NP-MRD: Showing NP-Card for 2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol (NP0306916)

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Record Information

Version

2.0

Created at

2022-09-10 23:41:38 UTC

Updated at

2022-09-10 23:41:39 UTC

NP-MRD ID

NP0306916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol

Description

Macrophyllosaponin D belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol is found in Astragalus oleifolius. Based on a literature review very few articles have been published on Macrophyllosaponin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201412D          

 63 70  0  0  1  0            999 V2000
    0.3077   -3.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -3.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562   -2.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8971   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -0.0491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9895    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411   -0.6798    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5214    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532   -0.5346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3335    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    0.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774   -0.2441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020   -0.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    0.3804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6974    1.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    0.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    0.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1492    0.8060    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6555    1.4573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4728    1.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7837    0.5803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6009    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1073    1.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9245    1.0059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7964    1.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3027    2.5343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9791    1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6682    2.7600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1746    3.4113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9918    3.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4982    3.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1873    4.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6937    5.3653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3701    4.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0592    5.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8637    4.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0465    4.2884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4601    0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6959   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2243    0.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7710   -0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313   -1.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -1.0201    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1995   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850   -1.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047   -1.9412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8365   -2.5719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2654   -2.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5369   -2.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195   -1.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -2.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -4.2191    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  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  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
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  0  0  0  0
 22 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
 17 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 15 48  1  0  0  0  0
 48 49  1  6  0  0  0
 48 50  1  0  0  0  0
 12 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  1  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 10 54  1  0  0  0  0
 54 55  1  0  0  0  0
  6 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
  4 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  1  0  0  0  0
  2 62  1  0  0  0  0
 62 63  1  0  0  0  0
M  END

     RDKit          3D

141148  0  0  0  0  0  0  0  0999 V2000
    2.0198   -1.3149   -1.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0212   -0.9461   -0.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9657   -1.9578    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3214   -2.0319   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223   -0.7540    0.0749 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3790   -1.1561   -0.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5796   -0.4257   -1.6389 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2652   -1.2922   -2.7632 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8966   -0.8500   -3.9052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9701    0.6520   -3.9128 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3877    1.0938   -5.1735 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9599    1.1309   -2.8589 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2439    1.2589   -3.3632 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9916    0.0232   -1.7928 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5428    0.4338   -0.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6871   -0.2833   -0.2627 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5082   -1.0168    0.8832 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4196   -0.8084    1.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5312    0.6447    2.2897 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4614    0.9727    3.0939 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5906    1.5443    1.0781 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3197    2.1241    0.9247 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8282    0.6987   -0.1511 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.0651    0.0720   -0.1239 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4445   -0.3343    1.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -1.4172    2.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3449    0.2715    2.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4007    0.7202    1.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7477   -1.0307    0.4628 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8175   -0.6312    1.9191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6295   -0.2925    2.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4219   -0.7464    1.1538 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4366   -2.2828    1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7939   -0.1878    1.0293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2225    0.7156    2.1422 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0968    2.0642    1.8912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7551    0.5452    2.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2309    1.1286    0.9163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7443    1.1142    0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1274    1.4446    2.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2907    2.2615    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3435   -0.2036    0.6273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.5174   -0.0568   -0.0718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5991   -0.6748    0.5549 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.9888   -1.7312   -0.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4034   -1.3806   -1.5206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.3958   -1.9518   -2.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5961    0.0516   -1.8295 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.4977    0.5711   -2.5123 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9565    0.9216   -0.6643 C   0  0  1  0  0  0  0  0  0  0  0  0
  -12.2740    1.3833   -0.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7895    0.2316    0.6642 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.7933    1.0788    1.7380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4179   -1.0609   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6175   -0.1791   -1.1615 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0895   -1.0764   -2.0567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6333    0.5582   -0.3040 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5730    1.4619   -0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2223    0.2313   -0.3235 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6181   -0.8098   -1.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252   -0.8397   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4712   -0.3427    0.0072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2042    1.1273    0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1043   -1.4331   -2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6315   -0.6114   -2.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178   -2.2918   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713    0.0309   -0.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4499   -2.9655    0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8701   -1.8527    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -2.7553    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5027   -2.5169   -1.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957    0.0572   -0.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8509    0.3919   -1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9083   -1.3004   -4.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2285   -1.1416   -4.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868    1.0748   -3.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3726    1.2060   -5.1259 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6219    2.0521   -2.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5907    2.1482   -3.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6119   -0.8285   -2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8599   -1.0409   -1.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3779   -1.2710    1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0260   -1.3424    2.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4691    0.7656    2.8516 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6923    0.8355    4.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112201412D          

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  4 58  1  0  0  0  0
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 60 62  1  0  0  0  0
  2 62  1  0  0  0  0
 62 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306916

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC[C@H](OC1OCC(O)C(O)C1OC1OCC(O)C(O)C1O)C(C)(C)O)C1CC[C@@]2(C)C3[C@@H](O)CC4[C@]5(C[C@@]35CC[C@]12C)[C@@H](O)C[C@H](OC1OC(C)C(O)C(O)C1O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C46H78O17/c1-20(9-10-28(42(5,6)57)61-40-36(32(53)25(49)18-59-40)63-38-34(55)31(52)24(48)17-58-38)22-11-12-44(8)37-23(47)15-26-41(3,4)29(62-39-35(56)33(54)30(51)21(2)60-39)16-27(50)46(26)19-45(37,46)14-13-43(22,44)7/h20-40,47-57H,9-19H2,1-8H3/t20-,21?,22?,23+,24?,25?,26?,27+,28+,29+,30?,31?,32?,33?,34?,35?,36?,37?,38?,39?,40?,43-,44+,45+,46-/m1/s1

> <INCHI_KEY>
BJQSXYMSMSHSIP-QMOAYLFTSA-N

> <FORMULA>
C46H78O17

> <MOLECULAR_WEIGHT>
903.113

> <EXACT_MASS>
902.523901052

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
141

> <JCHEM_AVERAGE_POLARIZABILITY>
98.70583221044804

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(1S,3S,4S,6S,10S,12S,16R)-15-[(2R,5S)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol

> <JCHEM_LOGP>
-0.21007338766666542

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.364473205306133

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.881521264908304

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806826167054

> <JCHEM_POLAR_SURFACE_AREA>
277.90999999999997

> <JCHEM_REFRACTIVITY>
221.2164000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(1S,3S,4S,6S,10S,12S,16R)-15-[(2R,5S)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.574  -7.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.418  -6.156   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.105  -4.708   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.888  -3.531   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.365  -2.082   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.151  -1.811   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.675  -0.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.191  -0.092   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.714   1.357   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.183  -1.269   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.707   0.179   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.699  -0.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.222   0.451   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.738   0.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.731  -0.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.403   0.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.270  -0.506   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.216   0.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.635   2.137   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.741   0.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.686   1.715   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.212   1.505   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.157   2.720   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      17.683   2.510   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      18.263   1.083   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      19.788   0.873   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.734   2.088   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      22.259   1.878   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      20.153   3.515   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      21.098   4.731   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      18.628   3.726   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      18.047   5.152   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      18.993   6.368   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      20.518   6.157   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      21.463   7.373   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.883   8.799   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      21.828  10.015   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.357   9.010   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      18.777  10.437   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      18.412   7.794   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      16.887   8.005   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      15.792   0.078   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      14.366  -0.502   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.219   0.658   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      16.372  -1.348   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      10.698  -1.985   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.424  -2.849   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       8.208  -1.904   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.839  -3.399   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.692  -2.175   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.169  -3.624   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       7.162  -4.801   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       4.653  -3.895   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       3.660  -2.717   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.144  -2.988   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       2.362  -4.513   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       1.002  -4.022   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -2.404  -3.802   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -3.396  -2.624   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -2.927  -5.250   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -4.443  -5.521   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      -1.934  -6.427   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -2.457  -7.876   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   62                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   58                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   55                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   54                                             
CONECT   11   10   12                                                       
CONECT   12   11   10   13   50                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   48                                             
CONECT   16   15                                                            
CONECT   17   15   18   46                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   42                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   33   41                                                  
CONECT   41   40                                                            
CONECT   42   22   43   44   45                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   42                                                            
CONECT   46   17   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   15   49   50                                             
CONECT   49   48                                                            
CONECT   50   48   12   51                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54                                                       
CONECT   54   53   10   55                                                  
CONECT   55   54    6   56   57                                             
CONECT   56   55                                                            
CONECT   57   55                                                            
CONECT   58    4   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60    2   63                                                  
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  140    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₆H₇₈O₁₇

Average Mass

903.1130 Da

Monoisotopic Mass

902.52390 Da

IUPAC Name

2-{[(1S,3S,4S,6S,10S,12S,16R)-15-[(2R,5S)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H](CC[C@H](OC1OCC(O)C(O)C1OC1OCC(O)C(O)C1O)C(C)(C)O)C1CC[C@@]2(C)C3[C@@H](O)CC4[C@]5(C[C@@]35CC[C@]12C)[C@@H](O)C[C@H](OC1OC(C)C(O)C(O)C1O)C4(C)C

InChI Identifier

InChI=1S/C46H78O17/c1-20(9-10-28(42(5,6)57)61-40-36(32(53)25(49)18-59-40)63-38-34(55)31(52)24(48)17-58-38)22-11-12-44(8)37-23(47)15-26-41(3,4)29(62-39-35(56)33(54)30(51)21(2)60-39)16-27(50)46(26)19-45(37,46)14-13-43(22,44)7/h20-40,47-57H,9-19H2,1-8H3/t20-,21?,22?,23+,24?,25?,26?,27+,28+,29+,30?,31?,32?,33?,34?,35?,36?,37?,38?,39?,40?,43-,44+,45+,46-/m1/s1

InChI Key

BJQSXYMSMSHSIP-QMOAYLFTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Astragalus oleifolius	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Triterpene saponin
Triterpene glycoside
Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
25-hydroxysteroid
Trihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
7-hydroxysteroid
7-alpha-hydroxysteroid
1-hydroxysteroid
Hydroxysteroid
O-glycosyl compound
Glycosyl compound
Disaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Oxacycle
Acetal
Organoheterocyclic compound
Polyol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
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	-0.21	ChemAxon
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	277.91 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	221.22 m³·mol⁻¹	ChemAxon
Polarizability	98.71 Å³	ChemAxon
Number of Rings	8	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

4509075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352120

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol (NP0306916)

MOL for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)

3D MOL for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)

3D SDF for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)

3D-SDF for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)

PDB for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)

3D PDB for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)

SMILES for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)

INCHI for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)

Structure for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)

3D Structure for NP0306916 (2-{[(1s,3s,4s,6s,10s,12s,16r)-15-[(2r,5s)-5-({4,5-dihydroxy-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl}oxy)-6-hydroxy-6-methylheptan-2-yl]-4,10-dihydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxy}-6-methyloxane-3,4,5-triol)