NP-MRD: Showing NP-Card for methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate (NP0246513)

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Record Information

Version

2.0

Created at

2022-09-07 08:01:18 UTC

Updated at

2022-09-07 08:01:18 UTC

NP-MRD ID

NP0246513

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate

Description

Globostellatic acid F methyl ester belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate is found in Rhabdastrella globostellata. Based on a literature review very few articles have been published on globostellatic acid F methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210012D          

 40 42  0  0  1  0            999 V2000
    0.7610   -3.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924   -2.9094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2075   -2.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9912   -2.6174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2729   -1.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.8508    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2203   -0.8765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102   -1.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348   -1.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756   -2.3048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.7992    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6435   -0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.7735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6108   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0758   -0.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7203   -1.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7978   -2.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -2.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8752   -3.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0990   -3.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4689   -3.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9527   -4.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -5.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0302   -5.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539   -6.1757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6602   -6.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2903   -6.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276   -7.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928   -5.7990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -1.4747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0183   -2.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -1.5262    0.0000 C   0  0  1  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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 20 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  1  0  0  0
 14 40  1  0  0  0  0
  5 40  1  0  0  0  0
M  END

     RDKit          3D

 88 90  0  0  0  0  0  0  0  0999 V2000
   -5.8647    3.5412   -1.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4774    2.2821   -0.9922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8719    2.0896    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6690    3.1222    0.9144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5043    0.7286    0.6687 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9463    0.9568    2.1026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7021   -0.1718    0.8881 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2145    0.0421    2.1933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5150    0.3938    2.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0835    0.6256    3.7882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2880    0.5325    1.4386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1853   -1.5951    0.8812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6850   -2.0042   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8263   -0.9539   -1.1345 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6837   -0.3491   -2.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5812   -1.4094   -1.7809 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5717   -2.7576   -2.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1692   -2.6505   -3.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -3.1565   -4.1174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3655   -1.8951   -2.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9429   -1.7933   -2.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5954   -2.4565   -3.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7346   -1.0892   -1.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445   -0.9076   -1.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7533   -0.1769   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0979   -0.0334   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7385   -0.6482   -1.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8230    0.6887    0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1088    0.8677    0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8438    1.6221    1.7497 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1486    1.7067    2.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2069    1.0419    2.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0725    1.0480    0.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8864    1.9755    3.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1705   -0.2233    2.5521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2937   -1.3550   -1.0393 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1656   -2.2638    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583    0.0935   -0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3671    0.9112   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4418    0.0491   -0.0870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3676    3.3756   -2.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5450    3.9946   -0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9710    4.2062   -1.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6201    0.0166    2.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0972    1.6713    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7413    1.4879    2.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5322    0.0017    0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0904    1.7270    3.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1627    0.3120    3.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5352    0.0689    4.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0126   -2.2739    1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3621   -1.6513    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6413   -2.1608   -1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2590   -2.9991   -0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2768    0.5526   -2.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7294   -0.2312   -2.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6972   -1.0896   -3.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3800   -0.7064   -2.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6604   -3.6044   -1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2921   -2.7992   -3.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -3.5322   -3.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6746   -2.4097   -3.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2289   -2.0212   -4.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2481   -0.6655   -0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5969   -1.3125   -2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2577    0.2611    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5199   -1.7391   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8064   -0.5111   -1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2902   -0.2356   -2.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2517    1.1040    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6902    0.4649   -0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0021    2.6531    1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0063    2.6225    3.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8220    1.8970    0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1242    1.1834    1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0462    0.0748    0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7233    1.4873    3.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1033    2.2168    3.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1518    2.9384    2.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3750   -0.2904    3.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3667   -3.0243    0.0106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042   -1.6959    1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590   -2.8222    0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4073    0.6399   -1.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7389    0.1255    0.3938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608    1.8197   -0.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004    1.0935   -1.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8904   -0.5938    0.6877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  5  3  1  6
  5  6  1  0
  5  7  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
 20 36  1  0
 36 37  1  1
 36 38  1  0
 38 39  1  0
 39 40  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 40  5  1  0
 40 14  1  0
 36 16  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  6 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  6
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  6
 17 59  1  0
 17 60  1  0
 22 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 24 65  1  0
 25 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 29 71  1  0
 30 72  1  6
 31 73  1  0
 33 74  1  0
 33 75  1  0
 33 76  1  0
 34 77  1  0
 34 78  1  0
 34 79  1  0
 35 80  1  0
 37 81  1  0
 37 82  1  0
 37 83  1  0
 38 84  1  0
 38 85  1  0
 39 86  1  0
 39 87  1  0
 40 88  1  1
 10 48  1  0
 10 49  1  0
 10 50  1  0
M  END


  Mrv1652309072210012D          

 40 42  0  0  1  0            999 V2000
    0.7610   -3.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924   -2.9094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2075   -2.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9912   -2.6174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -1.5520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2729   -1.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.8508    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2203   -0.8765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102   -1.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348   -1.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756   -2.3048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.7992    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6435   -0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.7735    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6108   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0758   -0.0207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9440   -1.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7203   -1.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7978   -2.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215   -2.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8752   -3.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0990   -3.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4689   -3.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9527   -4.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -5.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0302   -5.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539   -6.1757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6602   -6.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2903   -6.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276   -7.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928   -5.7990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -1.4747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0183   -2.1267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -1.5262    0.0000 C   0  0  1  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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 20 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  1  0  0  0
 14 40  1  0  0  0  0
  5 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)[C@@H](CC[C@]2(C)[C@@H]3CC(=O)\C(=C(/C)\C=C\C=C(/C)\C=C\C(O)C(C)(C)O)[C@@]3(C)CC[C@@H]12)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H48O7/c1-20(13-14-26(36)30(4,5)38)11-10-12-21(2)28-23(35)19-25-31(6)18-16-27(40-22(3)34)33(8,29(37)39-9)24(31)15-17-32(25,28)7/h10-14,24-27,36,38H,15-19H2,1-9H3/b12-10+,14-13+,20-11+,28-21-/t24-,25+,26?,27-,31+,32+,33-/m1/s1

> <INCHI_KEY>
RPQIPTLEYKHMBM-GNHKJRBKSA-N

> <FORMULA>
C33H48O7

> <MOLECULAR_WEIGHT>
556.74

> <EXACT_MASS>
556.340003886

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
63.59829917853273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3E,3aS,5aR,6R,7R,9aR,9bS)-7-(acetyloxy)-3-[(3E,5E,7E)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-dodecahydro-1H-cyclopenta[a]naphthalene-6-carboxylate

> <JCHEM_LOGP>
4.469944095999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.182010171947155

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.542221836096374

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1167820689480283

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
158.133

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3E,3aS,5aR,6R,7R,9aR,9bS)-7-(acetyloxy)-3-[(3E,5E,7E)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.420  -6.938   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.106  -5.431   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.254  -4.405   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.717  -4.886   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.939  -2.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.509  -3.469   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.128  -1.588   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.411  -1.636   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.139  -2.993   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.678  -3.041   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.328  -4.302   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.856  -0.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.395  -0.183   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.207  -1.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.935  -0.135   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.746  -1.444   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.740  -0.268   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.166  -0.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.475  -0.039   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.053  -2.386   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.229  -3.380   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.678  -2.859   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.956  -4.896   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.507  -5.417   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.234  -6.933   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.785  -7.454   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.609  -6.460   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.512  -8.970   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.063  -9.491   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.790 -11.007   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.341 -11.528   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.966 -12.001   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.142 -12.995   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.972 -13.177   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.960 -10.825   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.557  -2.753   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.501  -3.970   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.829  -4.110   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.290  -4.158   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.479  -2.849   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   40                                             
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   40                                             
CONECT   15   14                                                            
CONECT   16   14   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   36                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   20   16   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   14    5                                                  
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Value	Source
Globostellatate F methyl ester	Generator

Chemical Formula

C₃₃H₄₈O₇

Average Mass

556.7400 Da

Monoisotopic Mass

556.34000 Da

IUPAC Name

methyl (3E,3aS,5aR,6R,7R,9aR,9bS)-7-(acetyloxy)-3-[(3E,5E,7E)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-dodecahydro-1H-cyclopenta[a]naphthalene-6-carboxylate

Traditional Name

methyl (3E,3aS,5aR,6R,7R,9aR,9bS)-7-(acetyloxy)-3-[(3E,5E,7E)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)[C@@H](CC[C@]2(C)[C@@H]3CC(=O)\C(=C(/C)\C=C\C=C(/C)\C=C\C(O)C(C)(C)O)[C@@]3(C)CC[C@@H]12)OC(C)=O

InChI Identifier

InChI=1S/C33H48O7/c1-20(13-14-26(36)30(4,5)38)11-10-12-21(2)28-23(35)19-25-31(6)18-16-27(40-22(3)34)33(8,29(37)39-9)24(31)15-17-32(25,28)7/h10-14,24-27,36,38H,15-19H2,1-9H3/b12-10+,14-13+,20-11+,28-21-/t24-,25+,26?,27-,31+,32+,33-/m1/s1

InChI Key

RPQIPTLEYKHMBM-GNHKJRBKSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rhabdastrella globostellata	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
Fatty alcohol
Dicarboxylic acid or derivatives
Fatty acyl
Methyl ester
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.47	ChemAxon
pKa (Strongest Acidic)	13.54	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	158.13 m³·mol⁻¹	ChemAxon
Polarizability	63.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23076337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44434367

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate (NP0246513)

MOL for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)

3D MOL for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)

3D SDF for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)

3D-SDF for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)

PDB for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)

3D PDB for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)

SMILES for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)

INCHI for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)

Structure for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)

3D Structure for NP0246513 (methyl (3e,3as,5ar,6r,7r,9ar,9bs)-7-(acetyloxy)-3-[(3e,5e,7e)-9,10-dihydroxy-6,10-dimethylundeca-3,5,7-trien-2-ylidene]-3a,6,9a-trimethyl-2-oxo-octahydrocyclopenta[a]naphthalene-6-carboxylate)