NP-MRD: Showing NP-Card for Isoobacunoic acid 17-O-beta-D-glucoside (NP0086454)

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Record Information

Version

2.0

Created at

2022-04-29 06:45:12 UTC

Updated at

2022-04-29 06:45:12 UTC

NP-MRD ID

NP0086454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoobacunoic acid 17-O-beta-D-glucoside

Description

(1S,3'S,3aR,5aR,6R,7S,9aR,9bR)-1-(carboxymethyl)-7-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-3,3,5a,7,9b-pentamethyl-5-oxo-decahydro-1H-spiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid 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. Isoobacunoic acid 17-O-beta-D-glucoside is found in Citrus paradisii. Based on a literature review very few articles have been published on (1S,3'S,3aR,5aR,6R,7S,9aR,9bR)-1-(carboxymethyl)-7-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-3,3,5a,7,9b-pentamethyl-5-oxo-decahydro-1H-spiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208452D          

 48 53  0  0  1  0            999 V2000
   -2.3842   -3.2789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638   -2.5690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1388   -2.5783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7343   -3.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906   -3.3065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4951   -4.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146   -4.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771   -4.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -5.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1512   -4.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111   -2.5967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2610   -2.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -1.7859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1474   -1.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3899   -1.0075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5422   -0.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    0.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0838    0.3406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -1.5124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5941   -0.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3724   -0.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9985   -0.9654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2347   -0.1750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8461   -1.7762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7794   -2.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702   -2.1717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6759   -2.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373   -3.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -4.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0930   -2.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1700   -1.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -0.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5166   -0.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057   -0.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6608    0.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0678   -2.0497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.9155   -2.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371   -3.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -1.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1229   -1.1494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7024   -0.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1069    0.2794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9478   -1.1402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3523   -0.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683   -1.8500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1932   -1.8408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
 11  5  1  1  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
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 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 20 35  2  0  0  0  0
 19 36  1  1  0  0  0
 19 37  1  0  0  0  0
 24 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 11 40  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
  2 47  1  0  0  0  0
 47 48  1  1  0  0  0
M  END

     RDKit          3D

 90 95  0  0  0  0  0  0  0  0999 V2000
   -6.1931   -0.2534   -1.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3757    0.2854   -0.1958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2845    0.2325    0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0238    1.5840   -0.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6595    1.5260   -0.9594 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2193    2.9215   -1.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8157    2.8927   -2.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7683    4.8711   -2.5877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0883    0.6616    0.1090 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3154    1.3438    1.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1341   -0.4638   -0.1065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9902   -1.5637    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6327   -2.1077    0.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4976   -3.2342    0.2379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840   -1.1818    0.7335 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4423   -0.8341    2.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8069    0.0122   -0.1216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5425    0.8014   -0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422    0.0448   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036   -1.3606   -0.6106 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5395   -2.2137   -1.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622   -1.2458   -0.3144 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4889   -0.3128    0.6942 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2877    0.7159    0.2482 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6116    0.5424    0.7790 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3760    1.5019    0.0952 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8212    1.0350    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6401    1.9227   -0.5675 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2114    2.7965    0.8757 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6354    3.9029    0.1594 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8067    2.8902    1.3699 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.6601    2.8609   -0.6613 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6719   -3.0939   -1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -4.1170   -0.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2022   -4.0754    0.6471 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2057   -1.8977    0.4187 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.1734   -3.2047    1.0605 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.3620   -5.5414    1.0825 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324   -4.7849   -0.4482 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5245   -1.2840   -1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3 52  1  0
M  END


  Mrv1652304292208452D          

 48 53  0  0  1  0            999 V2000
   -2.3842   -3.2789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9638   -2.5690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1388   -2.5783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7343   -3.2973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906   -3.3065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4951   -4.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146   -4.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771   -4.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -5.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1512   -4.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111   -2.5967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2610   -2.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6634   -1.7859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1474   -1.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3899   -1.0075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5422   -0.1967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    0.0768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0838    0.3406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -1.5124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5941   -0.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3724   -0.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9985   -0.9654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2347   -0.1750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8461   -1.7762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7794   -2.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702   -2.1717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6759   -2.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373   -3.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -4.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0930   -2.8068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1700   -1.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -0.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5166   -0.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057   -0.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6608    0.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8157   -0.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0678   -2.0497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2894   -2.3232    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155   -2.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1371   -3.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7184   -1.8684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1229   -1.1494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7024   -0.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1069    0.2794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9478   -1.1402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3523   -0.4212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683   -1.8500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1932   -1.8408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
 11  5  1  1  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 20 35  2  0  0  0  0
 19 36  1  1  0  0  0
 19 37  1  0  0  0  0
 24 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 11 40  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
  2 47  1  0  0  0  0
 47 48  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0086454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(=O)[C@]3(C)[C@]([H])(CC[C@@](C)([C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C4=COC=C4)[C@@]33O[C@@H]3C(O)=O)[C@@]1(C)[C@H](CC(O)=O)OC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H44O14/c1-28(2)17-10-18(34)31(5)16(30(17,4)19(45-28)11-20(35)36)6-8-29(3,32(31)25(46-32)26(40)41)24(14-7-9-42-13-14)44-27-23(39)22(38)21(37)15(12-33)43-27/h7,9,13,15-17,19,21-25,27,33,37-39H,6,8,10-12H2,1-5H3,(H,35,36)(H,40,41)/t15-,16-,17+,19+,21-,22+,23-,24+,25-,27+,29+,30-,31+,32-/m1/s1

> <INCHI_KEY>
GFDDIOAHWBGUTE-UJIBJULZSA-N

> <FORMULA>
C32H44O14

> <MOLECULAR_WEIGHT>
652.69

> <EXACT_MASS>
652.273106097

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
65.53316788270865

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3'S,3aR,5aR,6R,7S,9aR,9bR)-1-(carboxymethyl)-7-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-3,3,5a,7,9b-pentamethyl-5-oxo-decahydro-1H-spiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid

> <ALOGPS_LOGP>
1.51

> <JCHEM_LOGP>
0.638184402666663

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.421089230851881

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.726116738230075

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083688337913

> <JCHEM_POLAR_SURFACE_AREA>
225.94999999999996

> <JCHEM_REFRACTIVITY>
152.34220000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3'S,3aR,5aR,6R,7S,9aR,9bR)-1-(carboxymethyl)-7-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-3,3,5a,7,9b-pentamethyl-5-oxo-hexahydrospiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -4.451  -6.121   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.666  -4.796   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.126  -4.813   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.371  -6.155   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.169  -6.172   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.924  -7.514   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.454  -7.692   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.757  -9.202   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.415  -9.957   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.282  -8.914   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.954  -4.847   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.487  -4.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.238  -3.334   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.275  -3.049   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.728  -1.881   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.012  -0.367   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.465   0.143   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.156   0.636   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.691  -2.823   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.976  -1.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.429  -0.799   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.597  -1.802   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       6.038  -0.327   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       5.313  -3.316   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.188  -4.851   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.664  -4.054   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.862  -5.581   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.283  -6.174   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.480  -7.701   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.507  -5.239   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.784  -2.996   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.124  -1.605   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.431  -0.790   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.104  -0.065   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.100   0.225   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.523  -1.820   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.860  -3.826   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0       2.407  -4.337   0.000  0.00  0.00           H+0
HETATM   39  C   UNK     0       3.576  -5.340   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.123  -5.850   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.341  -3.488   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.096  -2.146   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -1.311  -0.821   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.066   0.522   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -3.636  -2.128   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -4.391  -0.786   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -4.421  -3.453   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -5.961  -3.436   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   47                                                  
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    5   12   13   40                                             
CONECT   12   11                                                            
CONECT   13   11   14   15   19                                             
CONECT   14   13   15                                                       
CONECT   15   14   13   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20   36   37                                             
CONECT   20   19   21   35                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   32                                             
CONECT   23   22                                                            
CONECT   24   22   25   26   37                                             
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   32                                                       
CONECT   32   31   22   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   20                                                            
CONECT   36   19                                                            
CONECT   37   19   24   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   11                                                       
CONECT   41    3   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43                                                            
CONECT   45   42   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45    2   48                                                  
CONECT   48   47                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  106    0
END

View in JSmol

Synonyms

Value	Source
(1S,3's,3AR,5ar,6R,7S,9ar,9BR)-1-(carboxymethyl)-7-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-3,3,5a,7,9b-pentamethyl-5-oxo-decahydro-1H-spiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylate	Generator

Chemical Formula

C₃₂H₄₄O₁₄

Average Mass

652.6900 Da

Monoisotopic Mass

652.27311 Da

IUPAC Name

Traditional Name

(1S,3'S,3aR,5aR,6R,7S,9aR,9bR)-1-(carboxymethyl)-7-[(R)-furan-3-yl({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-3,3,5a,7,9b-pentamethyl-5-oxo-hexahydrospiro[naphtho[1,2-c]furan-6,2'-oxirane]-3'-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(=O)[C@]3(C)[C@]([H])(CC[C@@](C)([C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C4=COC=C4)[C@@]33O[C@@H]3C(O)=O)[C@@]1(C)[C@H](CC(O)=O)OC2(C)C

InChI Identifier

InChI=1S/C32H44O14/c1-28(2)17-10-18(34)31(5)16(30(17,4)19(45-28)11-20(35)36)6-8-29(3,32(31)25(46-32)26(40)41)24(14-7-9-42-13-14)44-27-23(39)22(38)21(37)15(12-33)43-27/h7,9,13,15-17,19,21-25,27,33,37-39H,6,8,10-12H2,1-5H3,(H,35,36)(H,40,41)/t15-,16-,17+,19+,21-,22+,23-,24+,25-,27+,29+,30-,31+,32-/m1/s1

InChI Key

GFDDIOAHWBGUTE-UJIBJULZSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus paradisii	Plant	KNApSAcK

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
Naphthofuran
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Monosaccharide
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Oxane
Furan
Heteroaromatic compound
Tetrahydrofuran
Ketone
Secondary alcohol
Polyol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Acetal
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Alcohol
Primary alcohol
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	1.51	ALOGPS
logP	0.64	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	225.95 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	152.34 m³·mol⁻¹	ChemAxon
Polarizability	65.53 Å³	ChemAxon
Number of Rings	6	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

C00056729

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

162891278

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isoobacunoic acid 17-O-beta-D-glucoside (NP0086454)

MOL for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)

3D MOL for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)

3D SDF for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)

3D-SDF for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)

PDB for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)

3D PDB for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)

SMILES for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)

INCHI for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)

Structure for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)

3D Structure for NP0086454 (Isoobacunoic acid 17-O-beta-D-glucoside)