NP-MRD: Showing NP-Card for methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate (NP0310530)

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Record Information

Version

2.0

Created at

2022-09-11 05:54:13 UTC

Updated at

2022-09-11 05:54:14 UTC

NP-MRD ID

NP0310530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate

Description

Methyl 3-[(3R,3aS,4R,5aR,6S,7S,9aR,9bR)-4-(acetyloxy)-3-[(2S,4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate is found in Alnus japonica. Based on a literature review very few articles have been published on methyl 3-[(3R,3aS,4R,5aR,6S,7S,9aR,9bR)-4-(acetyloxy)-3-[(2S,4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112207542D          

 39 41  0  0  1  0            999 V2000
   -3.8423    2.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051    1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7924    1.0444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6169    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3915   -0.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7425   -0.3837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3054   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6927   -1.8118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2555   -2.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4310   -2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -3.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5172   -1.8406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0475   -2.4726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8479   -3.2731    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0474   -3.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6484   -3.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6483   -4.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2418   -4.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0348   -4.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6282   -4.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2217   -5.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -5.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2013   -4.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8124   -2.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7548   -1.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9543   -1.1409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6383   -0.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3552    0.3447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6137   -0.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    0.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    1.5822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    0.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  6  0  0  0
 18 19  1  1  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  1  6  0  0  0
  9 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

 93 95  0  0  0  0  0  0  0  0999 V2000
    5.0121   -1.1914    2.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418   -0.9180    0.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7154   -1.9234    0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630    0.2693    0.4164 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7022    1.1738    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965    0.8232    2.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273    0.2687    1.0073 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2515   -1.1544    1.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9069    0.6390   -0.3384 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9387    0.5631   -1.4339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4850    0.1912   -1.0706 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7401   -1.1802   -1.3206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5180   -1.6962   -2.3121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7770   -3.1355   -2.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0841   -0.8766   -3.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9543    0.6895    0.2332 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8974   -0.1987    1.0050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3462    0.1691    0.8579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1288   -0.8378    1.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5081    1.4229    1.4635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9176    0.2267   -0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3703    0.6260   -0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3554   -0.1617   -0.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7647    0.2117   -0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6665   -0.4184   -1.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3283   -0.1299    0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8589    1.6104   -0.7131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    0.0669    2.4918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    0.8671    2.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1455    1.1087    1.1799 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3751    2.5599    0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3223    0.0848   -0.7077 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2064   -1.3624   -1.0602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690    0.9421   -1.8917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8693    0.8161   -2.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1163    1.1873   -2.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2050    2.4482   -1.7385 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1956    0.4455   -1.6969 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3158    1.0197   -1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5335   -2.0973    2.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5760   -0.5276    3.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3896   -2.9701    0.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9163   -1.6621   -0.8348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7479   -1.9052    0.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1800    0.8887    0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4742    1.2486    2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228    2.2060    1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9782    1.7594    2.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4669    0.1408    2.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1802   -1.5585    1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4655   -1.3416    2.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0465   -1.8727    0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1805    1.7415   -0.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8965    1.5519   -1.9923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1847   -0.1406   -2.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148    0.6818   -1.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232   -3.4249   -3.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8627   -3.3598   -2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3246   -3.7915   -1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5949    1.6194    0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7900   -1.2686    0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8536   -0.2975    2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6183   -1.5640    1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597   -1.3983    2.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4228    1.5110    1.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8976   -0.7330   -1.0527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4810    1.0561   -1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6484    1.5610    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0326   -1.1065   -1.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5328   -1.5095   -1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7164   -0.2289   -1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5744    0.0443   -2.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7707   -1.1571    0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1047    0.6223    1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5396   -0.0678    1.5773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0211    2.0480    0.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6306   -0.8493    3.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017    0.7164    2.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    0.3334    3.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4865    1.8567    3.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030    2.8210   -0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4233    3.1061    1.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3434    2.9831    1.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9677   -1.6001   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651   -2.0193   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -1.6372   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6407    2.0552   -1.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7890    0.9840   -2.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584   -0.1513   -3.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7756    1.5559   -3.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4813    0.5801   -0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1164    2.0918   -0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2487    0.8788   -1.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 38  1  0
 38 36  1  0
 36 37  2  0
 36 35  1  0
 35 34  1  0
 32 34  1  6
 32 33  1  0
 32  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 11 16  1  0
 16 17  1  0
 17 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
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 18 19  1  0
 18 20  1  1
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
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 24 26  1  0
 24 27  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  9 32  1  0
 30 16  1  0
 30  7  1  0
 39 91  1  0
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  4 45  1  6
  5 46  1  0
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  6 48  1  0
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  8 50  1  0
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  8 52  1  0
  9 53  1  1
 10 54  1  0
 10 55  1  0
 11 56  1  6
 14 57  1  0
 14 58  1  0
 14 59  1  0
 16 60  1  6
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 28 77  1  0
 28 78  1  0
 29 79  1  0
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 31 81  1  0
 31 82  1  0
 31 83  1  0
 19 62  1  0
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 21 66  1  0
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 22 68  1  0
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 25 70  1  0
 25 71  1  0
 25 72  1  0
 26 73  1  0
 26 74  1  0
 26 75  1  0
 27 76  1  0
  3 42  1  0
  3 43  1  0
  3 44  1  0
  1 40  1  0
  1 41  1  0
M  END


  Mrv1652309112207542D          

 39 41  0  0  1  0            999 V2000
   -3.8423    2.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051    1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5806    1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7924    1.0444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6169    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0042    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5670   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3915   -0.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7425   -0.3837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3054   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6927   -1.8118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2555   -2.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4310   -2.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0437   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -3.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5172   -1.8406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0475   -2.4726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8479   -3.2731    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0474   -3.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6484   -3.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6483   -4.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2418   -4.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0348   -4.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6282   -4.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2217   -5.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -5.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2013   -4.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8124   -2.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7548   -1.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9543   -1.1409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6383   -0.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3552    0.3447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6137   -0.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263    0.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2118    1.5822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    0.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  6  0  0  0
 18 19  1  1  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 16 30  1  0  0  0  0
  7 30  1  0  0  0  0
 30 31  1  6  0  0  0
  9 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0310530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC[C@@]1(C)[C@@H](CC[C@]2(C)[C@@H]1C[C@@H](OC(C)=O)[C@H]1[C@@H](CC[C@@]21C)[C@@](C)(O)C\C=C\C(C)(C)O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H54O6/c1-21(2)23-12-18-31(7)26(30(23,6)17-14-27(35)38-10)20-25(39-22(3)34)28-24(13-19-32(28,31)8)33(9,37)16-11-15-29(4,5)36/h11,15,23-26,28,36-37H,1,12-14,16-20H2,2-10H3/b15-11+/t23-,24+,25+,26+,28+,30-,31+,32+,33-/m0/s1

> <INCHI_KEY>
QCYLSMCCPZUBCM-CACPWKPASA-N

> <FORMULA>
C33H54O6

> <MOLECULAR_WEIGHT>
546.789

> <EXACT_MASS>
546.392039459

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
63.75412795579837

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-[(3R,3aS,4R,5aR,6S,7S,9aR,9bR)-4-(acetyloxy)-3-[(2S,4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate

> <JCHEM_LOGP>
5.018578809666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.78126084031512

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.710226414046211

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5822732912444177

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
154.96070000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-[(3R,3aS,4R,5aR,6S,7S,9aR,9bR)-4-(acetyloxy)-3-[(2S,4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -7.172   4.615   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.356   3.309   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.817   3.363   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.079   1.949   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.618   1.896   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.341   0.536   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.525  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.064  -0.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.986  -0.716   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.170  -2.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.893  -3.382   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.077  -4.688   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.538  -4.634   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.815  -3.274   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.722  -5.940   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -8.432  -3.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.422  -4.615   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.049  -6.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.555  -5.737   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -10.544  -6.482   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -8.677  -7.604   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.785  -8.674   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -11.265  -8.249   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -12.373  -9.319   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -13.481 -10.389   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -11.303 -10.427   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -13.443  -8.211   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -10.850  -4.039   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -10.742  -2.502   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -9.248  -2.130   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.525  -1.269   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.263   0.643   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.879  -0.032   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.929   1.413   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.596   0.643   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.262   1.413   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.262   2.953   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -0.928   0.643   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.405   1.413   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   30                                             
CONECT    8    7                                                            
CONECT    9    7   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17   30                                                  
CONECT   17   16   18   28                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   17   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   16    7   31                                             
CONECT   31   30                                                            
CONECT   32    9    4   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3-[(3R,3as,4R,5ar,6S,7S,9ar,9BR)-4-(acetyloxy)-3-[(2S,4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoic acid	Generator

Chemical Formula

C₃₃H₅₄O₆

Average Mass

546.7890 Da

Monoisotopic Mass

546.39204 Da

IUPAC Name

methyl 3-[(3R,3aS,4R,5aR,6S,7S,9aR,9bR)-4-(acetyloxy)-3-[(2S,4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]propanoate

Traditional Name

methyl 3-[(3R,3aS,4R,5aR,6S,7S,9aR,9bR)-4-(acetyloxy)-3-[(2S,4E)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC[C@@]1(C)[C@@H](CC[C@]2(C)[C@@H]1C[C@@H](OC(C)=O)[C@H]1[C@@H](CC[C@@]21C)[C@@](C)(O)C\C=C\C(C)(C)O)C(C)=C

InChI Identifier

InChI=1S/C33H54O6/c1-21(2)23-12-18-31(7)26(30(23,6)17-14-27(35)38-10)20-25(39-22(3)34)28-24(13-19-32(28,31)8)33(9,37)16-11-15-29(4,5)36/h11,15,23-26,28,36-37H,1,12-14,16-20H2,2-10H3/b15-11+/t23-,24+,25+,26+,28+,30-,31+,32+,33-/m0/s1

InChI Key

QCYLSMCCPZUBCM-CACPWKPASA-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
Alnus japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	5.02	ChemAxon
pKa (Strongest Acidic)	14.71	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	154.96 m³·mol⁻¹	ChemAxon
Polarizability	63.75 Å³	ChemAxon
Number of Rings	3	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

162886910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate (NP0310530)

MOL for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D MOL for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D SDF for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D-SDF for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

PDB for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D PDB for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

SMILES for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

INCHI for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

Structure for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)

3D Structure for NP0310530 (methyl 3-[(3r,3as,4r,5ar,6s,7s,9ar,9br)-4-(acetyloxy)-3-[(2s,4e)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-6,9a,9b-trimethyl-7-(prop-1-en-2-yl)-decahydrocyclopenta[a]naphthalen-6-yl]propanoate)