NP-MRD: Showing NP-Card for (2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid (NP0259151)

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Record Information

Version

2.0

Created at

2022-09-08 00:55:17 UTC

Updated at

2022-09-08 00:55:17 UTC

NP-MRD ID

NP0259151

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid

Description

Nocardicin C, also known as FR-29038, 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. Nocardicin C is a very strong basic compound (based on its pKa). (2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid is found in Apis cerana. (2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid was first documented in 2004 (PMID: 15252031). A monobactam that is produced by Nocardia uniformis subsp (PMID: 15629944).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306032018052D          

 35 37  0  0  1  0            999 V2000
    1.9702    0.4704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9710   -0.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -0.3456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7849    0.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932   -0.9362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567    1.1866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8465    0.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299    1.1812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5865    0.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -0.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299    2.0084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4747   -0.7658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1892   -0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9036   -0.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743   -1.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499   -2.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1790   -1.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180   -0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180    0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9036    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3239    0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009    1.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155    0.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155   -0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009   -0.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5865   -0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392   -0.4770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4537   -0.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682   -0.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8825   -0.0644    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5971   -0.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8825    0.7605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3239   -0.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5971   -1.3017    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
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  1  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  1  1  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 13 21  2  0  0  0  0
 19 22  1  0  0  0  0
  9 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  9 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  6  0  0  0
 32 34  1  0  0  0  0
 32 35  2  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
   -7.8812    1.6103   -2.7143 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0447    2.1484   -1.6168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1048    1.1491   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2480    1.6935    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9439    1.8650    0.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0546    0.8938   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2366   -0.4671   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2511   -1.3791   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238   -0.9457   -0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564   -1.9162   -1.2784 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3201   -1.5556   -2.5028 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151   -1.9877   -0.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4024   -2.2750    1.0146 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430   -1.7122   -0.4080 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -1.7728    0.6858 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4474   -2.6633    0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090   -1.4576    0.2073 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5455   -1.1660   -0.2957 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4960   -0.1465   -1.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5097    0.1280   -2.0427 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2996    0.5068   -1.5941 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3436   -0.6583    0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3072   -1.3656    2.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0165   -0.9546    3.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8008    0.1819    3.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5245    0.6107    4.2433 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8454    0.8853    1.9511 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1232    0.4665    0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2191   -0.6182    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950    0.5707    1.1992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8053    0.4133   -0.9176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7797    1.2980   -0.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6546    3.4100   -1.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8133    3.7363   -1.5829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0242    4.2752   -0.2916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8676    1.9099   -2.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8584    0.5554   -2.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0106    2.2747   -1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1729    1.0610   -0.1116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7791    0.1622   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6807    2.5945    1.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2998    0.9129    1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1915   -0.8615    0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4290   -2.4436   -0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4693   -2.9055   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0059   -1.0888   -3.1451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1558   -2.3520   -2.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7139   -1.4682   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514   -2.0208    1.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951   -3.3534    1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3267   -3.2058   -0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0401   -2.0901   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    1.4719   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6973   -2.2500    2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9883   -1.5049    4.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0680    1.2577    4.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4478    1.7933    1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1757    1.0475   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8173    0.7522   -1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5986    2.3678   -0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0554    4.5823   -0.4540 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 31  1  0
 31 32  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
 18 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 17 29  1  0
 29 30  2  0
  2 33  1  0
 33 35  1  0
 33 34  2  0
 32  6  1  0
 29 15  1  0
 28 22  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  6
  3 39  1  0
  3 40  1  0
  4 41  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  0
 31 59  1  0
 32 60  1  0
 10 45  1  6
 11 46  1  0
 11 47  1  0
 14 48  1  0
 15 49  1  1
 16 50  1  0
 16 51  1  0
 18 52  1  6
 21 53  1  0
 23 54  1  0
 24 55  1  0
 26 56  1  0
 27 57  1  0
 28 58  1  0
 35 61  1  0
M  END


  Mrv1652306032018052D          

 35 37  0  0  1  0            999 V2000
    1.9702    0.4704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9710   -0.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486   -0.3456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7849    0.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932   -0.9362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567    1.1866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8465    0.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299    1.1812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5865    0.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8505   -0.0597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1299    2.0084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4747   -0.7658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1892   -0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9036   -0.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743   -1.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499   -2.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1790   -1.9980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180   -0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180    0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9036    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892    0.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3239    0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009    1.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155    0.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155   -0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3009   -0.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5865   -0.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7392   -0.4770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4537   -0.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1682   -0.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8825   -0.0644    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5971   -0.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8825    0.7605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3239   -0.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5971   -1.3017    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
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  1  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 11  1  1  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 13 21  2  0  0  0  0
 19 22  1  0  0  0  0
  9 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  9 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  6  0  0  0
 32 34  1  0  0  0  0
 32 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0259151

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@H](CCOC1=CC=C(C=C1)[C@@H](N)C(=O)N[C@H]1CN([C@@H](C(O)=O)C2=CC=C(O)C=C2)C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N4O8/c24-16(22(31)32)9-10-35-15-7-3-12(4-8-15)18(25)20(29)26-17-11-27(21(17)30)19(23(33)34)13-1-5-14(28)6-2-13/h1-8,16-19,28H,9-11,24-25H2,(H,26,29)(H,31,32)(H,33,34)/t16-,17+,18-,19-/m1/s1

> <INCHI_KEY>
CWTCWGGPTVMMLT-FCGDIQPGSA-N

> <FORMULA>
C23H26N4O8

> <MOLECULAR_WEIGHT>
486.481

> <EXACT_MASS>
486.175063813

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.43899176127332

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-4-{4-[(R)-amino({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl})methyl]phenoxy}butanoic acid

> <ALOGPS_LOGP>
-2.18

> <JCHEM_LOGP>
-5.255286655734564

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.0823872776641315

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8655122069837935

> <JCHEM_PKA_STRONGEST_BASIC>
9.061062047196714

> <JCHEM_POLAR_SURFACE_AREA>
205.51

> <JCHEM_REFRACTIVITY>
120.08840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-amino-4-{4-[(R)-amino({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl})methyl]phenoxy}butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-20         0                                  
HETATM    1  C   UNK     0       3.678   0.878   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.679  -0.655   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.131  -0.645   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.198   0.883   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.601  -1.748   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       2.906   2.215   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.580   1.433   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.243   2.205   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.095   1.433   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.588  -0.111   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       0.243   3.749   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.486  -1.429   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.820  -0.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.153  -1.429   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.485  -2.969   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.133  -3.749   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.801  -3.730   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.487  -0.659   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.487   0.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.153   1.651   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.820   0.880   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.805   1.641   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.428   2.203   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.762   1.433   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.762  -0.107   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.428  -0.877   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.095  -0.107   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.113  -0.890   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.447  -0.120   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.781  -0.890   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -9.114  -0.120   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.448  -0.890   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      -9.114   1.420   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0     -11.805  -0.107   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -10.448  -2.430   0.000  0.00  0.00           O+0
CONECT    1    2    4    6                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    1                                                       
CONECT    5    2                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   23   27                                                  
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    3   13   15                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13   18                                                       
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   13                                                       
CONECT   22   19                                                            
CONECT   23    9   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26    9                                                       
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31   34   35                                                  
CONECT   33   31                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
(-)-Nocardicin C	ChEBI
Antibiotic FR 29038	ChEBI
FR-29038	ChEBI

Chemical Formula

C₂₃H₂₆N₄O₈

Average Mass

486.4810 Da

Monoisotopic Mass

486.17506 Da

IUPAC Name

(2R)-2-amino-4-{4-[(R)-amino({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl})methyl]phenoxy}butanoic acid

Traditional Name

(2R)-2-amino-4-{4-[(R)-amino({[(3S)-1-[(R)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl})methyl]phenoxy}butanoic acid

CAS Registry Number

Not Available

SMILES

N[C@H](CCOC1=CC=C(C=C1)[C@@H](N)C(=O)N[C@H]1CN([C@@H](C(O)=O)C2=CC=C(O)C=C2)C1=O)C(O)=O

InChI Identifier

InChI=1S/C23H26N4O8/c24-16(22(31)32)9-10-35-15-7-3-12(4-8-15)18(25)20(29)26-17-11-27(21(17)30)19(23(33)34)13-1-5-14(28)6-2-13/h1-8,16-19,28H,9-11,24-25H2,(H,26,29)(H,31,32)(H,33,34)/t16-,17+,18-,19-/m1/s1

InChI Key

CWTCWGGPTVMMLT-FCGDIQPGSA-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

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
Monobactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Phenylacetamide
Phenoxy compound
Phenol ether
Phenol
Alkyl aryl ether
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
Beta-lactam
Tertiary carboxylic acid amide
Amino acid
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Azetidine
Organoheterocyclic compound
Carboxylic acid
Azacycle
Ether
Organic nitrogen compound
Primary aliphatic amine
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monobactam (CHEBI:81021 )

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	-2.2	ALOGPS
logP	-5.3	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	205.51 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	120.09 m³·mol⁻¹	ChemAxon
Polarizability	49.44 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

30791686

KEGG Compound ID

C17351

BioCyc ID

CPD-9415

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13770100

PDB ID

Not Available

ChEBI ID

81021

Good Scents ID

Not Available

References

General References

Kelly WL, Townsend CA: Mutational analysis of nocK and nocL in the nocardicin a producer Nocardia uniformis. J Bacteriol. 2005 Jan;187(2):739-46. doi: 10.1128/JB.187.2.739-746.2005. [PubMed:15629944 ]
Kelly WL, Townsend CA: Mutational analysis and characterization of nocardicin C-9' epimerase. J Biol Chem. 2004 Sep 10;279(37):38220-7. doi: 10.1074/jbc.M405450200. Epub 2004 Jul 13. [PubMed:15252031 ]
LOTUS database [Link]

Showing NP-Card for (2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid (NP0259151)

MOL for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)

3D MOL for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)

3D SDF for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)

3D-SDF for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)

PDB for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)

3D PDB for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)

SMILES for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)

INCHI for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)

Structure for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)

3D Structure for NP0259151 ((2r)-2-amino-4-{4-[(r)-amino({[(3s)-1-[(r)-carboxy(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]-c-hydroxycarbonimidoyl})methyl]phenoxy}butanoic acid)