NP-MRD: Showing NP-Card for (2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone (NP0244392)

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Record Information

Version

2.0

Created at

2022-09-07 05:10:27 UTC

Updated at

2022-09-07 05:10:27 UTC

NP-MRD ID

NP0244392

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone

Description

Apratoxin C belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. (2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone was first documented in 2010 (PMID: 20704304). Based on a literature review a small amount of articles have been published on apratoxin C (PMID: 26584466) (PMID: 25093538).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207102D          

 58 61  0  0  1  0            999 V2000
   11.5697    3.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0995    3.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2774    3.0919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.9253    3.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8072    2.4139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1593    1.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6892    0.9899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9815    1.5996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5823    2.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3056    1.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1519    0.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3335    0.8535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8517    0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0463    0.2685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9560   -0.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2099   -1.0804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0562   -1.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2773   -2.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6812   -2.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6445   -0.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7489   -0.3660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2642   -1.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3969    0.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5747    0.4483    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1045   -0.2297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2226    1.1944    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6928    1.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4004    1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484    2.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2262    2.0768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8742    2.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3443    3.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1665    3.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9922    4.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1701    4.3152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4624    4.9249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2845    4.8568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7547    5.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    6.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5804    6.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    7.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6985    7.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3465    8.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5243    8.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5207    7.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8727    6.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6366    4.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6547    3.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4588    4.0425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9289    4.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8108    3.2964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3407    2.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6330    3.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1031    3.9061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9851    2.4821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5149    1.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0659    1.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7438    0.7631    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  1  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12  8  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 30 29  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  4  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 42 45  1  0  0  0  0
 45 46  2  0  0  0  0
 39 46  1  0  0  0  0
 37 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 51 52  1  6  0  0  0
 51 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
  5 55  1  0  0  0  0
 55 56  1  0  0  0  0
 30 57  1  0  0  0  0
 57 58  1  0  0  0  0
 28 58  1  0  0  0  0
M  END

     RDKit          3D

125128  0  0  0  0  0  0  0  0999 V2000
   -2.8718   -5.7841   -1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8649   -4.9407   -1.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772   -4.7240   -1.2653 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0812   -6.0688   -1.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -3.8078   -0.0933 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6406   -4.0357    0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4480   -4.8397    1.8840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124   -3.4282    0.8908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2056   -3.9292    1.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351   -3.3390    0.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4785   -2.4221   -0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2377   -2.1179    0.3692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5819   -1.2931    1.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6800   -1.3406    2.4726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344   -0.6319    1.6260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2027    0.6364    1.3944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5852    0.6180    0.7406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2763    1.9601    0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4164   -0.3787    1.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2865    1.6291    0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2063    1.6612   -0.6983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9397    2.8879   -1.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7323    1.8979   -1.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2593    3.2530   -0.5894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1134    4.1687   -1.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210    3.1546    0.1155 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0014    4.1038    1.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    3.5794   -0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117    3.3488   -0.6261 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2162    4.4802   -0.8574 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6426    4.1702   -0.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    3.5784    0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5486    4.1947    0.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8580    2.3359    0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704    2.2677    2.2331 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191    1.3374    0.2168 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6566    0.9269   -1.1231 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8204   -0.0402   -1.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0476    0.4832   -0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9733    1.1916   -1.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1318    1.6959   -0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4148    1.5058    0.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5686    1.9982    1.1923 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7946    1.7701    2.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5119    0.8096    1.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3644    0.3143    0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510    0.3702   -1.7751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9468    1.0648   -2.7225 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8121   -0.8443   -1.4524 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559   -1.7155   -2.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5702   -1.2998   -0.0982 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3398   -0.7252    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8777   -3.2527   -0.2039 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7497   -3.6878    0.5090 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1348   -4.5766    1.6235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8861    5.0261   -2.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1016    4.5618   -2.2849 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397   -5.3063   -1.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4144   -6.1445   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0697   -6.7523   -1.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5919   -5.4841   -2.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -3.9737   -2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1070   -4.2651   -2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4063   -6.6561   -0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -5.9034   -0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0162   -6.6164   -1.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -2.7612   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663   -3.5405    2.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2757   -5.0251    1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7063   -4.1497   -0.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0835   -2.8865    0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1730   -2.9435   -1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0386   -1.5251   -0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -1.6579   -0.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4390    1.0628    2.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5469    0.2818   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5512    2.6833    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6588    2.3030   -0.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1374    1.9186    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7750   -1.1923    0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3357    0.0845    1.9496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8497   -0.8578    2.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5139    2.6706    1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2634    1.4319    1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4970    0.7493   -1.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1257    3.6387   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8884    2.6436   -1.6889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366    3.4465   -1.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888    1.8665   -2.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1733    1.1343   -0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0391    3.6249    0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4158    5.0824   -1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309072207102D          

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 30 57  1  0  0  0  0
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 28 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244392

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H]1N(C)C(=O)[C@H](C)N(C)C(=O)[C@H](CC2=CC=C(OC)C=C2)N=C(O)\C(C)=C\[C@H]2CSC(=N2)[C@@H](C)[C@@H](O)C[C@H](C)C[C@H](OC(=O)[C@@H]2CCCN2C1=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C44H67N5O8S/c1-12-27(5)38-43(54)49-19-13-14-35(49)44(55)57-37(25(2)3)21-26(4)20-36(50)29(7)40-45-32(24-58-40)22-28(6)39(51)46-34(23-31-15-17-33(56-11)18-16-31)42(53)47(9)30(8)41(52)48(38)10/h15-18,22,25-27,29-30,32,34-38,50H,12-14,19-21,23-24H2,1-11H3,(H,46,51)/b28-22+/t26-,27-,29-,30-,32-,34-,35-,36-,37-,38-/m0/s1

> <INCHI_KEY>
OIRVOJCFIYCVDL-ADWUXKIFSA-N

> <FORMULA>
C44H67N5O8S

> <MOLECULAR_WEIGHT>
826.11

> <EXACT_MASS>
825.471035311

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
91.71461579200786

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-[(2S)-butan-2-yl]-3,24-dihydroxy-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-7-(propan-2-yl)-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0^{10,14}]triaconta-1(30),23,25-triene-9,15,18,21-tetrone

> <JCHEM_LOGP>
5.839109660100923

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.806799904167963

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.904334768950481

> <JCHEM_PKA_STRONGEST_BASIC>
3.919810111544508

> <JCHEM_POLAR_SURFACE_AREA>
161.64000000000001

> <JCHEM_REFRACTIVITY>
226.7951

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-[(2S)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0^{10,14}]triaconta-1(30),23,25-triene-9,15,18,21-tetrone

> <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      21.597   6.910   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.719   5.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.184   5.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.527   7.164   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.307   4.506   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.964   3.113   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      18.086   1.848   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      20.499   2.986   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      21.620   4.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.971   3.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.684   1.788   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.156   1.593   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.257   0.168   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.753   0.501   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      20.451  -1.360   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      19.058  -2.017   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.772  -3.530   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.318  -4.038   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.938  -4.535   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.003  -0.895   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.331  -0.683   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.426  -1.929   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.674   0.709   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.139   0.837   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.262  -0.429   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.482   2.229   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.360   3.495   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.947   2.357   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      11.290   3.749   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       9.756   3.877   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.098   5.269   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.976   6.535   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.511   6.408   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.319   7.928   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.784   8.055   0.000  0.00  0.00           O+0
HETATM   36  N   UNK     0      10.196   9.193   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0      11.731   9.066   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.609  10.331   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.952  11.724   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.417  11.851   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.760  13.244   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.637  14.510   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       9.980  15.902   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.445  16.030   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.172  14.382   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.829  12.990   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.388   7.673   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      12.422   6.134   0.000  0.00  0.00           O+0
HETATM   49  N   UNK     0      13.923   7.546   0.000  0.00  0.00           N+0
HETATM   50  C   UNK     0      14.801   8.811   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      14.580   6.153   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      13.703   4.888   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      16.115   6.026   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      16.993   7.291   0.000  0.00  0.00           O+0
HETATM   55  N   UNK     0      16.772   4.633   0.000  0.00  0.00           N+0
HETATM   56  C   UNK     0      15.895   3.368   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       9.456   2.302   0.000  0.00  0.00           C+0
HETATM   58  S   UNK     0      10.722   1.424   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   55                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   58                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   57                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   47                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   46                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43                                                            
CONECT   45   42   46                                                       
CONECT   46   45   39                                                       
CONECT   47   37   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53    5   56                                                  
CONECT   56   55                                                            
CONECT   57   30   58                                                       
CONECT   58   57   28                                                       
MASTER        0    0    0    0    0    0    0    0   58    0  122    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-[(2S)-Butan-2-yl]-3-hydroxy-22-(4-methoxybenzyl)-2,5,17,19,20,25-hexamethyl-7-(propan-2-yl)-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0(10,14)]triaconta-1(30),25-diene-9,15,18,21,24-pentone	ChEBI
N-((2E)-3-((4S)-2-((1S,2S,4S,6S)-2,6-Dihydroxy-1,4,7-trimethyloctyl)-4,5-dihydro-4-thiazolyl)-2-methyl-1-oxo-2-propenyl)-O-methyl-L-tyrosyl-N-methyl-L-alanyl-N-methyl-L-isoleucyl-L-proline (4-16)-lactone	ChEBI

Chemical Formula

C₄₄H₆₇N₅O₈S

Average Mass

826.1100 Da

Monoisotopic Mass

825.47104 Da

IUPAC Name

(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-[(2S)-butan-2-yl]-3,24-dihydroxy-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-7-(propan-2-yl)-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0^{10,14}]triaconta-1(30),23,25-triene-9,15,18,21-tetrone

Traditional Name

(2S,3S,5S,7S,10S,16S,19S,22S,25E,27S)-16-[(2S)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0^{10,14}]triaconta-1(30),23,25-triene-9,15,18,21-tetrone

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H]1N(C)C(=O)[C@H](C)N(C)C(=O)[C@H](CC2=CC=C(OC)C=C2)N=C(O)\C(C)=C\[C@H]2CSC(=N2)[C@@H](C)[C@@H](O)C[C@H](C)C[C@H](OC(=O)[C@@H]2CCCN2C1=O)C(C)C

InChI Identifier

InChI=1S/C44H67N5O8S/c1-12-27(5)38-43(54)49-19-13-14-35(49)44(55)57-37(25(2)3)21-26(4)20-36(50)29(7)40-45-32(24-58-40)22-28(6)39(51)46-34(23-31-15-17-33(56-11)18-16-31)42(53)47(9)30(8)41(52)48(38)10/h15-18,22,25-27,29-30,32,34-38,50H,12-14,19-21,23-24H2,1-11H3,(H,46,51)/b28-22+/t26-,27-,29-,30-,32-,34-,35-,36-,37-,38-/m0/s1

InChI Key

OIRVOJCFIYCVDL-ADWUXKIFSA-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 cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Alpha-amino acid ester
Macrolactam
Alpha-amino acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Imidothiolactone
Benzenoid
Pyrrolidine
Meta-thiazoline
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Secondary alcohol
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Ether
Oxacycle
Carboxylic acid derivative
Organic oxide
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

apratoxin (CHEBI:35216 )

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	5.84	ChemAxon
pKa (Strongest Acidic)	5.9	ChemAxon
pKa (Strongest Basic)	3.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	161.64 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	226.8 m³·mol⁻¹	ChemAxon
Polarizability	91.71 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

C00027886

Chemspider ID

5256890

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6857554

PDB ID

Not Available

ChEBI ID

35216

Good Scents ID

Not Available

References

General References

Matthew S, Salvador LA, Schupp PJ, Paul VJ, Luesch H: Cytotoxic halogenated macrolides and modified peptides from the apratoxin-producing marine cyanobacterium Lyngbya bouillonii from Guam. J Nat Prod. 2010 Sep 24;73(9):1544-52. doi: 10.1021/np1004032. [PubMed:20704304 ]
Yoshida M, Onda Y, Masuda Y, Doi T: Potent oxazoline analog of apratoxin C: Synthesis, biological evaluation, and conformational analysis. Biopolymers. 2016 Nov 4;106(4):404-14. doi: 10.1002/bip.22781. [PubMed:26584466 ]
Masuda Y, Suzuki J, Onda Y, Fujino Y, Yoshida M, Doi T: Total synthesis and conformational analysis of apratoxin C. J Org Chem. 2014 Sep 5;79(17):8000-9. doi: 10.1021/jo501130b. Epub 2014 Aug 18. [PubMed:25093538 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone (NP0244392)

MOL for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)

3D MOL for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)

3D SDF for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)

3D-SDF for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)

PDB for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)

3D PDB for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)

SMILES for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)

INCHI for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)

Structure for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)

3D Structure for NP0244392 ((2s,3s,5s,7s,10s,16s,19s,22s,25e,27s)-16-[(2s)-butan-2-yl]-3,24-dihydroxy-7-isopropyl-22-[(4-methoxyphenyl)methyl]-2,5,17,19,20,25-hexamethyl-8-oxa-29-thia-14,17,20,23,30-pentaazatricyclo[25.2.1.0¹⁰,¹⁴]triaconta-1(30),23,25-triene-9,15,18,21-tetrone)