NP-MRD: Showing NP-Card for (1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate (NP0221640)

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Record Information

Version

2.0

Created at

2022-09-05 23:16:17 UTC

Updated at

2022-09-05 23:16:17 UTC

NP-MRD ID

NP0221640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate

Description

(2S,5S,7R,11S,13S,14R,15R)-5-[(3,4-dihydroxy-6-methyl-5-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-13-yl propanoate 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,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate is found in Cryptostegia grandiflora. Based on a literature review very few articles have been published on (2S,5S,7R,11S,13S,14R,15R)-5-[(3,4-dihydroxy-6-methyl-5-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-13-yl propanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062201162D          

 53 59  0  0  1  0            999 V2000
    2.4033    0.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  1  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  2  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  0  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  0  0  0  0  0  0  0  0  0  0
    9.0171   -3.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5489   -3.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2686   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3610   -3.5371    0.0000 C   0  0  0  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 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7974   -3.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0777   -2.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5458   -1.6949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3292   -3.7322    0.0000 C   0  0  1  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  0  0  0  0  0  0  0  0  0  0
   13.5807   -5.1388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2368   -4.6533    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
   10.6413   -2.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4534   -2.6160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1095   -2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3898   -1.3546    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  0  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  1  0  0  0  0
  3  4  2  0  0  0  0
  3  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  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 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
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  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
 25 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  6  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  0  0  0  0
 15 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 13 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 10 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
  8 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
  6 47  1  0  0  0  0
 47 48  1  1  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 48 53  1  0  0  0  0
M  END

     RDKit          3D

111117  0  0  0  0  0  0  0  0999 V2000
   -7.1601   -3.6767   -0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2514   -4.4749    0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7209   -3.7353    1.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8083   -4.1943    2.9279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1145   -2.5175    1.5902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5824   -1.7472    2.6406 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0538   -1.7763    2.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0746   -0.9685    1.0592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4371   -1.8974    0.0564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7437   -0.4189    0.6848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8566    0.0152    1.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214    1.2210    1.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5781    1.3733    0.0941 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1437    2.8334   -0.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071    2.8734   -1.4193 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5094    1.8294   -1.3773 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8198    2.2389   -1.5705 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6144    1.9569   -0.4556 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9694    2.1230   -0.8479 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8307    2.2977    0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4028    0.9743   -1.7161 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3113    0.1237   -1.2092 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4717   -0.1232   -1.8466 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5163   -1.4789   -2.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8061   -2.3208   -1.1260 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7296   -2.4361   -0.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2181   -3.3327    0.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1083   -2.0048   -0.4194 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9915   -3.0792   -0.4269 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7174   -0.8333   -1.1863 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8436   -0.4246   -0.4925 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6769    0.2905   -1.0374 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4536    0.4204    0.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1300    0.3283   -2.2385 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3242   -0.1475   -1.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3410    1.5298   -2.8062 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1996    2.3664   -3.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4090    2.5866   -2.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7363    2.1094   -1.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5775    1.0118   -0.9407 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0553   -0.2058   -1.7224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276    0.6227   -0.4051 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7906    1.7534   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6472    1.4628    1.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1918    0.0525    1.1845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1008   -0.0538   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8014   -0.2871    2.4832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1773    0.1793    2.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1150   -0.6727    3.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3755    0.0318    3.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4951   -0.4657    3.6696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1285    1.3343    3.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7916    1.4936    2.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4276   -2.6316   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9470   -4.0208   -1.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6824   -5.4153    0.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3387   -4.6976    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7483   -2.1761    3.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7578   -2.8322    2.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5832   -1.3110    3.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6429   -2.2278   -0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861   -1.2479    0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3839    0.2515    2.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1675   -0.8363    2.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5341    2.1481    1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.1441    2.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3752    0.7856   -0.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107    3.5238   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217    3.1436    0.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081    3.8518   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236    3.3217   -1.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896    3.1103   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7335    2.8311    0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9646    1.3792    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2384    3.0066    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8481    1.4286   -2.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5872    0.4148   -2.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9334   -3.3348   -1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5054   -1.4955    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8070   -2.9237   -0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5983   -2.8368    1.6578 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9142   -1.6734    0.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7985   -3.6141   -1.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8854   -1.0880   -2.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5959   -1.0648   -0.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6489    1.3235    0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752   -0.3576   -3.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628   -0.3750   -0.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5267    1.1563   -3.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4855    1.9024   -4.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3013    2.9795   -1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
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 37 92  1  0
M  END


  Mrv1652309062201162D          

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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
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  8 45  1  0  0  0  0
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 52 53  1  0  0  0  0
 48 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)O[C@H]1C[C@]2(O)C3CC[C@@H]4C[C@H](CC[C@]4(C)C3CC[C@]2(C)[C@H]1C1=CC(=O)OC1)OC1OC(C)C(O[C@@H]2OC(CO)[C@@H](O)C(O)[C@@H]2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C38H58O15/c1-5-25(40)51-23-14-38(47)22-7-6-19-13-20(8-10-36(19,3)21(22)9-11-37(38,4)27(23)18-12-26(41)48-16-18)50-34-32(46)30(44)33(17(2)49-34)53-35-31(45)29(43)28(42)24(15-39)52-35/h12,17,19-24,27-35,39,42-47H,5-11,13-16H2,1-4H3/t17?,19-,20+,21?,22?,23+,24?,27+,28-,29?,30?,31+,32?,33?,34?,35+,36+,37-,38+/m1/s1

> <INCHI_KEY>
XRXCJPMZYAWJHD-JJGULWAKSA-N

> <FORMULA>
C38H58O15

> <MOLECULAR_WEIGHT>
754.867

> <EXACT_MASS>
754.377571168

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
80.60184526381826

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7R,11S,13S,14R,15R)-5-[(3,4-dihydroxy-6-methyl-5-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-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 propanoate

> <JCHEM_LOGP>
0.3326957166666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.938156899848572

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.819471836393047

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835652577543

> <JCHEM_POLAR_SURFACE_AREA>
231.12999999999997

> <JCHEM_REFRACTIVITY>
182.25080000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7R,11S,13S,14R,15R)-5-[(3,4-dihydroxy-6-methyl-5-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-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 propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       4.486   1.380   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.757  -0.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.580  -1.129   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.132  -0.605   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.832  -5.696   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      17.825  -6.874   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.301  -8.322   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.341  -6.603   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      20.333  -7.780   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      21.849  -7.509   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      22.372  -6.061   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.888  -5.789   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.412  -4.341   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      23.419  -3.164   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      24.881  -6.967   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      26.397  -6.696   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      24.358  -8.415   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      25.351  -9.592   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      22.842  -8.686   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      22.319 -10.135   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      19.864  -5.154   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      21.380  -4.883   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      18.871  -3.977   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      19.394  -2.529   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       5.210  -7.342   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       3.936  -8.206   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       3.886  -9.746   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       2.720  -7.261   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       3.243  -5.813   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   47                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   45                                             
CONECT    9    8                                                            
CONECT   10    8   11   42                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   40                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   38                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   33                                                  
CONECT   33   32                                                            
CONECT   34   21   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   17   37                                                  
CONECT   37   36                                                            
CONECT   38   15   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   13   41   42                                             
CONECT   41   40                                                            
CONECT   42   40   10   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44    8   46   47                                             
CONECT   46   45                                                            
CONECT   47   45    6   48                                                  
CONECT   48   47   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   48                                                       
MASTER        0    0    0    0    0    0    0    0   53    0  118    0
END

View in JSmol

Synonyms

Value	Source
(2S,5S,7R,11S,13S,14R,15R)-5-[(3,4-Dihydroxy-6-methyl-5-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0,.0,]heptadecan-13-yl propanoic acid	Generator

Chemical Formula

C₃₈H₅₈O₁₅

Average Mass

754.8670 Da

Monoisotopic Mass

754.37757 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(=O)O[C@H]1C[C@]2(O)C3CC[C@@H]4C[C@H](CC[C@]4(C)C3CC[C@]2(C)[C@H]1C1=CC(=O)OC1)OC1OC(C)C(O[C@@H]2OC(CO)[C@@H](O)C(O)[C@@H]2O)C(O)C1O

InChI Identifier

InChI=1S/C38H58O15/c1-5-25(40)51-23-14-38(47)22-7-6-19-13-20(8-10-36(19,3)21(22)9-11-37(38,4)27(23)18-12-26(41)48-16-18)50-34-32(46)30(44)33(17(2)49-34)53-35-31(45)29(43)28(42)24(15-39)52-35/h12,17,19-24,27-35,39,42-47H,5-11,13-16H2,1-4H3/t17?,19-,20+,21?,22?,23+,24?,27+,28-,29?,30?,31+,32?,33?,34?,35+,36+,37-,38+/m1/s1

InChI Key

XRXCJPMZYAWJHD-JJGULWAKSA-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
Cryptostegia grandiflora	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
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	0.33	ChemAxon
pKa (Strongest Acidic)	6.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	231.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	182.25 m³·mol⁻¹	ChemAxon
Polarizability	80.6 Å³	ChemAxon
Number of Rings	7	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

163030815

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate (NP0221640)

MOL for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)

3D MOL for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)

3D SDF for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)

3D-SDF for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)

PDB for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)

3D PDB for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)

SMILES for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)

INCHI for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)

Structure for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)

3D Structure for NP0221640 ((1r,2s,3as,5ar,7s,9as,11ar)-7-[(3,4-dihydroxy-6-methyl-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2h-furan-3-yl)-tetradecahydrocyclopenta[a]phenanthren-2-yl propanoate)