NP-MRD: Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid (NP0197795)

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Record Information

Version

2.0

Created at

2022-09-04 16:07:21 UTC

Updated at

2022-09-04 16:07:22 UTC

NP-MRD ID

NP0197795

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid

Description

Belactosin A 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. (2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid was first documented in 2014 (PMID: 24814885). Based on a literature review a small amount of articles have been published on belactosin A (PMID: 34990553) (PMID: 24524217) (PMID: 24452398) (PMID: 24321833).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042218072D          

 26 27  0  0  1  0            999 V2000
    1.1940    5.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190    5.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4315    5.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190    4.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2565    5.2372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8399    5.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399    6.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    5.2372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399    4.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399    3.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5544    3.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1254    3.4163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1254    2.5913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5379    1.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7129    1.8768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9984    1.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984    0.6393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7129    0.2268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7129   -0.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984   -1.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4274   -1.0107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1419   -0.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4274   -1.8357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840    0.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -0.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695    0.6393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  6  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
   -6.1289   -1.9368    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5586   -1.1535   -0.7869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2704    0.2822   -0.3808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5747    0.9461    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416    0.2965    0.6719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3938    1.4718    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3062    2.7044    0.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4509    0.5425    1.4279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9082   -0.2877    0.2908 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3459    0.2272   -0.9582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0492    0.2276   -2.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597    0.7074   -1.0209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3292    0.7563    0.1432 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0381   -0.5859    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0741    0.2592    0.0892 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0376    0.9302    1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4416    0.3707    0.9185 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8716    0.5896   -0.4380 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0962    0.4810   -0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4846    0.6967   -2.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1110    0.1302    0.2587 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0971    1.2838    0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8802   -1.0375   -0.1388 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -1.0575    1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899   -1.8805    0.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1480   -1.5336    2.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7701   -2.7444   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2990   -2.4345    0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6466   -1.2900    1.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038   -1.6294   -1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2262   -1.1464   -1.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0079    0.8394   -1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4542    0.4559   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5934    2.0222   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6014    0.8871    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5999   -0.1337    1.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7643   -1.3561    0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8882   -0.5212   -2.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    1.6320    0.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0487   -0.6409    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411   -1.5047    0.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5248   -0.0767   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822    2.0129    0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7045    0.8617    2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412    0.9553    1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1694    0.1272   -2.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7324   -0.0462    1.2680 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6251    1.3327    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8519    1.2410   -0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5683    2.2715    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8923   -0.8839   -0.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5438   -1.3506   -1.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5682   -2.3104    2.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 17 24  1  0
 24 26  1  0
 24 25  2  0
  6  5  1  0
 15 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  6
  4 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  1
  9 37  1  1
 11 38  1  0
 13 39  1  1
 14 40  1  0
 14 41  1  0
 15 42  1  6
 16 43  1  0
 16 44  1  0
 17 45  1  1
 20 46  1  0
 21 47  1  1
 22 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 26 53  1  0
M  END


  Mrv1652309042218072D          

 26 27  0  0  1  0            999 V2000
    1.1940    5.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190    5.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4315    5.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190    4.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2565    5.2372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8399    5.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399    6.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4233    5.2372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399    4.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8399    3.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5544    3.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1254    3.4163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1254    2.5913    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5379    1.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7129    1.8768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9984    1.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984    0.6393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7129    0.2268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7129   -0.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984   -1.0107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4274   -1.0107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1419   -0.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4274   -1.8357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840    0.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -0.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695    0.6393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  3  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  6  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197795

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)[C@H]1C(OC1=O)C(O)=N[C@H]1C[C@@H]1C[C@H](N=C(O)[C@H](C)N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H27N3O6/c1-4-7(2)12-13(26-17(12)25)15(22)19-10-5-9(10)6-11(16(23)24)20-14(21)8(3)18/h7-13H,4-6,18H2,1-3H3,(H,19,22)(H,20,21)(H,23,24)/t7?,8-,9+,10-,11-,12-,13?/m0/s1

> <INCHI_KEY>
ZSYIAUXMQLVKIL-AYWHVKGUSA-N

> <FORMULA>
C17H27N3O6

> <MOLECULAR_WEIGHT>
369.418

> <EXACT_MASS>
369.189985601

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.00916551526174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-3-[(1R,2S)-2-({[(3S)-3-(butan-2-yl)-4-oxooxetan-2-yl](hydroxy)methylidene}amino)cyclopropyl]propanoic acid

> <JCHEM_LOGP>
-3.969943878377821

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.289084513152159

> <JCHEM_PKA_STRONGEST_ACIDIC>
-5.160645751130706

> <JCHEM_PKA_STRONGEST_BASIC>
11.620774494581166

> <JCHEM_POLAR_SURFACE_AREA>
154.79999999999998

> <JCHEM_REFRACTIVITY>
90.46770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-3-[(1R,2S)-2-({hydroxy[(3S)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid

> <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       2.229  11.110   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.769  11.110   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.539   9.776   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.769   8.442   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.079   9.776   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.168  10.865   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.168  12.405   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.257   9.776   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.168   8.687   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.168   7.147   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.501   6.377   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       5.834   6.377   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.834   4.837   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.604   3.503   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.064   3.503   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.730   2.733   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.730   1.193   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.064   0.423   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.064  -1.117   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.730  -1.887   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.398  -1.887   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.731  -1.117   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       6.398  -3.427   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       2.397   0.423   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.397  -1.117   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.063   1.193   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₇N₃O₆

Average Mass

369.4180 Da

Monoisotopic Mass

369.18999 Da

IUPAC Name

(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-3-[(1R,2S)-2-({[(3S)-3-(butan-2-yl)-4-oxooxetan-2-yl](hydroxy)methylidene}amino)cyclopropyl]propanoic acid

Traditional Name

(2S)-2-{[(2S)-2-amino-1-hydroxypropylidene]amino}-3-[(1R,2S)-2-({hydroxy[(3S)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)[C@H]1C(OC1=O)C(O)=N[C@H]1C[C@@H]1C[C@H](N=C(O)[C@H](C)N)C(O)=O

InChI Identifier

InChI=1S/C17H27N3O6/c1-4-7(2)12-13(26-17(12)25)15(22)19-10-5-9(10)6-11(16(23)24)20-14(21)8(3)18/h7-13H,4-6,18H2,1-3H3,(H,19,22)(H,20,21)(H,23,24)/t7?,8-,9+,10-,11-,12-,13?/m0/s1

InChI Key

ZSYIAUXMQLVKIL-AYWHVKGUSA-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

Not Available

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
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alanine or derivatives
Alpha-amino acid or derivatives
Carbocyclic fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Beta_propiolactone
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Amino acid
Lactone
Oxetane
Secondary carboxylic acid amide
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Primary aliphatic amine
Amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Primary amine
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-4	ChemAxon
pKa (Strongest Acidic)	-5.2	ChemAxon
pKa (Strongest Basic)	11.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	154.8 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	90.47 m³·mol⁻¹	ChemAxon
Polarizability	38.01 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

C00015484

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101011058

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Engelbrecht A, Wolf F, Esch A, Kulik A, Kozhushkov SI, de Meijere A, Hughes CC, Kaysser L: Discovery of a Cryptic Nitro Intermediate in the Biosynthesis of the 3-(trans-2'-Aminocyclopropyl)alanine Moiety of Belactosin A. Org Lett. 2022 Jan 21;24(2):736-740. doi: 10.1021/acs.orglett.1c04205. Epub 2022 Jan 6. [PubMed:34990553 ]
Kawamura S, Unno Y, Asai A, Arisawa M, Shuto S: Development of a new class of proteasome inhibitors with an epoxyketone warhead: Rational hybridization of non-peptidic belactosin derivatives and peptide epoxyketones. Bioorg Med Chem. 2014 Jun 15;22(12):3091-5. doi: 10.1016/j.bmc.2014.04.032. Epub 2014 Apr 24. [PubMed:24814885 ]
Kawamura S, Unno Y, Asai A, Arisawa M, Shuto S: Structurally novel highly potent proteasome inhibitors created by the structure-based hybridization of nonpeptidic belactosin derivatives and peptide boronates. J Med Chem. 2014 Mar 27;57(6):2726-35. doi: 10.1021/jm500045x. Epub 2014 Feb 25. [PubMed:24524217 ]
Kawamura S, Unno Y, Hirokawa T, Asai A, Arisawa M, Shuto S: Rational hopping of a peptidic scaffold into non-peptidic scaffolds: structurally novel potent proteasome inhibitors derived from a natural product, belactosin A. Chem Commun (Camb). 2014 Mar 7;50(19):2445-7. doi: 10.1039/c3cc48818g. Epub 2014 Jan 22. [PubMed:24452398 ]
Hasegawa M, Yasuda Y, Tanaka M, Nakata K, Umeda E, Wang Y, Watanabe C, Uetake S, Kunoh T, Shionyu M, Sasaki R, Shiina I, Mizukami T: A novel tamoxifen derivative, ridaifen-F, is a nonpeptidic small-molecule proteasome inhibitor. Eur J Med Chem. 2014 Jan;71:290-305. doi: 10.1016/j.ejmech.2013.11.009. Epub 2013 Nov 16. [PubMed:24321833 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid (NP0197795)

MOL for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)

3D MOL for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)

3D SDF for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)

3D-SDF for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)

PDB for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)

3D PDB for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)

SMILES for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)

INCHI for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)

Structure for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)

3D Structure for NP0197795 ((2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-[(1r,2s)-2-({hydroxy[(3s)-4-oxo-3-(sec-butyl)oxetan-2-yl]methylidene}amino)cyclopropyl]propanoic acid)