NP-MRD: Showing NP-Card for 4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0316216)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 15:15:41 UTC

Updated at

2022-09-11 15:15:41 UTC

NP-MRD ID

NP0316216

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

4-[(1R,2S,5S,7R,10S,11S,14R,15R)-5-{[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2,5-dihydrofuran-2-one 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. 4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one is found in Nerium oleander. Based on a literature review very few articles have been published on 4-[(1R,2S,5S,7R,10S,11S,14R,15R)-5-{[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217152D          

 38 43  0  0  1  0            999 V2000
    7.0405    4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    3.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920    2.8855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1041    3.0307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3844    3.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6360    2.4000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4481    2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    1.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435    1.4789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    2.1096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1996    1.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 19 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  1  0  0  0
 16 36  1  0  0  0  0
 11 36  1  0  0  0  0
  9 37  1  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END

     RDKit          3D

 84 89  0  0  0  0  0  0  0  0999 V2000
    7.0350    0.6773    2.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0822    0.0887    1.7330 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3613    0.2702    0.4011 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5596   -1.0261   -0.3460 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8448   -2.0808    0.1817 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3503   -0.7951   -1.8025 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5699   -2.1367   -2.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1237   -0.3029   -2.1526 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4267    0.3353   -1.1596 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7500   -0.5948   -0.3965 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3561   -0.3884   -0.4013 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6633   -1.5762   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1881   -1.1754   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3142   -1.2026    0.2804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2076   -2.6618    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457   -0.3339    1.2404 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1568    1.0285    1.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004    1.4949    0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    0.5220   -0.1998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7590   -0.8232    0.4217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6952   -1.7470   -0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0742   -1.4791    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4471   -0.0181    0.3656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7570    0.0724    1.8698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6073    0.2220   -0.5085 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5548    1.3008   -0.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6561    2.1939    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8190    3.0426    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1481    3.9905    1.1953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3927    2.5804   -0.7203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6885    1.4995   -1.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9458    0.4935   -1.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9384    1.5625   -1.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4325    0.9700   -0.0577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3752    2.0670    0.8340 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9210   -0.2940    1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3017    1.1495   -0.2298 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8416    2.2603   -0.8726 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7839    0.5151    3.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0671    1.7895    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0508    0.2406    2.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3160    0.8642    0.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6495   -1.2941   -0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7797   -1.9680    1.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1987   -0.1377   -2.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4392   -2.9880   -1.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8854   -2.2073   -3.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6033   -2.2270   -2.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7107    1.0570   -1.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1105    0.4892   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219   -2.5104   -0.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226   -1.6757   -2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1434   -0.2155   -1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902   -1.9240   -1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2737   -3.3478   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7301   -2.8355    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0377   -2.8858    1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3200   -0.8409    2.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7053    1.7475    1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7325    1.1477    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028    2.4464    0.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3056    1.8609   -0.5254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8291    0.3852   -1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9883   -0.7727    1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5190   -1.6088   -1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4146   -2.7724   -0.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359   -2.1019    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7582   -1.9892   -0.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3451   -0.8378    2.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2435    0.9040    2.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8417   -0.0231    2.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2114   -0.7244   -0.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9635    2.2685    1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3423    0.5659   -1.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3869    1.5864   -2.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4114   -0.3958   -2.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5709    0.9056   -2.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5161    2.4765   -1.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1026    1.6529   -2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4695    2.9261    0.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4576   -1.1061    1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093    0.6537    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6155    1.5360    0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8393    2.1849   -0.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23 25  1  0
 25 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  1
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 16 36  1  0
  9 37  1  0
 37 38  1  0
 37  3  1  0
 36 11  1  0
 20 14  1  0
 34 23  1  0
 31 26  1  0
 34 19  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  1
  4 43  1  6
  5 44  1  0
  6 45  1  6
  7 46  1  0
  7 47  1  0
  7 48  1  0
  9 49  1  6
 11 50  1  6
 12 51  1  0
 12 52  1  0
 13 53  1  0
 13 54  1  0
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  1
 17 59  1  0
 17 60  1  0
 18 61  1  0
 18 62  1  0
 19 63  1  6
 20 64  1  1
 21 65  1  0
 21 66  1  0
 22 67  1  0
 22 68  1  0
 24 69  1  0
 24 70  1  0
 24 71  1  0
 25 72  1  6
 32 76  1  0
 32 77  1  0
 33 78  1  0
 33 79  1  0
 35 80  1  0
 27 73  1  0
 31 74  1  0
 31 75  1  0
 36 81  1  0
 36 82  1  0
 37 83  1  1
 38 84  1  0
M  END


  Mrv1652309112217152D          

 38 43  0  0  1  0            999 V2000
    7.0405    4.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    3.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920    2.8855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1041    3.0307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3844    3.8066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6360    2.4000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4481    2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    1.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435    1.4789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889   -1.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -2.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    2.1096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1996    1.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 19 34  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  1  0  0  0
 16 36  1  0  0  0  0
 11 36  1  0  0  0  0
  9 37  1  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0316216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@@H](O)[C@@H](C)O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@H]4[C@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=CC(=O)OC3)C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O8/c1-16-24(32)26(35-4)25(33)27(37-16)38-19-7-10-28(2)18(14-19)5-6-22-21(28)8-11-29(3)20(9-12-30(22,29)34)17-13-23(31)36-15-17/h13,16,18-22,24-27,32-34H,5-12,14-15H2,1-4H3/t16-,18-,19+,20-,21-,22+,24+,25-,26+,27+,28+,29-,30+/m1/s1

> <INCHI_KEY>
VPUNMTHWNSJUOG-RJHIURMFSA-N

> <FORMULA>
C30H46O8

> <MOLECULAR_WEIGHT>
534.69

> <EXACT_MASS>
534.319268441

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
59.457472090307036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1R,2S,5S,7R,10S,11S,14R,15R)-5-{[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
2.986555411666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.296494958925228

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182632881668664

> <JCHEM_PKA_STRONGEST_BASIC>
0.24224545289204225

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
139.26139999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <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      13.142   8.012   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.619   6.564   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.612   5.386   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.128   5.657   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.651   7.106   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.636   4.751   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      15.597   3.032   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.131  -3.824   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.081  -5.363   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.084  -2.878   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.089   3.938   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.573   3.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   37                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   36                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   20                                             
CONECT   15   14                                                            
CONECT   16   14   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   14   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   34                                             
CONECT   24   23                                                            
CONECT   25   23   26   32                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26                                                       
CONECT   32   25   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   19   23   35                                             
CONECT   35   34                                                            
CONECT   36   16   11                                                       
CONECT   37    9    3   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₈

Average Mass

534.6900 Da

Monoisotopic Mass

534.31927 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@@H](O)[C@@H](C)O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@H]4[C@H]3CC[C@]3(C)[C@H](CC[C@]43O)C3=CC(=O)OC3)C2)[C@@H]1O

InChI Identifier

InChI=1S/C30H46O8/c1-16-24(32)26(35-4)25(33)27(37-16)38-19-7-10-28(2)18(14-19)5-6-22-21(28)8-11-29(3)20(9-12-30(22,29)34)17-13-23(31)36-15-17/h13,16,18-22,24-27,32-34H,5-12,14-15H2,1-4H3/t16-,18-,19+,20-,21-,22+,24+,25-,26+,27+,28+,29-,30+/m1/s1

InChI Key

VPUNMTHWNSJUOG-RJHIURMFSA-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
Nerium oleander	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
14-hydroxysteroid
Hydroxysteroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
2-furanone
Monosaccharide
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Lactone
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Dialkyl ether
Ether
Oxacycle
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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

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

162915452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one (NP0316216)

MOL for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D MOL for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D SDF for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D-SDF for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

PDB for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D PDB for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

SMILES for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

INCHI for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

Structure for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)

3D Structure for NP0316216 (4-[(1r,3as,3bs,5ar,7s,9as,9br,11ar)-7-{[(2r,3r,4s,5s,6r)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-5h-furan-2-one)