NP-MRD: Showing NP-Card for (4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid (NP0317871)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 18:00:55 UTC

Updated at

2022-09-11 18:00:55 UTC

NP-MRD ID

NP0317871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid

Description

Micacocidin belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. (4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid was first documented in 2013 (PMID: 23790487). Based on a literature review a small amount of articles have been published on Micacocidin (PMID: 31293678) (PMID: 30533677) (PMID: 26507693) (PMID: 24202877).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112220002D          

 37 40  0  0  1  0            999 V2000
   -1.5356    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6486   -1.9986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4736   -1.9986    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7285   -2.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0611   -3.2681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0611   -4.0931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3466   -4.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7756   -4.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3631   -5.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881   -3.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4900   -4.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2437   -4.5826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7958   -5.1957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3478   -4.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4632   -5.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2169   -5.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3770   -6.5011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3833   -5.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5763   -5.7386    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937   -2.7832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6090   -3.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 S   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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 33  1  0  0  0  0
 19 34  1  0  0  0  0
 16 34  1  1  0  0  0
 34 35  1  0  0  0  0
 15 36  1  0  0  0  0
 36 37  1  0  0  0  0
 13 37  1  0  0  0  0
M  END

     RDKit          3D

 76 79  0  0  0  0  0  0  0  0999 V2000
   -2.1336   -0.2475   -3.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314   -1.1755   -2.0122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0649   -0.3854   -0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6545   -1.2598    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0533   -0.6056    1.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0176    0.4683    1.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3655    0.0994    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3265    0.9672    0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9107    2.2203    0.3498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5780    2.6708    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3186    3.9431    0.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6448    1.7293    0.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618    2.1678    1.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658    1.6279    1.7147 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542    2.2812    1.8396 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1930    1.6204    2.0603 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3451    0.6314    3.6159 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735   -0.0904    3.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0315    0.4204    1.6872 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9118   -0.3732    0.7688 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4074   -1.6497    0.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0954    0.2683   -0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7632    0.4359   -1.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7420    1.6185   -0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9483   -0.6024   -1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4413   -1.7297   -1.2380 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144   -2.3689   -2.1813 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6850   -2.2257   -1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656   -3.8270   -2.1651 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4409   -4.5970   -2.9525 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9223   -4.3101   -1.2919 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0145   -1.8067   -3.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -0.1303   -3.0956 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6574    0.5680    1.1802 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0857   -0.6669    1.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    3.2406    0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6491    3.7787    0.6047 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2960   -0.6723   -4.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0448   -0.0936   -2.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6261    0.7522   -3.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5991   -1.6814   -2.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9569   -1.9448   -1.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1258    0.0957   -0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7592    0.4185   -1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5654   -1.8059   -0.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9270   -2.1054    0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6177   -1.4061    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1928   -0.3246    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6499   -0.9010    1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3803    0.6738    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6247    2.9752   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6469    4.5814    0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1914    3.0168    2.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0638    2.3608    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0077   -1.1634    3.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7794    0.4180    3.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    1.4874    1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9266   -0.5384    1.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062   -2.3739    0.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2302    1.3460   -0.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -0.4784   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9312    0.5026   -2.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963    1.8272   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5711    1.6785    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9974    2.4390   -0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9771   -1.1751   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2758   -2.8621   -2.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7474   -2.5939   -0.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191   -4.8934   -0.5197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2068   -2.2863   -4.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9718   -1.7420   -4.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -1.1457    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8794   -0.4850    2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614   -1.4473    1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5714    2.7524   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600    4.0886    0.9609 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  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 36  1  0
 36 37  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 32  1  0
 32 33  1  0
 27 29  1  6
 29 31  1  0
 29 30  2  0
 19 34  1  0
 34 35  1  0
 12  6  1  0
 37 13  1  0
 34 16  1  0
 33 25  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
  4 46  1  0
  5 47  1  0
  5 48  1  0
  7 49  1  0
  8 50  1  0
  9 51  1  0
 11 52  1  0
 15 53  1  1
 36 75  1  0
 36 76  1  0
 16 54  1  1
 18 55  1  0
 18 56  1  0
 19 57  1  1
 20 58  1  1
 21 59  1  0
 23 60  1  0
 23 61  1  0
 23 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 28 66  1  0
 28 67  1  0
 28 68  1  0
 32 70  1  0
 32 71  1  0
 31 69  1  0
 35 72  1  0
 35 73  1  0
 35 74  1  0
M  END


  Mrv1652309112220002D          

 37 40  0  0  1  0            999 V2000
   -1.5356    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6486   -1.9986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4736   -1.9986    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7285   -2.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0611   -3.2681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0611   -4.0931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3466   -4.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7756   -4.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3631   -5.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1881   -3.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4900   -4.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2437   -4.5826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7958   -5.1957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3478   -4.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4632   -5.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2169   -5.3450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3770   -6.5011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3833   -5.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5763   -5.7386    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937   -2.7832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6090   -3.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 S   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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 33  1  0  0  0  0
 19 34  1  0  0  0  0
 16 34  1  1  0  0  0
 34 35  1  0  0  0  0
 15 36  1  0  0  0  0
 36 37  1  0  0  0  0
 13 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=CC=CC(O)=C1C1=N[C@H](CS1)[C@H]1SC[C@@H]([C@@H](O)C(C)(C)C2=N[C@](C)(CS2)C(O)=O)N1C

> <INCHI_IDENTIFIER>
InChI=1S/C27H39N3O4S3/c1-6-7-8-10-16-11-9-12-19(31)20(16)22-28-17(13-35-22)23-30(5)18(14-36-23)21(32)26(2,3)24-29-27(4,15-37-24)25(33)34/h9,11-12,17-18,21,23,31-32H,6-8,10,13-15H2,1-5H3,(H,33,34)/t17-,18+,21-,23-,27-/m1/s1

> <INCHI_KEY>
GGWOUCUSNYVHOC-QJKBBIFYSA-N

> <FORMULA>
C27H39N3O4S3

> <MOLECULAR_WEIGHT>
565.81

> <EXACT_MASS>
565.21027027

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
59.873522166156086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-2-[(1S)-1-hydroxy-1-[(2R,4R)-2-[(4R)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid

> <JCHEM_LOGP>
4.704691297244372

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.71981757053879

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.613080301440582

> <JCHEM_PKA_STRONGEST_BASIC>
5.499212939085599

> <JCHEM_POLAR_SURFACE_AREA>
105.72

> <JCHEM_REFRACTIVITY>
155.10609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-2-[(1S)-1-hydroxy-1-[(2R,4R)-2-[(4R)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5H-1,3-thiazole-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.867   1.425   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.533   2.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.199   1.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.134   2.195   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.468   1.425   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.802   3.735   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.136   4.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.469   3.735   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.803   1.425   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.381  -1.020   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       5.906  -2.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.811  -3.731   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0       8.351  -3.731   0.000  0.00  0.00           S+0
HETATM   18  C   UNK     0       8.827  -5.195   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.581  -6.101   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.581  -7.641   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.247  -8.411   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.914  -8.411   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.144  -9.744   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.684  -7.077   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.248  -9.181   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      11.655  -8.554   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      12.685  -9.699   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.716  -8.554   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.931 -10.604   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.338  -9.977   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.770 -12.135   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.915 -11.032   0.000  0.00  0.00           C+0
HETATM   33  S   UNK     0      10.409 -10.712   0.000  0.00  0.00           S+0
HETATM   34  N   UNK     0       6.335  -5.195   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       4.870  -5.671   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.366  -2.485   0.000  0.00  0.00           C+0
HETATM   37  S   UNK     0       3.890  -1.020   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12   14   37                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   36                                                  
CONECT   16   15   17   34                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29   32                                             
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   27   33                                                       
CONECT   33   32   25                                                       
CONECT   34   19   16   35                                                  
CONECT   35   34                                                            
CONECT   36   15   37                                                       
CONECT   37   36   13                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉N₃O₄S₃

Average Mass

565.8100 Da

Monoisotopic Mass

565.21027 Da

IUPAC Name

(4S)-2-[(1S)-1-hydroxy-1-[(2R,4R)-2-[(4R)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid

Traditional Name

(4S)-2-[(1S)-1-hydroxy-1-[(2R,4R)-2-[(4R)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5H-1,3-thiazole-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC=CC(O)=C1C1=N[C@H](CS1)[C@H]1SC[C@@H]([C@@H](O)C(C)(C)C2=N[C@](C)(CS2)C(O)=O)N1C

InChI Identifier

InChI=1S/C27H39N3O4S3/c1-6-7-8-10-16-11-9-12-19(31)20(16)22-28-17(13-35-22)23-30(5)18(14-36-23)21(32)26(2,3)24-29-27(4,15-37-24)25(33)34/h9,11-12,17-18,21,23,31-32H,6-8,10,13-15H2,1-5H3,(H,33,34)/t17-,18+,21-,23-,27-/m1/s1

InChI Key

GGWOUCUSNYVHOC-QJKBBIFYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic 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	4.7	ChemAxon
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.72 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	155.11 m³·mol⁻¹	ChemAxon
Polarizability	59.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00016026

Chemspider ID

34485487

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135415284

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Diettrich J, Kage H, Nett M: Genomics-inspired discovery of massiliachelin, an agrochelin epimer from Massilia sp. NR 4-1. Beilstein J Org Chem. 2019 Jun 13;15:1298-1303. doi: 10.3762/bjoc.15.128. eCollection 2019. [PubMed:31293678 ]
Montecillo AD, Raymundo AK, Papa IA, Aquino GMB, Jacildo AJ, Stothard P, Rosana ARR: Near-Complete Genome Sequence of Ralstonia solanacearum T523, a Phylotype I Tomato Phytopathogen Isolated from the Philippines. Microbiol Resour Announc. 2018 Sep 27;7(12). pii: MRA01048-18. doi: 10.1128/MRA.01048-18. eCollection 2018 Sep. [PubMed:30533677 ]
Kage H, Riva E, Parascandolo JS, Kreutzer MF, Tosin M, Nett M: Chemical chain termination resolves the timing of ketoreduction in a partially reducing iterative type I polyketide synthase. Org Biomol Chem. 2015 Dec 21;13(47):11414-7. doi: 10.1039/c5ob02009c. Epub 2015 Oct 28. [PubMed:26507693 ]
Kreutzer MF, Kage H, Herrmann J, Pauly J, Hermenau R, Muller R, Hoffmeister D, Nett M: Precursor-directed biosynthesis of micacocidin derivatives with activity against Mycoplasma pneumoniae. Org Biomol Chem. 2014 Jan 7;12(1):113-8. doi: 10.1039/c3ob41839a. Epub 2013 Nov 8. [PubMed:24202877 ]
Kage H, Kreutzer MF, Wackler B, Hoffmeister D, Nett M: An iterative type I polyketide synthase initiates the biosynthesis of the antimycoplasma agent micacocidin. Chem Biol. 2013 Jun 20;20(6):764-71. doi: 10.1016/j.chembiol.2013.04.010. [PubMed:23790487 ]
LOTUS database [Link]

Showing NP-Card for (4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid (NP0317871)

MOL for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)

3D MOL for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)

3D SDF for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)

3D-SDF for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)

PDB for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)

3D PDB for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)

SMILES for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)

INCHI for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)

Structure for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)

3D Structure for NP0317871 ((4s)-2-[(1s)-1-hydroxy-1-[(2r,4r)-2-[(4r)-2-(2-hydroxy-6-pentylphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidin-4-yl]-2-methylpropan-2-yl]-4-methyl-5h-1,3-thiazole-4-carboxylic acid)