NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid (NP0265774)

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Record Information

Version

1.0

Created at

2022-09-08 09:52:32 UTC

Updated at

2022-09-08 09:52:32 UTC

NP-MRD ID

NP0265774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid

Description

Asp-Leu-Asp-Gln, also known as D-L-D-Q or DLDQ, 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. Asp-Leu-Asp-Gln 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-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid is found in Trypanosoma brucei. Based on a literature review very few articles have been published on Asp-Leu-Asp-Gln.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082211522D          

 34 33  0  0  1  0            999 V2000
    7.4250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2500    5.7158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.2868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5375    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    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  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  4  0  0  0
 15 17  2  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  4  0  0  0
 23 25  2  0  0  0  0
 26 25  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

 65 64  0  0  0  0  0  0  0  0999 V2000
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    5.4135    0.4225   -2.5652 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7835   -0.4017   -1.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4480   -1.7500   -1.6623 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6174    0.0638   -0.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5582   -0.6962   -1.9832 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702    0.6503   -0.4268 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2746    0.9387    1.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4329   -0.3306    1.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4648   -0.3925    3.0338 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5523   -1.5101    1.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539   -0.2173   -0.7358 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8016   -0.7601   -0.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672   -1.7362   -1.5089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -0.5972    0.5687 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0238   -1.8431    1.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6603   -2.9768    0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0319   -2.6409    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9024   -4.0740    1.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083   -0.0125    0.0395 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0005    1.1346   -0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    1.8127   -0.6703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2361    1.7473   -1.0957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3943    0.9027   -0.8794 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5007    3.0694   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7132    3.7239   -0.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4489    3.2314   -1.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0681    4.9485   -0.3627 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9285    1.9875    0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845    2.4743    1.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4632    2.7475   -0.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910   -2.1839   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7485    1.1833   -0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6149   -0.3471   -0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4761    0.3389    1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7674   -1.2497    1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514    0.3523    1.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -1.3441   -2.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1794    1.6335   -0.9985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    1.5720    1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788    1.5488    1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4005   -2.0641    1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755   -1.4338   -2.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712    0.1486    1.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311   -2.1975    1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6505   -1.6005    2.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971   -3.4494   -0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5417   -1.9472    0.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062   -2.2718   -0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6420   -3.5740   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3283   -3.5416    2.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9430   -4.5218    2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6348   -4.8128    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6728    2.6242   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1527    1.9653   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3494    0.1248   -1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3409    4.9567    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7648    2.4462   -1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 23  1  0
 21 20  1  0
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 19 24  1  0
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 30 32  1  0
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 17 18  1  0
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 13 15  1  0
 13 14  2  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  7 33  1  0
 33 35  1  0
 33 34  2  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
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 32 64  1  0
 18 47  1  0
 11 43  1  6
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 15 46  1  0
 10 42  1  0
  7 41  1  1
  6 39  1  0
  6 40  1  0
  5 37  1  0
  5 38  1  0
  4 36  1  0
  2  1  1  0
 35 65  1  0
M  END


  Mrv1652309082211522D          

 34 33  0  0  1  0            999 V2000
    7.4250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    3.5724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4250    4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625    5.0013    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2500    5.7158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7250    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4875    6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    4.2868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    4.2868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5375    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    4.2868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    5.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    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
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  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
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 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  5 15  1  0  0  0  0
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 18 19  1  0  0  0  0
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 18 23  1  0  0  0  0
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 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265774

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H31N5O10/c1-8(2)5-11(23-16(30)9(20)6-14(26)27)17(31)24-12(7-15(28)29)18(32)22-10(19(33)34)3-4-13(21)25/h8-12H,3-7,20H2,1-2H3,(H2,21,25)(H,22,32)(H,23,30)(H,24,31)(H,26,27)(H,28,29)(H,33,34)/t9-,10-,11-,12-/m0/s1

> <INCHI_KEY>
CMBDUPIBCOEWNE-BJDJZHNGSA-N

> <FORMULA>
C19H31N5O10

> <MOLECULAR_WEIGHT>
489.482

> <EXACT_MASS>
489.207092218

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.51055412156596

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

> <JCHEM_LOGP>
-2.693349412911342

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.200499607550693

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7134213022606986

> <JCHEM_PKA_STRONGEST_BASIC>
9.702334958855444

> <JCHEM_POLAR_SURFACE_AREA>
279.77

> <JCHEM_REFRACTIVITY>
123.24819999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      13.860   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.090   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.550   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.860   5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.090   6.668   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      13.860   8.002   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      15.400   8.002   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      16.170   6.668   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.170   9.336   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      15.400  10.669   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      17.710   9.336   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.480  10.669   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      20.020  10.669   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      17.710  12.003   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.780   5.335   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      10.780   8.002   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       9.240   8.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.470   9.336   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.930   9.336   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.160   8.002   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.160  10.669   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.470   6.668   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.240   5.335   0.000  0.00  0.00           O+0
HETATM   25  N   UNK     0       6.930   6.668   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.850   4.001   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       1.540   2.667   0.000  0.00  0.00           N+0
HETATM   31  O   UNK     0       1.540   5.335   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.470   4.001   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.160   2.667   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   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    5   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol

Synonyms

Value	Source
D-L-D-Q	ChEBI
DLDQ	ChEBI
L-Asp-L-leu-L-asp-L-GLN	ChEBI

Chemical Formula

C₁₉H₃₁N₅O₁₀

Average Mass

489.4820 Da

Monoisotopic Mass

489.20709 Da

IUPAC Name

(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

Traditional Name

(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C[C@H](N=C(O)[C@@H](N)CC(O)=O)C(O)=N[C@@H](CC(O)=O)C(O)=N[C@@H](CCC(O)=N)C(O)=O

InChI Identifier

InChI=1S/C19H31N5O10/c1-8(2)5-11(23-16(30)9(20)6-14(26)27)17(31)24-12(7-15(28)29)18(32)22-10(19(33)34)3-4-13(21)25/h8-12H,3-7,20H2,1-2H3,(H2,21,25)(H,22,32)(H,23,30)(H,24,31)(H,26,27)(H,28,29)(H,33,34)/t9-,10-,11-,12-/m0/s1

InChI Key

CMBDUPIBCOEWNE-BJDJZHNGSA-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
Glutamine or derivatives
Leucine or derivatives
Aspartic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
N-acyl-l-glutamine
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
N-acyl-amine
Fatty acyl
Fatty amide
Primary carboxylic acid amide
Secondary carboxylic acid amide
Carboxamide group
Amino acid
Amino acid or derivatives
Carboxylic acid
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

tetrapeptide (CHEBI:73428 )

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	-2.7	ChemAxon
pKa (Strongest Acidic)	2.71	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	279.77 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	123.25 m³·mol⁻¹	ChemAxon
Polarizability	47.51 Å³	ChemAxon
Number of Rings	0	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

28639307

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464689

PDB ID

Not Available

ChEBI ID

73428

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid (NP0265774)

MOL for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D MOL for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D SDF for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D-SDF for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

PDB for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D PDB for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

SMILES for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

INCHI for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

Structure for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)

3D Structure for NP0265774 ((2s)-2-{[(2s)-2-{[(2s)-2-{[(2s)-2-amino-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid)