NP-MRD: Showing NP-Card for (3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0303093)

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Record Information

Version

2.0

Created at

2022-09-10 17:08:41 UTC

Updated at

2022-09-10 17:08:41 UTC

NP-MRD ID

NP0303093

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Description

Hebelomic acid B, also known as hebelomate b, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid is found in Hebeloma senescens. Based on a literature review very few articles have been published on hebelomic acid B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102219082D          

 52 56  0  0  1  0            999 V2000
    4.3959   -5.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6762   -4.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4883   -4.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351   -0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0458   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5140   -0.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8580   -0.7239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974   -2.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5489   -3.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2158   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5062   -4.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1731   -3.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7049   -4.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5171   -3.8774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4246   -4.7986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -4.4435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0429   -5.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5365   -5.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3915   -4.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6942   -5.6012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  1  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  1  0  0  0  0
  7 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  1  0  0  0
  8 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 44 47  1  0  0  0  0
 43 48  1  0  0  0  0
 48 49  1  0  0  0  0
 40 49  1  0  0  0  0
 49 50  1  6  0  0  0
 39 51  1  0  0  0  0
  5 51  1  0  0  0  0
 35 51  1  0  0  0  0
 51 52  1  1  0  0  0
M  END

     RDKit          3D

114118  0  0  0  0  0  0  0  0999 V2000
   -2.8416   -3.8426    2.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6511   -2.3847    1.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -1.6297    2.7932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1621   -1.8094    0.6948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0123   -0.4087    0.5859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5225   -0.1379    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0330   -0.3219   -0.8372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6621   -0.5518   -1.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0593   -0.6735   -3.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -1.1489   -3.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624   -1.4418   -1.8569 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2503   -1.9233   -1.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605   -3.4641   -1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0901   -1.5040   -3.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036   -1.6350   -0.5454 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3404   -1.9605   -0.6291 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9927   -2.9424    0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4269   -3.1986   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3365   -3.6202    0.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7242   -0.2389   -0.0451 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5537    0.0871    1.0198 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4701    1.0987    1.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5998    1.8262    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3296    1.3954    2.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292    2.5538    1.9798 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1661    2.3286    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4919    3.7236    1.7681 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0746    2.8025    3.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9227    1.6572    3.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4331    0.7344    4.2802 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2501    1.5576    3.2069 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337   -0.2555    0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5143   -0.2568   -1.0162 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8192    1.0704   -1.6562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219   -0.6934   -1.8054 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4477   -2.1366   -1.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3239   -0.1062   -2.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1024   -0.0220   -0.7863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0271    1.0437   -0.2851 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4210    0.5223   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5198    1.2612    0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2363    1.1036    1.5210 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.3653    1.7578    2.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5955    3.1620    1.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6297    0.9560    1.9598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1404    1.7541    3.6519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0840    1.7856    1.7711 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9496    2.2595    1.4756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    0.1532   -0.6409 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1598    1.5534   -0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -4.4143    1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1146    0.2890   -3.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5374   -2.3243    0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9910   -2.4501    0.5371 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9883    0.5075    2.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9421    2.0129   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.5319    2.3302   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4601    0.7604   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6669    3.7657    1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.2189    1.4476    1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1877    0.7995    2.8930 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7122    0.3281    1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7231    2.0888    2.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4231    1.6150   -1.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 29 31  1  0
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 35 36  1  1
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 39 40  1  0
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 36 90  1  0
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 38 95  1  0
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 41 99  1  0
 42100  1  0
 42101  1  0
 43102  1  1
 49110  1  1
 50111  1  0
 45103  1  0
 45104  1  0
 45105  1  0
 46106  1  0
 46107  1  0
 46108  1  0
 47109  1  0
 52112  1  0
 52113  1  0
 52114  1  0
M  END


  Mrv1652309102219082D          

 52 56  0  0  1  0            999 V2000
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    9.2974   -2.2757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5489   -3.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2158   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5062   -4.3493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1731   -3.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7049   -4.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5171   -3.8774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4246   -4.7986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -4.4435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0429   -5.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5365   -5.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3915   -4.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6942   -5.6012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  1  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  1  0  0  0  0
  7 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  1  0  0  0
  8 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  6  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 44 47  1  0  0  0  0
 43 48  1  0  0  0  0
 48 49  1  0  0  0  0
 40 49  1  0  0  0  0
 49 50  1  6  0  0  0
 39 51  1  0  0  0  0
  5 51  1  0  0  0  0
 35 51  1  0  0  0  0
 51 52  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0303093

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC2=C(CC[C@H]3C(C)(C)[C@@H](OC(C)=O)[C@@H](C[C@]23C)OC(=O)C[C@@](C)(O)CC(O)=O)[C@]2(C)CC[C@H]([C@H]3CC[C@@H](O[C@@H]3O)C(C)(C)O)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C40H62O12/c1-21(41)49-30-17-26-25(39(9)16-15-24(40(30,39)10)23-11-14-29(36(5,6)47)52-34(23)46)12-13-28-35(3,4)33(50-22(2)42)27(18-38(26,28)8)51-32(45)20-37(7,48)19-31(43)44/h23-24,27-30,33-34,46-48H,11-20H2,1-10H3,(H,43,44)/t23-,24-,27-,28+,29-,30+,33+,34+,37+,38-,39+,40+/m1/s1

> <INCHI_KEY>
NWNZSOBRAQBTIG-YXLXRQEESA-N

> <FORMULA>
C40H62O12

> <MOLECULAR_WEIGHT>
734.924

> <EXACT_MASS>
734.424127436

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
114

> <JCHEM_AVERAGE_POLARIZABILITY>
81.5100547871115

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5-{[(2S,4R,5R,7R,11S,14R,15R,16S)-5,16-bis(acetyloxy)-14-[(2S,3R,6R)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-4-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <JCHEM_LOGP>
3.3834037516666644

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.165348561106716

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7581625362872524

> <JCHEM_PKA_STRONGEST_BASIC>
-3.008398902096703

> <JCHEM_POLAR_SURFACE_AREA>
186.11999999999998

> <JCHEM_REFRACTIVITY>
188.14450000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5-{[(2S,4R,5R,7R,11S,14R,15R,16S)-5,16-bis(acetyloxy)-14-[(2S,3R,6R)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-4-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.206  -9.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.729  -8.500   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.245  -8.229   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.886  -1.622   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.893  -0.445   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.402  -1.351   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      17.355  -4.248   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.069  -5.087   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      19.612  -8.119   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      20.857  -6.332   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.849  -7.509   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      23.365  -7.238   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      21.326  -8.957   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.947  -9.510   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       1.001 -10.726   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.731  -8.565   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       3.162 -10.456   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       2.312  -6.868   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       2.676  -4.226   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   51                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   33                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   32                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   20   33                                                       
CONECT   33   32    7   11   34                                             
CONECT   34   33                                                            
CONECT   35    8   36   37   51                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   51                                                  
CONECT   40   39   41   49                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   48                                                  
CONECT   44   43   45   46   47                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   44                                                            
CONECT   48   43   49                                                       
CONECT   49   48   40   50                                                  
CONECT   50   49                                                            
CONECT   51   39    5   35   52                                             
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

View in JSmol

Synonyms

Value	Source
Hebelomate b	Generator

Chemical Formula

C₄₀H₆₂O₁₂

Average Mass

734.9240 Da

Monoisotopic Mass

734.42413 Da

IUPAC Name

(3S)-5-{[(2S,4R,5R,7R,11S,14R,15R,16S)-5,16-bis(acetyloxy)-14-[(2S,3R,6R)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-4-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CC2=C(CC[C@H]3C(C)(C)[C@@H](OC(C)=O)[C@@H](C[C@]23C)OC(=O)C[C@@](C)(O)CC(O)=O)[C@]2(C)CC[C@H]([C@H]3CC[C@@H](O[C@@H]3O)C(C)(C)O)[C@@]12C

InChI Identifier

InChI=1S/C40H62O12/c1-21(41)49-30-17-26-25(39(9)16-15-24(40(30,39)10)23-11-14-29(36(5,6)47)52-34(23)46)12-13-28-35(3,4)33(50-22(2)42)27(18-38(26,28)8)51-32(45)20-37(7,48)19-31(43)44/h23-24,27-30,33-34,46-48H,11-20H2,1-10H3,(H,43,44)/t23-,24-,27-,28+,29-,30+,33+,34+,37+,38-,39+,40+/m1/s1

InChI Key

NWNZSOBRAQBTIG-YXLXRQEESA-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
Hebeloma senescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid ester
14-alpha-methylsteroid
Steroid
Tetracarboxylic acid or derivatives
Fatty acid ester
Oxane
Fatty acyl
Tertiary alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.38	ChemAxon
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	186.12 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	188.14 m³·mol⁻¹	ChemAxon
Polarizability	81.51 Å³	ChemAxon
Number of Rings	5	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

C00023930

Chemspider ID

24711482

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44584160

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid (NP0303093)

MOL for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D MOL for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D SDF for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D-SDF for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

PDB for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D PDB for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

SMILES for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

INCHI for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

Structure for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)

3D Structure for NP0303093 ((3s)-5-{[(1r,3as,5ar,7r,8r,9as,11s,11ar)-7,11-bis(acetyloxy)-1-[(2s,3r,6r)-2-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}-3-hydroxy-3-methyl-5-oxopentanoic acid)