NP-MRD: Showing NP-Card for Spiroconazole A (NP0072346)

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Record Information

Version

2.0

Created at

2022-04-28 17:42:08 UTC

Updated at

2022-04-28 17:42:09 UTC

NP-MRD ID

NP0072346

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Spiroconazole A

Description

(25R)-3beta-[2-O,3-O-Bis(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]spirosta-5-ene-17-ol belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Spiroconazole A is found in Dioscorea bulbifera, Dioscorea bulbifera var.sativa and Dracaena arborea. Based on a literature review very few articles have been published on (25R)-3beta-[2-O,3-O-Bis(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyloxy]spirosta-5-ene-17-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219422D          

 62 70  0  0  1  0            999 V2000
   10.8476    1.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2179    2.0253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7645    2.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9409    2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4876    3.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6640    3.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2937    2.5708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7470    1.8815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5707    1.9294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0240    1.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2004    1.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3768    1.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5532    1.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0998    1.7856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4701    2.5228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8834    3.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1505    2.7240    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2843    1.9099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5514    1.5312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9646    2.1111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3349    2.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734    1.3392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594    1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3365    1.8436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6277    2.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417    2.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    1.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4270    0.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4180    1.0959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8909    0.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0415    2.0732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4948    1.3840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.1245    0.6467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5778   -0.0426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.4014    0.0054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7717    0.7426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3184    1.4319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.6887    2.1691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2354    2.8584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.6056    3.5957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1523    4.2849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3287    4.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9584    3.4998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4118    2.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1348    3.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8754    4.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5226    5.0222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4293    3.6436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5953    0.7905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0486    0.1012    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.8723    0.1492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3256   -0.5401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9553   -1.2773    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1317   -1.3253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6784   -0.6360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7614   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4086   -1.9666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1492   -0.4922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2425    0.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8548   -0.6839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2075   -0.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6609   -1.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 17 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 24 27  1  6  0  0  0
 19 28  1  6  0  0  0
 18 29  1  6  0  0  0
 14 30  1  1  0  0  0
  2 31  1  1  0  0  0
 32 31  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
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 51 59  1  6  0  0  0
 35 60  1  6  0  0  0
 34 61  1  1  0  0  0
 61 62  1  0  0  0  0
M  END

     RDKit          3D

134142  0  0  0  0  0  0  0  0999 V2000
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   -8.2496   -0.5787    3.7354 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9210   -0.3814    3.3550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7908   -0.1582    1.9770 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4455    0.0025    1.7290 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2359    1.9682    2.3631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9288    2.0365    3.5675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425    3.3854    1.8660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4053    4.2956    2.8751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0620    4.2396    4.1067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981    3.4429    0.6588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1465    2.2394    0.0469 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0021    1.5916    0.4819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0335    1.4804   -0.4796 C   0  0  1  0  0  0  0  0  0  0  0  0
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   12.3380   -1.2302   -2.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.9746    0.9276   -2.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7032   -1.7714   -0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9002   -0.0100   -0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4000   -2.5963    0.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2157   -1.2915    2.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5728   -3.0264    2.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7383   -1.7089    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3613    0.5203    2.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4665   -2.2876    1.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5178   -0.2242    2.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    1.2474    1.7797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2781    0.9527    2.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921   -0.8213    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2078    1.3247    0.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6375   -0.1659   -1.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481    1.0473   -5.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0724   -1.2708   -3.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061   -1.0793   -5.0489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2757   -1.5464   -4.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12  9  1  0
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 55127  1  1
 56128  1  0
M  END


  Mrv1652304282219422D          

 62 70  0  0  1  0            999 V2000
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   11.2179    2.0253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7645    2.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9409    2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4876    3.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6640    3.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2937    2.5708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7470    1.8815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5707    1.9294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0240    1.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2004    1.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3768    1.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5532    1.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0998    1.7856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4701    2.5228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.3365    1.8436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.4417    2.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224    1.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4180    1.0959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1245    0.6467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3184    1.4319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   13.2354    2.8584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.6056    3.5957    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1523    4.2849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3287    4.2370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9584    3.4998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4118    2.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1348    3.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8754    4.9263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5226    5.0222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4293    3.6436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5953    0.7905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0486    0.1012    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.8723    0.1492    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3256   -0.5401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9553   -1.2773    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1317   -1.3253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6784   -0.6360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7614   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4086   -1.9666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1492   -0.4922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2425    0.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8548   -0.6839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2075   -0.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6609   -1.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 17 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 20 26  1  0  0  0  0
 24 27  1  6  0  0  0
 19 28  1  6  0  0  0
 18 29  1  6  0  0  0
 14 30  1  1  0  0  0
  2 31  1  1  0  0  0
 32 31  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  6  0  0  0
 39 38  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 39 44  1  0  0  0  0
 43 45  1  1  0  0  0
 42 46  1  6  0  0  0
 41 47  1  1  0  0  0
 40 48  1  1  0  0  0
 36 49  1  1  0  0  0
 50 49  1  1  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 50 55  1  0  0  0  0
 54 56  1  6  0  0  0
 53 57  1  1  0  0  0
 52 58  1  6  0  0  0
 51 59  1  6  0  0  0
 35 60  1  6  0  0  0
 34 61  1  1  0  0  0
 61 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072346

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@]2(CC[C@@H](C)CO2)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@H](CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@]12O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C45H72O17/c1-19-9-14-44(55-18-19)22(4)45(54)29(62-44)16-27-25-8-7-23-15-24(10-12-42(23,5)26(25)11-13-43(27,45)6)58-41-38(61-40-36(53)34(51)31(48)21(3)57-40)37(32(49)28(17-46)59-41)60-39-35(52)33(50)30(47)20(2)56-39/h7,19-22,24-41,46-54H,8-18H2,1-6H3/t19-,20+,21+,22-,24+,25-,26+,27+,28-,29+,30+,31+,32-,33-,34-,35-,36-,37+,38-,39+,40+,41-,42+,43+,44-,45-/m1/s1

> <INCHI_KEY>
NLMRPYJFEJTQEC-JQHDQEQCSA-N

> <FORMULA>
C45H72O17

> <MOLECULAR_WEIGHT>
885.054

> <EXACT_MASS>
884.476950858

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
134

> <JCHEM_AVERAGE_POLARIZABILITY>
95.59569101758734

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1'R,2R,2'S,4'S,5R,7'S,8'S,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-8'-oloxy]-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.0442590263333351

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.339920342561392

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.867794124981227

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6084076074852627

> <JCHEM_POLAR_SURFACE_AREA>
255.90999999999994

> <JCHEM_REFRACTIVITY>
215.35470000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1'R,2R,2'S,4'S,5R,7'S,8'S,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-8'-oloxy]-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      20.249   2.404   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.940   3.781   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.094   5.067   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.556   4.978   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.710   6.264   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.173   6.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.482   4.799   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.328   3.512   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.865   3.602   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.711   2.315   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.174   2.225   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.637   2.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.099   2.046   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.253   3.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.944   4.709   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.849   5.792   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.481   5.085   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.731   3.565   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.363   2.858   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.267   3.941   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.959   5.317   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.724   2.500   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.204   2.250   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.228   3.441   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.772   4.882   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.291   5.132   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.708   3.192   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.130   1.336   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.980   2.046   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.863   1.843   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      22.477   3.870   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      23.324   2.583   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      22.632   1.207   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      23.479  -0.079   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      25.016   0.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      25.707   1.386   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      24.861   2.673   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      25.552   4.049   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      24.706   5.336   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      25.397   6.712   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      24.551   7.999   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      23.014   7.909   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      22.322   6.533   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      23.169   5.246   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      20.785   6.443   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      22.167   9.196   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      25.242   9.375   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      26.935   6.801   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      27.245   1.476   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      28.091   0.189   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      29.628   0.278   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      30.474  -1.008   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      29.783  -2.384   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      28.246  -2.474   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      27.400  -1.187   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      27.555  -3.850   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      30.629  -3.671   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      32.012  -0.919   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      30.319   1.655   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      25.862  -1.277   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      22.787  -1.456   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      23.634  -2.742   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18   30                                             
CONECT   15   14    7   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   14   19   29                                             
CONECT   19   18   20   28                                                  
CONECT   20   19   21   22   26                                             
CONECT   21   20   17                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   20                                                       
CONECT   27   24                                                            
CONECT   28   19                                                            
CONECT   29   18                                                            
CONECT   30   14                                                            
CONECT   31    2   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   61                                                  
CONECT   35   34   36   60                                                  
CONECT   36   35   37   49                                                  
CONECT   37   36   32   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41   48                                                  
CONECT   41   40   42   47                                                  
CONECT   42   41   43   46                                                  
CONECT   43   42   44   45                                                  
CONECT   44   43   39                                                       
CONECT   45   43                                                            
CONECT   46   42                                                            
CONECT   47   41                                                            
CONECT   48   40                                                            
CONECT   49   36   50                                                       
CONECT   50   49   51   55                                                  
CONECT   51   50   52   59                                                  
CONECT   52   51   53   58                                                  
CONECT   53   52   54   57                                                  
CONECT   54   53   55   56                                                  
CONECT   55   54   50                                                       
CONECT   56   54                                                            
CONECT   57   53                                                            
CONECT   58   52                                                            
CONECT   59   51                                                            
CONECT   60   35                                                            
CONECT   61   34   62                                                       
CONECT   62   61                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  140    0
END

View in JSmol

Synonyms

Value	Source
(25R)-3b-[2-O,3-O-Bis(a-L-rhamnopyranosyl)-b-D-glucopyranosyloxy]spirosta-5-ene-17-ol	Generator
(25R)-3Β-[2-O,3-O-bis(α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]spirosta-5-ene-17-ol	Generator

Chemical Formula

C₄₅H₇₂O₁₇

Average Mass

885.0540 Da

Monoisotopic Mass

884.47695 Da

IUPAC Name

(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-[(1'R,2R,2'S,4'S,5R,7'S,8'S,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-8'-oloxy]-4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@]2(CC[C@@H](C)CO2)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@H](CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@]12O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C45H72O17/c1-19-9-14-44(55-18-19)22(4)45(54)29(62-44)16-27-25-8-7-23-15-24(10-12-42(23,5)26(25)11-13-43(27,45)6)58-41-38(61-40-36(53)34(51)31(48)21(3)57-40)37(32(49)28(17-46)59-41)60-39-35(52)33(50)30(47)20(2)56-39/h7,19-22,24-41,46-54H,8-18H2,1-6H3/t19-,20+,21+,22-,24+,25-,26+,27+,28-,29+,30+,31+,32-,33-,34-,35-,36-,37+,38-,39+,40+,41-,42+,43+,44-,45-/m1/s1

InChI Key

NLMRPYJFEJTQEC-JQHDQEQCSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dioscorea bulbifera	LOTUS Database	35616633
Dioscorea bulbifera var.sativa	Plant	KNApSAcK
Dracaena arborea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Substituents

Steroidal saponin
Triterpenoid
Spirostane skeleton
Oligosaccharide
Hydroxysteroid
17-hydroxysteroid
Delta-5-steroid
Glycosyl compound
O-glycosyl compound
Ketal
Oxane
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Organooxygen compound
Organic oxygen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.33	ALOGPS
logP	1.04	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.87	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	255.91 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	215.35 m³·mol⁻¹	ChemAxon
Polarizability	95.6 Å³	ChemAxon
Number of Rings	9	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

46186821

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Spiroconazole A (NP0072346)

MOL for NP0072346 (Spiroconazole A)

3D MOL for NP0072346 (Spiroconazole A)

3D SDF for NP0072346 (Spiroconazole A)

3D-SDF for NP0072346 (Spiroconazole A)

PDB for NP0072346 (Spiroconazole A)

3D PDB for NP0072346 (Spiroconazole A)

SMILES for NP0072346 (Spiroconazole A)

INCHI for NP0072346 (Spiroconazole A)

Structure for NP0072346 (Spiroconazole A)

3D Structure for NP0072346 (Spiroconazole A)