidic)	3.21	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	189.77 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	118.86 m³·mol⁻¹	ChemAxon
Polarizability	48.21 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

28639275

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464563

PDB ID

Not Available

ChEBI ID

73365

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid (NP0177149)

MOL for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D MOL for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D SDF for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D-SDF for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

PDB for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D PDB for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

SMILES for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

INCHI for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

Structure for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)

3D Structure for NP0177149 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-(3h-imidazol-4-yl)propanoic acid)