NP-MRD: Showing NP-Card for 1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate (NP0316199)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 15:13:39 UTC

Updated at

2022-09-11 15:13:39 UTC

NP-MRD ID

NP0316199

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate

Description

1-[16-(Acetyloxy)-5,10,11,14-tetrahydroxy-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]ethyl pyridine-2-carboxylate belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. 1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate is found in Marsdenia rostrata. 1-[16-(Acetyloxy)-5,10,11,14-tetrahydroxy-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]ethyl pyridine-2-carboxylate is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502492D          

 37 41  0  0  0  0            999 V2000
   -0.4191   -3.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1127   -2.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -1.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3643   -1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764   -1.2123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0840   -0.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282   -0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085    0.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4766    1.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    0.3396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844   -1.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274   -4.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -4.2774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -1.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5328   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525    0.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449   -0.7000    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 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
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 16 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  0  0  0  0
 19 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END

     RDKit          3D

 76 80  0  0  0  0  0  0  0  0999 V2000
    2.3119   -1.4716   -3.8933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2992   -0.4460   -3.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237    0.2973   -4.4187 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8996   -0.3263   -2.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0582    0.6014   -1.7532 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7929    1.5596   -0.8578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486    0.6465    0.0580 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6421    1.2942    0.8357 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0990    2.2008    1.9532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181    2.2910   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2848    1.6130   -1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3659    0.9114   -0.2022 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3554    0.3672   -0.9947 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6938   -0.1592    0.5587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    0.2200    1.3818 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7844   -1.0625    1.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3303   -0.9070    1.9437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5837   -0.0673    0.9700 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0561    0.9509    1.7228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4949   -0.8040    0.2729 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5585   -0.9553    1.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1849   -2.1491   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591   -2.4426   -1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984   -1.1209   -1.7312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3939   -1.2384   -3.0531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923   -0.8863   -1.7687 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9408   -1.9554   -2.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8819   -0.7384   -0.5109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5136    0.4009   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5634    1.3785   -0.8479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1196    0.5092    1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7387    1.6789    1.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3272    1.8334    2.8890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2909    0.7775    3.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6696   -0.3937    3.3768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1023   -0.4965    2.1389 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0715   -0.0928   -0.9291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0835   -1.0427   -4.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -2.2891   -4.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.8776   -3.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5280    1.1999   -2.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0626    2.1747   -0.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    2.0858   -1.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -0.1403   -0.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9219    2.9211    2.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8558    1.6590    2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    2.8394    1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649    3.0699   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1182    2.7957    0.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7011    2.3627   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7062    0.8207   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7529    1.6980    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1583    0.9463   -0.9589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3501   -0.9430   -0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4361   -0.6727    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9098    0.5838    2.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2344   -1.6069    2.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8918   -1.7682    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1410   -0.6203    3.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8940   -1.9508    1.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4038    0.5631    2.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4605   -1.7956    1.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695   -2.9723    0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151   -2.2272   -0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2643   -2.7468   -0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021   -3.2343   -1.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8600   -0.5889   -3.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4370    0.0848   -2.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7108   -1.5642   -3.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1598   -2.4173   -3.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3670   -2.7843   -1.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7723    2.5077    0.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8145    2.7573    3.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7541    0.8811    4.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6568   -1.2078    4.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7625    0.6809   -0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 26 24  1  0
 24 25  1  6
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  1  1
 20 37  1  0
 37  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 36 31  1  0
 37 24  1  0
 18  7  1  0
 18 20  1  0
 15  8  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 26 68  1  6
 32 72  1  0
 33 73  1  0
 34 74  1  0
 35 75  1  0
 25 67  1  0
 23 65  1  0
 23 66  1  0
 22 63  1  0
 22 64  1  0
 21 62  1  0
 37 76  1  1
  5 41  1  6
  6 42  1  0
  6 43  1  0
  7 44  1  6
  9 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 12 52  1  1
 13 53  1  0
 14 54  1  0
 14 55  1  0
 15 56  1  1
 16 57  1  0
 16 58  1  0
 17 59  1  0
 17 60  1  0
 19 61  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
M  END


  Mrv1533004201502492D          

 37 41  0  0  0  0            999 V2000
   -0.4191   -3.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1127   -2.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -1.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3643   -1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1764   -1.2123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0840   -0.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282   -0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085    0.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4766    1.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    0.3396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844   -1.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2274   -4.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -4.2774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -1.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5328   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525    0.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3449   -0.7000    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 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
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 16 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  1  0  0  0  0
 19 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316199

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(OC(=O)C1=CC=CC=N1)C1(O)CCC2(O)C1C(CC1C3(C)CCC(O)CC3CCC21O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H39NO8/c1-16(36-24(32)20-6-4-5-13-29-20)26(33)11-12-28(35)23(26)21(37-17(2)30)15-22-25(3)9-8-19(31)14-18(25)7-10-27(22,28)34/h4-6,13,16,18-19,21-23,31,33-35H,7-12,14-15H2,1-3H3

> <INCHI_KEY>
AJEYBRIZNAXITC-UHFFFAOYSA-N

> <FORMULA>
C28H39NO8

> <MOLECULAR_WEIGHT>
517.619

> <EXACT_MASS>
517.26756722

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.815904366286546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[16-(acetyloxy)-5,10,11,14-tetrahydroxy-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethyl pyridine-2-carboxylate

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.0558724160000006

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.610246306772744

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.925326378742533

> <JCHEM_PKA_STRONGEST_BASIC>
2.169005373217509

> <JCHEM_POLAR_SURFACE_AREA>
146.41

> <JCHEM_REFRACTIVITY>
131.46749999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[16-(acetyloxy)-5,10,11,14-tetrahydroxy-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethyl pyridine-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -0.782  -5.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.210  -4.618   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.313  -3.169   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.680  -1.992   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.196  -2.263   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.157  -0.543   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.359  -0.272   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.882   1.176   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.890   2.353   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.626   2.082   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.149   0.634   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.838  -3.353   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.158  -7.782   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.724  -7.984   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.735  -2.213   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.728  -1.036   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.205   0.413   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.244  -1.307   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    2   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   32                                             
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18   20   34                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   23   24   29                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   22   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   16   21   33                                             
CONECT   33   32                                                            
CONECT   34   19   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
1-[16-(Acetyloxy)-5,10,11,14-tetrahydroxy-2-methyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]ethyl pyridine-2-carboxylic acid	Generator
1-[16-(Acetyloxy)-5,10,11,14-tetrahydroxy-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethyl pyridine-2-carboxylic acid	Generator

Chemical Formula

C₂₈H₃₉NO₈

Average Mass

517.6190 Da

Monoisotopic Mass

517.26757 Da

IUPAC Name

1-[16-(acetyloxy)-5,10,11,14-tetrahydroxy-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethyl pyridine-2-carboxylate

Traditional Name

1-[16-(acetyloxy)-5,10,11,14-tetrahydroxy-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]ethyl pyridine-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC(OC(=O)C1=CC=CC=N1)C1(O)CCC2(O)C1C(CC1C3(C)CCC(O)CC3CCC21O)OC(C)=O

InChI Identifier

InChI=1S/C28H39NO8/c1-16(36-24(32)20-6-4-5-13-29-20)26(33)11-12-28(35)23(26)21(37-17(2)30)15-22-25(3)9-8-19(31)14-18(25)7-10-27(22,28)34/h4-6,13,16,18-19,21-23,31,33-35H,7-12,14-15H2,1-3H3

InChI Key

AJEYBRIZNAXITC-UHFFFAOYSA-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
Marsdenia rostrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
3-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
17-hydroxysteroid
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Dicarboxylic acid or derivatives
Pyridine
Tertiary alcohol
Heteroaromatic compound
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Polyol
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.55	ALOGPS
logP	1.06	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	2.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.41 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131.47 m³·mol⁻¹	ChemAxon
Polarizability	55.82 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate (NP0316199)

MOL for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)

3D MOL for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)

3D SDF for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)

3D-SDF for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)

PDB for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)

3D PDB for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)

SMILES for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)

INCHI for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)

Structure for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)

3D Structure for NP0316199 (1-[11-(acetyloxy)-1,3a,3b,7-tetrahydroxy-9a-methyl-dodecahydro-2h-cyclopenta[a]phenanthren-1-yl]ethyl pyridine-2-carboxylate)