NP-MRD: Showing NP-Card for 2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid (NP0176245)

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Record Information

Version

2.0

Created at

2022-09-03 13:52:18 UTC

Updated at

2022-09-03 13:52:18 UTC

NP-MRD ID

NP0176245

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

2-Amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-C-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid belongs to the class of organic compounds known as monobactams. Monobactams are compounds comprising beta-lactam ring is alone and not fused to another ring. 2-Amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-C-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161502432D          

 37 39  0  0  0  0            999 V2000
    6.0117   -5.9459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117   -6.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972   -7.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828   -6.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683   -7.1834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538   -6.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394   -7.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -6.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394   -5.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538   -5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104   -5.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104   -4.7084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -4.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2959   -5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2959   -6.7709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185   -5.5334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1330   -5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465   -6.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -5.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.4667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299   -5.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424   -5.0179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262   -7.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4407   -6.7709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262   -8.0084    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
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 18 33  1  0  0  0  0
 33 34  2  0  0  0  0
  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END

     RDKit          3D

 60 62  0  0  0  0  0  0  0  0999 V2000
    7.8248   -3.4512   -0.7012 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4863   -2.1779   -1.3711 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9733   -2.0223   -1.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434   -0.7969   -1.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0784   -0.6836   -1.7502 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -0.4548   -0.6846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7565   -0.2124    0.5719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9432    0.0160    1.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5505    0.0125    1.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7752    0.1853    2.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -0.0853    3.8877 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452   -0.5238    4.3033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5721    0.6943    2.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1112    0.7319    3.9499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3295    1.1410    1.6843 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7107    1.6066    1.9655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3832    2.2984    0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4482    1.3406    0.9723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8299    1.2487    0.6166 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6458    2.4273    0.8019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8931    2.3541    0.5934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1319    3.6774    1.2072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9026    0.8187   -0.8258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1620    1.3601   -1.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2815    0.8751   -3.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1323   -0.1443   -3.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2507   -0.6276   -4.7705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8877   -0.7023   -2.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9802   -2.0091   -2.8558 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.7582   -0.2090   -1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6376    0.4371    1.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6073   -0.7342    2.1237 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.2313    0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -0.4608   -0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1417   -1.1307   -0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1437    0.0746   -0.8815 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7548   -1.4304    0.6974 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4175   -4.2496   -1.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4059   -3.5132    0.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8472   -2.1626   -2.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7644   -2.0125   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4687   -2.9289   -1.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7039   -0.7258   -2.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8968    0.0836   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8331   -0.1798    0.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3984    0.2229    2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6707   -1.5179    4.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    1.2283    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7834    1.9844    2.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420    3.3417    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7938    2.2899   -0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3182    0.3626    1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9694    4.3939    0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4986    2.1612   -1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6732    1.3321   -3.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7094   -0.2477   -5.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
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  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 33  1  0
 33 34  2  0
  9 10  1  0
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 11 12  1  0
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 13 15  1  0
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 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
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 23 24  2  0
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 28 29  1  0
 28 30  2  0
 18 31  1  0
 31 32  2  0
  2 35  1  0
 35 37  1  0
 35 36  2  0
 34  6  1  0
 31 16  1  0
 30 23  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  6
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  7 45  1  0
  8 46  1  0
 33 58  1  0
 34 59  1  0
 12 47  1  0
 15 48  1  0
 16 49  1  1
 17 50  1  0
 17 51  1  0
 19 52  1  1
 22 53  1  0
 24 54  1  0
 25 55  1  0
 27 56  1  0
 30 57  1  0
 37 60  1  0
M  END


  Mrv1533004161502432D          

 37 39  0  0  0  0            999 V2000
    6.0117   -5.9459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117   -6.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972   -7.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828   -6.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683   -7.1834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538   -6.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394   -7.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -6.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394   -5.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1538   -5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104   -5.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0104   -4.7084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -4.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2959   -5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2959   -6.7709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185   -5.5334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1330   -5.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465   -6.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.5292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -6.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5724   -8.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7158   -5.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.4667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3424   -5.0179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262   -7.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4407   -6.7709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7262   -8.0084    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 25 32  1  0  0  0  0
 20 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  2  0  0  0  0
  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0176245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCOC1=CC=C(C=C1)C(=NO)C(=O)NC1CN(C(C(O)=O)C2=CC=C(O)C(Cl)=C2)C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H23ClN4O9/c24-14-9-12(3-6-17(14)29)19(23(34)35)28-10-16(21(28)31)26-20(30)18(27-36)11-1-4-13(5-2-11)37-8-7-15(25)22(32)33/h1-6,9,15-16,19,29,36H,7-8,10,25H2,(H,26,30)(H,32,33)(H,34,35)

> <INCHI_KEY>
UMDAIHWMUXNVSB-UHFFFAOYSA-N

> <FORMULA>
C23H23ClN4O9

> <MOLECULAR_WEIGHT>
534.91

> <EXACT_MASS>
534.115356

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
52.06725029467678

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-1.8525327821466426

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.08770220659603

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.741656543601005

> <JCHEM_PKA_STRONGEST_BASIC>
9.278320444042217

> <JCHEM_POLAR_SURFACE_AREA>
212.07999999999996

> <JCHEM_REFRACTIVITY>
126.60929999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.90e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  N   UNK     0      11.222 -11.099   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      11.222 -12.639   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.888 -13.409   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.555 -12.639   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.221 -13.409   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.887 -12.639   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.553 -13.409   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.220 -12.639   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.220 -11.099   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.553 -10.329   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.887 -11.099   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.886 -10.329   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.886  -8.789   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       3.220  -8.019   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.552 -11.099   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.552 -12.639   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -0.781 -10.329   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.115 -11.099   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.514 -12.586   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -4.001 -12.188   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -5.335 -12.958   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335 -14.498   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.668 -15.268   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.001 -15.268   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.668 -12.188   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.002 -12.958   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.336 -12.188   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.336 -10.648   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -10.669  -9.878   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -8.002  -9.878   0.000  0.00  0.00           C+0
HETATM   31 Cl   UNK     0      -8.002  -8.338   0.000  0.00  0.00          Cl+0
HETATM   32  C   UNK     0      -6.668 -10.648   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.602 -10.700   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.372  -9.367   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.556 -13.409   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      13.889 -12.639   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      12.556 -14.949   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25                                                       
CONECT   33   20   18   34                                                  
CONECT   34   33                                                            
CONECT   35    2   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-C-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoate	Generator

Chemical Formula

C₂₃H₂₃ClN₄O₉

Average Mass

534.9100 Da

Monoisotopic Mass

534.11536 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

NC(CCOC1=CC=C(C=C1)C(=NO)C(=O)NC1CN(C(C(O)=O)C2=CC=C(O)C(Cl)=C2)C1=O)C(O)=O

InChI Identifier

InChI=1S/C23H23ClN4O9/c24-14-9-12(3-6-17(14)29)19(23(34)35)28-10-16(21(28)31)26-20(30)18(27-36)11-1-4-13(5-2-11)37-8-7-15(25)22(32)33/h1-6,9,15-16,19,29,36H,7-8,10,25H2,(H,26,30)(H,32,33)(H,34,35)

InChI Key

UMDAIHWMUXNVSB-UHFFFAOYSA-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 monobactams. Monobactams are compounds comprising beta-lactam ring is alone and not fused to another ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Monobactams

Alternative Parents

Substituents

Monobactam
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
2-chlorophenol
Phenoxy compound
Phenol ether
2-halophenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Halobenzene
Chlorobenzene
Monocyclic benzene moiety
Aryl halide
Benzenoid
Dicarboxylic acid or derivatives
Aryl chloride
Tertiary carboxylic acid amide
Ketoxime
Amino acid or derivatives
Amino acid
Azetidine
Carboxamide group
Azacycle
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Organic oxide
Organohalogen compound
Carbonyl group
Organochloride
Organic oxygen compound
Primary aliphatic amine
Amine
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	0.17	ALOGPS
logP	-1.9	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	9.28	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	212.08 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	126.61 m³·mol⁻¹	ChemAxon
Polarizability	52.07 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

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

85038827

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid (NP0176245)

MOL for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)

3D MOL for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)

3D SDF for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)

3D-SDF for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)

PDB for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)

3D PDB for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)

SMILES for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)

INCHI for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)

Structure for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)

3D Structure for NP0176245 (2-amino-4-{4-[({1-[carboxy(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl}-c-hydroxycarbonimidoyl)(hydroxyimino)methyl]phenoxy}butanoic acid)