NP-MRD: Showing NP-Card for methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate (NP0176065)

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Record Information

Version

2.0

Created at

2022-09-03 13:40:00 UTC

Updated at

2022-09-03 13:40:01 UTC

NP-MRD ID

NP0176065

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate

Description

Hirtin belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate is found in Trichilia martiana and Trichilia pallida. methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate was first documented in 2012 (PMID: 22305073). Based on a literature review a small amount of articles have been published on Hirtin (PMID: 26330216) (PMID: 23442935).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032215402D          

 43 48  0  0  1  0            999 V2000
    1.9965    4.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    3.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    2.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911    3.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934    1.6241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3055    1.4789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8373    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449    3.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889    3.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0540    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2063   -1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2019   -1.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9153   -2.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1176    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547   -0.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.2889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0923    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    0.9666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3693    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742    2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    2.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    0.9934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6017    1.7357    0.0000 C   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  1  0  0  0
  6  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
 12  7  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  2  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
 19 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  6  0  0  0
 13 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 37 41  2  0  0  0  0
 36 42  1  0  0  0  0
  6 42  1  0  0  0  0
 32 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END

     RDKit          3D

 79 84  0  0  0  0  0  0  0  0999 V2000
   -4.9517    2.6667    0.8701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5711    2.6489   -0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989    1.7600   -0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9479    1.6306   -2.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657    1.0544    0.1730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444    0.2157   -0.1152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5115    0.8255    0.7350 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6038    2.1937    0.4870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1727    3.1232    1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2251    4.5545    0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6538    2.7428    2.4196 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7676    0.1403    0.6940 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9410    0.7258   -0.0063 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7752    0.8801   -1.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3243    2.0834    0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5691    2.5265    0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1091   -0.1959    0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953   -1.4058    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -2.2237    1.0673 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6924   -2.0235    1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5527   -2.9855    1.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5619   -1.3151    0.4097 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6973   -1.7953   -0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7127   -1.8094    0.9776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7957   -2.6455    2.0575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9331   -3.2953    0.8589 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2554   -3.4212    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5109   -2.1002   -0.5271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9415   -1.8401   -0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581   -1.2581   -1.9757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8094   -1.1789   -1.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1170   -1.6737   -0.7044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0676   -2.0739   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8995   -1.0471    1.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9784    3.0629    0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2485    3.6830   -0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2944    5.0667    1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775    4.7311   -0.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593    5.0862    1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1596    0.1638    1.7733 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2211    0.0893   -2.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7049    1.1060   -1.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3065    1.8116   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6239    2.7362    0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8643    3.5340    0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083   -0.8994    1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6053   -0.2222    2.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781    0.8833    1.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1973   -0.5086   -2.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5203   -2.0461   -1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6602   -1.1879   -3.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2362   -3.0587    0.4832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -1.2406   -1.7904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7567   -2.0868   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1144   -3.9895    0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0354   -3.7391    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1276   -4.2492   -0.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9946   -2.0299   -1.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8456   -0.9405   -2.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5299   -0.7792   -2.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0852   -2.5176    0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4662   -0.4673    2.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0252   -2.0821    2.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8397   -0.5284    1.3815 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
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
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 19 20  1  0
 19 21  1  6
 21 22  2  0
 21 23  1  0
 23 24  1  0
 19 25  1  0
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 32 33  1  1
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  1 44  1  0
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  2 47  1  0
  2 48  1  0
  6 49  1  6
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 10 51  1  0
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 31 67  1  0
 31 68  1  0
 31 69  1  0
 34 70  1  6
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 35 72  1  0
 36 73  1  6
 41 76  1  0
 39 75  1  0
 38 74  1  0
 43 77  1  0
 43 78  1  0
 43 79  1  0
M  END


  Mrv1652309032215402D          

 43 48  0  0  1  0            999 V2000
    1.9965    4.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4646    3.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    2.9647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911    3.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934    1.6241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3055    1.4789    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8373    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5571    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449    3.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0889    3.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0540    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2063   -1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2019   -1.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9153   -2.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1176    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547   -0.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.2889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0923    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    0.9666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3693    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742    2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    2.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    0.9934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6017    1.7357    0.0000 C   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  1  0  0  0
  6  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
 12  7  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  2  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
 19 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  6  0  0  0
 13 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 37 41  2  0  0  0  0
 36 42  1  0  0  0  0
  6 42  1  0  0  0  0
 32 42  1  0  0  0  0
 42 43  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0176065

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)O[C@H]1[C@H](OC(C)=O)[C@@H]2[C@@]3(C)C=CC(=O)[C@](C)(C(=O)OC)C3=C(O)C(=O)C2(C)C23O[C@H]2C[C@@H](C2=COC=C2)[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C32H36O11/c1-8-20(35)42-26-22(41-15(2)33)24-28(3)11-9-18(34)29(4,27(38)39-7)23(28)21(36)25(37)31(24,6)32-19(43-32)13-17(30(26,32)5)16-10-12-40-14-16/h9-12,14,17,19,22,24,26,36H,8,13H2,1-7H3/t17-,19-,22+,24+,26-,28-,29-,30+,31?,32?/m0/s1

> <INCHI_KEY>
MSPSOUKLPSVQMY-PPERBCCSSA-N

> <FORMULA>
C32H36O11

> <MOLECULAR_WEIGHT>
596.629

> <EXACT_MASS>
596.225761979

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.959801868225334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (4S,6R,7R,8R,9R,10R,11R,15R)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadeca-12,16-diene-15-carboxylate

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
3.1442531403333343

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.004146513205676

> <JCHEM_PKA_STRONGEST_BASIC>
-2.858128080906891

> <JCHEM_POLAR_SURFACE_AREA>
158.94

> <JCHEM_REFRACTIVITY>
148.81749999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4S,6R,7R,8R,9R,10R,11R,15R)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadeca-12,16-diene-15-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.727   8.283   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.734   7.106   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.616   5.534   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.650   6.028   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.264   4.480   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.788   3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.304   2.761   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.296   3.938   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.773   5.386   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.257   5.657   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.766   6.564   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.827   1.312   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.834   0.135   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.254  -1.292   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.357  -1.314   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.365  -2.491   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.873  -1.585   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.397  -3.033   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.866  -0.407   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.382  -0.678   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.852  -2.124   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.714  -1.452   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.049  -0.685   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.710  -2.992   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.042  -3.765   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.375   0.499   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.891   0.228   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.852   1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.336   2.218   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.343   1.041   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.820   2.489   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.318   0.406   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.529  -1.120   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.102  -0.539   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.172   0.325   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.256   1.804   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.689   3.020   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.229   2.970   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.752   4.418   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.536   5.364   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -0.261   4.499   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.795   1.854   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.123   3.240   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                                                       
CONECT    6    5    7   42                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   30                                                  
CONECT   13   12   14   15   32                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   30                                                  
CONECT   20   19   21   22   26                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   20   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   19   12   31                                             
CONECT   31   30                                                            
CONECT   32   13   33   34   42                                             
CONECT   33   32   34                                                       
CONECT   34   33   32   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   42                                                  
CONECT   37   36   38   41                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   37                                                       
CONECT   42   36    6   32   43                                             
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₆O₁₁

Average Mass

596.6290 Da

Monoisotopic Mass

596.22576 Da

IUPAC Name

methyl (4S,6R,7R,8R,9R,10R,11R,15R)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0^{2,4}.0^{2,7}.0^{11,16}]octadeca-12,16-diene-15-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(=O)O[C@H]1[C@H](OC(C)=O)[C@@H]2[C@@]3(C)C=CC(=O)[C@](C)(C(=O)OC)C3=C(O)C(=O)C2(C)C23O[C@H]2C[C@@H](C2=COC=C2)[C@]13C

InChI Identifier

InChI=1S/C32H36O11/c1-8-20(35)42-26-22(41-15(2)33)24-28(3)11-9-18(34)29(4,27(38)39-7)23(28)21(36)25(37)31(24,6)32-19(43-32)13-17(30(26,32)5)16-10-12-40-14-16/h9-12,14,17,19,22,24,26,36H,8,13H2,1-7H3/t17-,19-,22+,24+,26-,28-,29-,30+,31?,32?/m0/s1

InChI Key

MSPSOUKLPSVQMY-PPERBCCSSA-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
Trichilia martiana	LOTUS Database	35616633
Trichilia pallida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
17-furanylsteroid skeleton
Steroid ester
7-oxosteroid
7-hydroxysteroid
Oxosteroid
Hydroxysteroid
3-oxo-delta-1-steroid
Steroid
Delta-1-steroid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Cyclohexenone
Pyran
Oxane
Heteroaromatic compound
Methyl ester
Furan
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Enol
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.29	ALOGPS
logP	3.14	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	158.94 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	148.82 m³·mol⁻¹	ChemAxon
Polarizability	59.96 Å³	ChemAxon
Number of Rings	6	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

C00045829

Chemspider ID

95601471

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44145739

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ji KL, Zhang P, Li XN, Guo J, Hu HB, Xiao CF, Xie XQ, Xu YK: Cytotoxic limonoids from Trichilia americana leaves. Phytochemistry. 2015 Oct;118:61-7. doi: 10.1016/j.phytochem.2015.08.014. Epub 2015 Aug 29. [PubMed:26330216 ]
Vieira IJ, Azevedo Ode A, de Souza JJ, Braz-Filho R, Goncalves Mdos S, de Araujo MF: Hirtinone, a Novel cycloartane-type triterpene and other compounds from Trichilia hirta L. (Meliaceae). Molecules. 2013 Feb 26;18(3):2589-97. doi: 10.3390/molecules18032589. [PubMed:23442935 ]
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LOTUS database [Link]

Showing NP-Card for methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate (NP0176065)

MOL for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D MOL for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D SDF for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D-SDF for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

PDB for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D PDB for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

SMILES for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

INCHI for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

Structure for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)

3D Structure for NP0176065 (methyl (4s,6s,7r,8r,9r,10r,11r,15r)-9-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-1,7,11,15-tetramethyl-14,18-dioxo-8-(propanoyloxy)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-15-carboxylate)