NP-MRD: Showing NP-Card for (2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid (NP0191674)

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Record Information

Version

2.0

Created at

2022-09-04 08:42:39 UTC

Updated at

2022-09-04 08:42:39 UTC

NP-MRD ID

NP0191674

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid

Description

Leupeptin, also known as ac-leu-leu-arg-H or ac-LLR-H, belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Leupeptin 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)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid is found in Apis cerana, Streptomyces lavendulae, Streptomyces roseus and Trypanosoma brucei. (2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid was first documented in 2022 (PMID: 36058890). Based on a literature review a small amount of articles have been published on leupeptin (PMID: 36049162) (PMID: 36006781) (PMID: 35966002) (PMID: 35929479).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042210422D          

 30 29  0  0  1  0            999 V2000
    0.2019    2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    1.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019   -0.0651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3382   -0.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -1.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420   -1.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082   -2.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5521    0.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821   -1.0005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -1.1565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3623   -1.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1724   -2.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   -1.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425   -2.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323   -0.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623    0.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425   -0.6887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.0651    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    0.8704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4931    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0332    1.3381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -0.0651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
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 13 18  1  0  0  0  0
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 21 22  1  0  0  0  0
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 26 27  1  0  0  0  0
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 28 30  1  0  0  0  0
M  END

     RDKit          3D

 68 67  0  0  0  0  0  0  0  0999 V2000
    8.3696    3.1460   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5918    2.3086   -0.1351 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9397    1.2118   -0.2897 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3614    2.1055    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1936    2.9775    1.0057 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6544   -0.1096    0.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6928   -2.6264   -0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1405   -3.9685    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9453   -0.2014    0.7970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3024   -1.5271    1.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0262    0.7829    0.7439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7779    0.8079   -0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2762   -0.4690   -1.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0949   -0.0769   -2.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1255   -1.3073   -1.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5985    2.0991    1.1877 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4369    2.9350    1.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8909    2.7704    1.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9119    4.1807    2.0264 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1791    0.1005    1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9805   -0.6754   -0.7798 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4342    1.1825    0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9640   -0.8704    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6011   -1.3849    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6984   -1.3489   -1.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420   -2.3807   -0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -3.5995   -1.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2392   -2.4963    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296   -3.4928   -1.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8730   -1.7825   -1.3415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2595   -3.4489    1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8314   -4.8060    0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042210422D          

 30 29  0  0  1  0            999 V2000
    0.2019    2.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720    1.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    1.1822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2019   -0.0651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3382   -0.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681   -1.4683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420   -1.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082   -2.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0121   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0922   -1.1565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.6323   -0.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3623    0.2467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4425   -0.6887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9825   -0.0651    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2526    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7927   -0.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1429    0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    0.8704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4931    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0332    1.3381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -0.0651    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0191674

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H38N6O4/c1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23)/t15-,16-,17-/m0/s1

> <INCHI_KEY>
GDBQQVLCIARPGH-ULQDDVLXSA-N

> <FORMULA>
C20H38N6O4

> <MOLECULAR_WEIGHT>
426.562

> <EXACT_MASS>
426.295453728

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.61054378705707

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-N-[(1S)-1-{[(2S)-5-carbamimidamido-1-oxopentan-2-yl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid

> <JCHEM_LOGP>
0.14205696576107324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
4.760262110872671

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9098591633659163

> <JCHEM_PKA_STRONGEST_BASIC>
12.079594693333803

> <JCHEM_POLAR_SURFACE_AREA>
176.74

> <JCHEM_REFRACTIVITY>
125.94859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
leupeptin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.377   3.953   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.881   2.498   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.393   2.207   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -0.127   1.334   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.377  -0.121   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.631  -1.286   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.127  -2.741   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.385  -3.032   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.135  -3.905   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.889  -0.413   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.897   0.752   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       2.393  -1.868   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.906  -2.159   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.410  -3.614   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.922  -3.905   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.930  -2.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.426  -5.360   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.914  -0.995   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.410   0.461   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       6.426  -1.286   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       7.434  -0.121   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.938   2.498   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.946  -0.413   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.954   0.752   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.467   0.461   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      12.475   1.625   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      13.987   1.334   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      14.995   2.498   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0      14.491  -0.121   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   58    0
END

View in JSmol

Synonyms

Value	Source
Ac-L-leu-L-leu-L-arg-H	ChEBI
Ac-leu-leu-arg-H	ChEBI
Ac-leu-leu-argininal	ChEBI
Ac-LLR-H	ChEBI
Acetyl-L-leucyl-L-leucyl-L-argininal	ChEBI
N-Acetyl-L-leucyl-L-leucyl-L-argininal	ChEBI
N-Acetyl-leucylleucylargininal	ChEBI
Leupeptin, (S)-isomer	MeSH
Leupeptin, monoacetate, (S)-isomer	MeSH
Acetyl-L-leucyl-L-leucyl-L-arginal	MeSH

Chemical Formula

C₂₀H₃₈N₆O₄

Average Mass

426.5620 Da

Monoisotopic Mass

426.29545 Da

IUPAC Name

(2S)-N-[(1S)-1-{[(2S)-5-carbamimidamido-1-oxopentan-2-yl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid

Traditional Name

leupeptin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H38N6O4/c1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22/h11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23)/t15-,16-,17-/m0/s1

InChI Key

GDBQQVLCIARPGH-ULQDDVLXSA-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
Apis cerana	LOTUS Database	35616633
Streptomyces lavendulae	LOTUS Database	35616633
Streptomyces roseus	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Guanidine
Carboximidic acid
Carboximidic acid derivative
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Imine
Organic nitrogen compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	0.14	ChemAxon
pKa (Strongest Acidic)	3.91	ChemAxon
pKa (Strongest Basic)	12.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	176.74 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	125.95 m³·mol⁻¹	ChemAxon
Polarizability	47.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

65357

KEGG Compound ID

Not Available

BioCyc ID

LEUPEPTIN

BiGG ID

Not Available

Wikipedia Link

Leupeptin

METLIN ID

Not Available

PubChem Compound

72429

PDB ID

Not Available

ChEBI ID

6426

Good Scents ID

Not Available

References

General References

Lu R, Chen J, Wang F, Wang L, Liu J, Lin Y: Lysosome Inhibition Reduces Basal and Nutrient-Induced Fat Accumulation in Caenorhabditis elegans. Mol Cells. 2022 Sep 30;45(9):649-659. doi: 10.14348/molcells.2022.0073. Epub 2022 Aug 29. [PubMed:36058890 ]
Gurevich M, Iocolano K, Achonu JU, Badalamente MA, Hurst LC, Komatsu DE: Leupeptin accelerates recovery after sciatic transection and repair, but not crush injuries in rats. Neuroreport. 2022 Sep 7;33(13):590-596. doi: 10.1097/WNR.0000000000001821. Epub 2022 Aug 3. [PubMed:36049162 ]
Li JZ, Dong LM, Zheng LL, Fu WL, Zhang JJ, Zhang L, Hu Q, Chen P, Gao ZF, Xia F: Molecular Visual Sensing, Boolean Logic Computing, and Data Security Using a Droplet-Based Superwetting Paradigm. ACS Appl Mater Interfaces. 2022 Sep 7;14(35):40447-40459. doi: 10.1021/acsami.2c11532. Epub 2022 Aug 25. [PubMed:36006781 ]
Ma L, Han Z, Yin H, Tian J, Zhang J, Li N, Ding C, Zhang L: Characterization of Cathepsin B in Mediating Silica Nanoparticle-Induced Macrophage Pyroptosis via an NLRP3-Dependent Manner. J Inflamm Res. 2022 Aug 8;15:4537-4545. doi: 10.2147/JIR.S371536. eCollection 2022. [PubMed:35966002 ]
McCoin CS, Franczak E, Washburn MP, Sardiu ME, Thyfault JP: Acute exercise dynamically modulates the hepatic mitochondrial proteome. Mol Omics. 2022 Oct 31;18(9):840-852. doi: 10.1039/d2mo00143h. [PubMed:35929479 ]
LOTUS database [Link]

Showing NP-Card for (2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid (NP0191674)

MOL for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)

3D MOL for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)

3D SDF for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)

3D-SDF for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)

PDB for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)

3D PDB for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)

SMILES for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)

INCHI for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)

Structure for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)

3D Structure for NP0191674 ((2s)-n-[(1s)-1-{[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-2-[(1-hydroxyethylidene)amino]-4-methylpentanimidic acid)