NP-MRD: Showing NP-Card for 8-epi-thienamycin (NP0021913)

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Record Information

Version

2.0

Created at

2021-01-06 07:09:42 UTC

Updated at

2021-07-15 17:37:38 UTC

NP-MRD ID

NP0021913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-epi-thienamycin

Provided By

NPAtlas

Description

(5R,6S)-3-[(2-aminoethyl)sulfanyl]-6-[(1S)-1-hydroxyethyl]-7-oxo-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. 8-epi-thienamycin is found in Streptomyces cattleya and Streptomyces MA4297. 8-epi-thienamycin was first documented in 1983 (PMID: 6630073). Based on a literature review very few articles have been published on (5R,6S)-3-[(2-aminoethyl)sulfanyl]-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]Hept-2-ene-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105193D          

 34 35  0  0  0  0            999 V2000
   -4.7313    0.0452    0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3348    0.4978    1.3937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2503    1.8827    1.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564   -0.0961    0.4271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5604    0.3018   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4773    0.6238   -1.7798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1715    0.1665   -1.1570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517   -0.0573   -1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563   -0.1170   -2.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -0.3197   -3.2698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3621    0.0472   -3.9738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2045   -0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315   -0.5056   -0.6732 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -0.6372    0.9981 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9055   -0.8890    0.8712 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4971    0.2080    0.1640 N   0  0  2  0  0  0  0  0  0  0  0  0
    0.1887   -0.0795    0.6977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0636    0.6342    0.2428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3009    0.8712    0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2903   -0.3661    1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6771   -0.7658    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1381    0.0575    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    2.2228    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -1.1727    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4926   -0.5287   -4.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    0.3048    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9241   -1.4493    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3503   -1.0094    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -1.8701    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8160    0.7034   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3534   -0.1015   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.5425    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334   -1.0818    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    1.7196    0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18  4  1  0  0  0  0
 18  7  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  1  0  0  0
  3 23  1  0  0  0  0
  4 24  1  6  0  0  0
 11 25  1  0  0  0  0
 14 26  1  0  0  0  0
 14 27  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
 16 30  1  0  0  0  0
 16 31  1  0  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 18 34  1  6  0  0  0
M  END

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.7313    0.0452    0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3348    0.4978    1.3937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2503    1.8827    1.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564   -0.0961    0.4271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5604    0.3018   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4773    0.6238   -1.7798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1715    0.1665   -1.1570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517   -0.0573   -1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563   -0.1170   -2.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -0.3197   -3.2698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3621    0.0472   -3.9738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2045   -0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315   -0.5056   -0.6732 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -0.6372    0.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055   -0.8890    0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971    0.2080    0.1640 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1887   -0.0795    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0636    0.6342    0.2428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3009    0.8712    0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2903   -0.3661    1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6771   -0.7658    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1381    0.0575    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    2.2228    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -1.1727    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4926   -0.5287   -4.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    0.3048    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9241   -1.4493    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3503   -1.0094    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -1.8701    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8160    0.7034   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3534   -0.1015   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.5425    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334   -1.0818    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    1.7196    0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18  4  1  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  4 24  1  6
 11 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  6
M  END


  Mrv1652306242105193D          

 34 35  0  0  0  0            999 V2000
   -4.7313    0.0452    0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3348    0.4978    1.3937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2503    1.8827    1.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564   -0.0961    0.4271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5604    0.3018   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4773    0.6238   -1.7798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1715    0.1665   -1.1570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517   -0.0573   -1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563   -0.1170   -2.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -0.3197   -3.2698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3621    0.0472   -3.9738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2045   -0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315   -0.5056   -0.6732 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -0.6372    0.9981 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9055   -0.8890    0.8712 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4971    0.2080    0.1640 N   0  0  2  0  0  0  0  0  0  0  0  0
    0.1887   -0.0795    0.6977 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0636    0.6342    0.2428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3009    0.8712    0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2903   -0.3661    1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6771   -0.7658    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1381    0.0575    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    2.2228    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -1.1727    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4926   -0.5287   -4.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    0.3048    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9241   -1.4493    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3503   -1.0094    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -1.8701    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8160    0.7034   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3534   -0.1015   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.5425    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334   -1.0818    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    1.7196    0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18  4  1  0  0  0  0
 18  7  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  1  0  0  0
  3 23  1  0  0  0  0
  4 24  1  6  0  0  0
 11 25  1  0  0  0  0
 14 26  1  0  0  0  0
 14 27  1  0  0  0  0
 15 28  1  0  0  0  0
 15 29  1  0  0  0  0
 16 30  1  0  0  0  0
 16 31  1  0  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 18 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0021913

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N2O4S/c1-5(14)8-6-4-7(18-3-2-12)9(11(16)17)13(6)10(8)15/h5-6,8,14H,2-4,12H2,1H3,(H,16,17)/t5-,6+,8+/m0/s1

> <INCHI_KEY>
WKDDRNSBRWANNC-SHYZEUOFSA-N

> <FORMULA>
C11H16N2O4S

> <MOLECULAR_WEIGHT>
272.32

> <EXACT_MASS>
272.083078177

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.911304903352864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.18

> <JCHEM_LOGP>
-4.309641918399189

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.000692926264293

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.666431404972687

> <JCHEM_PKA_STRONGEST_BASIC>
9.653061608872273

> <JCHEM_POLAR_SURFACE_AREA>
103.86

> <JCHEM_REFRACTIVITY>
68.71090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.70e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.7313    0.0452    0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3348    0.4978    1.3937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2503    1.8827    1.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564   -0.0961    0.4271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5604    0.3018   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4773    0.6238   -1.7798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1715    0.1665   -1.1570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517   -0.0573   -1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563   -0.1170   -2.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -0.3197   -3.2698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3621    0.0472   -3.9738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2045   -0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315   -0.5056   -0.6732 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -0.6372    0.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055   -0.8890    0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971    0.2080    0.1640 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1887   -0.0795    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0636    0.6342    0.2428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3009    0.8712    0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2903   -0.3661    1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6771   -0.7658    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1381    0.0575    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    2.2228    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -1.1727    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4926   -0.5287   -4.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    0.3048    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9241   -1.4493    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3503   -1.0094    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -1.8701    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8160    0.7034   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3534   -0.1015   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.5425    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334   -1.0818    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    1.7196    0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18  4  1  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  4 24  1  6
 11 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  6
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      -4.731   0.045   0.984  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.335   0.498   1.394  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.250   1.883   1.408  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.356  -0.096   0.427  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.560   0.302  -0.996  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.477   0.624  -1.780  0.00  0.00           O+0
HETATM    7  N   UNK     0      -1.172   0.167  -1.157  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.152  -0.057  -1.587  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.556  -0.117  -2.977  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.751  -0.320  -3.270  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.362   0.047  -3.974  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.969  -0.205  -0.552  0.00  0.00           C+0
HETATM   13  S   UNK     0       2.732  -0.506  -0.673  0.00  0.00           S+0
HETATM   14  C   UNK     0       3.431  -0.637   0.998  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.906  -0.889   0.871  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.497   0.208   0.164  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.189  -0.080   0.698  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.064   0.634   0.243  0.00  0.00           C+0
HETATM   19  H   UNK     0      -5.301   0.871   0.549  0.00  0.00           H+0
HETATM   20  H   UNK     0      -5.290  -0.366   1.861  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.677  -0.766   0.247  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.138   0.058   2.386  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.179   2.223   1.499  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.186  -1.173   0.554  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.493  -0.529  -4.773  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.265   0.305   1.559  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.924  -1.449   1.592  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.350  -1.009   1.897  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.040  -1.870   0.374  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.816   0.703  -0.456  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.353  -0.102  -0.345  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.743   0.543   1.442  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.033  -1.082   1.079  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.069   1.720   0.314  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3    4   22                                             
CONECT    3    2   23                                                       
CONECT    4    2    5   18   24                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   25                                                       
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   26   27                                             
CONECT   15   14   16   28   29                                             
CONECT   16   15   30   31                                                  
CONECT   17   12   18   32   33                                             
CONECT   18   17    4    7   34                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25   11                                                            
CONECT   26   14                                                            
CONECT   27   14                                                            
CONECT   28   15                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   16                                                            
CONECT   32   17                                                            
CONECT   33   17                                                            
CONECT   34   18                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

RDKit          3D

34 35  0  0  0  0  0  0  0  0999 V2000
   -4.7313    0.0452    0.9841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3348    0.4978    1.3937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2503    1.8827    1.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564   -0.0961    0.4271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5604    0.3018   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4773    0.6238   -1.7798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1715    0.1665   -1.1570 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517   -0.0573   -1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563   -0.1170   -2.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7506   -0.3197   -3.2698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3621    0.0472   -3.9738 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9693   -0.2045   -0.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315   -0.5056   -0.6732 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -0.6372    0.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055   -0.8890    0.8712 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4971    0.2080    0.1640 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1887   -0.0795    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0636    0.6342    0.2428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3009    0.8712    0.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2903   -0.3661    1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6771   -0.7658    0.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1381    0.0575    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793    2.2228    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -1.1727    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4926   -0.5287   -4.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    0.3048    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9241   -1.4493    1.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3503   -1.0094    1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0402   -1.8701    0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8160    0.7034   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3534   -0.1015   -0.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.5425    1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334   -1.0818    1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    1.7196    0.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  8 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18  4  1  0
 18  7  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  4 24  1  6
 11 25  1  0
 14 26  1  0
 14 27  1  0
 15 28  1  0
 15 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 18 34  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(5R,6S)-3-[(2-Aminoethyl)sulfanyl]-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
(5R,6S)-3-[(2-Aminoethyl)sulphanyl]-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
(5R,6S)-3-[(2-Aminoethyl)sulphanyl]-6-[(1S)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid	Generator
Thienamycin, (5R-(5alpha,6alpha(r*)))-isomer	MeSH
Thienamycin	MeSH
Thienamycin, ((5alpha,6alpha(s*))-(+-))-isomer	MeSH
Thienamycin, (5R-(5alpha,6alpha(s*)))-isomer	MeSH
Thienamycin, (5R-(5alpha,6beta(s*)))-isomer	MeSH
Tienamycin	MeSH

Chemical Formula

C₁₁H₁₆N₂O₄S

Average Mass

272.3200 Da

Monoisotopic Mass

272.08308 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@@H]1[C@H]2CC(SCCN)=C(N2C1=O)C(O)=O

InChI Identifier

InChI=1S/C11H16N2O4S/c1-5(14)8-6-4-7(18-3-2-12)9(11(16)17)13(6)10(8)15/h5-6,8,14H,2-4,12H2,1H3,(H,16,17)/t5-,6+,8+/m0/s1

InChI Key

WKDDRNSBRWANNC-SHYZEUOFSA-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 cattleya	NPAtlas	6630073
Streptomyces MA4297	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
Tertiary carboxylic acid amide
Pyrroline
Amino acid or derivatives
Amino acid
Azetidine
Carboxamide group
Thioenolether
Secondary alcohol
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfenyl compound
Amine
Primary aliphatic amine
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary amine
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	-1.2	ALOGPS
logP	-4.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	9.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	68.71 m³·mol⁻¹	ChemAxon
Polarizability	27.91 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

NPA020940

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59702318

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13018200

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wilson KE, Kempf AJ, Liesch JM, Arison BH: Northienamycin and 8-epi-thienamycin, new carbapenems from Streptomyces cattleya. J Antibiot (Tokyo). 1983 Sep;36(9):1109-17. doi: 10.7164/antibiotics.36.1109. [PubMed:6630073 ]

Showing NP-Card for 8-epi-thienamycin (NP0021913)

MOL for NP0021913 (8-epi-thienamycin)

3D MOL for NP0021913 (8-epi-thienamycin)

3D SDF for NP0021913 (8-epi-thienamycin)

3D-SDF for NP0021913 (8-epi-thienamycin)

PDB for NP0021913 (8-epi-thienamycin)

3D PDB for NP0021913 (8-epi-thienamycin)

SMILES for NP0021913 (8-epi-thienamycin)

INCHI for NP0021913 (8-epi-thienamycin)

Structure for NP0021913 (8-epi-thienamycin)

3D Structure for NP0021913 (8-epi-thienamycin)