NP-MRD: Showing NP-Card for (2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid (NP0314083)

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Record Information

Version

2.0

Created at

2022-09-11 11:59:53 UTC

Updated at

2022-09-11 11:59:54 UTC

NP-MRD ID

NP0314083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

GammaGluCys(4MeOI3M)Gly 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. GammaGluCys(4MeOI3M)Gly 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-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid is found in Arabidopsis thaliana. Based on a literature review very few articles have been published on gammaGluCys(4MeOI3M)Gly.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112213592D          

 32 33  0  0  1  0            999 V2000
   -2.8658   -7.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4178   -7.1079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2248   -7.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4797   -8.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2867   -8.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8387   -7.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5838   -6.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9963   -6.1233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4443   -5.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6906   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9761   -5.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2616   -5.8458    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5472   -5.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327   -5.8458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1182   -5.4333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -6.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -5.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0252   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397   -5.4333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7397   -4.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4541   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -5.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4541   -6.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327   -6.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5472   -7.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1182   -7.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1182   -7.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -8.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -7.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -9.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768   -6.6663    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  4  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 10 32  1  0  0  0  0
  3 32  2  0  0  0  0
  7 32  1  0  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
   -3.1101    3.7042    2.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    2.7170    1.1881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0091    2.1203    0.6042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779    2.4991    0.9979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3877    1.9060    0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2456    0.9257   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9819    0.5480   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5742   -0.3549   -1.8653 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2088   -0.3512   -1.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7816    0.5834   -0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4006    0.9624   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2626   -0.0635   -1.5694 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779   -1.7781   -1.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220   -1.8792    0.3693 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5818   -1.4796    0.5493 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629   -1.1377    0.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7780   -2.0251    0.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648    0.2699    1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1065    0.7987    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4525    2.2135    0.5586 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3165    3.0975    0.5504 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5479    2.8123   -0.2302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6078    2.1642   -0.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3944    4.0592   -0.7735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0192   -3.2642    0.8639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9228   -3.3726    1.9052 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4682   -4.3246    0.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4018   -4.4782   -0.6751 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442   -5.6841   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0745   -6.3676    0.6823 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2527   -6.0515   -1.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8962    1.1525   -0.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6410    3.3070    3.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157    4.4462    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1806    4.2599    2.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4593    3.2504    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4038    2.1605    0.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1167    0.4582   -1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1120   -0.9879   -2.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5797   -0.9581   -2.5045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2479    2.0310   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808    0.8865    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315   -2.1109   -0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2021   -2.4617   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981   -1.2003    0.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5337   -1.9715    1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5027    0.3262    2.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1851    0.9188    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7477    0.8500   -0.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0272    0.1747    0.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7951    2.1488    1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    3.4404   -0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032    2.9177    1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2043    4.6356   -0.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4409   -2.5743    2.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028   -4.7433   -1.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0725   -3.6228   -0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1037   -5.5028   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 32  2  0
 32 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 24  1  0
 22 23  2  0
 14 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  1  0
 29 31  1  0
 29 30  2  0
 10  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  7 32  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  1
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  1
 21 52  1  0
 21 53  1  0
 24 54  1  0
 26 55  1  0
 28 56  1  0
 28 57  1  0
 31 58  1  0
  9 40  1  0
  8 39  1  0
  6 38  1  0
  5 37  1  0
  4 36  1  0
M  END


  Mrv1652309112213592D          

 32 33  0  0  1  0            999 V2000
   -2.8658   -7.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4178   -7.1079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2248   -7.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4797   -8.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2867   -8.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8387   -7.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5838   -6.8378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9963   -6.1233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4443   -5.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6906   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9761   -5.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2616   -5.8458    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5472   -5.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327   -5.8458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1182   -5.4333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -6.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -5.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0252   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7397   -5.4333    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7397   -4.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4541   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -5.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4541   -6.6708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8327   -6.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5472   -7.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1182   -7.0833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1182   -7.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -8.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -7.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038   -9.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768   -6.6663    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  4  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 10 32  1  0  0  0  0
  3 32  2  0  0  0  0
  7 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(CSC[C@H](N=C(O)CC[C@H](N)C(O)=O)C(O)=NCC(O)=O)=CNC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H26N4O7S/c1-31-15-4-2-3-13-18(15)11(7-22-13)9-32-10-14(19(28)23-8-17(26)27)24-16(25)6-5-12(21)20(29)30/h2-4,7,12,14,22H,5-6,8-10,21H2,1H3,(H,23,28)(H,24,25)(H,26,27)(H,29,30)/t12-,14-/m0/s1

> <INCHI_KEY>
VQCJUVLBCCMWJY-JSGCOSHPSA-N

> <FORMULA>
C20H26N4O7S

> <MOLECULAR_WEIGHT>
466.51

> <EXACT_MASS>
466.152220367

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.443291827685826

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.3862428942117144

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.4361341178169966

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9737238592720194

> <JCHEM_PKA_STRONGEST_BASIC>
9.5361303925171

> <JCHEM_POLAR_SURFACE_AREA>
190.81999999999996

> <JCHEM_REFRACTIVITY>
117.02079999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.349 -14.412   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.380 -13.268   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.886 -13.588   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.362 -15.053   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.868 -15.373   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.899 -14.229   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.423 -12.764   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0     -11.193 -11.430   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0     -10.163 -10.286   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.756 -10.912   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.422 -10.142   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      -6.088 -10.912   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      -4.755 -10.142   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.421 -10.912   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.087 -10.142   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -0.754 -10.912   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.754 -12.452   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.580 -10.142   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.914 -10.912   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.247 -10.142   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.247  -8.602   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       4.581 -10.912   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.915 -10.142   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.581 -12.452   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.421 -12.452   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.755 -13.222   0.000  0.00  0.00           O+0
HETATM   27  N   UNK     0      -2.087 -13.222   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -2.087 -14.762   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.754 -15.532   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.580 -14.762   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.754 -17.072   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -8.917 -12.444   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   32                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   14   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   10    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
L-GammaGlu-L-cys-(4meoi3m)-gly	ChEBI
S-(4-Methoxyindol-3-ylmethyl)-glutathione	ChEBI

Chemical Formula

C₂₀H₂₆N₄O₇S

Average Mass

466.5100 Da

Monoisotopic Mass

466.15222 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C2C(CSC[C@H](N=C(O)CC[C@H](N)C(O)=O)C(O)=NCC(O)=O)=CNC2=CC=C1

InChI Identifier

InChI=1S/C20H26N4O7S/c1-31-15-4-2-3-13-18(15)11(7-22-13)9-32-10-14(19(28)23-8-17(26)27)24-16(25)6-5-12(21)20(29)30/h2-4,7,12,14,22H,5-6,8-10,21H2,1H3,(H,23,28)(H,24,25)(H,26,27)(H,29,30)/t12-,14-/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:65007 )
tripeptide (CHEBI:65007 )
glutathione derivative (CHEBI:65007 )
S-conjugate (CHEBI:65007 )

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)	1.97	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	190.82 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	117.02 m³·mol⁻¹	ChemAxon
Polarizability	46.44 Å³	ChemAxon
Number of Rings	2	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

28532788

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70678641

PDB ID

Not Available

ChEBI ID

65007

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid (NP0314083)

MOL for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D MOL for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D SDF for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D-SDF for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

PDB for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D PDB for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

SMILES for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

INCHI for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

Structure for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)

3D Structure for NP0314083 ((2s)-2-amino-4-{[(1r)-1-(carboxymethyl-c-hydroxycarbonimidoyl)-2-{[(4-methoxy-1h-indol-3-yl)methyl]sulfanyl}ethyl]-c-hydroxycarbonimidoyl}butanoic acid)