NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid (NP0227920)

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Record Information

Version

2.0

Created at

2022-09-06 07:24:11 UTC

Updated at

2022-09-06 07:24:11 UTC

NP-MRD ID

NP0227920

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid

Description

Leu-Phe-Asp, also known as L-F-D or L-leu-L-phe-L-asp, 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. Leu-Phe-Asp 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-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid is found in Trypanosoma brucei. (2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid was first documented in 2000 (PMID: 10666163). Based on a literature review very few articles have been published on Leu-Phe-Asp.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062209242D          

 28 28  0  0  1  0            999 V2000
   -6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    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
  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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  4  0  0  0
 18 20  2  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END

     RDKit          3D

 55 55  0  0  0  0  0  0  0  0999 V2000
    5.5904   -1.9075   -1.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6457   -2.7285   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3891   -3.3563    0.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170   -1.9122    0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867   -1.3063   -0.8247 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5075   -0.4560   -1.6343 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334   -0.5810   -0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115   -1.3003    0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2650    0.6386   -0.4769 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213    1.2840    0.1319 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0028    2.6525   -0.4654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1197    3.4588    0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007    3.4294   -0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4040    4.1508   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3550    4.9356    0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1784    4.9601    1.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0733    4.2429    1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704    0.4311   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5188    0.2605   -1.4065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -0.1314    0.8564 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8034   -0.9714    0.8103 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1024   -0.1715    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2344   -1.1264    0.5951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8899   -1.3561   -0.4818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6749   -1.8538    1.7163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774   -2.0686   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944   -2.2454   -0.9230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322   -2.9564   -0.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2729   -1.9490   -2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6355   -2.2979   -1.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6214   -0.8620   -0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2669   -3.5778   -0.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521   -3.5212    0.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2467   -2.6554    1.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8751   -4.3271    1.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8654   -2.5568    0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9186   -1.0630    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3439   -2.1648   -1.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3853   -0.5720   -2.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4997    0.5412   -1.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324   -2.3094    0.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3427    1.3262    1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611    2.5864   -1.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    3.2211   -0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896    2.8255   -1.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3106    4.1042   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2198    5.5286    1.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1080    5.5713    2.4313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1355    4.2531    1.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0553    0.5891   -2.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124   -1.4205    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2073    0.5076    1.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0961    0.4118   -0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9599   -2.8433    1.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1474   -3.3612   -1.1866 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
  5  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
 21 26  1  0
 26 28  1  0
 26 27  2  0
 17 12  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  6
  6 39  1  0
  6 40  1  0
  8 41  1  0
 10 42  1  1
 11 43  1  0
 11 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 19 50  1  0
 21 51  1  1
 22 52  1  0
 22 53  1  0
 25 54  1  0
 28 55  1  0
M  END


  Mrv1652309062209242D          

 28 28  0  0  1  0            999 V2000
   -6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    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
  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  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  4  0  0  0
 18 20  2  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227920

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H27N3O6/c1-11(2)8-13(20)17(25)21-14(9-12-6-4-3-5-7-12)18(26)22-15(19(27)28)10-16(23)24/h3-7,11,13-15H,8-10,20H2,1-2H3,(H,21,25)(H,22,26)(H,23,24)(H,27,28)/t13-,14-,15-/m0/s1

> <INCHI_KEY>
ZAVCJRJOQKIOJW-KKUMJFAQSA-N

> <FORMULA>
C19H27N3O6

> <MOLECULAR_WEIGHT>
393.44

> <EXACT_MASS>
393.189985601

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.289451949032504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid

> <JCHEM_LOGP>
-0.3484377693704096

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.739584281027678

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1697815452669427

> <JCHEM_PKA_STRONGEST_BASIC>
9.605409109148813

> <JCHEM_POLAR_SURFACE_AREA>
165.79999999999998

> <JCHEM_REFRACTIVITY>
100.4635

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.669  -6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -8.002  -7.700   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -6.668  -3.850   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -5.335  -6.160   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      -2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000  -1.540   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   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   10   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol

Synonyms

Value	Source
L-F-D	ChEBI
L-Leu-L-phe-L-asp	ChEBI
LFD	ChEBI

Chemical Formula

C₁₉H₂₇N₃O₆

Average Mass

393.4400 Da

Monoisotopic Mass

393.18999 Da

IUPAC Name

(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid

Traditional Name

(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H27N3O6/c1-11(2)8-13(20)17(25)21-14(9-12-6-4-3-5-7-12)18(26)22-15(19(27)28)10-16(23)24/h3-7,11,13-15H,8-10,20H2,1-2H3,(H,21,25)(H,22,26)(H,23,24)(H,27,28)/t13-,14-,15-/m0/s1

InChI Key

ZAVCJRJOQKIOJW-KKUMJFAQSA-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
Aspartic acid or derivatives
Leucine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Acyl-homoserine
Acyl-l-homoserine
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Dicarboxylic acid or derivatives
N-acyl-amine
Fatty acyl
Benzenoid
Fatty amide
Monocyclic benzene moiety
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Amine
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Primary aliphatic amine
Primary amine
Organooxygen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tripeptide (CHEBI:73571 )

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	-0.35	ChemAxon
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	9.61	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	165.8 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	100.46 m³·mol⁻¹	ChemAxon
Polarizability	40.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

28639372

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464636

PDB ID

Not Available

ChEBI ID

73571

Good Scents ID

Not Available

References

General References

Tzioufas AG, Tzortzakis NG, Panou-Pomonis E, Boki KA, Sakarellos-Daitsiotis M, Sakarellos C, Moutsopoulos HM: The clinical relevance of antibodies to ribosomal-P common epitope in two targeted systemic lupus erythematosus populations: a large cohort of consecutive patients and patients with active central nervous system disease. Ann Rheum Dis. 2000 Feb;59(2):99-104. doi: 10.1136/ard.59.2.99. [PubMed:10666163 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid (NP0227920)

MOL for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)

3D MOL for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)

3D SDF for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)

3D-SDF for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)

PDB for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)

3D PDB for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)

SMILES for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)

INCHI for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)

Structure for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)

3D Structure for NP0227920 ((2s)-2-{[(2s)-2-{[(2s)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid)