NP-MRD: Showing NP-Card for Asparenomycin B (NP0022009)

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Record Information

Version

2.0

Created at

2021-01-06 07:14:24 UTC

Updated at

2021-07-15 17:37:53 UTC

NP-MRD ID

NP0022009

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asparenomycin B

Provided By

NPAtlas

Description

(6E)-3-{2-[(1-hydroxyethylidene)amino]ethanesulfinyl}-6-(1-hydroxypropan-2-ylidene)-7-oxo-1-azabicyclo[3.2.0]Hept-2-ene-2-carboxylic acid belongs to the class of organic compounds known as carbapenems. These are beta-lactam derivatives in which the beta-lactam ring shares the nitrogen atom with a pyrrole-2-carboxylic acid. Asparenomycin B is found in Streptomyces and Streptomyces tokunonensis sp. nov. PA-31088. Asparenomycin B was first documented in 1982 (PMID: 7068508). Based on a literature review very few articles have been published on (6E)-3-{2-[(1-hydroxyethylidene)amino]ethanesulfinyl}-6-(1-hydroxypropan-2-ylidene)-7-oxo-1-azabicyclo[3.2.0]Hept-2-ene-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105203D          

 41 42  0  0  0  0            999 V2000
    5.3892    1.1205    1.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830    0.4251    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594    1.0786    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -0.9607    0.3892 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598   -1.8108   -0.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6404   -1.6792   -1.4407 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8361   -0.2299   -2.0030 S   0  0  1  0  0  4  0  0  0  0  0  0
    1.4822   -0.3042   -3.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3799    0.1931   -1.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    1.4176   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461    2.6590   -1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980    2.7081   -1.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2224    3.8428   -0.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2040    1.3671    0.0044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047    1.6531    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9419    2.6444    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    0.2621    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9676   -0.2908    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081    0.5136    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9853   -1.7612   -0.1926 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7877   -2.3283    0.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3722   -0.0391    0.4199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7396   -0.7760   -0.7415 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2389    2.2061    1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    0.7231    2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2893    0.8870    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1111   -1.4537    0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973   -1.8273    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332   -2.8873    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8829   -2.5421   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4307   -2.0061   -2.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    4.0372   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872    0.6639    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0428    1.5561   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0204    0.0546   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899   -2.2064   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4152   -1.9493   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7235   -2.0618    0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -0.2662    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2494   -1.7184   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -0.9141   -1.5856 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
  7  6  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23  9  1  0  0  0  0
 22 14  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
 13 32  1  0  0  0  0
 19 33  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
 20 37  1  0  0  0  0
 21 38  1  0  0  0  0
 22 39  1  1  0  0  0
 23 40  1  0  0  0  0
 23 41  1  0  0  0  0
M  END

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3892    1.1205    1.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830    0.4251    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594    1.0786    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -0.9607    0.3892 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598   -1.8108   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6404   -1.6792   -1.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -0.2299   -2.0030 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.4822   -0.3042   -3.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3799    0.1931   -1.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    1.4176   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461    2.6590   -1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980    2.7081   -1.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2224    3.8428   -0.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2040    1.3671    0.0044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047    1.6531    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9419    2.6444    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    0.2621    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9676   -0.2908    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081    0.5136    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9853   -1.7612   -0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7877   -2.3283    0.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3722   -0.0391    0.4199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7396   -0.7760   -0.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389    2.2061    1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    0.7231    2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2893    0.8870    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1111   -1.4537    0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973   -1.8273    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332   -2.8873    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8829   -2.5421   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4307   -2.0061   -2.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    4.0372   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872    0.6639    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0428    1.5561   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0204    0.0546   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899   -2.2064   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4152   -1.9493   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7235   -2.0618    0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -0.2662    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2494   -1.7184   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -0.9141   -1.5856 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
  7  6  1  1
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23  9  1  0
 22 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
 13 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  1
 23 40  1  0
 23 41  1  0
M  END


  Mrv1652306242105203D          

 41 42  0  0  0  0            999 V2000
    5.3892    1.1205    1.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830    0.4251    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594    1.0786    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -0.9607    0.3892 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598   -1.8108   -0.0810 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6404   -1.6792   -1.4407 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8361   -0.2299   -2.0030 S   0  0  1  0  0  4  0  0  0  0  0  0
    1.4822   -0.3042   -3.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3799    0.1931   -1.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    1.4176   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461    2.6590   -1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980    2.7081   -1.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2224    3.8428   -0.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2040    1.3671    0.0044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047    1.6531    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9419    2.6444    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    0.2621    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9676   -0.2908    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081    0.5136    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9853   -1.7612   -0.1926 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7877   -2.3283    0.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3722   -0.0391    0.4199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7396   -0.7760   -0.7415 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2389    2.2061    1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    0.7231    2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2893    0.8870    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1111   -1.4537    0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973   -1.8273    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332   -2.8873    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8829   -2.5421   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4307   -2.0061   -2.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    4.0372   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872    0.6639    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0428    1.5561   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0204    0.0546   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899   -2.2064   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4152   -1.9493   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7235   -2.0618    0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -0.2662    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2494   -1.7184   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -0.9141   -1.5856 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
  7  6  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23  9  1  0  0  0  0
 22 14  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
 13 32  1  0  0  0  0
 19 33  1  0  0  0  0
 19 34  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
 20 37  1  0  0  0  0
 21 38  1  0  0  0  0
 22 39  1  1  0  0  0
 23 40  1  0  0  0  0
 23 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022009

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C([S@](=O)C([H])([H])C([H])([H])N([H])C(=O)C([H])([H])[H])C([H])([H])[C@@]2([H])N1C(=O)\C2=C(/C([H])([H])[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O6S/c1-7(6-17)11-9-5-10(23(22)4-3-15-8(2)18)12(14(20)21)16(9)13(11)19/h9,17H,3-6H2,1-2H3,(H,15,18)(H,20,21)/b11-7+/t9-,23-/m1/s1

> <INCHI_KEY>
IATDYGCCUJUVGA-YRNVUSSQSA-N

> <FORMULA>
C14H18N2O6S

> <MOLECULAR_WEIGHT>
342.37

> <EXACT_MASS>
342.088557482

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
33.851548040441116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,6E)-3-[(R)-2-acetamidoethanesulfinyl]-6-(1-hydroxypropan-2-ylidene)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-0.66

> <JCHEM_LOGP>
-3.5571413243333327

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.838929328409883

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.558123862293751

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5723937673684243

> <JCHEM_POLAR_SURFACE_AREA>
124.01

> <JCHEM_REFRACTIVITY>
84.9769

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6E)-3-[(R)-2-acetamidoethanesulfinyl]-6-(1-hydroxypropan-2-ylidene)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3892    1.1205    1.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830    0.4251    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594    1.0786    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -0.9607    0.3892 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598   -1.8108   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6404   -1.6792   -1.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -0.2299   -2.0030 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.4822   -0.3042   -3.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3799    0.1931   -1.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    1.4176   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461    2.6590   -1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980    2.7081   -1.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2224    3.8428   -0.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2040    1.3671    0.0044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047    1.6531    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9419    2.6444    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    0.2621    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9676   -0.2908    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081    0.5136    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9853   -1.7612   -0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7877   -2.3283    0.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3722   -0.0391    0.4199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7396   -0.7760   -0.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389    2.2061    1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    0.7231    2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2893    0.8870    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1111   -1.4537    0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973   -1.8273    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332   -2.8873    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8829   -2.5421   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4307   -2.0061   -2.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    4.0372   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872    0.6639    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0428    1.5561   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0204    0.0546   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899   -2.2064   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4152   -1.9493   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7235   -2.0618    0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -0.2662    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2494   -1.7184   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -0.9141   -1.5856 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
  7  6  1  1
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23  9  1  0
 22 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
 13 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  1
 23 40  1  0
 23 41  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       5.389   1.121   1.073  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.183   0.425   0.580  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.159   1.079   0.334  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.189  -0.961   0.389  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.160  -1.811  -0.081  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.640  -1.679  -1.441  0.00  0.00           C+0
HETATM    7  S   UNK     0       1.836  -0.230  -2.003  0.00  0.00           S+0
HETATM    8  O   UNK     0       1.482  -0.304  -3.480  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.380   0.193  -1.091  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.004   1.418  -0.727  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.746   2.659  -1.039  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.798   2.708  -1.700  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.222   3.843  -0.556  0.00  0.00           O+0
HETATM   14  N   UNK     0      -1.204   1.367   0.004  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.405   1.653   0.654  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.942   2.644   1.256  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.803   0.262   0.334  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.968  -0.291   0.104  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.208   0.514   0.139  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.985  -1.761  -0.193  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.788  -2.328   0.825  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.372  -0.039   0.420  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.740  -0.776  -0.742  0.00  0.00           C+0
HETATM   24  H   UNK     0       5.239   2.206   1.195  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.611   0.723   2.097  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.289   0.887   0.464  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.111  -1.454   0.635  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.297  -1.827   0.666  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.533  -2.887   0.015  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.883  -2.542  -1.562  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.431  -2.006  -2.190  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.758   4.037  -0.729  0.00  0.00           H+0
HETATM   33  H   UNK     0      -5.587   0.664   1.176  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.043   1.556  -0.256  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.020   0.055  -0.474  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.990  -2.206  -0.087  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.415  -1.949  -1.189  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.723  -2.062   0.624  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.968  -0.266   1.404  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.249  -1.718  -0.436  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.416  -0.914  -1.586  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
CONECT    5    4    6   28   29                                             
CONECT    6    5    7   30   31                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   32                                                       
CONECT   14   10   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   33   34   35                                             
CONECT   20   18   21   36   37                                             
CONECT   21   20   38                                                       
CONECT   22   17   23   14   39                                             
CONECT   23   22    9   40   41                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32   13                                                            
CONECT   33   19                                                            
CONECT   34   19                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   20                                                            
CONECT   38   21                                                            
CONECT   39   22                                                            
CONECT   40   23                                                            
CONECT   41   23                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   84    0
END

RDKit          3D

41 42  0  0  0  0  0  0  0  0999 V2000
    5.3892    1.1205    1.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1830    0.4251    0.5796 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1594    1.0786    0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -0.9607    0.3892 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1598   -1.8108   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6404   -1.6792   -1.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -0.2299   -2.0030 S   0  0  0  0  0  4  0  0  0  0  0  0
    1.4822   -0.3042   -3.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3799    0.1931   -1.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0039    1.4176   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461    2.6590   -1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980    2.7081   -1.7002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2224    3.8428   -0.5556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2040    1.3671    0.0044 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047    1.6531    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9419    2.6444    1.2557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8027    0.2621    0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9676   -0.2908    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2081    0.5136    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9853   -1.7612   -0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7877   -2.3283    0.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3722   -0.0391    0.4199 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7396   -0.7760   -0.7415 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389    2.2061    1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    0.7231    2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2893    0.8870    0.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1111   -1.4537    0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973   -1.8273    0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332   -2.8873    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8829   -2.5421   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4307   -2.0061   -2.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    4.0372   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5872    0.6639    1.1760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0428    1.5561   -0.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0204    0.0546   -0.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899   -2.2064   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4152   -1.9493   -1.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7235   -2.0618    0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -0.2662    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2494   -1.7184   -0.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -0.9141   -1.5856 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
  7  6  1  1
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 17 22  1  0
 22 23  1  0
 23  9  1  0
 22 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
 13 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 20 36  1  0
 20 37  1  0
 21 38  1  0
 22 39  1  1
 23 40  1  0
 23 41  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(6E)-3-{2-[(1-hydroxyethylidene)amino]ethanesulfinyl}-6-(1-hydroxypropan-2-ylidene)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
(6E)-3-{2-[(1-hydroxyethylidene)amino]ethanesulphinyl}-6-(1-hydroxypropan-2-ylidene)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
(6E)-3-{2-[(1-hydroxyethylidene)amino]ethanesulphinyl}-6-(1-hydroxypropan-2-ylidene)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid	Generator
Asparenomycin a	MeSH
Asparenomycin C	MeSH
Asparenomycin	MeSH

Chemical Formula

C₁₄H₁₈N₂O₆S

Average Mass

342.3700 Da

Monoisotopic Mass

342.08856 Da

IUPAC Name

(5R,6E)-3-[(R)-2-acetamidoethanesulfinyl]-6-(1-hydroxypropan-2-ylidene)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Traditional Name

(5R,6E)-3-[(R)-2-acetamidoethanesulfinyl]-6-(1-hydroxypropan-2-ylidene)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NCCS(=O)C1=C(N2C(C1)\C(=C(\C)CO)C2=O)C(O)=O

InChI Identifier

InChI=1S/C14H18N2O6S/c1-7(6-17)11-9-5-10(23(22)4-3-15-8(2)18)12(14(20)21)16(9)13(11)19/h9,17H,3-6H2,1-2H3,(H,15,18)(H,20,21)/b11-7+

InChI Key

IATDYGCCUJUVGA-YRNVUSSQSA-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	NPAtlas	7068508
Streptomyces tokunonensis sp. nov. PA-31088	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbapenems. These are beta-lactam derivatives in which the beta-lactam ring shares the nitrogen atom with a pyrrole-2-carboxylic acid.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Carbapenems

Alternative Parents

Substituents

Carbapenem
Alpha-amino acid or derivatives
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Azepine
Acetamide
Tertiary carboxylic acid amide
Pyrroline
Azetidine
Carboxamide group
Sulfoxide
Secondary carboxylic acid amide
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfinyl compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary alcohol
Organic oxide
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	-0.66	ALOGPS
logP	-3.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.56	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	124.01 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.98 m³·mol⁻¹	ChemAxon
Polarizability	33.85 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

NPA021010

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8242864

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10067324

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kawamura Y, Yasuda Y, Mayama M, Tanaka K: Asparenomycins A, B and C, new carbapenem antibiotics. I. Taxonomic studies on the producing microorganisms. J Antibiot (Tokyo). 1982 Jan;35(1):10-4. doi: 10.7164/antibiotics.35.10. [PubMed:7068508 ]

Showing NP-Card for Asparenomycin B (NP0022009)

MOL for NP0022009 (Asparenomycin B)

3D MOL for NP0022009 (Asparenomycin B)

3D SDF for NP0022009 (Asparenomycin B)

3D-SDF for NP0022009 (Asparenomycin B)

PDB for NP0022009 (Asparenomycin B)

3D PDB for NP0022009 (Asparenomycin B)

SMILES for NP0022009 (Asparenomycin B)

INCHI for NP0022009 (Asparenomycin B)

Structure for NP0022009 (Asparenomycin B)

3D Structure for NP0022009 (Asparenomycin B)