NP-MRD: Showing NP-Card for Lactacystin (NP0007753)

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Record Information

Version

2.0

Created at

2020-12-09 04:33:00 UTC

Updated at

2021-07-15 16:58:27 UTC

NP-MRD ID

NP0007753

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lactacystin

Provided By

NPAtlas

Description

Lactacystin belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. Lactacystin is found in Streptomyces and Streptomyces lactacystinaeus. Lactacystin was first documented in 1991 (PMID: 1848215). Based on a literature review very few articles have been published on lactacystin (PMID: 34323419) (PMID: 34149689) (PMID: 33775797) (PMID: 33526051) (PMID: 33505626) (PMID: 33268710).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119023D          

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M  END

     RDKit          3D

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  Mrv1652306242119023D          

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 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 21 10  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5 30  1  6  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
 11 33  1  6  0  0  0
 12 34  1  0  0  0  0
 13 35  1  6  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
 14 38  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
 16 42  1  0  0  0  0
 19 43  1  1  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 21 47  1  1  0  0  0
 22 48  1  0  0  0  0
 25 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007753

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]([H])(N([H])C(=O)C([H])([H])[H])C([H])([H])SC(=O)[C@@]1(N([H])C(=O)[C@]([H])(C([H])([H])[H])[C@]1([H])O[H])[C@@]([H])(O[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10+,11+,15-/m1/s1

> <INCHI_KEY>
DAQAKHDKYAWHCG-RWTHQLGUSA-N

> <FORMULA>
C15H24N2O7S

> <MOLECULAR_WEIGHT>
376.42

> <EXACT_MASS>
376.130422295

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.790801052082266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-acetamido-3-[(2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid

> <ALOGPS_LOGP>
-0.66

> <JCHEM_LOGP>
-1.2231128766666677

> <ALOGPS_LOGS>
-1.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.432734173598336

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6402986161239665

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8403632828758094

> <JCHEM_POLAR_SURFACE_AREA>
153.03

> <JCHEM_REFRACTIVITY>
88.03269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lactacystin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 49  0  0  0  0  0  0  0  0999 V2000
    3.9431   -2.5534    0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252   -1.2328    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478   -1.2160   -0.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453   -0.0253    0.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312    1.2468    0.3612 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3532    1.9925    1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8054    1.1011    1.2271 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    0.9120   -0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567    1.3715   -1.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    0.1991   -0.5319 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0448   -1.1934   -0.0415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7598   -1.1582    1.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0580   -2.2186   -0.3469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4349   -1.9979    0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -3.5262    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6265    0.2362   -1.9424 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889    0.8575   -2.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551    0.8219   -3.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891    1.5406   -0.8531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1673    3.0450   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3494    0.9613    0.1881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7755    2.0764    0.8313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6409    2.0951    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926    1.6384    0.8942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778    3.3897   -0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5937   -2.4524    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4902   -3.1708    0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0161   -3.0830    1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0580   -0.0685    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1199    1.1084   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7414    2.1571    2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633    2.9880    0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672   -1.5749   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0855   -1.8438    1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141   -2.4684   -1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9566   -1.2180   -0.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0763   -2.9241    0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4678   -1.8628    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7671   -3.5150    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109   -4.3901   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4837   -3.6596    0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0516   -0.1271   -2.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3531    1.3353   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7941    3.5086   -0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1451    3.5100   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830    3.2709   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8486    0.3913    0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8697    2.0228    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4526    3.7028   -0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
 10  8  1  6
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  5 23  1  0
 23 24  2  0
 23 25  1  0
 21 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  0
  6 32  1  0
 11 33  1  6
 12 34  1  0
 13 35  1  6
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 19 43  1  1
 20 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  1
 22 48  1  0
 25 49  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.943  -2.553   0.809  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.625  -1.233   0.207  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.248  -1.216  -0.991  0.00  0.00           O+0
HETATM    4  N   UNK     0       3.745  -0.025   0.967  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.431   1.247   0.361  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.353   1.992   1.126  0.00  0.00           C+0
HETATM    7  S   UNK     0       0.805   1.101   1.227  0.00  0.00           S+0
HETATM    8  C   UNK     0       0.021   0.912  -0.358  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.557   1.371  -1.331  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.290   0.199  -0.532  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.045  -1.193  -0.042  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.760  -1.158   1.320  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.058  -2.219  -0.347  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.435  -1.998   0.182  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.562  -3.526   0.296  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.627   0.236  -1.942  0.00  0.00           N+0
HETATM   17  C   UNK     0      -2.889   0.858  -2.107  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.555   0.822  -3.170  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.289   1.541  -0.853  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.167   3.045  -0.971  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.349   0.961   0.188  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.776   2.076   0.831  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.641   2.095   0.390  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.693   1.638   0.894  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.678   3.390  -0.117  0.00  0.00           O+0
HETATM   26  H   UNK     0       4.594  -2.452   1.689  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.490  -3.171   0.061  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.016  -3.083   1.151  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.058  -0.069   1.950  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.120   1.108  -0.705  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.741   2.157   2.142  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.263   2.988   0.634  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.067  -1.575  -0.503  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.086  -1.844   1.579  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.114  -2.468  -1.436  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.957  -1.218  -0.390  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.076  -2.924   0.020  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.468  -1.863   1.281  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.767  -3.515   1.379  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.111  -4.390  -0.151  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.484  -3.660   0.138  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.052  -0.127  -2.723  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.353   1.335  -0.591  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.794   3.509  -0.044  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.145   3.510  -1.260  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.483   3.271  -1.836  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.849   0.391   0.969  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.870   2.023   1.797  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.453   3.703  -0.709  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   29                                                  
CONECT    5    4    6   23   30                                             
CONECT    6    5    7   31   32                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16   21                                             
CONECT   11   10   12   13   33                                             
CONECT   12   11   34                                                       
CONECT   13   11   14   15   35                                             
CONECT   14   13   36   37   38                                             
CONECT   15   13   39   40   41                                             
CONECT   16   10   17   42                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   43                                             
CONECT   20   19   44   45   46                                             
CONECT   21   19   22   10   47                                             
CONECT   22   21   48                                                       
CONECT   23    5   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   49                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   14                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   25                                                            
MASTER        0    0    0    0    0    0    0    0   49    0   98    0
END

RDKit          3D

49 49  0  0  0  0  0  0  0  0999 V2000
    3.9431   -2.5534    0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252   -1.2328    0.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478   -1.2160   -0.9908 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7453   -0.0253    0.9665 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312    1.2468    0.3612 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3532    1.9925    1.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8054    1.1011    1.2271 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    0.9120   -0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567    1.3715   -1.3310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2898    0.1991   -0.5319 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0448   -1.1934   -0.0415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7598   -1.1582    1.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0580   -2.2186   -0.3469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4349   -1.9979    0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -3.5262    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6265    0.2362   -1.9424 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889    0.8575   -2.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551    0.8219   -3.1699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891    1.5406   -0.8531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1673    3.0450   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3494    0.9613    0.1881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7755    2.0764    0.8313 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6409    2.0951    0.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6926    1.6384    0.8942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6778    3.3897   -0.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5937   -2.4524    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4902   -3.1708    0.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0161   -3.0830    1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0580   -0.0685    1.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1199    1.1084   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7414    2.1571    2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2633    2.9880    0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672   -1.5749   -0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0855   -1.8438    1.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1141   -2.4684   -1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9566   -1.2180   -0.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0763   -2.9241    0.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4678   -1.8628    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7671   -3.5150    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109   -4.3901   -0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4837   -3.6596    0.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0516   -0.1271   -2.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3531    1.3353   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7941    3.5086   -0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1451    3.5100   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4830    3.2709   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8486    0.3913    0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8697    2.0228    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4526    3.7028   -0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
 10  8  1  6
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  5 23  1  0
 23 24  2  0
 23 25  1  0
 21 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  6
  6 31  1  0
  6 32  1  0
 11 33  1  6
 12 34  1  0
 13 35  1  6
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 19 43  1  1
 20 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  1
 22 48  1  0
 25 49  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄N₂O₇S

Average Mass

376.4200 Da

Monoisotopic Mass

376.13042 Da

IUPAC Name

(2R)-2-acetamido-3-[(2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonylsulfanyl]propanoic acid

Traditional Name

lactacystin

CAS Registry Number

Not Available

SMILES

CC(C)[C@H](O)[C@]1(NC(=O)[C@H](C)[C@@H]1O)C(=O)SC[C@H](NC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10+,11+,15-/m1/s1

InChI Key

DAQAKHDKYAWHCG-RWTHQLGUSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Streptomyces	NPAtlas	1848215
Streptomyces lactacystinaeus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces sp. OM-6519	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cysteine or derivatives
Pyrrolidine carboxylic acid or derivatives
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Pyrrolidone
Fatty acyl
Fatty acid
2-pyrrolidone
Pyrrolidine
Acetamide
Carboxamide group
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Thiocarboxylic acid ester
Carbothioic s-ester
Organoheterocyclic compound
Azacycle
Carboxylic acid
Sulfenyl compound
Thiocarboxylic acid or derivatives
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organosulfur compound
Alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

lactam (CHEBI:52722 )
S-substituted L-cysteine (CHEBI:52722 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.66	ALOGPS
logP	-1.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.03 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	88.03 m³·mol⁻¹	ChemAxon
Polarizability	36.79 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA020681

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00017067

Chemspider ID

5042546

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lactacystin

METLIN ID

Not Available

PubChem Compound

6610292

PDB ID

Not Available

ChEBI ID

52722

Good Scents ID

Not Available

References

General References

Omura S, Fujimoto T, Otoguro K, Matsuzaki K, Moriguchi R, Tanaka H, Sasaki Y: Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells. J Antibiot (Tokyo). 1991 Jan;44(1):113-6. doi: 10.7164/antibiotics.44.113. [PubMed:1848215 ]
Zhang SY, Fan Q, Moktefi A, Ory V, Audard V, Pawlak A, Ollero M, Sahali D, Henique C: CMIP interacts with WT1 and targets it on the proteasome degradation pathway. Clin Transl Med. 2021 Jul;11(7):e460. doi: 10.1002/ctm2.460. [PubMed:34323419 ]
Holmen Olofsson G, Idorn M, Carnaz Simoes AM, Aehnlich P, Skadborg SK, Noessner E, Debets R, Moser B, Met O, Thor Straten P: Vgamma9Vdelta2 T Cells Concurrently Kill Cancer Cells and Cross-Present Tumor Antigens. Front Immunol. 2021 Jun 2;12:645131. doi: 10.3389/fimmu.2021.645131. eCollection 2021. [PubMed:34149689 ]
Leskela S, Huber N, Hoffmann D, Rostalski H, Remes AM, Takalo M, Hiltunen M, Haapasalo A: Expression of C9orf72 hexanucleotide repeat expansion leads to formation of RNA foci and dipeptide repeat proteins but does not influence autophagy or proteasomal function in neuronal cells. Biochim Biophys Acta Mol Cell Res. 2021 Jun;1868(7):119021. doi: 10.1016/j.bbamcr.2021.119021. Epub 2021 Mar 26. [PubMed:33775797 ]
Wang A, Liu J, Yang Y, Chen Z, Gao C, Wang Z, Fu C, Zou L, Wang S: Shikonin promotes ubiquitination and degradation of cIAP1/2-mediated apoptosis and necrosis in triple negative breast cancer cells. Chin Med. 2021 Feb 1;16(1):16. doi: 10.1186/s13020-021-00426-1. [PubMed:33526051 ]
Chiu CT, Lin CY, Yen CY, Tsai MT, Chang HC, Liu YC, Lin MH: Mechanistic and compositional studies of the autophagy-inducing areca nut ingredient. J Dent Sci. 2020 Dec;15(4):526-535. doi: 10.1016/j.jds.2020.05.007. Epub 2020 Jun 5. [PubMed:33505626 ]
Maki A, Lin Y, Aoyama M, Sato K, Gao JQ, Tsujino H, Nagano K, Higashisaka K, Tsutsumi Y: Silver Nanoparticles Induce DNA Hypomethylation through Proteasome-Mediated Degradation of DNA Methyltransferase 1. Biol Pharm Bull. 2020;43(12):1924-1930. doi: 10.1248/bpb.b20-00631. [PubMed:33268710 ]
Ekimova IV, Guzeev MA, Simonova VV, Pastukhov YF: [Age-related differences in sleep disturbances in rat models of preclinical Parkinson's disease]. Zh Nevrol Psikhiatr Im S S Korsakova. 2020;120(9. Vyp. 2):26-33. doi: 10.17116/jnevro202012009226. [PubMed:33076642 ]
Schneider SM, Lee BH, Nicola AV: Viral entry and the ubiquitin-proteasome system. Cell Microbiol. 2021 Feb;23(2):e13276. doi: 10.1111/cmi.13276. Epub 2020 Oct 26. [PubMed:33037857 ]

Showing NP-Card for Lactacystin (NP0007753)

MOL for NP0007753 (Lactacystin)

3D MOL for NP0007753 (Lactacystin)

3D SDF for NP0007753 (Lactacystin)

3D-SDF for NP0007753 (Lactacystin)

PDB for NP0007753 (Lactacystin)

3D PDB for NP0007753 (Lactacystin)

SMILES for NP0007753 (Lactacystin)

INCHI for NP0007753 (Lactacystin)

Structure for NP0007753 (Lactacystin)

3D Structure for NP0007753 (Lactacystin)