NP-MRD: Showing NP-Card for (3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid (NP0212486)

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Record Information

Version

1.0

Created at

2022-09-05 11:10:18 UTC

Updated at

2022-09-05 11:10:18 UTC

NP-MRD ID

NP0212486

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid

Description

Ala-Val-Asp-His, also known as a-V-D-H or AVDH, 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-Val-Asp-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. (3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid is found in Trypanosoma brucei. Based on a literature review very few articles have been published on Ala-Val-Asp-His.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052213102D          

 31 31  0  0  1  0            999 V2000
   -4.4335    4.8268    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
   -3.0046    4.8268    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757   -0.1232    0.0000 O   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  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  1  0  0  0
  4 11  1  0  0  0  0
 11 12  1  4  0  0  0
 11 13  2  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  4  0  0  0
 19 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 59 59  0  0  0  0  0  0  0  0999 V2000
   -3.3050   -1.3535    2.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1095   -0.6372    1.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2251   -1.6165    1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964    0.4727    0.8631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4320    0.0268   -0.1967 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6990    0.1353   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5250    0.7133    0.6381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3440   -0.4278   -1.5264 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0675    0.6408   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2404   -1.5234   -1.1378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358    1.2004    0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5743    2.2542   -0.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2423    0.8568    0.6260 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9193    1.5168    0.1135 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3314    2.5961    1.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2605    3.5975    1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1531    4.5613    0.5101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340    3.5005    2.3518 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.5344   -0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799   -0.0977    1.1494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5986    0.2946   -1.1285 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7093   -0.6461   -1.3420 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8925   -0.0877   -0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1464   -0.8515   -0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5081   -1.8748   -1.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7680   -2.2281   -1.2874 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2114   -1.4392   -0.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2239   -0.6065    0.0295 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2838   -1.9873   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0396   -2.9691   -0.6861 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308   -2.1125   -0.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -0.7631    3.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9250   -2.2926    2.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0058   -1.5993    1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5311   -0.2113    2.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7475   -2.6101    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2523   -1.8023    1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9723   -1.3140    0.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1076    1.2260    1.5332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2883    1.3131    0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5949   -0.8875   -2.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5684    0.8961   -3.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0656    1.5921   -1.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0942    0.2951   -2.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6970   -1.2282   -0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6310   -2.3698   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1525    2.1216   -1.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7314    1.9390   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5998    2.1511    2.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2342    3.1214    0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297    3.9678    2.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7051    0.4294    2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8633   -0.7281   -2.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6694    0.0867    0.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797    0.9241   -1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9270   -2.3164   -2.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1803   -1.4923    0.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2706    0.1208    0.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5717   -3.0118   -0.1265 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  4 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
 14 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 22 29  1  0
 29 31  1  0
 29 30  2  0
 28 24  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  1
  7 40  1  0
  8 41  1  6
  9 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 12 47  1  0
 14 48  1  6
 15 49  1  0
 15 50  1  0
 18 51  1  0
 20 52  1  0
 22 53  1  6
 23 54  1  0
 23 55  1  0
 25 56  1  0
 27 57  1  0
 28 58  1  0
 31 59  1  0
M  END


  Mrv1652309052213102D          

 31 31  0  0  1  0            999 V2000
   -4.4335    4.8268    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
   -3.0046    4.8268    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757   -0.1232    0.0000 O   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  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  1  0  0  0
  4 11  1  0  0  0  0
 11 12  1  4  0  0  0
 11 13  2  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  4  0  0  0
 19 21  2  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212486

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H28N6O7/c1-8(2)14(24-15(27)9(3)19)17(29)22-11(5-13(25)26)16(28)23-12(18(30)31)4-10-6-20-7-21-10/h6-9,11-12,14H,4-5,19H2,1-3H3,(H,20,21)(H,22,29)(H,23,28)(H,24,27)(H,25,26)(H,30,31)/t9-,11-,12-,14-/m0/s1

> <INCHI_KEY>
XIHHLOVIGNFBCR-HVTMNAMFSA-N

> <FORMULA>
C18H28N6O7

> <MOLECULAR_WEIGHT>
440.457

> <EXACT_MASS>
440.201947266

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.303874741910406

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}propanoic acid

> <JCHEM_LOGP>
-3.425057304869156

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.263200959780687

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7933048275572023

> <JCHEM_PKA_STRONGEST_BASIC>
9.570097140810118

> <JCHEM_POLAR_SURFACE_AREA>
227.06999999999994

> <JCHEM_REFRACTIVITY>
106.54729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1S)-1-carboxy-2-(3H-imidazol-4-yl)ethyl]-C-hydroxycarbonimidoyl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.276   9.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.942   8.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.609   9.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.942   6.700   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -8.276   5.930   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -9.610   6.700   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -9.610   8.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -10.943   5.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.277   6.700   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0     -10.943   4.390   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -5.609   5.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.275   6.700   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -5.609   4.390   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -4.275   3.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.275   2.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.941   1.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.608   2.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.941  -0.230   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.941   4.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.941   5.930   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      -1.608   3.620   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.060   6.700   0.000  0.00  0.00           O+0
HETATM   31  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   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   22   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Value	Source
a-V-D-H	ChEBI
AVDH	ChEBI
L-Ala-L-val-L-asp-L-his	ChEBI

Chemical Formula

C₁₈H₂₈N₆O₇

Average Mass

440.4570 Da

Monoisotopic Mass

440.20195 Da

IUPAC Name

(3S)-3-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1S)-1-carboxy-2-(1H-imidazol-5-yl)ethyl]-C-hydroxycarbonimidoyl}propanoic acid

Traditional Name

(3S)-3-{[(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1S)-1-carboxy-2-(3H-imidazol-4-yl)ethyl]-C-hydroxycarbonimidoyl}propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H28N6O7/c1-8(2)14(24-15(27)9(3)19)17(29)22-11(5-13(25)26)16(28)23-12(18(30)31)4-10-6-20-7-21-10/h6-9,11-12,14H,4-5,19H2,1-3H3,(H,20,21)(H,22,29)(H,23,28)(H,24,27)(H,25,26)(H,30,31)/t9-,11-,12-,14-/m0/s1

InChI Key

XIHHLOVIGNFBCR-HVTMNAMFSA-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
Aspartic acid or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Valine or derivatives
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 acyl
Dicarboxylic acid or derivatives
Fatty amide
Azole
Heteroaromatic compound
Imidazole
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Azacycle
Carboxylic acid
Organoheterocyclic compound
Primary amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tetrapeptide (CHEBI:73383 )

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	-3.4	ChemAxon
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	227.07 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	106.55 m³·mol⁻¹	ChemAxon
Polarizability	43.3 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

28639286

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71464591

PDB ID

Not Available

ChEBI ID

73383

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid (NP0212486)

MOL for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)

3D MOL for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)

3D SDF for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)

3D-SDF for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)

PDB for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)

3D PDB for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)

SMILES for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)

INCHI for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)

Structure for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)

3D Structure for NP0212486 ((3s)-3-{[(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-{[(1s)-1-carboxy-2-(3h-imidazol-4-yl)ethyl]-c-hydroxycarbonimidoyl}propanoic acid)