NP-MRD: Showing NP-Card for (3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate (NP0043285)

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Record Information

Version

2.0

Created at

2021-06-21 00:44:13 UTC

Updated at

2021-06-30 00:18:53 UTC

NP-MRD ID

NP0043285

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate

Provided By

JEOL Database JEOL Logo

Description

3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-tetradecahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position. (3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate is found in Aletris farinosa. (3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate was first documented in 2013 (Challinor, V. L., et al.). Based on a literature review very few articles have been published on 3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-tetradecahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102443D          

 82 84  0  0  0  0            999 V2000
    6.2277    1.9441    2.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4826    0.8313    2.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    0.7855    1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059    1.5833    0.3381 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6024   -0.4111    0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1760   -0.7575   -0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028   -2.0388   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.0193   -1.7506 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5916    1.2775   -1.9495 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0551    1.0719   -2.1421 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6854    0.4150   -3.5205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2940    1.0903   -4.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2018   -0.9290   -3.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1655    0.2615   -3.6810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6256    1.5268   -3.3841 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3316    2.0180   -1.9531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3727    3.0732   -1.3798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3619    4.3742   -2.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8135    2.4801   -1.4572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8637    3.2562   -0.6549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4783    3.4176    0.8164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4665    2.1015    1.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6518    1.6384    1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274    2.2162    1.8207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4731    0.2907    2.5264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7396    0.3450    3.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4065    1.3319    4.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -0.8884    4.2993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703    4.0647    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1340    5.5709    0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    3.9646    2.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    3.2739    0.1415 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.6504    3.5886   -2.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7578    2.8855    2.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3557   -1.0431    1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8980   -2.6782   -1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3272   -2.6148    0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3866   -0.6405   -2.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    1.8293   -2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7637    0.3323   -1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3878    1.0526   -4.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0763   -0.0918   -4.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4085    2.2895   -4.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856    1.1277   -1.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    5.0953   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1761    4.1764   -3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208    4.8968   -2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8023    1.4414   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.4458   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8104    2.7075   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0481    4.2360   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2244    4.0432    1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4636   -0.1425    2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9380   -0.3502    1.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.7215    5.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468    6.0396    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467    5.7857   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802    6.0902    1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304    4.5877    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    2.9361    2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238    4.3085    3.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311    2.2590    0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6842    3.8314    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5918    4.7368   -0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339    3.1614   -0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    1.8253    0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2212    3.5953   -3.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833    4.5431   -2.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    3.6280   -2.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 10  1  0  0  0  0
 29 32  1  0  0  0  0
 17 19  1  0  0  0  0
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 11 13  1  1  0  0  0
 10  9  1  0  0  0  0
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 23 22  1  0  0  0  0
 21 29  1  0  0  0  0
 26 25  1  0  0  0  0
 17 16  1  0  0  0  0
  8  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  3  1  0  0  0  0
  3  4  2  0  0  0  0
 32 33  1  0  0  0  0
  3  2  1  0  0  0  0
 33 34  1  0  0  0  0
  2  1  1  0  0  0  0
 34 35  1  0  0  0  0
 23 24  2  0  0  0  0
 16 35  1  0  0  0  0
 26 27  2  0  0  0  0
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 29 30  1  6  0  0  0
 25 23  1  0  0  0  0
 17 18  1  6  0  0  0
 35 36  1  6  0  0  0
 21 20  1  0  0  0  0
 11 12  1  0  0  0  0
 16 15  1  0  0  0  0
  6  7  1  0  0  0  0
 35 10  1  0  0  0  0
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M  END

     RDKit          3D

 82 84  0  0  0  0  0  0  0  0999 V2000
    6.2277    1.9441    2.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4826    0.8313    2.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    0.7855    1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059    1.5833    0.3381 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6024   -0.4111    0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1760   -0.7575   -0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028   -2.0388   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.0193   -1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916    1.2775   -1.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0551    1.0719   -2.1421 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6854    0.4150   -3.5205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2940    1.0903   -4.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2018   -0.9290   -3.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1655    0.2615   -3.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256    1.5268   -3.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    2.0180   -1.9531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3727    3.0732   -1.3798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3619    4.3742   -2.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8135    2.4801   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637    3.2562   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4783    3.4176    0.8164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4665    2.1015    1.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6518    1.6384    1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274    2.2162    1.8207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4731    0.2907    2.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7396    0.3450    3.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4065    1.3319    4.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -0.8884    4.2993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703    4.0647    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1340    5.5709    0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    3.9646    2.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    3.2739    0.1415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4367    3.7415    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323    2.7410   -0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956    2.3773   -1.7780 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6504    3.5886   -2.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1761    4.1764   -3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8023    1.4414   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.4458   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8104    2.7075   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0481    4.2360   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2244    4.0432    1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4636   -0.1425    2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9380   -0.3502    1.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.7215    5.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468    6.0396    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467    5.7857   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802    6.0902    1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304    4.5877    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    2.9361    2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238    4.3085    3.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311    2.2590    0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6842    3.8314    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5918    4.7368   -0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339    3.1614   -0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    1.8253    0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2212    3.5953   -3.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833    4.5431   -2.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    3.6280   -2.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0
 14 15  1  0
 11 10  1  0
 29 32  1  0
 17 19  1  0
 19 20  1  0
 17 32  1  0
 11 13  1  1
 10  9  1  0
  9  8  1  0
 23 22  1  0
 21 29  1  0
 26 25  1  0
 17 16  1  0
  8  6  1  0
  6  5  2  0
  5  3  1  0
  3  4  2  0
 32 33  1  0
  3  2  1  0
 33 34  1  0
  2  1  1  0
 34 35  1  0
 23 24  2  0
 16 35  1  0
 26 27  2  0
 28 26  1  0
 29 30  1  6
 25 23  1  0
 17 18  1  6
 35 36  1  6
 21 20  1  0
 11 12  1  0
 16 15  1  0
  6  7  1  0
 35 10  1  0
 29 31  1  0
 21 22  1  0
 28 68  1  0
 25 66  1  0
 25 67  1  0
 21 65  1  1
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 32 75  1  1
 33 76  1  0
 33 77  1  0
 34 78  1  0
 34 79  1  0
 16 57  1  1
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 10 48  1  1
  9 46  1  0
  9 47  1  0
 13 52  1  0
  8 44  1  0
  8 45  1  0
  5 40  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 30 69  1  0
 30 70  1  0
 30 71  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 36 80  1  0
 36 81  1  0
 36 82  1  0
 12 49  1  0
 12 50  1  0
 12 51  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
M  END


  Mrv1652306212102443D          

 82 84  0  0  0  0            999 V2000
    6.2277    1.9441    2.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4826    0.8313    2.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    0.7855    1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059    1.5833    0.3381 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6024   -0.4111    0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1760   -0.7575   -0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028   -2.0388   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.0193   -1.7506 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5916    1.2775   -1.9495 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0551    1.0719   -2.1421 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6854    0.4150   -3.5205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2940    1.0903   -4.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2018   -0.9290   -3.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1655    0.2615   -3.6810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6256    1.5268   -3.3841 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3316    2.0180   -1.9531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3727    3.0732   -1.3798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3619    4.3742   -2.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8135    2.4801   -1.4572 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8637    3.2562   -0.6549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4783    3.4176    0.8164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4665    2.1015    1.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6518    1.6384    1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274    2.2162    1.8207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4731    0.2907    2.5264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7396    0.3450    3.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4065    1.3319    4.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -0.8884    4.2993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703    4.0647    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1340    5.5709    0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    3.9646    2.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    3.2739    0.1415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4367    3.7415    0.3179 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4323    2.7410   -0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1956    2.3773   -1.7780 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6504    3.5886   -2.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7578    2.8855    2.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2641    1.8978    2.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2280    1.8927    4.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3557   -1.0431    1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8980   -2.6782   -1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3272   -2.6148    0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3842   -1.8357   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    0.3245   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3866   -0.6405   -2.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    1.8293   -2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707    1.9230   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7637    0.3323   -1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9800    2.1244   -4.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3878    1.0526   -4.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0069    0.5496   -5.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587   -1.3468   -4.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867   -0.5404   -3.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763   -0.0918   -4.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833    1.2742   -3.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4085    2.2895   -4.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856    1.1277   -1.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    5.0953   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1761    4.1764   -3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208    4.8968   -2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8023    1.4414   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.4458   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8104    2.7075   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0481    4.2360   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2244    4.0432    1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4636   -0.1425    2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9380   -0.3502    1.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.7215    5.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468    6.0396    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467    5.7857   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802    6.0902    1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304    4.5877    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    2.9361    2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238    4.3085    3.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311    2.2590    0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6842    3.8314    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5918    4.7368   -0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339    3.1614   -0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    1.8253    0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2212    3.5953   -3.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833    4.5431   -2.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    3.6280   -2.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 10  1  0  0  0  0
 29 32  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 32  1  0  0  0  0
 11 13  1  1  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
 23 22  1  0  0  0  0
 21 29  1  0  0  0  0
 26 25  1  0  0  0  0
 17 16  1  0  0  0  0
  8  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  3  1  0  0  0  0
  3  4  2  0  0  0  0
 32 33  1  0  0  0  0
  3  2  1  0  0  0  0
 33 34  1  0  0  0  0
  2  1  1  0  0  0  0
 34 35  1  0  0  0  0
 23 24  2  0  0  0  0
 16 35  1  0  0  0  0
 26 27  2  0  0  0  0
 28 26  1  0  0  0  0
 29 30  1  6  0  0  0
 25 23  1  0  0  0  0
 17 18  1  6  0  0  0
 35 36  1  6  0  0  0
 21 20  1  0  0  0  0
 11 12  1  0  0  0  0
 16 15  1  0  0  0  0
  6  7  1  0  0  0  0
 35 10  1  0  0  0  0
 29 31  1  0  0  0  0
 21 22  1  0  0  0  0
 28 68  1  0  0  0  0
 25 66  1  0  0  0  0
 25 67  1  0  0  0  0
 21 65  1  1  0  0  0
 19 61  1  0  0  0  0
 19 62  1  0  0  0  0
 20 63  1  0  0  0  0
 20 64  1  0  0  0  0
 32 75  1  1  0  0  0
 33 76  1  0  0  0  0
 33 77  1  0  0  0  0
 34 78  1  0  0  0  0
 34 79  1  0  0  0  0
 16 57  1  1  0  0  0
 14 53  1  0  0  0  0
 14 54  1  0  0  0  0
 15 55  1  0  0  0  0
 15 56  1  0  0  0  0
 10 48  1  1  0  0  0
  9 46  1  0  0  0  0
  9 47  1  0  0  0  0
 13 52  1  0  0  0  0
  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
  5 40  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
 30 69  1  0  0  0  0
 30 70  1  0  0  0  0
 30 71  1  0  0  0  0
 18 58  1  0  0  0  0
 18 59  1  0  0  0  0
 18 60  1  0  0  0  0
 36 80  1  0  0  0  0
 36 81  1  0  0  0  0
 36 82  1  0  0  0  0
 12 49  1  0  0  0  0
 12 50  1  0  0  0  0
 12 51  1  0  0  0  0
  7 41  1  0  0  0  0
  7 42  1  0  0  0  0
  7 43  1  0  0  0  0
 31 72  1  0  0  0  0
 31 73  1  0  0  0  0
 31 74  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043285

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C(=O)O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])C(=C(\[H])C(=O)OC([H])([H])[H])\C([H])([H])[H])[C@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]23[H])C1(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O7/c1-18(16-24(32)35-7)8-9-21-28(5)13-10-19-26(2,3)22(36-25(33)17-23(30)31)12-14-27(19,4)20(28)11-15-29(21,6)34/h16,19-22,34H,8-15,17H2,1-7H3,(H,30,31)/b18-16-/t19-,20+,21-,22+,27-,28+,29-/m0/s1

> <INCHI_KEY>
WZPRGXSKTPRFRQ-WSQSCVPOSA-N

> <FORMULA>
C29H46O7

> <MOLECULAR_WEIGHT>
506.68

> <EXACT_MASS>
506.324353821

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
56.08042085262662

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-tetradecahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
5.32

> <JCHEM_LOGP>
5.293290489

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.294547448939685

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4354567321796957

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
136.57809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-decahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 82 84  0  0  0  0  0  0  0  0999 V2000
    6.2277    1.9441    2.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4826    0.8313    2.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    0.7855    1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059    1.5833    0.3381 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6024   -0.4111    0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1760   -0.7575   -0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028   -2.0388   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.0193   -1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916    1.2775   -1.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0551    1.0719   -2.1421 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6854    0.4150   -3.5205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2940    1.0903   -4.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2018   -0.9290   -3.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1655    0.2615   -3.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256    1.5268   -3.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    2.0180   -1.9531 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3727    3.0732   -1.3798 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3619    4.3742   -2.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8135    2.4801   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637    3.2562   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4665    2.1015    1.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6518    1.6384    1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274    2.2162    1.8207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4731    0.2907    2.5264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7396    0.3450    3.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4065    1.3319    4.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -0.8884    4.2993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703    4.0647    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1340    5.5709    0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    3.9646    2.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    3.2739    0.1415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4367    3.7415    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323    2.7410   -0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956    2.3773   -1.7780 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6504    3.5886   -2.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7578    2.8855    2.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2641    1.8978    2.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2280    1.8927    4.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3557   -1.0431    1.6023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8980   -2.6782   -1.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3272   -2.6148    0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3842   -1.8357   -1.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5098    0.3245   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3866   -0.6405   -2.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0032    1.8293   -2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7707    1.9230   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7637    0.3323   -1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9800    2.1244   -4.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3878    1.0526   -4.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0069    0.5496   -5.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9587   -1.3468   -4.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867   -0.5404   -3.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763   -0.0918   -4.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833    1.2742   -3.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4085    2.2895   -4.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856    1.1277   -1.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    5.0953   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1761    4.1764   -3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208    4.8968   -2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8023    1.4414   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1568    2.4458   -2.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8104    2.7075   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0481    4.2360   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2244    4.0432    1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4636   -0.1425    2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9380   -0.3502    1.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.7215    5.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468    6.0396    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467    5.7857   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802    6.0902    1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304    4.5877    2.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4602    2.9361    2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238    4.3085    3.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311    2.2590    0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6842    3.8314    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5918    4.7368   -0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339    3.1614   -0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3936    1.8253    0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2212    3.5953   -3.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3833    4.5431   -2.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    3.6280   -2.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0
 14 15  1  0
 11 10  1  0
 29 32  1  0
 17 19  1  0
 19 20  1  0
 17 32  1  0
 11 13  1  1
 10  9  1  0
  9  8  1  0
 23 22  1  0
 21 29  1  0
 26 25  1  0
 17 16  1  0
  8  6  1  0
  6  5  2  0
  5  3  1  0
  3  4  2  0
 32 33  1  0
  3  2  1  0
 33 34  1  0
  2  1  1  0
 34 35  1  0
 23 24  2  0
 16 35  1  0
 26 27  2  0
 28 26  1  0
 29 30  1  6
 25 23  1  0
 17 18  1  6
 35 36  1  6
 21 20  1  0
 11 12  1  0
 16 15  1  0
  6  7  1  0
 35 10  1  0
 29 31  1  0
 21 22  1  0
 28 68  1  0
 25 66  1  0
 25 67  1  0
 21 65  1  1
 19 61  1  0
 19 62  1  0
 20 63  1  0
 20 64  1  0
 32 75  1  1
 33 76  1  0
 33 77  1  0
 34 78  1  0
 34 79  1  0
 16 57  1  1
 14 53  1  0
 14 54  1  0
 15 55  1  0
 15 56  1  0
 10 48  1  1
  9 46  1  0
  9 47  1  0
 13 52  1  0
  8 44  1  0
  8 45  1  0
  5 40  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
 30 69  1  0
 30 70  1  0
 30 71  1  0
 18 58  1  0
 18 59  1  0
 18 60  1  0
 36 80  1  0
 36 81  1  0
 36 82  1  0
 12 49  1  0
 12 50  1  0
 12 51  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
 31 72  1  0
 31 73  1  0
 31 74  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       6.228   1.944   2.962  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.483   0.831   2.466  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.405   0.786   1.110  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.906   1.583   0.338  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.602  -0.411   0.754  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.176  -0.758  -0.478  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.403  -2.039  -0.665  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.455   0.019  -1.751  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.592   1.278  -1.950  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.055   1.072  -2.142  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.685   0.415  -3.521  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.294   1.090  -4.757  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.202  -0.929  -3.521  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.166   0.262  -3.681  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.626   1.527  -3.384  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.332   2.018  -1.953  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.373   3.073  -1.380  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.362   4.374  -2.215  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.813   2.480  -1.457  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.864   3.256  -0.655  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.478   3.418   0.816  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.466   2.102   1.423  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.652   1.638   1.906  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.727   2.216   1.821  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.473   0.291   2.526  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.740   0.345   3.823  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.406   1.332   4.455  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.466  -0.888   4.299  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.070   4.065   1.004  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.134   5.571   0.682  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.696   3.965   2.509  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.018   3.274   0.142  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.437   3.741   0.318  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.432   2.741  -0.280  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.196   2.377  -1.778  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.650   3.589  -2.626  0.00  0.00           C+0
HETATM   37  H   UNK     0       5.758   2.886   2.660  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.264   1.898   2.613  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.228   1.893   4.054  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.356  -1.043   1.602  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.898  -2.678  -1.403  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.327  -2.615   0.264  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.384  -1.836  -1.004  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.510   0.325  -1.750  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.387  -0.641  -2.621  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.003   1.829  -2.801  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.771   1.923  -1.087  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.764   0.332  -1.383  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.980   2.124  -4.888  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.388   1.053  -4.739  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.007   0.550  -5.668  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.959  -1.347  -4.365  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.187  -0.540  -3.016  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.076  -0.092  -4.692  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.683   1.274  -3.502  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.409   2.289  -4.136  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.486   1.128  -1.320  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.618   5.095  -1.876  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.176   4.176  -3.275  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.321   4.897  -2.196  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.802   1.441  -1.101  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.157   2.446  -2.498  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.810   2.708  -0.732  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.048   4.236  -1.105  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.224   4.043   1.324  0.00  0.00           H+0
HETATM   66  H   UNK     0      -5.464  -0.143   2.701  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.938  -0.350   1.818  0.00  0.00           H+0
HETATM   68  H   UNK     0      -3.003  -0.722   5.148  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.147   6.040   0.744  0.00  0.00           H+0
HETATM   70  H   UNK     0      -2.547   5.786  -0.303  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.780   6.090   1.400  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.830   4.588   2.756  0.00  0.00           H+0
HETATM   73  H   UNK     0      -1.460   2.936   2.803  0.00  0.00           H+0
HETATM   74  H   UNK     0      -2.524   4.309   3.142  0.00  0.00           H+0
HETATM   75  H   UNK     0      -1.031   2.259   0.573  0.00  0.00           H+0
HETATM   76  H   UNK     0       0.684   3.831   1.381  0.00  0.00           H+0
HETATM   77  H   UNK     0       0.592   4.737  -0.107  0.00  0.00           H+0
HETATM   78  H   UNK     0       2.434   3.161  -0.135  0.00  0.00           H+0
HETATM   79  H   UNK     0       1.394   1.825   0.326  0.00  0.00           H+0
HETATM   80  H   UNK     0       1.221   3.595  -3.628  0.00  0.00           H+0
HETATM   81  H   UNK     0       1.383   4.543  -2.169  0.00  0.00           H+0
HETATM   82  H   UNK     0       2.738   3.628  -2.734  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3   40                                                  
CONECT    6    8    5    7                                                  
CONECT    7    6   41   42   43                                             
CONECT    8    9    6   44   45                                             
CONECT    9   10    8   46   47                                             
CONECT   10   11    9   35   48                                             
CONECT   11   14   10   13   12                                             
CONECT   12   11   49   50   51                                             
CONECT   13   11   52                                                       
CONECT   14   11   15   53   54                                             
CONECT   15   14   16   55   56                                             
CONECT   16   17   35   15   57                                             
CONECT   17   19   32   16   18                                             
CONECT   18   17   58   59   60                                             
CONECT   19   17   20   61   62                                             
CONECT   20   19   21   63   64                                             
CONECT   21   29   20   22   65                                             
CONECT   22   23   21                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   26   23   66   67                                             
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   68                                                       
CONECT   29   32   21   30   31                                             
CONECT   30   29   69   70   71                                             
CONECT   31   29   72   73   74                                             
CONECT   32   29   17   33   75                                             
CONECT   33   32   34   76   77                                             
CONECT   34   33   35   78   79                                             
CONECT   35   34   16   36   10                                             
CONECT   36   35   80   81   82                                             
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    5                                                            
CONECT   41    7                                                            
CONECT   42    7                                                            
CONECT   43    7                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47    9                                                            
CONECT   48   10                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   14                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   15                                                            
CONECT   57   16                                                            
CONECT   58   18                                                            
CONECT   59   18                                                            
CONECT   60   18                                                            
CONECT   61   19                                                            
CONECT   62   19                                                            
CONECT   63   20                                                            
CONECT   64   20                                                            
CONECT   65   21                                                            
CONECT   66   25                                                            
CONECT   67   25                                                            
CONECT   68   28                                                            
CONECT   69   30                                                            
CONECT   70   30                                                            
CONECT   71   30                                                            
CONECT   72   31                                                            
CONECT   73   31                                                            
CONECT   74   31                                                            
CONECT   75   32                                                            
CONECT   76   33                                                            
CONECT   77   33                                                            
CONECT   78   34                                                            
CONECT   79   34                                                            
CONECT   80   36                                                            
CONECT   81   36                                                            
CONECT   82   36                                                            
MASTER        0    0    0    0    0    0    0    0   82    0  168    0
END

RDKit          3D

82 84  0  0  0  0  0  0  0  0999 V2000
    6.2277    1.9441    2.9615 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4826    0.8313    2.4665 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4048    0.7855    1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9059    1.5833    0.3381 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6024   -0.4111    0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1760   -0.7575   -0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4028   -2.0388   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4555    0.0193   -1.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916    1.2775   -1.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0551    1.0719   -2.1421 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6854    0.4150   -3.5205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2940    1.0903   -4.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2018   -0.9290   -3.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1655    0.2615   -3.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6256    1.5268   -3.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3619    4.3742   -2.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8135    2.4801   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8637    3.2562   -0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4783    3.4176    0.8164 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4665    2.1015    1.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6518    1.6384    1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7274    2.2162    1.8207 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7396    0.3450    3.8231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4065    1.3319    4.4552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -0.8884    4.2993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703    4.0647    1.0037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1340    5.5709    0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6965    3.9646    2.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    3.2739    0.1415 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4367    3.7415    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9800    2.1244   -4.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3878    1.0526   -4.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0069    0.5496   -5.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4085    2.2895   -4.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856    1.1277   -1.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6180    5.0953   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1761    4.1764   -3.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208    4.8968   -2.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8023    1.4414   -1.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2244    4.0432    1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4636   -0.1425    2.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9380   -0.3502    1.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.7215    5.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468    6.0396    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5467    5.7857   -0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7802    6.0902    1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5238    4.3085    3.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6842    3.8314    1.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol

Synonyms

Value	Source
3-{[(2R,4ar,4BR,7S,8S,8ar,10ar)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-tetradecahydrophenanthren-2-yl]oxy}-3-oxopropanoate	Generator

Chemical Formula

C₂₉H₄₆O₇

Average Mass

506.6800 Da

Monoisotopic Mass

506.32435 Da

IUPAC Name

3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-tetradecahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid

Traditional Name

3-{[(2R,4aR,4bR,7S,8S,8aR,10aR)-7-hydroxy-8-[(3Z)-5-methoxy-3-methyl-5-oxopent-3-en-1-yl]-1,1,4a,7,8a-pentamethyl-decahydrophenanthren-2-yl]oxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])C(=O)O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[C@@]3(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])C(=C(\[H])C(=O)OC([H])([H])[H])\C([H])([H])[H])[C@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]23[H])C1(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C29H46O7/c1-18(16-24(32)35-7)8-9-21-28(5)13-10-19-26(2,3)22(36-25(33)17-23(30)31)12-14-27(19,4)20(28)11-15-29(21,6)34/h16,19-22,34H,8-15,17H2,1-7H3,(H,30,31)/b18-16-/t19-,20+,21-,22+,27-,28+,29-/m0/s1

InChI Key

WZPRGXSKTPRFRQ-WSQSCVPOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aletris farinosa	JEOL database	Challinor, V. L., et al, J. Nat. Prod. 76, 485 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Cheilanthane sesterterpenoids

Alternative Parents

Substituents

Cheilanthane sesterterpenoid
13-hydroxysteroid
Hydroxysteroid
Steroid
Hydrophenanthrene
Phenanthrene
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
1,3-dicarbonyl compound
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.32	ALOGPS
logP	5.29	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-0.44	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	136.58 m³·mol⁻¹	ChemAxon
Polarizability	56.08 Å³	ChemAxon
Number of Rings	3	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

Not Available

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

71665524

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Challinor, V. L., et al. (2013). Challinor, V. L., et al, J. Nat. Prod. 76, 485 (2013). J. Nat. Prod..

Showing NP-Card for (3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate (NP0043285)

MOL for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)

3D MOL for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)

3D SDF for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)

3D-SDF for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)

PDB for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)

3D PDB for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)

SMILES for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)

INCHI for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)

Structure for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)

3D Structure for NP0043285 ((3R)-malonyl-(13S)-hydroxy-cheilanth-17-en-19-oate)