NP-MRD: Showing NP-Card for (2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid (NP0292840)

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Record Information

Version

2.0

Created at

2022-09-10 00:34:10 UTC

Updated at

2022-09-10 00:34:10 UTC

NP-MRD ID

NP0292840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid

Description

GammaGluCys(IAN), also known as L-g-glu-L-cys-(ian), belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. GammaGluCys(IAN) 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-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid is found in Arabidopsis thaliana. (2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid was first documented in 2011 (PMID: 21239642). Based on a literature review very few articles have been published on gammaGluCys(IAN).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102202342D          

 28 29  0  0  1  0            999 V2000
    2.0240    1.0484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365    0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6740   -0.3805    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115    0.3340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3240    1.0484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1490    1.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5615    0.3340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5615    1.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3865    1.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7990    2.4774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3865    3.1918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6240    2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0365    3.1918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0365    1.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3240   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1490   -0.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115   -1.0950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365   -1.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7721   -1.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1590   -2.4007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445   -1.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599   -2.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -1.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183   -0.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -1.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  8  9  1  4  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  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
 20 28  1  0  0  0  0
 23 28  1  0  0  0  0
M  END

     RDKit          3D

 48 49  0  0  0  0  0  0  0  0999 V2000
    3.0664    2.8347    1.1790 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7870    1.7549    0.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3883    0.3952    0.3770 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0639    0.7014   -0.8586 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625    1.3724   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2419    0.4415    0.7009 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2989    1.2655    1.2606 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3054    1.6385    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2282    2.4401    1.3573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6429    1.3386   -0.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0263    0.7215   -0.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0783   -0.5518   -0.0881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1091   -1.4930   -0.5667 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4540   -1.1254   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4091   -0.4309    0.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6212   -2.4011   -0.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123   -0.3592    1.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517    0.0359    2.9457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548   -1.6190    1.4652 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4642   -0.3401   -0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2049   -1.3547   -1.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3591   -1.7958   -1.6888 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3637   -1.1361   -1.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7538   -1.2038   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5680   -0.3874   -0.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0437    0.5250    0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6576    0.5985    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8203   -0.2114   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0439   -0.1959    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151    2.2077    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0007    1.9547   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391   -0.2947   -0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6105    1.9932    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5901    2.2580   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9320    0.6354   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7729    1.4225   -0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2119    0.4909   -1.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885   -0.3022    0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4707   -1.8164    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6981   -1.2784   -1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5668   -2.7321   -0.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3770   -1.8212    0.5868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2195   -1.7119   -1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5066   -2.5615   -2.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1890   -1.9255   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6386   -0.4587   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6490    1.1803    0.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2283    1.3019    1.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  3  0
  3 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  6 17  1  0
 17 19  1  0
 17 18  2  0
 12 14  1  0
 14 16  1  0
 14 15  2  0
 28 20  1  0
 28 23  1  0
 13 39  1  0
 13 40  1  0
 12 38  1  1
 11 36  1  0
 11 37  1  0
 10 34  1  0
 10 35  1  0
  9 33  1  0
  6 32  1  6
  5 30  1  0
  5 31  1  0
  3 29  1  1
 21 43  1  0
 22 44  1  0
 24 45  1  0
 25 46  1  0
 26 47  1  0
 27 48  1  0
 19 42  1  0
 16 41  1  0
M  END


  Mrv1652309102202342D          

 28 29  0  0  1  0            999 V2000
    2.0240    1.0484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365    0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6740   -0.3805    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115    0.3340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3240    1.0484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1490    1.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5615    0.3340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5615    1.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3865    1.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7990    2.4774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3865    3.1918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6240    2.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0365    3.1918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0365    1.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3240   -0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1490   -0.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115   -1.0950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365   -1.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7721   -1.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1590   -2.4007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445   -1.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6599   -2.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468   -1.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183   -0.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029   -0.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -1.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  8  9  1  4  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  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
 20 28  1  0  0  0  0
 23 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292840

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H20N4O5S/c19-7-15(11-8-21-13-4-2-1-3-10(11)13)28-9-14(18(26)27)22-16(23)6-5-12(20)17(24)25/h1-4,8,12,14-15,21H,5-6,9,20H2,(H,22,23)(H,24,25)(H,26,27)/t12-,14-,15?/m0/s1

> <INCHI_KEY>
FGSKBDHSKRORJJ-XRJCJLGXSA-N

> <FORMULA>
C18H20N4O5S

> <MOLECULAR_WEIGHT>
404.44

> <EXACT_MASS>
404.115440934

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
39.162537741547034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-{[(1R)-1-carboxy-2-{[cyano(1H-indol-3-yl)methyl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <JCHEM_LOGP>
-1.444765728651799

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
2.64359851331531

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7079959825450421

> <JCHEM_PKA_STRONGEST_BASIC>
9.534835426659658

> <JCHEM_POLAR_SURFACE_AREA>
172.79

> <JCHEM_REFRACTIVITY>
102.14000000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-{[(1R)-1-carboxy-2-{[cyano(1H-indol-3-yl)methyl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  N   UNK     0       3.778   1.957   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.548   0.623   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.318  -0.710   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       6.858  -0.710   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       7.628   0.623   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.168   0.623   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       9.938   1.957   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      11.478   1.957   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.248   0.623   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.248   3.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.788   3.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.558   4.624   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      13.788   5.958   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      16.098   4.624   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.868   5.958   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      16.868   3.291   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.938  -0.710   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.478  -0.710   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.168  -2.044   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.548  -2.044   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.175  -3.451   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       4.030  -4.481   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       2.696  -3.711   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.232  -4.187   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.087  -3.157   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.408  -1.650   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.872  -1.174   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.017  -2.205   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    6   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    3   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   20   23                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Value	Source
Indole-3-acetonitrile-gamma-glutamylcysteine conjugate	ChEBI
Indole-3-acetonitrile-L-gamma-glutamyl-L-cysteine conjugate	ChEBI
L-gamma-Glu-L-cys-(ian)	ChEBI
Indole-3-acetonitrile-g-glutamylcysteine conjugate	Generator
Indole-3-acetonitrile-g-glutamylcysteine conjugic acid	Generator
Indole-3-acetonitrile-gamma-glutamylcysteine conjugic acid	Generator
Indole-3-acetonitrile-γ-glutamylcysteine conjugate	Generator
Indole-3-acetonitrile-γ-glutamylcysteine conjugic acid	Generator
Indole-3-acetonitrile-L-g-glutamyl-L-cysteine conjugate	Generator
Indole-3-acetonitrile-L-g-glutamyl-L-cysteine conjugic acid	Generator
Indole-3-acetonitrile-L-gamma-glutamyl-L-cysteine conjugic acid	Generator
Indole-3-acetonitrile-L-γ-glutamyl-L-cysteine conjugate	Generator
Indole-3-acetonitrile-L-γ-glutamyl-L-cysteine conjugic acid	Generator
L-g-Glu-L-cys-(ian)	Generator
L-Γ-glu-L-cys-(ian)	Generator

Chemical Formula

C₁₈H₂₀N₄O₅S

Average Mass

404.4400 Da

Monoisotopic Mass

404.11544 Da

IUPAC Name

(2S)-2-amino-4-{[(1R)-1-carboxy-2-{[cyano(1H-indol-3-yl)methyl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

Traditional Name

(2S)-2-amino-4-{[(1R)-1-carboxy-2-{[cyano(1H-indol-3-yl)methyl]sulfanyl}ethyl]-C-hydroxycarbonimidoyl}butanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CCC(O)=N[C@@H](CSC(C#N)C1=CNC2=CC=CC=C12)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C18H20N4O5S/c19-7-15(11-8-21-13-4-2-1-3-10(11)13)28-9-14(18(26)27)22-16(23)6-5-12(20)17(24)25/h1-4,8,12,14-15,21H,5-6,9,20H2,(H,22,23)(H,24,25)(H,26,27)/t12-,14-,15?/m0/s1

InChI Key

FGSKBDHSKRORJJ-XRJCJLGXSA-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
Arabidopsis thaliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Cysteine or derivatives
Alpha-amino acid
L-alpha-amino acid
3-alkylindole
Alpha-amino acid or derivatives
Indole
Indole or derivatives
Benzenoid
N-acyl-amine
Fatty acyl
Substituted pyrrole
Fatty amide
Dicarboxylic acid or derivatives
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Thioether
Sulfenyl compound
Carboxylic acid
Azacycle
Organoheterocyclic compound
Dialkylthioether
Carbonitrile
Nitrile
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organic oxide
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Primary amine
Amine
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:65022 )
dipeptide (CHEBI:65022 )
nitrile (CHEBI:65022 )
S-conjugate (CHEBI:65022 )

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	-1.4	ChemAxon
pKa (Strongest Acidic)	1.71	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.79 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	102.14 m³·mol⁻¹	ChemAxon
Polarizability	39.16 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

28532790

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70678683

PDB ID

Not Available

ChEBI ID

65022

Good Scents ID

Not Available

References

General References

Su T, Xu J, Li Y, Lei L, Zhao L, Yang H, Feng J, Liu G, Ren D: Glutathione-indole-3-acetonitrile is required for camalexin biosynthesis in Arabidopsis thaliana. Plant Cell. 2011 Jan;23(1):364-80. doi: 10.1105/tpc.110.079145. Epub 2011 Jan 14. [PubMed:21239642 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid (NP0292840)

MOL for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D MOL for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D SDF for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D-SDF for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

PDB for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D PDB for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

SMILES for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

INCHI for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

Structure for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D Structure for NP0292840 ((2s)-2-amino-4-{[(1r)-1-carboxy-2-{[cyano(1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)