NP-MRD: Showing NP-Card for (+)-Amaroxocane A (NP0081324)

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Record Information

Version

2.0

Created at

2022-04-29 02:17:16 UTC

Updated at

2022-04-29 02:17:16 UTC

NP-MRD ID

NP0081324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Amaroxocane A

Description

[(1R,2R,4S,5R,7S,8S,14R,15R)-14-[(2R)-4-[(1R,2S,4R,6R)-4-[(1S)-1-[(2S,4S,5R,6R,7S,8S,11R,14R,15R)-4,5-dihydroxy-2,6,15-trimethyl-8-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]ethyl]-1-hydroxy-7,7-dimethyl-3-oxabicyclo[4.2.1]Nonan-2-yl]butan-2-yl]-5-hydroxy-2,15-dimethyl-4-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-10-en-8-yl]oxidanesulfonic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-Amaroxocane A is found in Phorbas amaranthus. Based on a literature review very few articles have been published on [(1R,2R,4S,5R,7S,8S,14R,15R)-14-[(2R)-4-[(1R,2S,4R,6R)-4-[(1S)-1-[(2S,4S,5R,6R,7S,8S,11R,14R,15R)-4,5-dihydroxy-2,6,15-trimethyl-8-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]ethyl]-1-hydroxy-7,7-dimethyl-3-oxabicyclo[4.2.1]Nonan-2-yl]butan-2-yl]-5-hydroxy-2,15-dimethyl-4-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-10-en-8-yl]oxidanesulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204172D          

 75 84  0  0  1  0            999 V2000
    5.7786    2.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4983    3.6724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0301    4.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8422    4.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1225    3.3820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5907    2.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9471    3.4088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1764    4.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4935    4.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4534    2.7575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1425    1.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2707    2.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7770    2.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5943    2.3318    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0113    1.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8095    1.4115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5214    1.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7298    2.6267    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7034    2.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8028    3.1301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5146    3.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3128    3.3386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4687    4.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0504    3.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1451    3.6281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9224    0.5942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2710    0.0879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4785    0.3172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0156   -0.3656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.5219   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2978   -0.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1927   -0.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8328    0.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2958    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1187    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0100    0.4958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5470   -0.1870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9069   -0.9294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7297   -0.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4439   -1.6123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8038   -2.3546    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1636   -3.0970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0614   -2.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5461   -1.9948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242   -0.1275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3643    0.6149    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8273    1.2977    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6501    1.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4674    2.0401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5414    0.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -0.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4730    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0104    0.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6865    0.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4824    2.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7498    5.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9377    5.2243    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4059    4.5936    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6862    3.8176    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1543    3.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3422    3.3321    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0619    4.1081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5937    4.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498    4.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8104    2.7014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9983    2.8466    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    2.9919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    3.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8531    2.0345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9665    3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6574    6.0002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1892    6.6309    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8199    6.0991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585    7.1627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210    7.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  6  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  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  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 20 25  1  1  0  0  0
 16 26  1  6  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 27 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 35  1  0  0  0  0
 33 36  1  0  0  0  0
 37 36  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 32 39  1  0  0  0  0
 38 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  2  0  0  0  0
 41 44  1  0  0  0  0
 37 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 36 48  1  0  0  0  0
 47 49  1  1  0  0  0
 46 50  1  1  0  0  0
 45 51  1  1  0  0  0
 36 52  1  1  0  0  0
 28 53  1  1  0  0  0
 26 54  1  1  0  0  0
  5 55  1  6  0  0  0
  3 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
  2 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 58 63  1  6  0  0  0
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 59 70  1  6  0  0  0
 57 71  1  1  0  0  0
 71 72  1  0  0  0  0
 72 73  2  0  0  0  0
 72 74  2  0  0  0  0
 72 75  1  0  0  0  0
M  END

     RDKit          3D

163172  0  0  0  0  0  0  0  0999 V2000
   -1.9636    2.4864   -2.7912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8034    1.3477   -1.8099 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8979    0.0165   -2.5444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9443    0.0001   -3.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.1363   -4.6437 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0232   -2.2807   -3.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424   -2.8061   -3.0981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1388   -4.0970   -2.7471 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -2.7623   -4.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0922   -1.7856   -5.1773 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4403   -2.4932   -6.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587   -0.7248   -5.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6491   -1.8537   -1.9677 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3811   -2.6914   -0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0780   -1.8491    0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1358   -0.9782    0.4676 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9689   -0.1607    1.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012   -1.7610    0.5932 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6711   -2.6119   -0.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331   -2.5544   -0.9672 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7392   -1.7303    0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9741   -1.5920    0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0034   -2.4502   -0.1803 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0234   -1.4205   -0.6909 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.8675   -1.2142   -3.0784 S   0  0  1  0  0  6  0  0  0  0  0  0
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    7.7260    0.0242    1.3111 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4906    1.3480    0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4672   -0.7225    1.6037 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3438    0.1925    2.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0852   -0.6597    2.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434   -0.8991    0.7204 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5992    0.3638   -0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7536   -1.0566   -1.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.2544    0.3017    0.6471 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.8202    1.5293    0.3627 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.4675    0.6915    2.9981 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -8.0730    0.5937    2.4120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0280    1.0262    3.3820 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3776   -0.0737    3.9934 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304292204172D          

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    2.2498    4.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9983    2.8466    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1862    2.9919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    3.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8531    2.0345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9665    3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6574    6.0002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1892    6.6309    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8199    6.0991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5585    7.1627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210    7.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  6  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  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  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 20 25  1  1  0  0  0
 16 26  1  6  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 27 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 35  1  0  0  0  0
 33 36  1  0  0  0  0
 37 36  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 32 39  1  0  0  0  0
 38 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  2  0  0  0  0
 41 44  1  0  0  0  0
 37 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 36 48  1  0  0  0  0
 47 49  1  1  0  0  0
 46 50  1  1  0  0  0
 45 51  1  1  0  0  0
 36 52  1  1  0  0  0
 28 53  1  1  0  0  0
 26 54  1  1  0  0  0
  5 55  1  6  0  0  0
  3 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
  2 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 58 63  1  6  0  0  0
 62 64  1  6  0  0  0
 61 65  1  6  0  0  0
 65 66  1  0  0  0  0
 66 67  2  0  0  0  0
 66 68  2  0  0  0  0
 66 69  1  0  0  0  0
 59 70  1  6  0  0  0
 57 71  1  1  0  0  0
 71 72  1  0  0  0  0
 72 73  2  0  0  0  0
 72 74  2  0  0  0  0
 72 75  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC[C@@H]1O[C@H](C[C@@H]2C[C@@]1(O)CC2(C)C)[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)C[C@H](O)[C@H](O)[C@H](C)[C@@H]1[C@H](C3)OS(O)(=O)=O)[C@H]1CCC2=C3C[C@H](OS(O)(=O)=O)[C@H]4C[C@@H](O)[C@H](C[C@]4(C)[C@H]3CC[C@]12C)OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C55H88O17S3/c1-28(34-11-13-36-32-21-44(70-73(60,61)62)40-23-41(56)46(72-75(66,67)68)26-53(40,8)38(32)16-18-51(34,36)6)10-15-47-55(59)24-31(50(4,5)27-55)20-43(69-47)29(2)35-12-14-37-33-22-45(71-74(63,64)65)48-30(3)49(58)42(57)25-54(48,9)39(33)17-19-52(35,37)7/h28-31,34-35,37-38,40-49,56-59H,10-27H2,1-9H3,(H,60,61,62)(H,63,64,65)(H,66,67,68)/t28-,29+,30-,31-,34-,35-,37+,38+,40-,41-,42+,43-,44+,45+,46+,47+,48-,49-,51-,52-,53-,54-,55-/m1/s1

> <INCHI_KEY>
YKJFYWUVKGJDGY-PSUKIVINSA-N

> <FORMULA>
C55H88O17S3

> <MOLECULAR_WEIGHT>
1117.47

> <EXACT_MASS>
1116.518364896

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
163

> <JCHEM_AVERAGE_POLARIZABILITY>
122.01182046400568

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2R,4S,5R,7S,8S,14R,15R)-14-[(2R)-4-[(1R,2S,4R,6R)-4-[(1S)-1-[(2S,4S,5R,6R,7S,8S,11R,14R,15R)-4,5-dihydroxy-2,6,15-trimethyl-8-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]ethyl]-1-hydroxy-7,7-dimethyl-3-oxabicyclo[4.2.1]nonan-2-yl]butan-2-yl]-5-hydroxy-2,15-dimethyl-4-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-8-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
-0.18

> <JCHEM_LOGP>
1.6186604229189456

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
-1.5538258949620056

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.108363250057965

> <JCHEM_PKA_STRONGEST_BASIC>
-3.160799741123066

> <JCHEM_POLAR_SURFACE_AREA>
280.95

> <JCHEM_REFRACTIVITY>
278.3981

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R,4S,5R,7S,8S,14R,15R)-14-[(2R)-4-[(1R,2S,4R,6R)-4-[(1S)-1-[(2S,4S,5R,6R,7S,8S,11R,14R,15R)-4,5-dihydroxy-2,6,15-trimethyl-8-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]ethyl]-1-hydroxy-7,7-dimethyl-3-oxabicyclo[4.2.1]nonan-2-yl]butan-2-yl]-5-hydroxy-2,15-dimethyl-4-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-10-en-8-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      10.787   5.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.263   6.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.256   8.032   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.772   7.761   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.295   6.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.303   5.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.835   6.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.263   7.842   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.988   8.707   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.780   5.147   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.199   3.721   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.305   5.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.250   4.142   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.776   4.353   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      20.554   3.024   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      22.044   2.635   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.373   3.413   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.762   4.903   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.846   4.923   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.165   5.843   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.494   6.621   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      22.984   6.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.275   7.744   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.361   6.922   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.937   6.773   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      22.255   1.109   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.039   0.164   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.560   0.592   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.696  -0.683   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.641  -1.898   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      21.089  -1.375   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.160  -0.571   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.488   0.814   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.352   2.089   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.888   1.978   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.952   0.925   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.088  -0.349   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.760  -1.735   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.295  -1.846   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.895  -3.010   0.000  0.00  0.00           O+0
HETATM   41  S   UNK     0      14.567  -4.395   0.000  0.00  0.00           S+0
HETATM   42  O   UNK     0      15.239  -5.781   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      13.181  -5.067   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      15.953  -3.724   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      12.552  -0.238   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      11.880   1.148   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      12.744   2.422   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      14.280   2.311   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      12.072   3.808   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      10.344   1.259   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      11.688  -1.513   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      15.816   2.200   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      20.553   1.769   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      23.682   0.529   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      13.967   4.927   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      10.733   9.481   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       9.217   9.752   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       8.224   8.575   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       8.747   7.126   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       7.755   5.949   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       6.239   6.220   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       5.716   7.668   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       6.708   8.846   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       4.200   7.939   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       5.246   5.043   0.000  0.00  0.00           O+0
HETATM   66  S   UNK     0       3.730   5.314   0.000  0.00  0.00           S+0
HETATM   67  O   UNK     0       2.214   5.585   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0       4.001   6.830   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0       3.459   3.798   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0       9.271   5.678   0.000  0.00  0.00           C+0
HETATM   71  O   UNK     0       8.694  11.200   0.000  0.00  0.00           O+0
HETATM   72  S   UNK     0       9.687  12.378   0.000  0.00  0.00           S+0
HETATM   73  O   UNK     0      10.864  11.385   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0       8.509  13.370   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0      10.679  13.555   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   59                                                  
CONECT    3    2    4   56                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   55                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   14   21   25                                             
CONECT   21   20   22                                                       
CONECT   22   21   18   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20                                                            
CONECT   26   16   27   54                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29   35   53                                             
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   27                                                       
CONECT   32   29   33   39                                                  
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34   28                                                       
CONECT   36   33   37   48   52                                             
CONECT   37   36   38   45                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38   32                                                       
CONECT   40   38   41                                                       
CONECT   41   40   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41                                                            
CONECT   45   37   46   51                                                  
CONECT   46   45   47   50                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47   36                                                       
CONECT   49   47                                                            
CONECT   50   46                                                            
CONECT   51   45                                                            
CONECT   52   36                                                            
CONECT   53   28                                                            
CONECT   54   26                                                            
CONECT   55    5                                                            
CONECT   56    3   57                                                       
CONECT   57   56   58   71                                                  
CONECT   58   57   59   63                                                  
CONECT   59   58    2   60   70                                             
CONECT   60   59   61                                                       
CONECT   61   60   62   65                                                  
CONECT   62   61   63   64                                                  
CONECT   63   62   58                                                       
CONECT   64   62                                                            
CONECT   65   61   66                                                       
CONECT   66   65   67   68   69                                             
CONECT   67   66                                                            
CONECT   68   66                                                            
CONECT   69   66                                                            
CONECT   70   59                                                            
CONECT   71   57   72                                                       
CONECT   72   71   73   74   75                                             
CONECT   73   72                                                            
CONECT   74   72                                                            
CONECT   75   72                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  168    0
END

View in JSmol

Synonyms

Value	Source
[(1R,2R,4S,5R,7S,8S,14R,15R)-14-[(2R)-4-[(1R,2S,4R,6R)-4-[(1S)-1-[(2S,4S,5R,6R,7S,8S,11R,14R,15R)-4,5-Dihydroxy-2,6,15-trimethyl-8-(sulfooxy)tetracyclo[8.7.0.0,.0,]heptadec-1(10)-en-14-yl]ethyl]-1-hydroxy-7,7-dimethyl-3-oxabicyclo[4.2.1]nonan-2-yl]butan-2-yl]-5-hydroxy-2,15-dimethyl-4-(sulfooxy)tetracyclo[8.7.0.0,.0,]heptadec-10-en-8-yl]oxidanesulfonate	Generator
[(1R,2R,4S,5R,7S,8S,14R,15R)-14-[(2R)-4-[(1R,2S,4R,6R)-4-[(1S)-1-[(2S,4S,5R,6R,7S,8S,11R,14R,15R)-4,5-Dihydroxy-2,6,15-trimethyl-8-(sulphooxy)tetracyclo[8.7.0.0,.0,]heptadec-1(10)-en-14-yl]ethyl]-1-hydroxy-7,7-dimethyl-3-oxabicyclo[4.2.1]nonan-2-yl]butan-2-yl]-5-hydroxy-2,15-dimethyl-4-(sulphooxy)tetracyclo[8.7.0.0,.0,]heptadec-10-en-8-yl]oxidanesulphonate	Generator
[(1R,2R,4S,5R,7S,8S,14R,15R)-14-[(2R)-4-[(1R,2S,4R,6R)-4-[(1S)-1-[(2S,4S,5R,6R,7S,8S,11R,14R,15R)-4,5-Dihydroxy-2,6,15-trimethyl-8-(sulphooxy)tetracyclo[8.7.0.0,.0,]heptadec-1(10)-en-14-yl]ethyl]-1-hydroxy-7,7-dimethyl-3-oxabicyclo[4.2.1]nonan-2-yl]butan-2-yl]-5-hydroxy-2,15-dimethyl-4-(sulphooxy)tetracyclo[8.7.0.0,.0,]heptadec-10-en-8-yl]oxidanesulphonic acid	Generator

Chemical Formula

C₅₅H₈₈O₁₇S₃

Average Mass

1117.4700 Da

Monoisotopic Mass

1116.51836 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H](CC[C@@H]1O[C@H](C[C@@H]2C[C@@]1(O)CC2(C)C)[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)C[C@H](O)[C@H](O)[C@H](C)[C@@H]1[C@H](C3)OS(O)(=O)=O)[C@H]1CCC2=C3C[C@H](OS(O)(=O)=O)[C@H]4C[C@@H](O)[C@H](C[C@]4(C)[C@H]3CC[C@]12C)OS(O)(=O)=O

InChI Identifier

InChI=1S/C55H88O17S3/c1-28(34-11-13-36-32-21-44(70-73(60,61)62)40-23-41(56)46(72-75(66,67)68)26-53(40,8)38(32)16-18-51(34,36)6)10-15-47-55(59)24-31(50(4,5)27-55)20-43(69-47)29(2)35-12-14-37-33-22-45(71-74(63,64)65)48-30(3)49(58)42(57)25-54(48,9)39(33)17-19-52(35,37)7/h28-31,34-35,37-38,40-49,56-59H,10-27H2,1-9H3,(H,60,61,62)(H,63,64,65)(H,66,67,68)/t28-,29+,30-,31-,34-,35-,37+,38+,40-,41-,42+,43-,44+,45+,46+,47+,48-,49-,51-,52-,53-,54-,55-/m1/s1

InChI Key

YKJFYWUVKGJDGY-PSUKIVINSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phorbas amaranthus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cholesterol-skeleton
Cholestane-skeleton
25-hydroxysteroid
Sulfated steroid skeleton
3-beta-hydroxysteroid
Hydroxysteroid
2-hydroxysteroid
3-hydroxysteroid
Steroid
Oxepane
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Tertiary alcohol
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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
logP	-0.18	ALOGPS
logP	1.62	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	-2.1	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	280.95 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	278.4 m³·mol⁻¹	ChemAxon
Polarizability	122.01 Å³	ChemAxon
Number of Rings	10	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

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

25243332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Amaroxocane A (NP0081324)

MOL for NP0081324 ((+)-Amaroxocane A)

3D MOL for NP0081324 ((+)-Amaroxocane A)

3D SDF for NP0081324 ((+)-Amaroxocane A)

3D-SDF for NP0081324 ((+)-Amaroxocane A)

PDB for NP0081324 ((+)-Amaroxocane A)

3D PDB for NP0081324 ((+)-Amaroxocane A)

SMILES for NP0081324 ((+)-Amaroxocane A)

INCHI for NP0081324 ((+)-Amaroxocane A)

Structure for NP0081324 ((+)-Amaroxocane A)

3D Structure for NP0081324 ((+)-Amaroxocane A)