NP-MRD: Showing NP-Card for (1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one (NP0248740)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 11:06:19 UTC

Updated at

2022-09-07 11:06:19 UTC

NP-MRD ID

NP0248740

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one

Description

Thailandepsin B belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone. (1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one is found in Chromobacterium violaceum. (1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one was first documented in 2011 (PMID: 21793558). Based on a literature review a small amount of articles have been published on Thailandepsin B (PMID: 32725698) (PMID: 27373645) (PMID: 25558934) (PMID: 22531354).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213062D          

 35 36  0  0  1  0            999 V2000
   -0.7186    3.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6145    2.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1463    1.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2503    1.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    0.7862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0543    1.6101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511    1.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    2.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1615    0.8604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1417    0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9386   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1521   -0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688   -1.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -1.3168    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885   -1.9001    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3916   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114   -0.8897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6146   -0.6762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010    0.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003    0.3169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -2.3103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5502   -1.9001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1336   -1.3168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3471   -2.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1440   -2.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7637   -2.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -3.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -1.5303    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5716   -2.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138   -0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3003   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8836    0.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5034    0.0635    0.0000 O   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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  4  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
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  4  0  0  0
 18 22  1  0  0  0  0
 22 23  1  4  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 10 35  1  6  0  0  0
M  END

     RDKit          3D

 74 75  0  0  0  0  0  0  0  0999 V2000
    5.0663   -1.0034   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9593   -2.1624    0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5132   -2.4779    0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003   -1.2796    0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776   -1.6365    1.2084 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5624   -0.6392    1.7857 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714    0.4732    2.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6299    0.8191    3.6576 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2262    1.5940    1.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1520    2.7002    1.5222 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8505    4.0084    1.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282    4.6715    0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665    4.1241   -0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849    4.1004   -1.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7789    2.9974   -2.7911 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3568    0.9558   -2.3826 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052    0.5993   -2.4972 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3186   -0.8896   -2.2222 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5781   -1.3180   -0.9519 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7828   -2.1555   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5843   -3.5314   -0.0502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1324   -1.1038   -2.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4618   -0.9096   -3.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9358   -1.4240   -1.6779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713   -0.9210   -0.5358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6823   -1.8200   -0.0232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2059   -3.2742   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777   -1.4385    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2904   -2.4351    1.7270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0374    0.4863   -0.5756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4305    0.5267   -0.6147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6205    1.3120    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9290    2.5604    0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    3.4132   -0.3850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784    2.6482    0.3212 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0479   -0.9878   -1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8783   -0.0701   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148   -1.2287   -1.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5697   -1.9861    0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3691   -3.0533   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5020   -3.3606    0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0349   -2.7279   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -0.9908    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154   -0.4657    0.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169   -2.4594    1.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5003    0.9936    4.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1632    1.9824    1.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3652    1.2817    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5119    2.5103    2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8749    4.4493    2.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2136    5.7527    0.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655    3.1390   -0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803    4.7903   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098    3.8440   -1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8376    5.1191   -2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    1.2665   -1.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3311    0.7357   -3.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526   -1.3507   -3.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3318   -4.1119    0.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6636   -1.7496   -4.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8019   -0.9571    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5398   -1.7712   -0.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1183   -3.5945    1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2349   -3.3130   -0.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9514   -3.9183   -0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3556   -1.6384    2.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5697   -0.4340    1.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8273   -2.7666    0.8131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0059   -1.9785    2.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527   -3.3323    2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7361    1.0132   -1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7782    1.4456   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9767    0.7017    1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5094    1.6506    1.2302 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
  7  9  1  0
  9 10  1  0
 10 35  1  0
 35 33  1  0
 33 34  2  0
 33 32  1  0
 32 30  1  0
 30 31  1  0
 30 25  1  0
 25 24  1  0
 24 22  2  0
 22 23  1  0
 22 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 20  5  1  0
 11 10  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  1
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  1
 32 73  1  0
 32 74  1  0
 30 71  1  6
 31 72  1  0
 25 61  1  1
 23 60  1  0
 18 58  1  6
 17 56  1  0
 17 57  1  0
 14 54  1  0
 14 55  1  0
 13 52  1  0
 13 53  1  0
 12 51  1  0
 11 50  1  0
 21 59  1  0
 26 62  1  6
 27 63  1  0
 27 64  1  0
 27 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 29 70  1  0
M  END


  Mrv1652309072213062D          

 35 36  0  0  1  0            999 V2000
   -0.7186    3.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6145    2.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1463    1.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2503    1.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0111    0.7862    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0543    1.6101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511    1.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    2.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1615    0.8604    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1417    0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9386   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1521   -0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5688   -1.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -1.3168    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1885   -1.9001    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3916   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114   -0.8897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6146   -0.6762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4010    0.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4003    0.3169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7533   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -2.3103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5502   -1.9001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1336   -1.3168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3471   -2.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1440   -2.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7637   -2.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -3.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304   -1.5303    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5716   -2.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138   -0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3003   -0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8836    0.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5034    0.0635    0.0000 O   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
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  4  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
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  4  0  0  0
 18 22  1  0  0  0  0
 22 23  1  4  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 10 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0248740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC[C@H]1N=C(O)C[C@@H]2OC(=O)C[C@H](O)[C@H](N=C(O)[C@@H](CSSCCC=C2)N=C1O)C(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C24H39N3O6S2/c1-4-6-10-17-23(31)26-18-14-35-34-11-8-7-9-16(12-20(29)25-17)33-21(30)13-19(28)22(15(3)5-2)27-24(18)32/h7,9,15-19,22,28H,4-6,8,10-14H2,1-3H3,(H,25,29)(H,26,31)(H,27,32)/t15?,16-,17-,18-,19+,22-/m1/s1

> <INCHI_KEY>
MUNWAZFRKGVMPQ-WCXJMSLPSA-N

> <FORMULA>
C24H39N3O6S2

> <MOLECULAR_WEIGHT>
529.71

> <EXACT_MASS>
529.228028336

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.88544378935408

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5S,6R,9S,20R)-6-(butan-2-yl)-20-butyl-5,8,18,21-tetrahydroxy-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one

> <JCHEM_LOGP>
-2.487742742352096

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
-6.421346733062825

> <JCHEM_PKA_STRONGEST_ACIDIC>
-9.810677992973485

> <JCHEM_PKA_STRONGEST_BASIC>
15.642416521746982

> <JCHEM_POLAR_SURFACE_AREA>
144.3

> <JCHEM_REFRACTIVITY>
140.17899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,6R,9S,20R)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.341   5.714   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.147   4.187   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.273   3.591   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.467   2.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.887   1.468   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.968   3.005   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.455   3.404   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.007   4.842   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.294   2.112   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.902   1.606   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.865   0.119   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.352  -0.280   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.751  -1.768   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.662  -2.857   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0       5.174  -2.458   0.000  0.00  0.00           S+0
HETATM   16  S   UNK     0       4.085  -3.547   0.000  0.00  0.00           S+0
HETATM   17  C   UNK     0       2.598  -3.148   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.635  -1.661   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.147  -1.262   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.749   0.225   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.747   0.592   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.273  -3.148   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.265  -4.313   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       4.760  -3.547   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       5.849  -2.458   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.248  -3.945   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.735  -4.344   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.159  -5.034   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.558  -6.522   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.337  -2.857   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.534  -3.826   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.426  -1.768   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.027  -0.280   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.116   0.809   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       6.540   0.119   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   35                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19    5   21                                                  
CONECT   21   20                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   10                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₉N₃O₆S₂

Average Mass

529.7100 Da

Monoisotopic Mass

529.22803 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCC[C@H]1N=C(O)C[C@@H]2OC(=O)C[C@H](O)[C@H](N=C(O)[C@@H](CSSCCC=C2)N=C1O)C(C)CC

InChI Identifier

InChI=1S/C24H39N3O6S2/c1-4-6-10-17-23(31)26-18-14-35-34-11-8-7-9-16(12-20(29)25-17)33-21(30)13-19(28)22(15(3)5-2)27-24(18)32/h7,9,15-19,22,28H,4-6,8,10-14H2,1-3H3,(H,25,29)(H,26,31)(H,27,32)/t15?,16-,17-,18-,19+,22-/m1/s1

InChI Key

MUNWAZFRKGVMPQ-WCXJMSLPSA-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

Species Name	Source	Reference
Chromobacterium violaceum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cyclic peptides

Alternative Parents

Substituents

Cyclic alpha peptide
Macrolide
Cyclic carboximidic acid
Secondary alcohol
Organic disulfide
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587929

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang C, Henkes LM, Doughty LB, He M, Wang D, Meyer-Almes FJ, Cheng YQ: Thailandepsins: bacterial products with potent histone deacetylase inhibitory activities and broad-spectrum antiproliferative activities. J Nat Prod. 2011 Oct 28;74(10):2031-8. doi: 10.1021/np200324x. Epub 2011 Jul 27. [PubMed:21793558 ]
Brosowsky J, Lutterbeck M, Liebich A, Keller M, Herp D, Vogelmann A, Jung M, Breit B: Syntheses of Thailandepsin B Pseudo-Natural Products: Access to New Highly Potent HDAC Inhibitors via Late-Stage Modification. Chemistry. 2020 Dec 9;26(69):16241-16245. doi: 10.1002/chem.202002449. Epub 2020 Nov 3. [PubMed:32725698 ]
Narita K, Katoh T: Total Synthesis of Thailandepsin B, a Potent HDAC Inhibitor Isolated from a Microorganism. Chem Pharm Bull (Tokyo). 2016;64(7):913-7. doi: 10.1248/cpb.c16-00060. [PubMed:27373645 ]
Cheng Z, Ding L, Zhang Y, Chen G, Chen C, Cheng YQ, Jiang H: Determination of thailandepsin B in rat plasma with a LC-MS/MS method. Bioanalysis. 2015;7(1):39-52. doi: 10.4155/bio.14.264. [PubMed:25558934 ]
Wilson AJ, Cheng YQ, Khabele D: Thailandepsins are new small molecule class I HDAC inhibitors with potent cytotoxic activity in ovarian cancer cells: a preclinical study of epigenetic ovarian cancer therapy. J Ovarian Res. 2012 Apr 24;5(1):12. doi: 10.1186/1757-2215-5-12. [PubMed:22531354 ]
LOTUS database [Link]

Showing NP-Card for (1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one (NP0248740)

MOL for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)

3D MOL for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)

3D SDF for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)

3D-SDF for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)

PDB for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)

3D PDB for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)

SMILES for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)

INCHI for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)

Structure for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)

3D Structure for NP0248740 ((1s,5s,6r,9s,20r)-20-butyl-5,8,18,21-tetrahydroxy-6-(sec-butyl)-2-oxa-11,12-dithia-7,19,22-triazabicyclo[7.7.6]docosa-7,15,18,21-tetraen-3-one)