NP-MRD: Showing NP-Card for (1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate (NP0244698)

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Record Information

Version

2.0

Created at

2022-09-07 05:33:45 UTC

Updated at

2022-09-07 05:33:45 UTC

NP-MRD ID

NP0244698

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate

Description

Acetylgitoxin-alpha [German] belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. (1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate is found in Digitalis lanata. Based on a literature review very few articles have been published on Acetylgitoxin-alpha [German].

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072207332D          

 58 65  0  0  1  0            999 V2000
    2.5485   -0.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9178   -0.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1419   -0.3243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0630   -1.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2974   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5489   -3.6824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2686   -4.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8004   -5.0890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.6125   -4.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1443   -5.5745    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9565   -5.4293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8640   -6.3504    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.3959   -6.9811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0519   -6.4956    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7716   -7.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5201   -5.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8928   -4.1678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7049   -4.0226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9852   -3.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7974   -3.1015    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0777   -2.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3292   -3.7322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.1413   -3.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0489   -4.5081    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.5807   -5.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2368   -4.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6413   -2.7612    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1095   -2.1305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -3.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1084   -4.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816   -5.2209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570   -3.8899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -3.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  1  0  0  0
 31 30  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 31 39  1  0  0  0  0
 29 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  0  0  0  0
 16 42  1  0  0  0  0
 14 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 12 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
  9 47  1  0  0  0  0
 47 48  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
  7 50  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
  5 52  1  0  0  0  0
 52 53  1  1  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 55 57  1  0  0  0  0
 57 58  1  0  0  0  0
 53 58  1  0  0  0  0
M  END

     RDKit          3D

124131  0  0  0  0  0  0  0  0999 V2000
   10.0849   -1.7285   -3.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6102   -1.9048   -2.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9891   -2.8194   -1.8317 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6842   -1.0100   -2.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1810   -1.1004   -0.7938 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6972   -1.2464   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4154   -0.8762    0.7216 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8981   -1.8857    1.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9708   -0.6508    1.0071 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1249   -1.8299    0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491   -1.5038    0.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3726   -0.3590    1.4424 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9162   -0.1647    1.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1209    0.4929    0.6715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0820    0.9778    1.1668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146    0.4392    0.6017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0827    1.5880    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2934    1.0285   -0.6191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4113    1.8496   -0.4681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0066    2.2097   -1.6515 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1504    3.7215   -1.8080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5580    4.1829   -1.5925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5015    5.5793   -1.3752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2421    3.5429   -0.4304 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.9036    4.1632    0.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8513    2.0835   -0.3744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1111    1.3051   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3304    1.7215   -1.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6471   -0.2824    0.0634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9715   -0.6360   -0.0749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1150   -1.9012   -0.6263 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8485   -1.7878   -1.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3447   -3.1577   -2.3593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8909   -3.0626   -3.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3907   -3.6165   -1.3514 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.6676   -3.3618   -1.8154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1520   -2.8476   -0.0725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8750   -3.5028    1.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7971   -2.7912    0.1689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2591   -0.0861    1.5345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0187   -0.9958    2.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940   -0.1912    1.6616 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281    1.6848    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2367    1.4253   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0121    0.8803    0.8620 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0499    1.8897    2.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4111    0.5832    0.3794 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2505    1.7939    0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6343    1.5738    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2778    0.3387    0.8710 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5702    0.6020    2.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5186    0.0724    0.0709 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7497   -0.1611    0.8663 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8626    0.5913    0.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8616    0.0602    1.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0039    0.5621    1.9539 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3186   -1.0549    2.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0315   -1.2700    1.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2635   -1.8632   -4.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5625   -0.7389   -4.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8475   -2.4925   -4.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6633   -1.9919   -0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1864   -0.5629   -1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3874   -2.3120   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0642   -2.7350    1.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8700   -0.5554    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -2.1047   -0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3144   -2.7137    1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0864   -2.4319    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3538   -1.2159   -0.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8709   -0.5661    2.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373    0.3754    2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -1.2064    1.8600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0568   -0.2627   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0574   -0.3080   -0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193    2.1777   -0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292    2.2959    0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1270    0.8467   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5204    1.8004   -2.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8303    4.0585   -2.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5085    4.1896   -1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1549    4.0172   -2.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0474    5.7058   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3413    3.6692   -0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9321    4.2220    0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0949    1.9660    0.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8084    0.4316    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6684    1.0468   -0.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7421    1.9353    0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9610   -1.0866   -0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0950   -2.3022   -0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6818   -1.0865   -1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309072207332D          

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M  END
> <DATABASE_ID>
NP0244698

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](C[C@H](O)[C@@H]1O)O[C@H]1C[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H]([C@@H](CC43O)OC(C)=O)C3=CC(=O)OC3)C2)O[C@H](C)[C@H]1O[C@@H]1C[C@H](O)[C@H](O)[C@@H](C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C43H66O15/c1-20-38(48)29(45)15-34(52-20)57-31-17-36(54-22(3)40(31)58-35-16-30(46)39(49)21(2)53-35)56-26-9-11-41(5)25(14-26)7-8-28-27(41)10-12-42(6)37(24-13-33(47)51-19-24)32(55-23(4)44)18-43(28,42)50/h13,20-22,25-32,34-40,45-46,48-50H,7-12,14-19H2,1-6H3/t20-,21-,22-,25-,26+,27+,28-,29+,30+,31+,32-,34-,35-,36-,37+,38-,39-,40-,41+,42-,43?/m1/s1

> <INCHI_KEY>
SZHBGTRKQDNXNC-RIYHBKJUSA-N

> <FORMULA>
C43H66O15

> <MOLECULAR_WEIGHT>
822.986

> <EXACT_MASS>
822.440171425

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
124

> <JCHEM_AVERAGE_POLARIZABILITY>
89.06247166256675

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S,7R,10R,13R,14R,15R)-5-{[(2S,4S,5R,6R)-4,5-bis({[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

> <JCHEM_LOGP>
2.6570583463333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.825184414738658

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.819476929274381

> <JCHEM_PKA_STRONGEST_BASIC>
-3.203886689169476

> <JCHEM_POLAR_SURFACE_AREA>
209.12999999999997

> <JCHEM_REFRACTIVITY>
202.41770000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7R,10R,13R,14R,15R)-5-{[(2S,4S,5R,6R)-4,5-bis({[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.757  -0.136   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.580  -1.129   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.132  -0.605   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.301  -8.322   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.294  -9.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.810  -9.228   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.803 -10.406   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.319 -10.135   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.280 -11.854   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      21.272 -13.031   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      18.764 -12.125   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.240 -13.574   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.771 -10.948   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      21.849  -7.509   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.372  -6.061   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      23.888  -5.789   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      24.412  -4.341   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      24.881  -6.967   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      26.397  -6.696   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      24.358  -8.415   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      25.351  -9.592   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      22.842  -8.686   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.380  -4.883   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      18.871  -3.977   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       5.210  -7.342   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       3.936  -8.206   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       3.886  -9.746   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       2.720  -7.261   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       3.243  -5.813   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   52                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   50                                             
CONECT    8    7                                                            
CONECT    9    7   10   47                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   45                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   43                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   42                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20                                                       
CONECT   29   18   30   40                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   39                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   31                                                       
CONECT   40   29   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   16                                                       
CONECT   43   14   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   12   46   47                                             
CONECT   46   45                                                            
CONECT   47   45    9   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49    7   51   52                                             
CONECT   51   50                                                            
CONECT   52   50    5   53                                                  
CONECT   53   52   54   58                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   58                                                       
CONECT   58   57   53                                                       
MASTER        0    0    0    0    0    0    0    0   58    0  130    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₆₆O₁₅

Average Mass

822.9860 Da

Monoisotopic Mass

822.44017 Da

IUPAC Name

(1S,2S,5S,7R,10R,13R,14R,15R)-5-{[(2S,4S,5R,6R)-4,5-bis({[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

Traditional Name

(1S,2S,5S,7R,10R,13R,14R,15R)-5-{[(2S,4S,5R,6R)-4,5-bis({[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@@H](C[C@H](O)[C@@H]1O)O[C@H]1C[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H]([C@@H](CC43O)OC(C)=O)C3=CC(=O)OC3)C2)O[C@H](C)[C@H]1O[C@@H]1C[C@H](O)[C@H](O)[C@@H](C)O1

InChI Identifier

InChI=1S/C43H66O15/c1-20-38(48)29(45)15-34(52-20)57-31-17-36(54-22(3)40(31)58-35-16-30(46)39(49)21(2)53-35)56-26-9-11-41(5)25(14-26)7-8-28-27(41)10-12-42(6)37(24-13-33(47)51-19-24)32(55-23(4)44)18-43(28,42)50/h13,20-22,25-32,34-40,45-46,48-50H,7-12,14-19H2,1-6H3/t20-,21-,22-,25-,26+,27+,28-,29+,30+,31+,32-,34-,35-,36-,37+,38-,39-,40-,41+,42-,43?/m1/s1

InChI Key

SZHBGTRKQDNXNC-RIYHBKJUSA-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
Digitalis lanata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
Steroidal glycoside
Steroid ester
Hydroxysteroid
14-hydroxysteroid
O-glycosyl compound
Glycosyl compound
Disaccharide
Oxane
Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.66	ChemAxon
pKa (Strongest Acidic)	6.82	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	209.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	202.42 m³·mol⁻¹	ChemAxon
Polarizability	89.06 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

179533

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

207215

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate (NP0244698)

MOL for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D MOL for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D SDF for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D-SDF for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

PDB for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D PDB for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

SMILES for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

INCHI for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

Structure for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)

3D Structure for NP0244698 ((1r,2r,3br,5ar,7s,9as,9bs,11ar)-7-{[(2s,4s,5r,6r)-4,5-bis({[(2r,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy})-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl acetate)