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Teniposide
Teniposide ID: B184438
CAS:29767-20-2
Supplier:BEYOND PHARMATECH CORPORATION LIMITED

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SMILES:[C@@H]12[C@@H](c3c([C@H]([C@H]1C(=O)OC2)c1cc(c(c(c1)OC)O)OC)cc1c(c3)OCO1)OC1C(C(C2OC(c3sccc3)OCC2O1)O)O	
FORMULA: C32H32O13S
MASS: 656.6537
EXACT MASS: 656.1563621
INTERATOMIC DISTANCES

              C   1      C   2      C   3      C   4      C   5      C   6
              ------------------------------------------------------------------
   C   1    0.0000 
   C   2    0.7510     0.0000 
   C   3    1.2958     0.7546     0.0000 
   C   4    1.4972     1.3065     0.7500     0.0000 
   C   5    0.7500     1.3044     1.4972     1.2958     0.0000 
   C   6    1.2921     1.5000     1.2900     0.7426     0.7463     0.0000 
   C   7    3.4081     2.6728     2.5753     3.2482     3.9413     3.8652 
   C   8    1.9736     1.2843     1.4958     2.2458     2.5887     2.6892 
   O   9    4.1407     3.3996     3.2402     3.8704     4.6504     4.5247 
   C  10    2.2347     1.4838     1.2894     1.9764     2.6903     2.5794 
   C  11    2.9779     2.2270     1.9682     2.5846     3.4168     3.2451 
   O  12    2.5815     1.9621     2.2375     2.9875     3.2531     3.4142 
   O  13    1.2935     0.7375     1.2956     1.9805     1.9791     2.2375 
   C  14    3.2417     2.5665     2.6831     3.4167     3.8709     3.9372 
   C  15    1.9727     2.2458     1.9713     1.2864     1.2885     0.7458 
   C  16    4.6445     3.9265     3.8647     4.5316     5.2126     5.1547 
   C  17    1.2110     1.9239     2.2343     2.0213     0.7485     1.3694 
   C  18    1.9727     1.2918     0.7411     1.2915     2.2383     1.9673 
   C  19    2.2363     1.9795     1.2879     0.7391     1.9719     1.2875 
   C  20    3.4125     3.7333     3.4117     2.6790     2.6800     2.2333 
   O  21    1.2149     1.9548     2.4792     2.4779     1.2123     1.9491 
   C  22    5.3628     4.6357     4.5234     5.1598     5.9095     5.8106 
   C  23    0.7497     1.3666     2.0218     2.2361     1.2143     1.9180 
   O  24    4.5178     3.8487     3.9305     4.6468     5.1531     5.2018 
   C  25    3.2450     3.4206     2.9750     2.2250     2.5748     1.9673 
   C  26    2.9750     3.4183     3.2416     2.5707     2.2250     1.9660 
   C  27    2.6877     2.2404     1.4859     1.2875     2.5833     1.9693 
   C  28    2.5833     1.9751     1.2875     1.4900     2.6900     2.2326 
   C  29    2.5785     2.6921     2.2292     1.4792     1.9665     1.2864 
   C  30    2.2292     2.6892     2.5743     1.9610     1.4792     1.2843 
   S  31    5.6867     4.9412     4.7190     5.2897     6.1685     5.9818 
   C  32    3.8580     3.2252     3.4037     4.1432     4.5238     4.6399 
   O  33    3.2958     2.6460     2.0053     2.2212     3.4314     2.9629 
   O  34    3.4290     2.9704     2.2175     2.0044     3.2952     2.6413 
   C  35    3.7513     3.1773     2.4649     2.4675     3.7529     3.1732 
   C  36    5.9465     5.2377     5.1845     5.8436     6.5291     6.4744 
   O  37    1.9341     2.6101     2.8017     2.4237     1.3288     1.6884 
   C  38    6.4090     5.6657     5.4537     6.0233     6.9002     6.7167 
   C  39    6.5702     5.8449     5.7248     6.3472     7.1190     7.0092 
   O  40    2.6843     1.9653     1.4871     1.9777     2.9842     2.6872 
   O  41    3.4116     2.6797     2.2296     2.6872     3.7268     3.4109 
   O  42    4.1430     4.4750     4.1424     3.4035     3.4043     2.9750 
   O  43    3.4020     3.9399     3.8606     3.2334     2.6690     2.5707 
   O  44    3.8628     3.9426     3.4028     2.6700     3.2359     2.5707 
   C  45    4.1287     4.6434     4.5141     3.8498     3.3897     3.2302 
   C  46    3.9401     3.8771     3.2416     2.5707     3.4094     2.6816 

              C   7      C   8      O   9      C  10      C  11      O  12
              ------------------------------------------------------------------
   C   7    0.0000 
   C   8    1.4822     0.0000 
   O   9    0.7432     2.2255     0.0000 
   C  10    1.2859     0.7468     1.9651     0.0000 
   C  11    0.7417     1.2875     1.2859     0.7432     0.0000 
   O  12    1.2833     0.7417     1.9612     1.2900     1.4859     0.0000 
   O  13    2.2255     0.7432     2.9687     1.2875     1.9653     1.2879 
   C  14    0.7447     1.2822     1.2875     1.4875     1.2885     0.7375 
   C  15    4.5276     3.4183     5.1567     3.2476     3.8709     4.1493 
   C  16    1.2894     2.6755     0.7458     2.5753     1.9672     2.2239 
   C  17    4.5964     3.1821     5.3203     3.3779     4.1150     3.7878 
   C  18    1.9712     1.2993     2.5789     0.7500     1.2931     1.9766 
   C  19    3.4135     2.6921     3.9411     2.2375     2.6892     3.4166 
   C  20    5.9084     4.8876     6.4898     4.6513     5.2142     5.6237 
   O  21    4.5522     3.0786     5.2932     3.4326     4.1740     3.5790 
   C  22    1.9682     3.4019     1.2894     3.2402     2.5753     2.9671 
   C  23    3.8467     2.3651     4.5898     2.7907     3.5216     2.8314 
   O  24    1.4833     2.5644     1.2848     2.6751     2.2250     1.9560 
   C  25    5.3662     4.4708     5.9071     4.1451     4.6502     5.2125 
   C  26    5.8083     4.6502     6.4410     4.5256     5.1552     5.3672 
   C  27    2.9792     2.5856     3.4127     1.9727     2.2375     3.2488 
   C  28    2.2375     1.9790     2.6872     1.2956     1.4958     2.5856 
   C  29    4.6451     3.7250     5.2073     3.4101     3.9385     4.4667 
   C  30    5.1495     3.9385     5.8059     3.8637     4.5237     4.6463 
   S  31    2.2981     3.7801     1.5551     3.4796     2.7548     3.4591 
   C  32    1.2848     1.9554     1.4853     2.2250     1.9623     1.2765 
   O  33    2.1285     2.3651     2.3804     1.6191     1.4497     2.8314 
   O  34    3.2915     3.1788     3.5883     2.4952     2.5715     3.7842 
   C  35    2.8519     3.0742     3.0244     2.3351     2.1933     3.5726 
   C  36    2.6096     3.9730     1.9887     3.8952     3.2652     3.4528 
   O  37    5.2675     3.8873     5.9790     4.0189     4.7432     4.5154 
   C  38    3.0084     4.4861     2.2691     4.2103     3.4885     4.1213 
   C  39    3.1777     4.6050     2.4847     4.4456     3.7662     4.1355 
   O  40    1.4792     1.4838     1.9607     0.7370     0.7375     1.9610 
   O  41    1.2885     1.9685     1.4875     1.2875     0.7447     2.2305 
   O  42    6.6142     5.6237     7.1772     5.3681     5.9098     6.3612 
   O  43    6.4359     5.2064     7.0905     5.1500     5.8070     5.9020 
   O  44    5.6150     4.8810     6.0892     4.4625     4.8793     5.6169 
   C  45    7.0848     5.8980     7.7202     5.8008     6.4343     6.6035 
   C  46    5.2125     4.6548     5.6228     4.1471     4.4708     5.3712 

              O  13      C  14      C  15      C  16      C  17      C  18
              ------------------------------------------------------------------
   O  13    0.0000 
   C  14    1.9619     0.0000 
   C  15    2.9833     4.6491     0.0000 
   C  16    3.4019     1.4864     5.8139     0.0000 
   C  17    2.5010     4.4527     1.6238     5.8469     0.0000 
   C  18    1.4936     2.2375     2.5778     3.2466     2.9741     0.0000 
   C  19    2.5836     3.7250     1.4879     4.6519     2.6536     1.4875 
   C  20    4.4708     6.0932     1.4875     7.1796     2.7344     3.9373 
   O  21    2.3431     4.2903     2.3357     5.7446     0.7450     3.1814 
   C  22    4.1343     2.2296     6.4462     0.7432     6.5593     3.8683 
   C  23    1.6225     3.5492     2.4998     5.0138     1.2125     2.6536 
   O  24    3.2301     1.2822     5.9018     0.7406     5.7285     3.4078 
   C  25    4.1471     5.6186     1.2864     6.6158     2.8313     3.4068 
   C  26    4.1451     5.9031     1.2843     7.0958     2.1220     3.8621 
   C  27    2.6875     3.4141     2.2347     4.1474     3.3043     1.2864 
   C  28    2.2383     2.6901     2.6845     3.4160     3.4382     0.7447 
   C  29    3.4125     4.8782     0.7426     5.9057     2.3655     2.6780 
   C  30    3.4101     5.2034     0.7391     6.4390     1.4429     3.2376 
   S  31    4.5233     2.7357     6.5670     1.3271     6.8548     4.0146 
   C  32    2.5644     0.7375     5.3611     1.2876     5.0636     2.9750 
   O  33    2.7868     2.7381     3.3688     3.1260     4.1797     1.3570 
   O  34    3.3721     3.8336     2.7828     4.3340     4.0000     1.9062 
   C  35    3.4271     3.4815     3.4270     3.7618     4.4878     1.9413 
   C  36    4.6849     2.7299     7.1280     1.3211     7.1533     4.5545 
   O  37    3.2275     5.1656     1.5967     6.5338     0.7472     3.5383 
   C  38    5.2282     3.3874     7.2991     1.9172     7.5827     4.7494 
   C  39    5.3327     3.4017     7.6329     1.9308     7.7682     5.0568 
   O  40    1.9630     1.9609     3.2518     2.6760     3.7184     0.7460 
   O  41    2.5750     1.9696     3.9413     2.2333     4.4608     1.4885 
   O  42    5.2125     6.8202     2.2292     7.8770     3.3977     4.6445 
   O  43    4.6434     6.4783     1.9610     7.7253     2.3637     4.5181 
   O  44    4.6457     5.9500     1.9610     6.8195     3.5502     3.7125 
   C  45    5.3560     7.1616     2.5635     8.3730     3.1009     5.1413 
   C  46    4.5309     5.6220     2.2305     6.3641     3.8530     3.4076 

              C  19      C  20      O  21      C  22      C  23      O  24
              ------------------------------------------------------------------
   C  19    0.0000 
   C  20    2.5778     0.0000 
   O  21    3.1784     3.4757     0.0000 
   C  22    5.2135     7.7726     6.4772     0.0000 
   C  23    2.9741     3.8336     0.7552     5.7503     0.0000 
   O  24    4.8777     7.3249     5.5339     1.2876     4.7842     0.0000 
   C  25    1.9660     0.7468     3.5694     7.1781     3.7850     6.8146 
   C  26    2.6786     0.7432     2.8442     7.7305     3.2883     7.1664 
   C  27    0.7468     3.2467     3.7550     4.6508     3.4370     4.4625 
   C  28    1.2900     3.8678     3.7567     3.9423     3.3040     3.7209 
   C  29    1.2843     1.2935     3.0700     6.4866     3.1776     6.0833 
   C  30    2.2270     1.2915     2.1849     7.0930     2.5658     6.4751 
   S  31    5.2384     7.8162     6.8471     0.7463     6.1448     1.9917 
   C  32    4.4625     6.8153     4.8302     1.9677     4.0770     0.7432 
   O  33    1.9092     4.4493     4.4837     3.5449     4.0000     3.5621 
   O  34    1.3574     3.5492     4.4815     4.7418     4.1785     4.7514 
   C  35    1.9461     4.2903     4.8875     4.1017     4.4861     4.2519 
   C  36    5.9291     8.4772     7.0198     0.7409     6.2788     1.5516 
   O  37    2.9319     2.2957     1.3303     7.2354     1.9381     6.4456 
   C  38    5.9596     8.5370     7.5606     1.1972     6.8508     2.4723 
   C  39    6.3612     8.9331     7.6753     1.2097     6.9430     2.2858 
   O  40    1.9804     4.5369     3.8988     3.2367     3.3292     2.9625 
   O  41    2.5830     5.1609     4.6264     2.6831     4.0331     2.6780 
   O  42    3.2416     0.7417     4.1277     8.4540     4.5345     8.0432 
   O  43    3.4031     1.2875     3.0072     8.3781     3.5758     7.7536 
   O  44    2.2250     1.2875     4.2819     7.3289     4.4501     7.0901 
   C  45    3.9252     1.4797     3.7359     9.0096     4.3132     8.4309 
   C  46    1.9673     1.9693     4.5505     6.8268     4.5995     6.6958 

              C  25      C  26      C  27      C  28      C  29      C  30
              ------------------------------------------------------------------
   C  25    0.0000 
   C  26    1.2875     0.0000 
   C  27    2.5778     3.4086     0.0000 
   C  28    3.2416     3.9346     0.7417     0.0000 
   C  29    0.7458     1.4879     1.9673     2.5743     0.0000 
   C  30    1.4879     0.7458     2.9738     3.4059     1.2875     0.0000 
   S  31    7.1797     7.8449     4.6079     3.9484     6.5227     7.2484 
   C  32    6.3516     6.6038     4.1408     3.4108     5.6099     5.8939 
   O  33    3.7762     4.5876     1.2027     0.7418     3.1671     4.1009 
   O  34    2.8226     3.8410     0.7418     1.2027     2.3537     3.5109 
   C  35    3.5700     4.5474     1.2096     1.2070     3.0676     4.1647 
   C  36    7.8950     8.4112     5.3814     4.6666     7.1959     7.7587 
   O  37    2.5757     1.5942     3.6467     3.9061     2.2971     1.0879 
   C  38    7.8926     8.5757     5.3167     4.6699     7.2437     7.9825 
   C  39    8.3182     8.9168     5.7616     5.0767     7.6420     8.2895 
   O  40    3.9464     4.5305     1.5000     0.7583     3.2498     3.9387 
   O  41    4.5294     5.2087     1.9726     1.2931     3.8673     4.6444 
   O  42    1.2900     1.2879     3.8678     4.5254     1.9713     1.9699 
   O  43    1.9678     0.7426     4.1393     4.6412     2.2305     1.2864 
   O  44    0.7391     1.9637     2.6790     3.4035     1.2843     2.2270 
   C  45    2.2264     1.2792     4.6382     5.1974     2.6758     1.9595 
   C  46    1.2875     2.5750     2.2333     2.9750     1.4879     2.6808 

              S  31      C  32      O  33      O  34      C  35      C  36
              ------------------------------------------------------------------
   S  31    0.0000 
   C  32    2.6140     0.0000 
   O  33    3.4340     3.3993     0.0000 
   O  34    4.5810     4.5318     1.2083     0.0000 
   C  35    3.8833     4.1313     0.7475     0.7542     0.0000 
   C  36    1.2048     2.2947     4.2846     5.4825     4.8411     0.0000 
   O  37    7.4964     5.7919     4.6429     4.2854     4.8551     7.8473 
   C  38    0.7350     3.1649     4.1312     5.2525     4.5365     1.2032 
   C  39    1.2065     3.0252     4.6086     5.7734     5.0848     0.7552 
   O  40    3.3152     2.6689     0.8850     1.8740     1.6147     3.9489 
   O  41    2.6554     2.5733     0.8942     2.1011     1.5773     3.4182 
   O  42    8.4679     7.5453     5.0658     4.0829     4.8355     9.1659 
   O  43    8.5228     7.1601     5.3091     4.5833     5.2872     9.0451 
   O  44    7.2553     6.6875     3.8214     2.7247     3.4750     8.0603 
   C  45    9.1200     7.8534     5.8312     5.0042     5.7347     9.6892 
   C  46    6.6984     6.3554     3.2847     2.1204     2.8506     7.5650 

              O  37      C  38      C  39      O  40      O  41      O  42
              ------------------------------------------------------------------
   O  37    0.0000 
   C  38    8.2284     0.0000 
   C  39    8.4450     0.7442     0.0000 
   O  40    4.2825     4.0475     4.3995     0.0000 
   O  41    5.0225     3.3779     3.7914     0.7426     0.0000 
   O  42    2.8775     9.1820     9.6017     5.2181     5.8158     0.0000 
   O  43    1.6771     9.2559     9.5732     5.2087     5.9024     1.4900 
   O  44    3.3148     7.9475     8.4264     4.1493     4.6474     1.4900 
   C  45    2.4063     9.8499    10.1957     5.8070     6.4784     1.2876 
   C  46    3.7474     7.3729     7.8862     3.7333     4.1493     2.2326 

              O  43      O  44      C  45      C  46
              --------------------------------------------
   O  43    0.0000 
   O  44    2.5750     0.0000 
   C  45    0.7375     2.6785     0.0000 
   C  46    3.2416     0.7426     3.4048     0.0000 



ATOMIC CHARGES
   C   1    0.0864818698
   C   2    0.1439389886
   C   3    0.0043268648
   C   4   -0.0163694427
   C   5    0.1133603687
   C   6    0.0553704497
   C   7    0.1805533735
   C   8    0.2696847755
   O   9   -0.3239235389
   C  10    0.2404506499
   C  11    0.2166725182
   O  12   -0.3258470966
   O  13   -0.3264173602
   C  14    0.1770541402
   C  15   -0.0116604931
   C  16    0.2662895521
   C  17    0.3172921753
   C  18    0.0379452819
   C  19    0.0360105510
   C  20    0.2627185065
   O  21   -0.4483729643
   C  22    0.0631241876
   C  23    0.2116660983
   O  24   -0.3240429306
   C  25    0.1801577221
   C  26    0.1801577221
   C  27    0.1761001893
   C  28    0.1761643843
   C  29    0.0364934573
   C  30    0.0364934573
   S  31   -0.0858798892
   C  32    0.1771865521
   O  33   -0.4346402219
   O  34   -0.4346411082
   C  35    0.4294030464
   C  36    0.0075713249
   O  37   -0.2500936557
   C  38    0.0352780242
   C  39    0.0073135071
   O  40   -0.2148648858
   O  41   -0.2175112378
   O  42   -0.2800504403
   O  43   -0.4680980772
   O  44   -0.4680980772
   C  45    0.2526258406
   C  46    0.2526258406


BOND ANGLES
  13    2    1   O3   C3   C3    120.690
   2    1   23   C3   C3   C3    131.179
   4    3    2  Car  Car   C3    120.528
   3    2    1  Car   C3   C3    118.782
   3    2   13  Car   C3   O3    120.528
  17    5    1   C2   C3   C3    107.832
   5    1   23   C3   C3   C3    108.130
  15    6    5  Car   C3   C3    119.430
   6    5    1   C3   C3   C3    119.430
   6    5   17   C3   C3   C2    132.738
   7   11   10   C3   C3   C3    119.977
  11   10    8   C3   C3   C3    119.556
   1    2   13   C3   C3   O3    120.690
   5    6   15   C3   C3  Car    119.430
   9   16   24   O3   C3   O3    119.629
  16   24   32   C3   O3   C3    120.392
   1    5   17   C3   C3   C2    107.832
   5   17   21   C3   C2   O3    108.527
  20   25   29  Car  Car  Car    120.143
  25   29   15  Car  Car  Car    119.589
  28   27   19  Car  Car  Car    120.143
  27   19    4  Car  Car  Car    120.111
  34   35   33   O3   C3   O3    107.151
  35   33   28   C3   O3  Car    108.282
  38   39   36  Car  Car  Car    106.722
  39   36   22  Car  Car  Car    107.910
   2    3    4   C3  Car  Car    120.528
   3    4    6  Car  Car   C3    119.589
  19   27   28  Car  Car  Car    120.143
  27   28   18  Car  Car  Car    119.863
  29   25   20  Car  Car  Car    120.143
  25   20   26  Car  Car  Car    119.556
  10   11    7   C3   C3   C3    119.977
  11    7   14   C3   C3   C3    120.188
  33   35   34   O3   C3   O3    107.151
  35   34   27   C3   O3  Car    107.906
  24   16    9   O3   C3   O3    119.629
  16    9    7   C3   O3   C3    119.979
  36   39   38  Car  Car  Car    106.722
  39   38   31  Car  Car   S2    109.299


TORSION ANGLES
   3    2    1    5      0.026
   3    2    1   23    179.974
  13    2    1    5    179.974
  13    2    1   23      0.026
  18    3    2    1    179.974
  18    3    2   13      0.026
   4    3    2    1      0.026
   4    3    2   13    179.974
  19    4    6    5    179.974
  19    4    6   15      0.026
   3    4    6    5      0.026
   3    4    6   15    179.974
   6    5    1    2      0.026
   6    5    1   23    179.974
  17    5    1    2    179.974
  17    5    1   23      0.026
   4    6    5    1      0.026
   4    6    5   17    179.974
  15    6    5    1    179.974
  15    6    5   17      0.026
   9    7   14   12    179.974
   9    7   14   32      0.026
  11    7   14   12      0.026
  11    7   14   32    179.974
  10    8   13    2      0.026
  12    8   13    2    179.974
  16    9    7   14      0.026
  16    9    7   11    179.974
  11   10    8   13    179.974
  11   10    8   12      0.026
  40   10    8   13    179.974
  40   10    8   12      0.026
  41   11   10    8    179.974
  41   11   10   40      0.026
   7   11   10    8      0.026
   7   11   10   40    179.974
  14   12    8   13    179.974
  14   12    8   10      0.026
   1    2   13    8    179.974
   3    2   13    8      0.026
   7   14   12    8      0.026
  32   14   12    8    179.974
   4    6   15   29      0.026
   4    6   15   30    179.974
   5    6   15   29    179.974
   5    6   15   30      0.026
  22   16   24   32    179.974
   9   16   24   32      0.026
   1    5   17   37    179.974
   1    5   17   21      0.026
   6    5   17   37      0.026
   6    5   17   21    179.974
  28   18    3    2    179.974
  28   18    3    4      0.026
  27   19    4    6    179.974
  27   19    4    3      0.026
  42   20   26   30    179.974
  42   20   26   43      0.026
  25   20   26   30      0.026
  25   20   26   43    179.974
  17   21   23    1      0.026
  31   22   16   24    179.974
  31   22   16    9      0.026
  36   22   16   24      0.026
  36   22   16    9    179.974
   2    1   23   21    179.974
   5    1   23   21      0.026
  16   24   32   14      0.026
  44   25   29   15    179.974
  20   25   29   15      0.026
  20   26   30   15      0.026
  43   26   30   15    179.974
  34   27   19    4    179.974
  28   27   19    4      0.026
  33   28   18    3    179.974
  27   28   18    3      0.026
  25   29   15    6    179.974
  25   29   15   30      0.026
  26   30   15    6    179.974
  26   30   15   29      0.026
  38   31   22   16    179.974
  38   31   22   36      0.026
  24   32   14    7      0.026
  24   32   14   12    179.974
  35   33   28   18    179.974
  35   33   28   27      0.026
  35   34   27   19    179.974
  35   34   27   28      0.026
  34   35   33   28      0.026
  39   36   22   16    179.974
  39   36   22   31      0.026
  39   38   31   22      0.026
  38   39   36   22      0.026
  45   43   26   20      0.026
  45   43   26   30    179.974
  46   44   25   29      0.026
  46   44   25   20    179.974
   5   17   21   23      0.026
  37   17   21   23    179.974
   2    3    4    6      0.026
   2    3    4   19    179.974
  18    3    4    6    179.974
  18    3    4   19      0.026
  19   27   28   18      0.026
  19   27   28   33    179.974
  34   27   28   18    179.974
  34   27   28   33      0.026
  29   25   20   26      0.026
  29   25   20   42    179.974
  44   25   20   26    179.974
  44   25   20   42      0.026
  10   11    7   14      0.026
  10   11    7    9    179.974
  41   11    7   14    179.974
  41   11    7    9      0.026
  33   35   34   27      0.026
  24   16    9    7      0.026
  22   16    9    7    179.974
  36   39   38   31      0.026


CHIRAL ATOMS
   C     1 is chiral: counterclockwise
   C     2 is chiral: clockwise
   C     5 is chiral: clockwise
   C     6 is chiral: counterclockwise
   C     7 is chiral: counterclockwise
   C     8 is chiral: counterclockwise
   C    10 is chiral: counterclockwise
   C    11 is chiral: counterclockwise
   C    14 is chiral: counterclockwise
   C    16 is chiral: counterclockwise