NP-MRD: Showing NP-Card for sarsasapogenin (NP0030539)

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Record Information

Version

2.0

Created at

2021-06-19 21:52:20 UTC

Updated at

2021-08-20 00:00:18 UTC

NP-MRD ID

NP0030539

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sarsasapogenin

Provided By

JEOL Database JEOL Logo

Description

Sarsasapogenin, also known as smilagenin or parigenin, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, sarsasapogenin is considered to be a sterol. Sarsasapogenin has been detected, but not quantified in, a few different foods, such as asparagus (Asparagus officinalis), fenugreeks (Trigonella foenum-graecum), and herbs and spices. This could make sarsasapogenin a potential biomarker for the consumption of these foods. sarsasapogenin is found in Cordyline fruticosa, Dioscorea colletii, Doryanthes palmeri, Echinopora lamellosa, Narthecium ossifragum, Radix sarsaparilla, Radix sarsaparillae, Yucca carnerosana, Yucca gloriosa and Yucca treculeana. sarsasapogenin was first documented in 2006 (PMID: 17077534). Based on a literature review very few articles have been published on Sarsasapogenin.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306192123523D          

 74 79  0  0  0  0            999 V2000
    0.9308    7.9484    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    7.2889    0.8998 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6542    6.7938   -0.3650 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4963    5.5483   -0.0927 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6949    4.4829    0.6633 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1010    5.0342    1.8427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812    6.1219    1.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3098    3.9218   -0.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012    2.6969    0.4087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1849    1.6412   -0.5872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6209    0.3647    0.0274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6854   -0.9471   -0.7615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1235   -1.2808   -1.1782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2222   -2.6416   -1.8614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6105   -3.7847   -1.0330 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5271   -4.1185    0.1690 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9734   -5.2351    1.0494 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0109   -6.4575    0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -4.9387    1.4950 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3634   -4.6465    0.3028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1343   -3.4848   -0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7768   -3.5029   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0718   -2.0862    0.1169 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3336   -1.7075    0.6601 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3844   -0.3194    1.3266 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8230    0.7760    0.4083 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7560    0.9389   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411    2.1283    1.1276 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5639    3.2657    1.0383 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3807    3.4152    2.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    8.7748    1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    7.2432    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    8.3588    2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    8.0473    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022    6.5519   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    7.5837   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3752    5.8417    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8553    5.1517   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6141    5.7720    0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2136    6.4418    2.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    2.9121    1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    1.6253   -0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8128    1.8266   -1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    0.1952    0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1061   -0.8363   -1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858   -1.2528   -0.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4970   -0.5170   -1.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750   -2.8596   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216   -2.5878   -2.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044   -4.6749   -1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916   -3.2324    0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090   -4.4214   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -5.3626    1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697   -7.1586    0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5376   -4.0938    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1399   -5.8031    2.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808   -4.4570    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387   -5.5635   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8347   -3.4210   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -4.4449   -2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -2.6969   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -2.1533    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0774   -1.7471   -0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -2.4388    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -0.0874    1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067   -0.3625    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005    0.0453   -1.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4490    1.7638   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7864    1.1321   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    1.9316    2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676    3.0949    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0659    4.2656    2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796    2.5154    2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    3.5665    3.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0  0  0  0
 21 20  1  0  0  0  0
 21 15  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
 29 28  1  0  0  0  0
 28  9  1  0  0  0  0
 21 23  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
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 23 12  1  0  0  0  0
  9  8  1  0  0  0  0
  5 29  1  0  0  0  0
  2  7  1  0  0  0  0
 23 24  1  0  0  0  0
 12 11  1  0  0  0  0
 25 24  1  0  0  0  0
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 21 22  1  6  0  0  0
 26 11  1  0  0  0  0
 19 17  1  0  0  0  0
  7  6  1  0  0  0  0
  9 10  1  0  0  0  0
 28 26  1  0  0  0  0
 11 10  1  0  0  0  0
 29 30  1  0  0  0  0
  5  4  1  0  0  0  0
 26 27  1  6  0  0  0
 19 20  1  0  0  0  0
 17 18  1  0  0  0  0
 17 16  1  0  0  0  0
  2  1  1  0  0  0  0
  5  6  1  1  0  0  0
  5  8  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  2 34  1  6  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
 29 71  1  6  0  0  0
 28 70  1  1  0  0  0
  9 41  1  1  0  0  0
 25 65  1  0  0  0  0
 25 66  1  0  0  0  0
 19 55  1  0  0  0  0
 19 56  1  0  0  0  0
 17 53  1  1  0  0  0
 16 51  1  0  0  0  0
 16 52  1  0  0  0  0
 20 57  1  0  0  0  0
 20 58  1  0  0  0  0
 15 50  1  6  0  0  0
 14 48  1  0  0  0  0
 14 49  1  0  0  0  0
 13 46  1  0  0  0  0
 13 47  1  0  0  0  0
 23 62  1  1  0  0  0
 12 45  1  6  0  0  0
 24 63  1  0  0  0  0
 24 64  1  0  0  0  0
 22 59  1  0  0  0  0
 22 60  1  0  0  0  0
 22 61  1  0  0  0  0
 11 44  1  1  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 30 72  1  0  0  0  0
 30 73  1  0  0  0  0
 30 74  1  0  0  0  0
 27 67  1  0  0  0  0
 27 68  1  0  0  0  0
 27 69  1  0  0  0  0
 18 54  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
M  END

     RDKit          3D

 74 79  0  0  0  0  0  0  0  0999 V2000
    0.9308    7.9484    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    7.2889    0.8998 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6542    6.7938   -0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4963    5.5483   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6949    4.4829    0.6633 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1010    5.0342    1.8427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812    6.1219    1.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3098    3.9218   -0.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012    2.6969    0.4087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1849    1.6412   -0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209    0.3647    0.0274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6854   -0.9471   -0.7615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1235   -1.2808   -1.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2222   -2.6416   -1.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105   -3.7847   -1.0330 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5271   -4.1185    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9734   -5.2351    1.0494 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0109   -6.4575    0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -4.9387    1.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3634   -4.6465    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343   -3.4848   -0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7768   -3.5029   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0718   -2.0862    0.1169 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3336   -1.7075    0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3844   -0.3194    1.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230    0.7760    0.4083 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7560    0.9389   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411    2.1283    1.1276 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.6784    7.2432    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    8.3588    2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2822    7.5837   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3752    5.8417    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8553    5.1517   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4930    2.9121    1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    1.6253   -0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8128    1.8266   -1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6514   -2.4388    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -0.0874    1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067   -0.3625    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005    0.0453   -1.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4490    1.7638   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7864    1.1321   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    1.9316    2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676    3.0949    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0659    4.2656    2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796    2.5154    2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    3.5665    3.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 21 20  1  0
 21 15  1  0
  4  3  1  0
  3  2  1  0
 29 28  1  0
 28  9  1  0
 21 23  1  0
 15 14  1  0
 14 13  1  0
 12 13  1  0
 23 12  1  0
  9  8  1  0
  5 29  1  0
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 23 24  1  0
 12 11  1  0
 25 24  1  0
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 11 10  1  0
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 26 27  1  6
 19 20  1  0
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  2 34  1  6
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 27 67  1  0
 27 68  1  0
 27 69  1  0
 18 54  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
M  END

  Mrv1652306192123523D          

 74 79  0  0  0  0            999 V2000
    0.9308    7.9484    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    7.2889    0.8998 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6542    6.7938   -0.3650 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4963    5.5483   -0.0927 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6949    4.4829    0.6633 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1010    5.0342    1.8427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812    6.1219    1.5697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3098    3.9218   -0.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012    2.6969    0.4087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1849    1.6412   -0.5872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6209    0.3647    0.0274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6854   -0.9471   -0.7615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1235   -1.2808   -1.1782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2222   -2.6416   -1.8614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6105   -3.7847   -1.0330 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.3634   -4.6465    0.3028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1343   -3.4848   -0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7768   -3.5029   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0718   -2.0862    0.1169 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3336   -1.7075    0.6601 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3844   -0.3194    1.3266 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8230    0.7760    0.4083 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7560    0.9389   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411    2.1283    1.1276 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5639    3.2657    1.0383 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3807    3.4152    2.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    8.7748    1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    7.2432    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    8.3588    2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    8.0473    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022    6.5519   -1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    7.5837   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3752    5.8417    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4387   -5.5635   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8347   -3.4210   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -4.4449   -2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -2.6969   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -2.1533    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0774   -1.7471   -0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -2.4388    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -0.0874    1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067   -0.3625    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005    0.0453   -1.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4490    1.7638   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7864    1.1321   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    1.9316    2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676    3.0949    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0659    4.2656    2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796    2.5154    2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    3.5665    3.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0  0  0  0
 21 20  1  0  0  0  0
 21 15  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
 29 28  1  0  0  0  0
 28  9  1  0  0  0  0
 21 23  1  0  0  0  0
 15 14  1  0  0  0  0
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 12 13  1  0  0  0  0
 23 12  1  0  0  0  0
  9  8  1  0  0  0  0
  5 29  1  0  0  0  0
  2  7  1  0  0  0  0
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 25 26  1  0  0  0  0
 21 22  1  6  0  0  0
 26 11  1  0  0  0  0
 19 17  1  0  0  0  0
  7  6  1  0  0  0  0
  9 10  1  0  0  0  0
 28 26  1  0  0  0  0
 11 10  1  0  0  0  0
 29 30  1  0  0  0  0
  5  4  1  0  0  0  0
 26 27  1  6  0  0  0
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 17 18  1  0  0  0  0
 17 16  1  0  0  0  0
  2  1  1  0  0  0  0
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 29 71  1  6  0  0  0
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 30 72  1  0  0  0  0
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 27 67  1  0  0  0  0
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 18 54  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030539

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]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([H])[C@]4([H])C([H])([H])[C@]5([H])O[C@@]6(OC([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])C6([H])[H])[C@@]([H])(C([H])([H])[H])[C@]5([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])[C@]23[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18+,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

> <INCHI_KEY>
GMBQZIIUCVWOCD-WWASVFFGSA-N

> <FORMULA>
C27H44O3

> <MOLECULAR_WEIGHT>
416.646

> <EXACT_MASS>
416.329045277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.29193600162655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-16'-ol

> <ALOGPS_LOGP>
4.52

> <JCHEM_LOGP>
5.332884935333334

> <ALOGPS_LOGS>
-7.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963963211217

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3560752133131748

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
119.41590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-16'-ol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 74 79  0  0  0  0  0  0  0  0999 V2000
    0.9308    7.9484    1.8699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0538    7.2889    0.8998 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.4963    5.5483   -0.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6949    4.4829    0.6633 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1010    5.0342    1.8427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812    6.1219    1.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3098    3.9218   -0.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012    2.6969    0.4087 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.0718   -2.0862    0.1169 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3336   -1.7075    0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6916   -3.2324    0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090   -4.4214   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -5.3626    1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1399   -5.8031    2.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4387   -5.5635   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8347   -3.4210   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -4.4449   -2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -2.6969   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -2.1533    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0774   -1.7471   -0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -2.4388    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -0.0874    1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067   -0.3625    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005    0.0453   -1.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4490    1.7638   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7864    1.1321   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2676    3.0949    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0659    4.2656    2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796    2.5154    2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    3.5665    3.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 21 20  1  0
 21 15  1  0
  4  3  1  0
  3  2  1  0
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 28  9  1  0
 21 23  1  0
 15 14  1  0
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 28 26  1  0
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 29 30  1  0
  5  4  1  0
 26 27  1  6
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 17 18  1  0
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  2  1  1  0
  5  6  1  1
  5  8  1  0
  4 37  1  0
  4 38  1  0
  3 35  1  0
  3 36  1  0
  2 34  1  6
  7 39  1  0
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 29 71  1  6
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  9 41  1  1
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 27 67  1  0
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  1 31  1  0
  1 32  1  0
  1 33  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.931   7.948   1.870  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.054   7.289   0.900  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.654   6.794  -0.365  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.496   5.548  -0.093  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.695   4.483   0.663  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.101   5.034   1.843  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.781   6.122   1.570  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.310   3.922  -0.204  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.701   2.697   0.409  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.185   1.641  -0.587  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.621   0.365   0.027  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.685  -0.947  -0.762  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.123  -1.281  -1.178  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.222  -2.642  -1.861  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.611  -3.785  -1.033  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.527  -4.119   0.169  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.973  -5.235   1.049  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.011  -6.457   0.316  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.546  -4.939   1.495  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.363  -4.646   0.303  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.134  -3.485  -0.605  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.777  -3.503  -1.861  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.072  -2.086   0.117  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -1.708   0.660  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.384  -0.319   1.327  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.823   0.776   0.408  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.756   0.939  -0.819  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.541   2.128   1.128  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.564   3.266   1.038  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.381   3.415   2.316  0.00  0.00           C+0
HETATM   31  H   UNK     0       1.459   8.775   1.383  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.678   7.243   2.246  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.398   8.359   2.735  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.793   8.047   0.614  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.102   6.552  -1.123  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.282   7.584  -0.793  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.375   5.842   0.493  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.855   5.152  -1.050  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.614   5.772   0.948  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.214   6.442   2.524  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.493   2.912   1.138  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.278   1.625  -0.638  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.813   1.827  -1.600  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.190   0.195   0.958  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.106  -0.836  -1.683  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.786  -1.253  -0.305  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.497  -0.517  -1.871  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.275  -2.860  -2.080  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.722  -2.588  -2.836  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.604  -4.675  -1.679  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.692  -3.232   0.791  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.509  -4.421  -0.217  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.619  -5.363   1.926  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.670  -7.159   0.897  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.538  -4.094   2.192  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.140  -5.803   2.034  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.381  -4.457   0.662  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.439  -5.564  -0.298  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.835  -3.421  -1.591  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.663  -4.445  -2.410  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.554  -2.697  -2.563  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.708  -2.153   1.010  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.077  -1.747  -0.141  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.651  -2.439   1.411  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.417  -0.087   1.615  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.807  -0.363   2.259  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.801   0.045  -1.446  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.449   1.764  -1.469  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.786   1.132  -0.498  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.264   1.932   2.172  0.00  0.00           H+0
HETATM   71  H   UNK     0       2.268   3.095   0.220  0.00  0.00           H+0
HETATM   72  H   UNK     0       3.066   4.266   2.245  0.00  0.00           H+0
HETATM   73  H   UNK     0       2.980   2.515   2.492  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.744   3.567   3.194  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    7    1   34                                             
CONECT    3    4    2   35   36                                             
CONECT    4    3    5   37   38                                             
CONECT    5   29    4    6    8                                             
CONECT    6    7    5                                                       
CONECT    7    2    6   39   40                                             
CONECT    8    9    5                                                       
CONECT    9   28    8   10   41                                             
CONECT   10    9   11   42   43                                             
CONECT   11   12   26   10   44                                             
CONECT   12   13   23   11   45                                             
CONECT   13   14   12   46   47                                             
CONECT   14   15   13   48   49                                             
CONECT   15   16   21   14   50                                             
CONECT   16   15   17   51   52                                             
CONECT   17   19   18   16   53                                             
CONECT   18   17   54                                                       
CONECT   19   17   20   55   56                                             
CONECT   20   21   19   57   58                                             
CONECT   21   20   15   23   22                                             
CONECT   22   21   59   60   61                                             
CONECT   23   21   12   24   62                                             
CONECT   24   23   25   63   64                                             
CONECT   25   24   26   65   66                                             
CONECT   26   25   11   28   27                                             
CONECT   27   26   67   68   69                                             
CONECT   28   29    9   26   70                                             
CONECT   29   28    5   30   71                                             
CONECT   30   29   72   73   74                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   16                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   19                                                            
CONECT   57   20                                                            
CONECT   58   20                                                            
CONECT   59   22                                                            
CONECT   60   22                                                            
CONECT   61   22                                                            
CONECT   62   23                                                            
CONECT   63   24                                                            
CONECT   64   24                                                            
CONECT   65   25                                                            
CONECT   66   25                                                            
CONECT   67   27                                                            
CONECT   68   27                                                            
CONECT   69   27                                                            
CONECT   70   28                                                            
CONECT   71   29                                                            
CONECT   72   30                                                            
CONECT   73   30                                                            
CONECT   74   30                                                            
MASTER        0    0    0    0    0    0    0    0   74    0  158    0
END

RDKit          3D

74 79  0  0  0  0  0  0  0  0999 V2000
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   -0.0538    7.2889    0.8998 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.6949    4.4829    0.6633 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1010    5.0342    1.8427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812    6.1219    1.5697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3098    3.9218   -0.2038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7012    2.6969    0.4087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1849    1.6412   -0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209    0.3647    0.0274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6854   -0.9471   -0.7615 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.2222   -2.6416   -1.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105   -3.7847   -1.0330 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.3634   -4.6465    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1343   -3.4848   -0.6053 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7768   -3.5029   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0718   -2.0862    0.1169 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.7560    0.9389   -0.8186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5411    2.1283    1.1276 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5639    3.2657    1.0383 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3807    3.4152    2.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    8.7748    1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    7.2432    2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    8.3588    2.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7929    8.0473    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2822    7.5837   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3752    5.8417    0.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8553    5.1517   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6141    5.7720    0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2136    6.4418    2.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4930    2.9121    1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    1.6253   -0.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8128    1.8266   -1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1061   -0.8363   -1.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7858   -1.2528   -0.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4970   -0.5170   -1.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2750   -2.8596   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216   -2.5878   -2.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6044   -4.6749   -1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916   -3.2324    0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5090   -4.4214   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6188   -5.3626    1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6697   -7.1586    0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5376   -4.0938    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1399   -5.8031    2.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3808   -4.4570    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387   -5.5635   -0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8347   -3.4210   -1.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625   -4.4449   -2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -2.6969   -2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082   -2.1533    1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0774   -1.7471   -0.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6514   -2.4388    1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -0.0874    1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8067   -0.3625    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005    0.0453   -1.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4490    1.7638   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7864    1.1321   -0.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2640    1.9316    2.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676    3.0949    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0659    4.2656    2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796    2.5154    2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7445    3.5665    3.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 21 20  1  0
 21 15  1  0
  4  3  1  0
  3  2  1  0
 29 28  1  0
 28  9  1  0
 21 23  1  0
 15 14  1  0
 14 13  1  0
 12 13  1  0
 23 12  1  0
  9  8  1  0
  5 29  1  0
  2  7  1  0
 23 24  1  0
 12 11  1  0
 25 24  1  0
 25 26  1  0
 21 22  1  6
 26 11  1  0
 19 17  1  0
  7  6  1  0
  9 10  1  0
 28 26  1  0
 11 10  1  0
 29 30  1  0
  5  4  1  0
 26 27  1  6
 19 20  1  0
 17 18  1  0
 17 16  1  0
  2  1  1  0
  5  6  1  1
  5  8  1  0
  4 37  1  0
  4 38  1  0
  3 35  1  0
  3 36  1  0
  2 34  1  6
  7 39  1  0
  7 40  1  0
 29 71  1  6
 28 70  1  1
  9 41  1  1
 25 65  1  0
 25 66  1  0
 19 55  1  0
 19 56  1  0
 17 53  1  1
 16 51  1  0
 16 52  1  0
 20 57  1  0
 20 58  1  0
 15 50  1  6
 14 48  1  0
 14 49  1  0
 13 46  1  0
 13 47  1  0
 23 62  1  1
 12 45  1  6
 24 63  1  0
 24 64  1  0
 22 59  1  0
 22 60  1  0
 22 61  1  0
 11 44  1  1
 10 42  1  0
 10 43  1  0
 30 72  1  0
 30 73  1  0
 30 74  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 18 54  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3beta,5beta,25S)-Spirostan-3-ol	ChEBI
Parigenin	ChEBI
(25S)-5beta-Spirostan-3beta-ol	Kegg
(3b,5b,25S)-Spirostan-3-ol	Generator
(3Β,5β,25S)-spirostan-3-ol	Generator
(25S)-5b-Spirostan-3b-ol	Generator
(25S)-5Β-spirostan-3β-ol	Generator
Sarsasapogenine	HMDB
Spirostan-3-ol, (3beta,5beta,25S)- (9ci)	HMDB
Epi-sarsasapogenin	HMDB
Tigogenin	HMDB
Sarsaponin	HMDB
Sarsasapogenin, (3beta,5alpha,25S)-isomer	HMDB
Smilagenin	HMDB
Epismilagenin	HMDB
Sarsasapogenin, (3beta,5alpha,25R)-isomer	HMDB
Sarsasapogenin, (3beta,5beta)-isomer	HMDB
Sarsasapogenin, (3beta,5beta,25R)-isomer	HMDB
Sarsasapogenin, (3beta,5beta,25S)-isomer	HMDB
Sarsasapogenin	ChEBI

Chemical Formula

C₂₇H₄₄O₃

Average Mass

416.6460 Da

Monoisotopic Mass

416.32905 Da

IUPAC Name

(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-16'-ol

Traditional Name

(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-16'-ol

CAS Registry Number

Not Available

SMILES

[H]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([H])[C@]4([H])C([H])([H])[C@]5([H])O[C@@]6(OC([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])C6([H])[H])[C@@]([H])(C([H])([H])[H])[C@]5([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])[C@]23[H])C1([H])[H]

InChI Identifier

InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18+,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

InChI Key

GMBQZIIUCVWOCD-WWASVFFGSA-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
Anemarrhena asphodeloides	KNApSAcK Database	22123792
Asparagus broussonetii	KNApSAcK Database	22123792
Asparagus cochinchinensis	KNApSAcK Database	22123792
Asparagus officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Asparagus racemosus	KNApSAcK Database	22123792
Asparagus spp.	KNApSAcK Database	22123792
Cordyline fruticosa	LOTUS Database	35616633
Dioscorea colletii	Plant	KNApSAcK
Dioscorea collettii	KNApSAcK Database	22123792
Doryanthes palmeri	LOTUS Database	35616633
Echinopora lamellosa	LOTUS Database	35616633
Narthecium ossifragum	LOTUS Database	35616633
Radix sarsaparilla	-	KNApSAcK
Radix sarsaparillae	-	KNApSAcK
Smilax lanceolata	KNApSAcK Database	22123792
Smilax rotundifolia	KNApSAcK Database	22123792
Smilax spp.	KNApSAcK Database	22123792
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Yucca angustissima	KNApSAcK Database	22123792
Yucca arizonica	KNApSAcK Database	22123792
Yucca baccata	KNApSAcK Database	22123792
Yucca baileyi	KNApSAcK Database	22123792
Yucca brevifolia Engelm.	KNApSAcK Database	22123792
Yucca carnerosana	LOTUS Database	35616633
Yucca confinis	KNApSAcK Database	22123792
Yucca decipiens	KNApSAcK Database	22123792
Yucca elata Engelm.	KNApSAcK Database	22123792
Yucca filifera	KNApSAcK Database	22123792
Yucca glauca Nutt.	KNApSAcK Database	22123792
Yucca gloriosa	LOTUS Database	35616633
Yucca harrimannii	KNApSAcK Database	22123792
Yucca jalicensis	KNApSAcK Database	22123792
Yucca rigida	KNApSAcK Database	22123792
Yucca schidigera	KNApSAcK Database	22123792
Yucca schottii Engelm.	KNApSAcK Database	22123792
Yucca thornberi	KNApSAcK Database	22123792
Yucca torreyi	KNApSAcK Database	22123792
Yucca treculeana	LOTUS Database	35616633
Yucca treculeana Hook.	KNApSAcK Database	22123792
Yucca valida	KNApSAcK Database	22123792

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
Spirostane skeleton
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
Steroid
Ketal
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Alcohol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sapogenin (CHEBI:15578 )
spirostan (C03963 )
Spirostanols and derivatives (C03963 )
Spirostan and derivatives (C03963 )
Spirostanols and derivatives (LMST01080007 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	200.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	516.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.0066 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.210 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	4.52	ALOGPS
logP	5.33	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	119.42 m³·mol⁻¹	ChemAxon
Polarizability	51.29 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030024

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sarsasapogenin

METLIN ID

Not Available

PubChem Compound

92095

PDB ID

Not Available

ChEBI ID

15578

Good Scents ID

rw1281751

References

General References

Ren LX, Luo YF, Li X, Zuo DY, Wu YL: Antidepressant-like effects of sarsasapogenin from Anemarrhena asphodeloides BUNGE (Liliaceae). Biol Pharm Bull. 2006 Nov;29(11):2304-6. doi: 10.1248/bpb.29.2304. [PubMed:17077534 ]
Agrawal, P. K., et al. (1997). Agrawal, P. K., et al, Magn. Reson. Chem. 35, 441 (1997). Mag. Reson. Chem..

Showing NP-Card for sarsasapogenin (NP0030539)

MOL for NP0030539 (sarsasapogenin)

3D MOL for NP0030539 (sarsasapogenin)

3D SDF for NP0030539 (sarsasapogenin)

3D-SDF for NP0030539 (sarsasapogenin)

PDB for NP0030539 (sarsasapogenin)

3D PDB for NP0030539 (sarsasapogenin)

SMILES for NP0030539 (sarsasapogenin)

INCHI for NP0030539 (sarsasapogenin)

Structure for NP0030539 (sarsasapogenin)

3D Structure for NP0030539 (sarsasapogenin)