NP-MRD: Showing NP-Card for MM 17880 (NP0021435)

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Record Information

Version

2.0

Created at

2021-01-06 06:40:59 UTC

Updated at

2021-07-15 17:36:21 UTC

NP-MRD ID

NP0021435

Secondary Accession Numbers

None

Natural Product Identification

Common Name

MM 17880

Provided By

NPAtlas

Description

3-({2-[(1-Hydroxyethylidene)amino]ethyl}sulfanyl)-7-oxo-6-[1-(sulfooxy)ethyl]-1-azabicyclo[3.2.0]Hept-2-ene-2-carboxylic acid belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain. MM 17880 is found in Streptomyces olivaceus and Streptomyces olivaceus ATCC 21379. MM 17880 was first documented in 1979 (PMID: 468716). Based on a literature review very few articles have been published on 3-({2-[(1-hydroxyethylidene)amino]ethyl}sulfanyl)-7-oxo-6-[1-(sulfooxy)ethyl]-1-azabicyclo[3.2.0]Hept-2-ene-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105153D          

 43 44  0  0  0  0            999 V2000
    6.2200    2.2457   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    1.0060    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9212   -0.0877   -0.1529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.0856    0.6039 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -0.0945    0.7629 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0825   -0.7468   -0.5829 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0585   -2.2039   -0.5083 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -1.7755   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6306   -2.6730   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -4.1253    0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -4.8983    0.3541 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8286   -4.6281   -0.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -2.0585    0.1005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -1.7071    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -2.2250    0.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8733   -0.3940   -0.3841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7710    0.6968    0.1099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1939    0.3474   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369    1.8624   -0.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    3.1468    0.4006 S   0  0  2  0  0  6  0  0  0  0  0  0
   -4.2165    4.1062    0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    3.8975   -0.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756    2.7110    1.9310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6212   -0.6351    0.3793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3012   -0.4479   -0.3338 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5960    3.0969   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6150    2.4987    0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0592    2.0534   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242    1.9952    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.8155    1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    0.1145    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178    0.0584   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.9373   -1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -4.9388    0.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069   -0.3827   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    0.7980    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    1.2721   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1156   -0.2270   -1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6980   -0.2954    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128    3.5108    2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992   -0.3861    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -0.0802   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2718    0.2604    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  2  0  0  0  0
 20 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25  8  1  0  0  0  0
 24 13  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
 12 34  1  0  0  0  0
 16 35  1  6  0  0  0
 17 36  1  1  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 18 39  1  0  0  0  0
 23 40  1  0  0  0  0
 24 41  1  1  0  0  0
 25 42  1  0  0  0  0
 25 43  1  0  0  0  0
M  END

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
    6.2200    2.2457   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    1.0060    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9212   -0.0877   -0.1529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.0856    0.6039 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -0.0945    0.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825   -0.7468   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585   -2.2039   -0.5083 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -1.7755   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6306   -2.6730   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -4.1253    0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -4.8983    0.3541 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8286   -4.6281   -0.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -2.0585    0.1005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -1.7071    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -2.2250    0.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8733   -0.3940   -0.3841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7710    0.6968    0.1099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1939    0.3474   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369    1.8624   -0.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    3.1468    0.4006 S   0  0  2  0  0  6  0  0  0  0  0  0
   -4.2165    4.1062    0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    3.8975   -0.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756    2.7110    1.9310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6212   -0.6351    0.3793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3012   -0.4479   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5960    3.0969   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6150    2.4987    0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0592    2.0534   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242    1.9952    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.8155    1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    0.1145    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178    0.0584   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.9373   -1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -4.9388    0.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069   -0.3827   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    0.7980    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    1.2721   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1156   -0.2270   -1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6980   -0.2954    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128    3.5108    2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992   -0.3861    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -0.0802   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2718    0.2604    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 20 19  1  6
 20 21  2  0
 20 22  2  0
 20 23  1  0
 16 24  1  0
 24 25  1  0
 25  8  1  0
 24 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
 12 34  1  0
 16 35  1  6
 17 36  1  1
 18 37  1  0
 18 38  1  0
 18 39  1  0
 23 40  1  0
 24 41  1  1
 25 42  1  0
 25 43  1  0
M  END


  Mrv1652306242105153D          

 43 44  0  0  0  0            999 V2000
    6.2200    2.2457   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    1.0060    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9212   -0.0877   -0.1529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.0856    0.6039 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -0.0945    0.7629 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0825   -0.7468   -0.5829 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0585   -2.2039   -0.5083 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -1.7755   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6306   -2.6730   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -4.1253    0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -4.8983    0.3541 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8286   -4.6281   -0.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -2.0585    0.1005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -1.7071    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -2.2250    0.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8733   -0.3940   -0.3841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7710    0.6968    0.1099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1939    0.3474   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369    1.8624   -0.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    3.1468    0.4006 S   0  0  2  0  0  6  0  0  0  0  0  0
   -4.2165    4.1062    0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    3.8975   -0.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756    2.7110    1.9310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6212   -0.6351    0.3793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3012   -0.4479   -0.3338 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5960    3.0969   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6150    2.4987    0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0592    2.0534   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242    1.9952    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.8155    1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    0.1145    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178    0.0584   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.9373   -1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -4.9388    0.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069   -0.3827   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    0.7980    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    1.2721   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1156   -0.2270   -1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6980   -0.2954    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128    3.5108    2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992   -0.3861    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -0.0802   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2718    0.2604    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  2  0  0  0  0
 20 23  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25  8  1  0  0  0  0
 24 13  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5 30  1  0  0  0  0
  5 31  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
 12 34  1  0  0  0  0
 16 35  1  6  0  0  0
 17 36  1  1  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 18 39  1  0  0  0  0
 23 40  1  0  0  0  0
 24 41  1  1  0  0  0
 25 42  1  0  0  0  0
 25 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021435

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(SC([H])([H])C([H])([H])N([H])C(=O)C([H])([H])[H])C([H])([H])[C@]2([H])N1C(=O)[C@@]2([H])[C@@]([H])(O[S](=O)(=O)O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O8S2/c1-6(23-25(20,21)22)10-8-5-9(24-4-3-14-7(2)16)11(13(18)19)15(8)12(10)17/h6,8,10H,3-5H2,1-2H3,(H,14,16)(H,18,19)(H,20,21,22)/t6-,8-,10-/m0/s1

> <INCHI_KEY>
HZYSJDYRQDXUAB-UHFFFAOYSA-N

> <FORMULA>
C13H18N2O8S2

> <MOLECULAR_WEIGHT>
394.41

> <EXACT_MASS>
394.050457896

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
37.32661849979769

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6R)-3-[(2-acetamidoethyl)sulfanyl]-7-oxo-6-[(1S)-1-(sulfooxy)ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-3.9270287854268746

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.5036484398671384

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.038879472154134

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3967538684357197

> <JCHEM_POLAR_SURFACE_AREA>
150.31

> <JCHEM_REFRACTIVITY>
88.1465

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R)-3-[(2-acetamidoethyl)sulfanyl]-7-oxo-6-[(1S)-1-(sulfooxy)ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
    6.2200    2.2457   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    1.0060    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9212   -0.0877   -0.1529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.0856    0.6039 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -0.0945    0.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825   -0.7468   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585   -2.2039   -0.5083 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -1.7755   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6306   -2.6730   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -4.1253    0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -4.8983    0.3541 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8286   -4.6281   -0.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -2.0585    0.1005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -1.7071    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -2.2250    0.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8733   -0.3940   -0.3841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7710    0.6968    0.1099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1939    0.3474   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369    1.8624   -0.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    3.1468    0.4006 S   0  0  2  0  0  6  0  0  0  0  0  0
   -4.2165    4.1062    0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    3.8975   -0.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756    2.7110    1.9310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6212   -0.6351    0.3793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3012   -0.4479   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5960    3.0969   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6150    2.4987    0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0592    2.0534   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242    1.9952    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.8155    1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    0.1145    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178    0.0584   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.9373   -1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -4.9388    0.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069   -0.3827   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    0.7980    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    1.2721   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1156   -0.2270   -1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6980   -0.2954    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128    3.5108    2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992   -0.3861    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -0.0802   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2718    0.2604    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 20 19  1  6
 20 21  2  0
 20 22  2  0
 20 23  1  0
 16 24  1  0
 24 25  1  0
 25  8  1  0
 24 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
 12 34  1  0
 16 35  1  6
 17 36  1  1
 18 37  1  0
 18 38  1  0
 18 39  1  0
 23 40  1  0
 24 41  1  1
 25 42  1  0
 25 43  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.220   2.246  -0.028  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.408   1.006   0.134  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.921  -0.088  -0.153  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.086   1.086   0.604  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.272  -0.095   0.763  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.083  -0.747  -0.583  0.00  0.00           C+0
HETATM    7  S   UNK     0       2.059  -2.204  -0.508  0.00  0.00           S+0
HETATM    8  C   UNK     0       0.341  -1.776  -0.282  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.631  -2.673  -0.024  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.441  -4.125   0.113  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.390  -4.898   0.354  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.829  -4.628  -0.032  0.00  0.00           O+0
HETATM   13  N   UNK     0      -1.896  -2.059   0.101  0.00  0.00           N+0
HETATM   14  C   UNK     0      -3.260  -1.707   0.172  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.327  -2.225   0.529  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.873  -0.394  -0.384  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.771   0.697   0.110  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.194   0.347  -0.334  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.437   1.862  -0.574  0.00  0.00           O+0
HETATM   20  S   UNK     0      -3.069   3.147   0.401  0.00  0.00           S+0
HETATM   21  O   UNK     0      -4.216   4.106   0.539  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.919   3.898  -0.246  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.576   2.711   1.931  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.621  -0.635   0.379  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.301  -0.448  -0.334  0.00  0.00           C+0
HETATM   26  H   UNK     0       5.596   3.097  -0.365  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.615   2.499   0.980  0.00  0.00           H+0
HETATM   28  H   UNK     0       7.059   2.053  -0.701  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.624   1.995   0.861  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.853  -0.816   1.438  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.299   0.115   1.211  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.618   0.058  -1.228  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.067  -0.937  -1.070  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.373  -4.939   0.757  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.707  -0.383  -1.478  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.747   0.798   1.192  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.749   1.272  -0.576  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.116  -0.227  -1.279  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.698  -0.295   0.403  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.613   3.511   2.516  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.599  -0.386   1.437  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.444  -0.080  -1.373  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.272   0.260   0.270  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   29                                                  
CONECT    5    4    6   30   31                                             
CONECT    6    5    7   32   33                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   34                                                       
CONECT   13    9   14   24                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   24   35                                             
CONECT   17   16   18   19   36                                             
CONECT   18   17   37   38   39                                             
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   40                                                       
CONECT   24   16   25   13   41                                             
CONECT   25   24    8   42   43                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34   12                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   18                                                            
CONECT   39   18                                                            
CONECT   40   23                                                            
CONECT   41   24                                                            
CONECT   42   25                                                            
CONECT   43   25                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   88    0
END

RDKit          3D

43 44  0  0  0  0  0  0  0  0999 V2000
    6.2200    2.2457   -0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083    1.0060    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9212   -0.0877   -0.1529 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.0856    0.6039 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -0.0945    0.7629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825   -0.7468   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585   -2.2039   -0.5083 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -1.7755   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6306   -2.6730   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405   -4.1253    0.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3901   -4.8983    0.3541 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8286   -4.6281   -0.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -2.0585    0.1005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -1.7071    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -2.2250    0.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8733   -0.3940   -0.3841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7710    0.6968    0.1099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1939    0.3474   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369    1.8624   -0.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691    3.1468    0.4006 S   0  0  2  0  0  6  0  0  0  0  0  0
   -4.2165    4.1062    0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    3.8975   -0.2462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5756    2.7110    1.9310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6212   -0.6351    0.3793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3012   -0.4479   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5960    3.0969   -0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6150    2.4987    0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0592    2.0534   -0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6242    1.9952    0.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.8155    1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    0.1145    1.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178    0.0584   -1.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0669   -0.9373   -1.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -4.9388    0.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7069   -0.3827   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    0.7980    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490    1.2721   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1156   -0.2270   -1.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6980   -0.2954    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6128    3.5108    2.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992   -0.3861    1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -0.0802   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2718    0.2604    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 20 19  1  6
 20 21  2  0
 20 22  2  0
 20 23  1  0
 16 24  1  0
 24 25  1  0
 25  8  1  0
 24 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
 12 34  1  0
 16 35  1  6
 17 36  1  1
 18 37  1  0
 18 38  1  0
 18 39  1  0
 23 40  1  0
 24 41  1  1
 25 42  1  0
 25 43  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-({2-[(1-hydroxyethylidene)amino]ethyl}sulfanyl)-7-oxo-6-[1-(sulfooxy)ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
3-({2-[(1-hydroxyethylidene)amino]ethyl}sulphanyl)-7-oxo-6-[1-(sulphooxy)ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
3-({2-[(1-hydroxyethylidene)amino]ethyl}sulphanyl)-7-oxo-6-[1-(sulphooxy)ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid	Generator

Chemical Formula

C₁₃H₁₈N₂O₈S₂

Average Mass

394.4100 Da

Monoisotopic Mass

394.05046 Da

IUPAC Name

(5S,6R)-3-[(2-acetamidoethyl)sulfanyl]-7-oxo-6-[(1S)-1-(sulfooxy)ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Traditional Name

(5S,6R)-3-[(2-acetamidoethyl)sulfanyl]-7-oxo-6-[(1S)-1-(sulfooxy)ethyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(OS(O)(=O)=O)C1C2CC(SCCNC(C)=O)=C(N2C1=O)C(O)=O

InChI Identifier

InChI=1S/C13H18N2O8S2/c1-6(23-25(20,21)22)10-8-5-9(24-4-3-14-7(2)16)11(13(18)19)15(8)12(10)17/h6,8,10H,3-5H2,1-2H3,(H,14,16)(H,18,19)(H,20,21,22)

InChI Key

HZYSJDYRQDXUAB-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Streptomyces olivaceus	NPAtlas	468716
Streptomyces olivaceus ATCC 21379	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Thienamycins

Alternative Parents

Substituents

Thienamycin
Alpha-amino acid or derivatives
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Azepine
Vinylogous thioester
Sulfuric acid ester
Alkyl sulfate
Sulfuric acid monoester
Sulfate-ester
Organic sulfuric acid or derivatives
Acetamide
Pyrroline
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Secondary carboxylic acid amide
Thioenolether
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Sulfenyl compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-0.64	ALOGPS
logP	-3.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	150.31 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	88.15 m³·mol⁻¹	ChemAxon
Polarizability	37.33 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

NPAtlas ID

NPA016447

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

57468492

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73835220

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hood JD, Box SJ, Verrall MS: Olivanic acids, a family of beta-lactam antibiotics with beta-lactamase inhibitory properties produced by Streptomyces species. II. Isolation and characterisation of the olivanic acids MM 4550, MM 13902 and MM 17880 from Streptomyces olivaceus. J Antibiot (Tokyo). 1979 Apr;32(4):295-304. doi: 10.7164/antibiotics.32.295. [PubMed:468716 ]

Showing NP-Card for MM 17880 (NP0021435)

MOL for NP0021435 (MM 17880)

3D MOL for NP0021435 (MM 17880)

3D SDF for NP0021435 (MM 17880)

3D-SDF for NP0021435 (MM 17880)

PDB for NP0021435 (MM 17880)

3D PDB for NP0021435 (MM 17880)

SMILES for NP0021435 (MM 17880)

INCHI for NP0021435 (MM 17880)

Structure for NP0021435 (MM 17880)

3D Structure for NP0021435 (MM 17880)