NP-MRD: Showing NP-Card for Watasemycin A (NP0004162)

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Record Information

Version

2.0

Created at

2020-12-09 01:39:35 UTC

Updated at

2021-07-15 16:48:25 UTC

NP-MRD ID

NP0004162

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Watasemycin A

Provided By

NPAtlas

Description

(2S,4S)-2-[(4R,5S)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-thiazol-4-yl]-3,4-dimethyl-1,3-thiazolidine-4-carboxylic acid belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Watasemycin A is found in Streptomyces and Streptomyces sp. TP-A0597. Based on a literature review very few articles have been published on (2S,4S)-2-[(4R,5S)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-thiazol-4-yl]-3,4-dimethyl-1,3-thiazolidine-4-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118043D          

 43 45  0  0  0  0            999 V2000
    0.5192   -3.8097   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112   -2.5461   -0.8917 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1711   -1.6079   -1.7800 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.6520   -0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425    0.1465   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1265    0.8107    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    1.5695    1.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144    1.6802    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    1.0349   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8848    0.2611   -1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058   -0.3411   -2.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914   -0.7913    0.4899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3324   -1.5514    0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5793   -0.8169   -0.0748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5172    0.1131   -1.6370 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    1.3976   -1.1123 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1053    0.8456    0.2406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1828   -0.2098    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6038    1.9242    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6011    2.6378    0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0015    2.1935    2.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058    0.2842    0.8174 N   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8949    1.3468    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164   -4.5847   -0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1966   -4.1835   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1658   -3.5567    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088   -2.6955   -1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    0.7289    1.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3674    2.0756    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    2.2860    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565    1.0879   -1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606   -0.9110   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827   -2.1623    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -1.4882   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053    2.3912   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    1.2784   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416   -0.9482    0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793   -0.7276   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    0.2521    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4556    2.2815    3.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4027    1.2907   -0.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.3235    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813    2.3426    0.7043 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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13  2  1  0  0  0  0
 22 14  1  0  0  0  0
 10  5  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
  2 27  1  6  0  0  0
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 11 32  1  0  0  0  0
 13 33  1  1  0  0  0
 14 34  1  6  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 18 39  1  0  0  0  0
 21 40  1  0  0  0  0
 23 41  1  0  0  0  0
 23 42  1  0  0  0  0
 23 43  1  0  0  0  0
M  END

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    0.5192   -3.8097   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112   -2.5461   -0.8917 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1711   -1.6079   -1.7800 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.6520   -0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425    0.1465   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1265    0.8107    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    1.5695    1.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144    1.6802    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    1.0349   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8848    0.2611   -1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058   -0.3411   -2.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914   -0.7913    0.4899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3324   -1.5514    0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5793   -0.8169   -0.0748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5172    0.1131   -1.6370 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    1.3976   -1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053    0.8456    0.2406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1828   -0.2098    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6038    1.9242    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6011    2.6378    0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0015    2.1935    2.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058    0.2842    0.8174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949    1.3468    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164   -4.5847   -0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1966   -4.1835   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1658   -3.5567    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088   -2.6955   -1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    0.7289    1.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3674    2.0756    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    2.2860    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565    1.0879   -1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606   -0.9110   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827   -2.1623    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -1.4882   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053    2.3912   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    1.2784   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416   -0.9482    0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793   -0.7276   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    0.2521    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4556    2.2815    3.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4027    1.2907   -0.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.3235    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813    2.3426    0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  4 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 13  2  1  0
 22 14  1  0
 10  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 13 33  1  1
 14 34  1  6
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
M  END


  Mrv1652306242118043D          

 43 45  0  0  0  0            999 V2000
    0.5192   -3.8097   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112   -2.5461   -0.8917 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1711   -1.6079   -1.7800 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.6520   -0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425    0.1465   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1265    0.8107    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    1.5695    1.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144    1.6802    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    1.0349   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8848    0.2611   -1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058   -0.3411   -2.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914   -0.7913    0.4899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3324   -1.5514    0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5793   -0.8169   -0.0748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5172    0.1131   -1.6370 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    1.3976   -1.1123 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1053    0.8456    0.2406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1828   -0.2098    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6038    1.9242    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6011    2.6378    0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0015    2.1935    2.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058    0.2842    0.8174 N   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8949    1.3468    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164   -4.5847   -0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1966   -4.1835   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1658   -3.5567    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088   -2.6955   -1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    0.7289    1.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3674    2.0756    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    2.2860    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565    1.0879   -1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606   -0.9110   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827   -2.1623    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -1.4882   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053    2.3912   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    1.2784   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416   -0.9482    0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793   -0.7276   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    0.2521    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4556    2.2815    3.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4027    1.2907   -0.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.3235    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813    2.3426    0.7043 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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13  2  1  0  0  0  0
 22 14  1  0  0  0  0
 10  5  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
  2 27  1  6  0  0  0
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 11 32  1  0  0  0  0
 13 33  1  1  0  0  0
 14 34  1  6  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
 18 39  1  0  0  0  0
 21 40  1  0  0  0  0
 23 41  1  0  0  0  0
 23 42  1  0  0  0  0
 23 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1(N(C([H])([H])[H])[C@@]([H])(SC1([H])[H])[C@]1([H])N=C(S[C@@]1([H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O3S2/c1-9-12(14-18(3)16(2,8-22-14)15(20)21)17-13(23-9)10-6-4-5-7-11(10)19/h4-7,9,12,14,19H,8H2,1-3H3,(H,20,21)/t9-,12+,14-,16+/m0/s1

> <INCHI_KEY>
NOEXPDVJQLSPPC-UODBANLJSA-N

> <FORMULA>
C16H20N2O3S2

> <MOLECULAR_WEIGHT>
352.47

> <EXACT_MASS>
352.09153486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
37.069092529420274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S)-2-[(4R,5S)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-thiazol-4-yl]-3,4-dimethyl-1,3-thiazolidine-4-carboxylic acid

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
2.3030699103109815

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.614910111680866

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7494905066152224

> <JCHEM_PKA_STRONGEST_BASIC>
5.136988864515402

> <JCHEM_POLAR_SURFACE_AREA>
73.13000000000001

> <JCHEM_REFRACTIVITY>
94.30689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S)-2-[(4R,5S)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-thiazol-4-yl]-3,4-dimethyl-1,3-thiazolidine-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
    0.5192   -3.8097   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112   -2.5461   -0.8917 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1711   -1.6079   -1.7800 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.6520   -0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425    0.1465   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1265    0.8107    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    1.5695    1.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144    1.6802    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    1.0349   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8848    0.2611   -1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058   -0.3411   -2.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914   -0.7913    0.4899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3324   -1.5514    0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5793   -0.8169   -0.0748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5172    0.1131   -1.6370 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    1.3976   -1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053    0.8456    0.2406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1828   -0.2098    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6038    1.9242    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6011    2.6378    0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0015    2.1935    2.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058    0.2842    0.8174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949    1.3468    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164   -4.5847   -0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1966   -4.1835   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1658   -3.5567    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088   -2.6955   -1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    0.7289    1.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3674    2.0756    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    2.2860    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565    1.0879   -1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606   -0.9110   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827   -2.1623    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -1.4882   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053    2.3912   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    1.2784   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416   -0.9482    0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793   -0.7276   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    0.2521    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4556    2.2815    3.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4027    1.2907   -0.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.3235    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813    2.3426    0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  4 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 13  2  1  0
 22 14  1  0
 10  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 13 33  1  1
 14 34  1  6
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 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       0.519  -3.810  -0.391  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.111  -2.546  -0.892  0.00  0.00           C+0
HETATM    3  S   UNK     0       1.171  -1.608  -1.780  0.00  0.00           S+0
HETATM    4  C   UNK     0       1.712  -0.652  -0.377  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.942   0.147  -0.196  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.127   0.811   1.023  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.243   1.569   1.261  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.214   1.680   0.267  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.041   1.035  -0.923  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.885   0.261  -1.145  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.806  -0.341  -2.362  0.00  0.00           O+0
HETATM   12  N   UNK     0       0.791  -0.791   0.490  0.00  0.00           N+0
HETATM   13  C   UNK     0      -0.332  -1.551   0.258  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.579  -0.817  -0.075  0.00  0.00           C+0
HETATM   15  S   UNK     0      -1.517   0.113  -1.637  0.00  0.00           S+0
HETATM   16  C   UNK     0      -2.739   1.398  -1.112  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.105   0.846   0.241  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.183  -0.210   0.153  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.604   1.924   1.110  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.601   2.638   0.780  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.002   2.193   2.315  0.00  0.00           O+0
HETATM   22  N   UNK     0      -1.906   0.284   0.817  0.00  0.00           N+0
HETATM   23  C   UNK     0      -0.895   1.347   0.694  0.00  0.00           C+0
HETATM   24  H   UNK     0      -0.216  -4.585  -0.107  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.197  -4.184  -1.191  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.166  -3.557   0.478  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.009  -2.696  -1.490  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.385   0.729   1.788  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.367   2.076   2.211  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.097   2.286   0.469  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.757   1.088  -1.719  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.161  -0.911  -2.788  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.583  -2.162   1.166  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.432  -1.488  -0.132  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.305   2.391  -1.107  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.632   1.278  -1.762  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.042  -0.948   0.965  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.179  -0.728  -0.803  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.186   0.252   0.371  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.456   2.281   3.196  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.403   1.291  -0.307  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.183   1.323   1.538  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.381   2.343   0.704  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3   13   27                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9   30                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9   11    5                                                  
CONECT   11   10   32                                                       
CONECT   12    4   13                                                       
CONECT   13   12   14    2   33                                             
CONECT   14   13   15   22   34                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   35   36                                             
CONECT   17   16   18   19   22                                             
CONECT   18   17   37   38   39                                             
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   40                                                       
CONECT   22   17   23   14                                                  
CONECT   23   22   41   42   43                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   11                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   18                                                            
CONECT   38   18                                                            
CONECT   39   18                                                            
CONECT   40   21                                                            
CONECT   41   23                                                            
CONECT   42   23                                                            
CONECT   43   23                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

RDKit          3D

43 45  0  0  0  0  0  0  0  0999 V2000
    0.5192   -3.8097   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1112   -2.5461   -0.8917 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1711   -1.6079   -1.7800 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.6520   -0.3766 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425    0.1465   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1265    0.8107    1.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    1.5695    1.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144    1.6802    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    1.0349   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8848    0.2611   -1.1450 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058   -0.3411   -2.3620 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914   -0.7913    0.4899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3324   -1.5514    0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5793   -0.8169   -0.0748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5172    0.1131   -1.6370 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    1.3976   -1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053    0.8456    0.2406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1828   -0.2098    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6038    1.9242    1.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6011    2.6378    0.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0015    2.1935    2.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9058    0.2842    0.8174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949    1.3468    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2164   -4.5847   -0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1966   -4.1835   -1.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1658   -3.5567    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088   -2.6955   -1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849    0.7289    1.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3674    2.0756    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0971    2.2860    0.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7565    1.0879   -1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606   -0.9110   -2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5827   -2.1623    1.1664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4319   -1.4882   -0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3053    2.3912   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318    1.2784   -1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416   -0.9482    0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1793   -0.7276   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    0.2521    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4556    2.2815    3.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4027    1.2907   -0.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.3235    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813    2.3426    0.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  4 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 19 20  2  0
 19 21  1  0
 17 22  1  0
 22 23  1  0
 13  2  1  0
 22 14  1  0
 10  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  6
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 13 33  1  1
 14 34  1  6
 16 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S,4S)-2-[(4R,5S)-2-(2-Hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-thiazol-4-yl]-3,4-dimethyl-1,3-thiazolidine-4-carboxylate	Generator
Watasemycin b	MeSH

Chemical Formula

C₁₆H₂₀N₂O₃S₂

Average Mass

352.4700 Da

Monoisotopic Mass

352.09153 Da

IUPAC Name

(2S,4S)-2-[(4R,5S)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-thiazol-4-yl]-3,4-dimethyl-1,3-thiazolidine-4-carboxylic acid

Traditional Name

(2S,4S)-2-[(4R,5S)-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-thiazol-4-yl]-3,4-dimethyl-1,3-thiazolidine-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1SC(=N[C@H]1[C@@H]1SC[C@@](C)(N1C)C(O)=O)C1=CC=CC=C1O

InChI Identifier

InChI=1S/C16H20N2O3S2/c1-9-12(14-18(3)16(2,8-22-14)15(20)21)17-13(23-9)10-6-4-5-7-11(10)19/h4-7,9,12,14,19H,8H2,1-3H3,(H,20,21)/t9-,12+,14-,16+/m0/s1

InChI Key

NOEXPDVJQLSPPC-UODBANLJSA-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	12014439
Streptomyces sp. TP-A0597	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Imidothiolactone
Thiazolidine
Meta-thiazoline
Carboxylic acid
Monocarboxylic acid or derivatives
Thioether
Hemithioaminal
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Dialkylthioether
Azacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phenols (CHEBI:70582 )

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	2.12	ALOGPS
logP	2.3	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	2.75	ChemAxon
pKa (Strongest Basic)	5.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	73.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.31 m³·mol⁻¹	ChemAxon
Polarizability	37.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA008164

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26390429

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

136030744

PDB ID

Not Available

ChEBI ID

70582

Good Scents ID

Not Available

References

General References

Showing NP-Card for Watasemycin A (NP0004162)

MOL for NP0004162 (Watasemycin A)

3D MOL for NP0004162 (Watasemycin A)

3D SDF for NP0004162 (Watasemycin A)

3D-SDF for NP0004162 (Watasemycin A)

PDB for NP0004162 (Watasemycin A)

3D PDB for NP0004162 (Watasemycin A)

SMILES for NP0004162 (Watasemycin A)

INCHI for NP0004162 (Watasemycin A)

Structure for NP0004162 (Watasemycin A)

3D Structure for NP0004162 (Watasemycin A)