NP-MRD: Showing NP-Card for methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate (NP0223145)

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Record Information

Version

2.0

Created at

2022-09-06 01:09:23 UTC

Updated at

2022-09-06 01:09:23 UTC

NP-MRD ID

NP0223145

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate

Description

Shizukaol A belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate is found in Chloranthus fortunei, Chloranthus japonicus and Chloranthus serratus. methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate was first documented in 2021 (PMID: 33550145). Based on a literature review very few articles have been published on Shizukaol A (PMID: 34926189).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062203092D          

 37 44  0  0  1  0            999 V2000
    6.5863    3.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8441    3.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7887    2.6562    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5633    1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887    2.4546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5497    3.1531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2399    2.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784    3.7864    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7942    4.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814    4.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4262    5.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634    6.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424    5.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1605    5.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    4.4920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4527    4.0687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7369    3.2942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2082    2.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954    2.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1112    3.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6399    4.2099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3557    4.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409    5.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8831    5.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032    6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0332    7.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447    7.2312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162    8.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429    5.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026    5.7670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0142    4.4922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1284    4.6483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984    3.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4127    3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0614    2.7520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0060    1.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466    2.2924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  2  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  1  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 20  1  6  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 37 36  1  1  0  0  0
 19 37  1  0  0  0  0
 35 37  1  0  0  0  0
M  END

     RDKit          3D

 71 78  0  0  0  0  0  0  0  0999 V2000
    4.5414   -0.2714   -2.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334   -0.6718   -0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9515   -0.6168    1.4856 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.6464   -0.7080   -0.4402 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5957   -0.1762   -1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532    0.9441   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3853    2.0941   -1.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    2.6222   -2.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714    2.8742    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    4.0303    0.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1839    2.0827    1.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4273    0.7665    0.7627 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5062    0.0485    1.5553 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0873   -1.2994    2.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2522   -2.0575    1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504   -1.3680    0.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862    0.0568    0.9372 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0046    0.5898    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8472    1.4874    0.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548    2.0619    1.9365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9370    1.9870   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7676    2.9936    0.2448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8474    3.5127   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3415    0.8473   -2.1996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9905   -1.3942   -1.5498 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2531   -1.8940   -1.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466   -2.1264   -0.3049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9320   -2.3728    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971   -3.4245   -0.5175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8967   -4.2881    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570   -3.4063    0.4174 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9735    0.1132   -2.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6230   -0.3405   -2.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9134   -2.3095    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7911    0.6519    0.9565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0859   -0.8184    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6995   -1.2749    2.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1803    1.8364   -0.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1836    1.8224    0.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896    2.1960    1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4299   -1.7236   -0.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0203    0.1559   -2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8504   -0.9557   -1.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3557    3.3060   -2.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419    1.7885   -3.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4092    3.2354   -2.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289    0.6801    2.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3959   -1.2121    2.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8170    2.1032    2.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6965    4.6067   -0.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8273    3.3455   -0.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8606    3.0312   -1.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3984   -1.6420   -2.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6558   -1.5901    0.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3060   -3.3701    0.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7158   -2.3039    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -3.9137   -1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958   -5.3859    0.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5922   -4.0455    1.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2257   -3.8655    0.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 25  1  0
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 25 23  1  0
 23 24  1  0
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 22 21  1  0
 21 20  1  0
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 17  6  1  0
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  4  3  1  0
  3  2  1  0
  2  1  2  3
  2  8  1  0
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  9 10  1  0
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 11 12  1  0
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 16 21  1  0
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  5 43  1  1
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  3 40  1  6
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  1 39  1  0
  8 47  1  1
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 12 50  1  0
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 36 70  1  0
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 34 65  1  0
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 34 67  1  0
 31 63  1  6
 32 64  1  0
M  END


  Mrv1652309062203092D          

 37 44  0  0  1  0            999 V2000
    6.5863    3.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8441    3.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7887    2.6562    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5633    1.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9887    2.4546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5497    3.1531    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2399    2.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784    3.7864    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7942    4.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9814    4.7021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4262    5.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634    6.3383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424    5.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1605    5.9435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    4.4920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4527    4.0687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7369    3.2942    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2082    2.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3954    2.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1112    3.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6399    4.2099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3557    4.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409    5.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8831    5.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032    6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0332    7.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4447    7.2312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162    8.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5429    5.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026    5.7670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0142    4.4922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1284    4.6483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984    3.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4127    3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0614    2.7520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0060    1.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466    2.2924    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  2  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  1  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 20  1  6  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 37 36  1  1  0  0  0
 19 37  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223145

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(\C)=C1\[C@H]2C3=C(C[C@H]4[C@@]5(C)[C@@H]6C[C@@H]6C(=C)[C@@H]5CC5=C(C)C(=O)O[C@]245)[C@H]2C[C@H]2[C@]3(C)[C@@H](O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H34O6/c1-11-14-7-19(14)29(4)17(11)10-18-12(2)28(35)37-31(18)21(29)9-16-15-8-20(15)30(5)23(16)24(31)22(25(32)26(30)33)13(3)27(34)36-6/h14-15,17,19-21,24,26,33H,1,7-10H2,2-6H3/b22-13-/t14-,15-,17+,19-,20-,21+,24+,26+,29-,30+,31+/m1/s1

> <INCHI_KEY>
GQSUZVYXPAKHQW-SFVFYCNCSA-N

> <FORMULA>
C31H34O6

> <MOLECULAR_WEIGHT>
502.607

> <EXACT_MASS>
502.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.153735059652576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,2S,8S,10S,12R,13S,14S,17S,19R,20S,21R,23Z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0^{2,6}.0^{2,14}.0^{8,13}.0^{10,12}.0^{17,19}.0^{20,24}]tetracosa-5,16(24)-dien-23-ylidene]propanoate

> <JCHEM_LOGP>
3.166543965999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.283546890968438

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.947292167941628

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7287754752594457

> <JCHEM_POLAR_SURFACE_AREA>
89.90000000000002

> <JCHEM_REFRACTIVITY>
135.71869999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(1R,2S,8S,10S,12R,13S,14S,17S,19R,20S,21R,23Z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0^{2,6}.0^{2,14}.0^{8,13}.0^{10,12}.0^{17,19}.0^{20,24}]tetracosa-5,16(24)-dien-23-ylidene]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      12.294   7.309   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.909   6.495   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.806   4.958   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.385   3.477   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.312   4.582   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.493   5.886   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.914   4.313   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.480   7.068   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.949   8.514   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.432   8.777   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.396  10.062   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.838  11.832   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.119   9.705   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.033  11.095   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.996   8.385   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.445   7.595   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.976   6.149   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.989   4.967   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.471   5.230   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.941   6.676   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.928   7.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.397   9.304   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.490  10.900   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.248  10.870   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.233  12.530   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.795  13.083   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.430  13.498   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.190  15.019   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.880   9.568   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.685  10.765   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.893   8.386   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.240   8.677   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.424   6.940   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.770   6.518   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.981   5.137   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.878   3.601   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.260   4.279   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    4    3    6                                                  
CONECT    6    5    7    8   17                                             
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10   17   21                                             
CONECT   17   16    6   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   37                                                  
CONECT   20   19   21   33                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   22   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   20   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35   37                                                       
CONECT   37   36   19   35                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₄O₆

Average Mass

502.6070 Da

Monoisotopic Mass

502.23554 Da

IUPAC Name

methyl 2-[(1R,2S,8S,10S,12R,13S,14S,17S,19R,20S,21R,23Z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0^{2,6}.0^{2,14}.0^{8,13}.0^{10,12}.0^{17,19}.0^{20,24}]tetracosa-5,16(24)-dien-23-ylidene]propanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C(\C)=C1\[C@H]2C3=C(C[C@H]4[C@@]5(C)[C@@H]6C[C@@H]6C(=C)[C@@H]5CC5=C(C)C(=O)O[C@]245)[C@H]2C[C@H]2[C@]3(C)[C@@H](O)C1=O

InChI Identifier

InChI=1S/C31H34O6/c1-11-14-7-19(14)29(4)17(11)10-18-12(2)28(35)37-31(18)21(29)9-16-15-8-20(15)30(5)23(16)24(31)22(25(32)26(30)33)13(3)27(34)36-6/h14-15,17,19-21,24,26,33H,1,7-10H2,2-6H3/b22-13-/t14-,15-,17+,19-,20-,21+,24+,26+,29-,30+,31+/m1/s1

InChI Key

GQSUZVYXPAKHQW-SFVFYCNCSA-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
Chloranthus fortunei	LOTUS Database	35616633
Chloranthus japonicus	LOTUS Database	35616633
Chloranthus serratus	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
Naphthofuran
2-furanone
Dicarboxylic acid or derivatives
Cyclic alcohol
Dihydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
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	3.17	ChemAxon
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	135.72 m³·mol⁻¹	ChemAxon
Polarizability	54.15 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000502

Chemspider ID

58927726

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127045559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vardhan S, Sahoo SK: Exploring the therapeutic nature of limonoids and triterpenoids against SARS-CoV-2 by targeting nsp13, nsp14, and nsp15 through molecular docking and dynamics simulations. J Tradit Complement Med. 2022 Jan;12(1):44-54. doi: 10.1016/j.jtcme.2021.12.002. Epub 2021 Dec 13. [PubMed:34926189 ]
Tang P, Li Q, Liao S, Wei S, Cui L, Xu W, Zhu D, Luo J, Kong L: Shizukaol A exerts anti-inflammatory effect by regulating HMGB1/Nrf2/HO-1 pathway. Phytomedicine. 2021 Feb;82:153472. doi: 10.1016/j.phymed.2021.153472. Epub 2021 Jan 17. [PubMed:33550145 ]
LOTUS database [Link]

Showing NP-Card for methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate (NP0223145)

MOL for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)

3D MOL for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)

3D SDF for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)

3D-SDF for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)

PDB for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)

3D PDB for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)

SMILES for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)

INCHI for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)

Structure for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)

3D Structure for NP0223145 (methyl 2-[(1r,2s,8s,10s,12r,13s,14s,17s,19r,20s,21r,23z)-21-hydroxy-5,13,20-trimethyl-9-methylidene-4,22-dioxo-3-oxaoctacyclo[14.7.1.0²,⁶.0²,¹⁴.0⁸,¹³.0¹⁰,¹².0¹⁷,¹⁹.0²⁰,²⁴]tetracosa-5,16(24)-dien-23-ylidene]propanoate)