NP-MRD: Showing NP-Card for (2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0203762)

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Record Information

Version

2.0

Created at

2022-09-04 23:17:36 UTC

Updated at

2022-09-04 23:17:37 UTC

NP-MRD ID

NP0203762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Description

Azlocillin, also known as baye 6905 or securopen, 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. Azlocillin is a drug which is used for the treatment of infections caused by pseudomonas aeruginosa, escherichia coli, and haemophilus influenzae. (2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is found in Apis cerana. (2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid was first documented in 1982 (PMID: 6212725). Azlocillin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 10090000) (PMID: 11036013) (PMID: 19292999) (PMID: 20363776) (PMID: 21219695) (PMID: 21360610).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04191212162D          

 34 37  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7530   -3.1424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2380   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7530   -1.8076    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9567   -2.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9567   -2.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0080   -3.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8149   -4.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -4.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600   -3.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4130   -2.4749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9280   -1.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9281   -3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829   -1.0229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
 22  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  1  1  0  0  0  0
  5  6  2  0  0  0  0
  4  3  2  0  0  0  0
  2  3  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10  7  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  7 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  0  0  0  0
 23 24  1  0  0  0  0
 24 31  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  2  0  0  0  0
  8 26  2  0  0  0  0
 10 27  1  6  0  0  0
 22 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 30 34  2  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    3.6821    3.1666    1.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3658    2.0557    0.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6388    2.5009    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123    1.3160   -0.2329 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142   -0.3337    0.5626 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7919   -0.7864    1.0122 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6059   -0.1254    0.6015 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548   -0.8667    0.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4523   -2.1148    0.3410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164   -0.2582   -0.1824 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7990   -1.3465   -0.3779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0330   -1.3534    0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3802   -0.4207    1.0755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9553   -2.4068    0.0701 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7979   -3.5731   -0.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5622   -4.6351   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6117   -3.9300    0.6297 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2606   -2.5538    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9160   -1.5643    1.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7217    0.4131   -1.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8050    1.8031   -1.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7215    2.4664   -2.7112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5564    1.7458   -3.8976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4783    0.3695   -3.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5599   -0.3055   -2.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2189   -0.5739    2.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909   -0.9064    3.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3608    0.0995    1.9205 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466    0.9111    1.9502 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7191    0.0753    1.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5714   -1.1689    1.5616 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0134    0.5735    1.5510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5950    2.9646    1.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8967    4.1638    1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0112    3.1536    2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042    3.4883   -0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313    1.7892   -0.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4321    2.7534    1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8025   -1.0694    0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -1.8999    0.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5780    0.9376    0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2706    0.4226    0.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5498   -2.1220   -1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2610   -3.3398   -1.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7373   -3.8523   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527   -5.1564    0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9811   -5.3303   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4864   -4.3144    1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9350    2.3867   -0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7775    3.5307   -2.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875    2.2308   -4.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3486   -0.2522   -4.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -1.3782   -2.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6949    1.3504    2.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6040    0.4127    0.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 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  2  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 32  1  0
 30 31  2  0
 29  2  1  0
  2  1  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
 10 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 14  1  0
  5  6  1  0
 25 20  1  0
  5 28  1  0
 10 42  1  1
 11 43  1  0
 15 44  1  0
 15 45  1  0
 16 46  1  0
 16 47  1  0
 17 48  1  0
  7 41  1  0
  6 40  1  1
 29 54  1  1
 32 55  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  5 39  1  6
 21 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
 25 53  1  0
M  END


  Mrv0541 04191212162D          

 34 37  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7530   -3.1424    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2380   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7530   -1.8076    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9567   -2.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9567   -2.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0080   -3.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8149   -4.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -4.5402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5600   -3.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4130   -2.4749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9280   -1.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9281   -3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1829   -1.0229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
 22  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  1  1  0  0  0  0
  5  6  2  0  0  0  0
  4  3  2  0  0  0  0
  2  3  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10  7  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 11 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  7 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  0  0  0  0
 23 24  1  0  0  0  0
 24 31  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  2  0  0  0  0
  8 26  2  0  0  0  0
 10 27  1  6  0  0  0
 22 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 30 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0203762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](NC(=O)N1CCNC1=O)(C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@]12[H])C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1

> <INCHI_KEY>
JTWOMNBEOCYFNV-NFFDBFGFSA-N

> <FORMULA>
C20H23N5O6S

> <MOLECULAR_WEIGHT>
461.492

> <EXACT_MASS>
461.136904183

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
45.021513352290285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <ALOGPS_LOGP>
0.20

> <JCHEM_LOGP>
-0.3251712750000002

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.901647305261674

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4850654855904257

> <JCHEM_PKA_STRONGEST_BASIC>
-5.940777343638934

> <JCHEM_POLAR_SURFACE_AREA>
148.15

> <JCHEM_REFRACTIVITY>
111.71099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azlocillin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.541  -5.390   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.541  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.006  -5.866   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.911  -4.620   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0       7.006  -3.374   0.000  0.00  0.00           S+0
HETATM   14  C   UNK     0       9.253  -5.376   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.253  -3.864   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.482  -7.331   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.988  -7.651   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.451  -8.475   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -1.334  -3.850   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.912  -6.479   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       5.541  -2.310   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.334  -2.310   0.000  0.00  0.00           H+0
HETATM   29  N   UNK     0      -6.371  -4.620   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -5.466  -3.374   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -4.001  -3.850   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.466  -5.866   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.941  -1.909   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2                                                       
CONECT    4   22    5    3                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    8   10   19                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    7   13   27                                             
CONECT   11    9   12   16                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12   10                                                       
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   11   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    7   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22    4   20   23   28                                             
CONECT   23   24   22                                                       
CONECT   24   23   31   25                                                  
CONECT   25   24                                                            
CONECT   26    8                                                            
CONECT   27   10                                                            
CONECT   28   22                                                            
CONECT   29   30   33                                                       
CONECT   30   29   31   34                                                  
CONECT   31   24   30   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
CONECT   34   30                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
Azlocilina	ChEBI
Azlocilline	ChEBI
Azlocillinum	ChEBI
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
Azlocillin sodium salt	HMDB
Azlocillin, sodium	HMDB
Baye 6905	HMDB
Bayer brand OF azlocillin	HMDB
Securopen	HMDB
Azlocillin sodium	HMDB
Azlin	HMDB
Sodium azlocillin	HMDB
Sodium, azlocillin	HMDB
Azlocillin bayer brand	HMDB
Bay e 6905	HMDB
Bay-e 6905	HMDB

Chemical Formula

C₂₀H₂₃N₅O₆S

Average Mass

461.4920 Da

Monoisotopic Mass

461.13690 Da

IUPAC Name

(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

azlocillin

CAS Registry Number

Not Available

SMILES

[H][C@](NC(=O)N1CCNC1=O)(C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@]12[H])C1=CC=CC=C1

InChI Identifier

InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1

InChI Key

JTWOMNBEOCYFNV-NFFDBFGFSA-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 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
Penicillin
N-acyl-alpha amino acid or derivatives
N-carbamoyl-alpha-amino acid or derivatives
Alpha-amino acid amide
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Phenylacetamide
Penam
Imidazolidinone
Monocyclic benzene moiety
Benzenoid
Imidazolidine
Beta-lactam
Tertiary carboxylic acid amide
Thiazolidine
Azetidine
Urea
Carbonic acid derivative
Carboxamide group
Secondary carboxylic acid amide
Lactam
Organoheterocyclic compound
Azacycle
Hemithioaminal
Carboxylic acid
Monocarboxylic acid or derivatives
Dialkylthioether
Thioether
Organic nitrogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:2956 )

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	0.2	ALOGPS
logP	-0.33	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	148.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.71 m³·mol⁻¹	ChemAxon
Polarizability	45.02 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015194

DrugBank ID

DB01061

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4980416

KEGG Compound ID

C06839

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azlocillin

METLIN ID

Not Available

PubChem Compound

6479523

PDB ID

Not Available

ChEBI ID

2956

Good Scents ID

Not Available

References

General References

Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. doi: 10.4065/74.3.290. [PubMed:10090000 ]
Franceschini N, Caravelli B, Docquier JD, Galleni M, Frere JM, Amicosante G, Rossolini GM: Purification and biochemical characterization of the VIM-1 metallo-beta-lactamase. Antimicrob Agents Chemother. 2000 Nov;44(11):3003-7. doi: 10.1128/AAC.44.11.3003-3007.2000. [PubMed:11036013 ]
Marina M, Ivanova M, Kantardjiev T: Antimicrobial susceptibility of anaerobic bacteria in Bulgaria. Anaerobe. 2009 Aug;15(4):127-32. doi: 10.1016/j.anaerobe.2009.03.002. Epub 2009 Mar 16. [PubMed:19292999 ]
Radomski N, Cambau E, Moulin L, Haenn S, Moilleron R, Lucas FS: Comparison of culture methods for isolation of nontuberculous mycobacteria from surface waters. Appl Environ Microbiol. 2010 Jun;76(11):3514-20. doi: 10.1128/AEM.02659-09. Epub 2010 Apr 2. [PubMed:20363776 ]
Peres RL, Palaci M, Loureiro RB, Dietze R, Johnson JL, Maciel EL: Reduction of contamination of mycobacterial growth indicator tubes using increased PANTA concentration. Int J Tuberc Lung Dis. 2011 Feb;15(2):281-3, i. [PubMed:21219695 ]
Asandei A, Apetrei A, Luchian T: Uni-molecular detection and quantification of selected beta-lactam antibiotics with a hybrid alpha-hemolysin protein pore. J Mol Recognit. 2011 Mar-Apr;24(2):199-207. doi: 10.1002/jmr.1038. [PubMed:21360610 ]
Subramanyam B, Sivaramakrishnan GN, Dusthackeer A, Nagamiah S, Kumar V: Phage lysin as a substitute for antibiotics to detect Mycobacterium tuberculosis from sputum samples with the BACTEC MGIT 960 system. Clin Microbiol Infect. 2012 May;18(5):497-501. doi: 10.1111/j.1469-0691.2011.03601.x. Epub 2011 Aug 29. [PubMed:21883661 ]
Roy C, Segura C, Fuster C, Tirado M, Foz A: [Antibacterial spectrum of mezlocillin and azlocillin, two new antibiotics of the ureidopenicillin group (author's transl)]. Med Clin (Barc). 1982 May 1;78(9):363-71. [PubMed:6212725 ]
Godard J, Aubertin J, Borderon JC, Dureux JB, Motin J: [Monotherapy of Pseudomonas aeruginosa septicemia with azlocillin]. Presse Med. 1984 Mar 29;13(13):819-21. [PubMed:6231603 ]
Fass RJ: Comparative in vitro activities of azlocillin-cefotaxime and azlocillin-tobramycin combinations against blood and multi-drug resistant bacterial isolates. Antimicrob Agents Chemother. 1982 Jul;22(1):167-9. doi: 10.1128/AAC.22.1.167. [PubMed:6289737 ]
Petit JC, Richard G, Burghoffer B, Daguet GL: [Synergistic activity between ticarcillin, azlocillin, cefsulodin, ceftazidime and tobramycin or amikacin against Pseudomonas aeruginosa (author's transl)]. Pathol Biol (Paris). 1982 Jun;30(6):426-31. [PubMed:6810286 ]
LOTUS database [Link]

Showing NP-Card for (2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0203762)

MOL for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D MOL for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D SDF for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D-SDF for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

PDB for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D PDB for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

SMILES for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

INCHI for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

Structure for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D Structure for NP0203762 ((2s,5r,6r)-6-{[(2r)-1-hydroxy-2-{[hydroxy(2-hydroxy-4,5-dihydroimidazol-1-yl)methylidene]amino}-2-phenylethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)