NP-MRD: Showing NP-Card for methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate (NP0146238)

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Record Information

Version

2.0

Created at

2022-09-02 01:35:47 UTC

Updated at

2022-09-02 01:35:47 UTC

NP-MRD ID

NP0146238

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

Description

Turrapubesin A belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate is found in Turraea pubescens. methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate was first documented in 2006 (PMID: 16898832). Based on a literature review very few articles have been published on Turrapubesin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203352D          

 41 44  0  0  1  0            999 V2000
    0.7655   -2.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9397   -1.9211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -1.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883   -1.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5237   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3972   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8344   -0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214   -1.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3468   -1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6589   -0.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4108   -1.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694    0.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5214    1.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309   -0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1008   -0.6244    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9076    0.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865    3.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    4.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    4.0549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4568    2.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9289    3.0450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973    3.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2262    4.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    3.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7075    2.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061    3.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    4.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0353    3.9489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  2  0  0  0  0
 24 30  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END

     RDKit          3D

 80 83  0  0  0  0  0  0  0  0999 V2000
   -5.6125    1.1664    3.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7313    0.3156    2.8793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4877    0.7757    2.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127    1.9754    2.7941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135   -0.0419    1.7467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4995   -0.2026    0.3019 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7380   -0.7723   -0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0946   -2.0243    0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8986    0.1079   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4138   -1.2675   -1.6754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8108   -2.3937   -2.0338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6400   -0.3995   -2.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8995    0.5319   -1.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    0.8182   -0.5267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3954    2.1204   -0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2723    0.7386   -0.2395 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5600    1.9346   -0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1427    3.1160   -1.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468    4.3133   -1.7314 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8462    1.8655   -0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0583    2.6900   -0.0232 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1336    3.9724   -0.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1778    1.7981   -0.5493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511    0.5609    0.2090 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6466    0.2973    1.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0388   -1.0066    1.7571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7552   -0.9512    2.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8028    0.2907    3.2656 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640    1.0660    2.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3388    0.5218    0.4460 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0029    0.2558    1.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446   -0.4304   -0.6044 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4807   -1.6578   -0.6790 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1450   -2.2030   -1.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7592   -3.5469   -1.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2012   -1.5404   -2.8014 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122   -0.5730   -0.5518 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0092   -1.1948   -1.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844   -2.5715   -1.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107   -3.2709   -3.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2603   -3.2066   -0.7552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3971    2.2484    3.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6680    1.0214    3.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6113    1.0121    4.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256    0.2576    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6320   -1.0765    2.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7873   -1.1235    0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2010   -2.4937    0.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5009   -2.8273   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9203   -1.8397    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3713    0.6131    0.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7157   -0.5907   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7053    0.7363   -1.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -0.5394   -3.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3405    1.1277   -2.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642    2.7820   -1.1157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4790    1.9984    0.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9252    2.5748    0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2848    0.7319    0.9227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5418    3.7782   -0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    2.9915   -2.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3033    2.6449    1.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364    4.5762    0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1634    2.2127   -0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0140    1.7024   -1.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435   -0.2838   -0.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8211   -1.9085    1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941   -1.7956    3.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0743    2.1295    2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3123   -0.5827    1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286    0.1062    2.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5327    1.1480    2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0072    0.0699   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7275   -3.3908   -1.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233   -3.8825   -2.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0961   -4.2642   -1.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1738   -1.3599    0.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229   -2.5528   -3.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2538   -3.9489   -3.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4678   -3.9804   -2.8763 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  6
 14 16  1  0
 16 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  2  0
 37 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 32 30  1  0
 30 31  1  1
 30 24  1  0
 24 23  1  0
 23 21  1  0
 21 22  1  0
 21 20  1  0
 20 17  2  0
 17 18  1  0
 18 19  1  0
 24 25  1  0
 25 29  2  0
 29 28  1  0
 28 27  1  0
 27 26  2  0
 14  6  1  0
 17 16  1  0
 26 25  1  0
 20 30  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  1
  8 48  1  0
  8 49  1  0
  8 50  1  0
  9 51  1  0
  9 52  1  0
  9 53  1  0
 12 54  1  0
 13 55  1  0
 15 56  1  0
 15 57  1  0
 15 58  1  0
 16 59  1  1
 37 77  1  1
 40 78  1  0
 40 79  1  0
 40 80  1  0
 32 73  1  6
 35 74  1  0
 35 75  1  0
 35 76  1  0
 31 70  1  0
 31 71  1  0
 31 72  1  0
 24 66  1  6
 23 64  1  0
 23 65  1  0
 21 62  1  1
 22 63  1  0
 18 60  1  0
 18 61  1  0
 29 69  1  0
 27 68  1  0
 26 67  1  0
M  END


  Mrv1652309022203352D          

 41 44  0  0  1  0            999 V2000
    0.7655   -2.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9397   -1.9211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -1.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1883   -1.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5237   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3972   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8344   -0.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214   -1.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3468   -1.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6589   -0.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4108   -1.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0462    0.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6694    0.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5214    1.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309   -0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1008   -0.6244    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9076    0.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865    3.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    4.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    4.0549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831    3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4568    2.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9289    3.0450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973    3.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2262    4.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    3.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7075    2.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061    3.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    4.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0353    3.9489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  2  0  0  0  0
 24 30  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 32 37  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0146238

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1C(C)(C)C(=O)C=C[C@]1(C)[C@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](C[C@@H](O)C2=C1CCl)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H39ClO9/c1-16(33)40-27-26(30(5)10-8-23(36)29(3,4)22(30)13-24(37)38-7)19(14-32)25-21(35)12-20(18-9-11-39-15-18)31(25,6)28(27)41-17(2)34/h8-11,15,20-22,26-28,35H,12-14H2,1-7H3/t20-,21+,22-,26+,27+,28-,30-,31-/m0/s1

> <INCHI_KEY>
GPBIXXJZJVXGOC-DRIGCWSYSA-N

> <FORMULA>
C31H39ClO9

> <MOLECULAR_WEIGHT>
591.09

> <EXACT_MASS>
590.2282605

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
60.45389993778114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,2S)-2-[(1R,3R,5R,6R,7R,7aS)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.082170420666668

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.55592238844951

> <JCHEM_PKA_STRONGEST_BASIC>
-2.874880557352695

> <JCHEM_POLAR_SURFACE_AREA>
129.34000000000003

> <JCHEM_REFRACTIVITY>
150.27870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,2S)-2-[(1R,3R,5R,6R,7R,7aS)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.429  -5.154   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.754  -3.586   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.904  -1.955   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.352  -2.418   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.844  -0.381   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.475  -0.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.291  -1.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.707  -2.911   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.247  -2.741   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.830  -1.309   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.234  -2.154   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.553   0.051   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.850   0.936   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.573   2.089   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.738  -0.422   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       0.188  -1.166   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.694   0.826   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.744   5.553   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.161   6.799   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.744   8.045   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.208   7.569   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.208   6.029   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.853   5.121   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.601   5.684   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.035   6.550   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.022   8.052   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.570   5.652   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.054   5.021   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.985   6.703   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.783   8.045   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.533   7.371   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17   37                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   30                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25                                                       
CONECT   30   24   20   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   32   16   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₉ClO₉

Average Mass

591.0900 Da

Monoisotopic Mass

590.22826 Da

IUPAC Name

methyl 2-[(1R,2S)-2-[(1R,3R,5R,6R,7R,7aS)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

Traditional Name

methyl [(1R,2S)-2-[(1R,3R,5R,6R,7R,7aS)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1C(C)(C)C(=O)C=C[C@]1(C)[C@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](C[C@@H](O)C2=C1CCl)C1=COC=C1

InChI Identifier

InChI=1S/C31H39ClO9/c1-16(33)40-27-26(30(5)10-8-23(36)29(3,4)22(30)13-24(37)38-7)19(14-32)25-21(35)12-20(18-9-11-39-15-18)31(25,6)28(27)41-17(2)34/h8-11,15,20-22,26-28,35H,12-14H2,1-7H3/t20-,21+,22-,26+,27+,28-,30-,31-/m0/s1

InChI Key

GPBIXXJZJVXGOC-DRIGCWSYSA-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
Turraea pubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Cyclohexenone
Cyclic alcohol
Furan
Heteroaromatic compound
Methyl ester
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Oxacycle
Organoheterocyclic compound
Organochloride
Organohalogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alkyl halide
Organooxygen compound
Alkyl chloride
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.71	ALOGPS
logP	3.08	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.56	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	129.34 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	150.28 m³·mol⁻¹	ChemAxon
Polarizability	60.45 Å³	ChemAxon
Number of Rings	4	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

17240386

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16081674

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang XN, Yin S, Fan CQ, Wang FD, Lin LP, Ding J, Yue JM: Turrapubesins A and B, first examples of halogenated and maleimide-bearing limonoids in nature from Turraea pubescens. Org Lett. 2006 Aug 17;8(17):3845-8. doi: 10.1021/ol061466a. [PubMed:16898832 ]
LOTUS database [Link]

Showing NP-Card for methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate (NP0146238)

MOL for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D MOL for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D SDF for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D-SDF for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)

PDB for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D PDB for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)

SMILES for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)

INCHI for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)

Structure for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)

3D Structure for NP0146238 (methyl 2-[(1r,2s)-2-[(1s,3r,5r,6r,7r,7as)-6,7-bis(acetyloxy)-4-(chloromethyl)-1-(furan-3-yl)-3-hydroxy-7a-methyl-1,2,3,5,6,7-hexahydroinden-5-yl]-2,6,6-trimethyl-5-oxocyclohex-3-en-1-yl]acetate)