NP-MRD: Showing NP-Card for Ikemagenin (NP0072147)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 17:31:45 UTC

Updated at

2022-04-28 17:31:45 UTC

NP-MRD ID

NP0072147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ikemagenin

Description

Ikemagenin belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Ikemagenin is found in Araujia sericifera, Asclepias tuberosa and Cynanchum caudatum Max.. Ikemagenin was first documented in 2003 (PMID: 12951444). Based on a literature review a small amount of articles have been published on Ikemagenin (PMID: 23308358) (PMID: 19182408).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219312D          

 36 40  0  0  1  0            999 V2000
    6.1708   -0.2182    0.0000 C   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
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  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  2  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
    4.8269    0.2673    0.0000 C   0  0  1  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
    4.5466   -0.5086    0.0000 C   0  0  0  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  2  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  1  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
    2.0195    1.1139    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
    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
    1.3705   -1.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424   -0.6800    0.0000 C   0  0  0  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
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6421   -1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1739   -2.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936   -2.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -2.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5178   -2.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3299   -2.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6102   -1.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4223   -1.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6739   -3.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8618   -3.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1721    1.5170    0.0000 O   0  0  0  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
  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  1  0  0  0
 14 23  1  1  0  0  0
 13 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
  7 35  1  1  0  0  0
  2 36  1  1  0  0  0
M  END

     RDKit          3D

 74 78  0  0  0  0  0  0  0  0999 V2000
    2.8339   -3.9971   -0.8630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0640   -2.9375   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6846   -2.1820    0.5554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6475   -2.8782   -0.3249 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1280   -2.7847   -1.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3684   -2.7435   -1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483   -2.0415   -0.1151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9336   -3.0187    0.8061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4811   -0.9169   -0.0950 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3866   -1.0768    0.9891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4276   -0.8775   -1.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3958    0.2244   -1.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2196    1.2115   -0.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3122    2.2128   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0201    3.3184    0.8533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5963    3.0161    2.1034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6074    3.7571    0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5673    2.7923    0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9985    1.3437    0.6300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2152    1.0532    2.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9419    0.4721   -0.0051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5973    0.6108    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2722   -0.3611   -0.2251 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6021   -0.0188   -0.1513 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3376    0.4329   -1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244    0.5158   -2.3515 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.7888   -1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198    0.7129   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8171    1.0600    0.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5901    1.5009   -0.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9371    1.8232   -0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4933    1.6880    0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7244    1.2462    1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4134    0.9336    1.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -1.6970    0.2727 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0994   -1.7441    1.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7033   -4.3453   -0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1686   -3.6827   -1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1769   -4.9090   -0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1136   -3.8032    0.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3918   -3.7431   -2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -1.9198   -2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6713   -3.8305   -1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9495   -2.3372   -2.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -3.9341    0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0299   -1.7828    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -0.5405   -2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9760   -1.8059   -1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3231    0.1454   -1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2720    1.7411    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4664    2.6494   -1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6174    4.2134    0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4239    2.4876    1.9592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4301    4.7247    0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4615    4.0753    2.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6651    2.9322    1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2740    3.0391   -0.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821    0.4087    2.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2146    0.6488    2.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1280    1.9848    2.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8201    0.8934   -1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143    0.3281    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215    1.6268    0.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0542   -0.2393   -1.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2421    1.1243   -2.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8557    0.3637    0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1686    1.6134   -1.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5072    2.1680   -1.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5495    1.9287    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1871    1.1483    2.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7969    0.5784    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4425   -2.7634    2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9070   -1.0604    2.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617   -1.5659    2.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7 35  1  0
 35 36  1  1
 35 23  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  1  1
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11  9  1  0
  9 10  1  1
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 35  4  1  0
  9 21  1  0
 34 29  1  0
  9  7  1  0
 13 19  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  4 40  1  1
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  8 45  1  0
 36 72  1  0
 36 73  1  0
 36 74  1  0
 23 64  1  6
 22 62  1  0
 22 63  1  0
 21 61  1  6
 20 58  1  0
 20 59  1  0
 20 60  1  0
 18 56  1  0
 18 57  1  0
 17 54  1  0
 17 55  1  0
 15 52  1  6
 16 53  1  0
 14 50  1  0
 14 51  1  0
 12 49  1  0
 11 47  1  0
 11 48  1  0
 10 46  1  0
 27 65  1  0
 28 66  1  0
 30 67  1  0
 31 68  1  0
 32 69  1  0
 33 70  1  0
 34 71  1  0
M  END


  Mrv1652304282219312D          

 36 40  0  0  1  0            999 V2000
    6.1708   -0.2182    0.0000 C   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
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  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  2  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
    4.8269    0.2673    0.0000 C   0  0  1  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
    4.5466   -0.5086    0.0000 C   0  0  0  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  2  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  1  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
    2.0195    1.1139    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
    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
    1.3705   -1.5571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424   -0.6800    0.0000 C   0  0  0  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
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6421   -1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1739   -2.2057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936   -2.9816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -2.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5178   -2.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3299   -2.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6102   -1.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4223   -1.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6739   -3.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8618   -3.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1721    1.5170    0.0000 O   0  0  0  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
  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  1  0  0  0
 14 23  1  1  0  0  0
 13 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
  7 35  1  1  0  0  0
  2 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0072147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)[C@@H]1CC[C@@]2(O)[C@]1(C)[C@@H](C[C@@H]1[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21O)OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O6/c1-19(31)23-13-16-30(35)28(23,3)25(36-26(33)10-9-20-7-5-4-6-8-20)18-24-27(2)14-12-22(32)17-21(27)11-15-29(24,30)34/h4-11,22-25,32,34-35H,12-18H2,1-3H3/b10-9+/t22-,23-,24+,25+,27-,28-,29-,30+/m0/s1

> <INCHI_KEY>
JSEOJMNUDFVEQJ-HWEYXPBISA-N

> <FORMULA>
C30H38O6

> <MOLECULAR_WEIGHT>
494.628

> <EXACT_MASS>
494.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.55784158807001

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,10S,11R,14R,15S,16R)-14-acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.2996997636666667

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.36416778641447

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.009105493420137

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972422311332444

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
137.6651

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,10S,11R,14R,15S,16R)-14-acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.558  -2.907   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.932  -2.940   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.925  -4.117   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.401  -5.566   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.441  -3.846   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.433  -5.024   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.949  -4.752   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.472  -3.304   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.988  -3.033   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.981  -4.210   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.458  -5.659   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.942  -5.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.921   2.832   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15   35                                             
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   18   23                                             
CONECT   15   14    7   16   22                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24   13   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35    7                                                            
CONECT   36    2                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₈O₆

Average Mass

494.6280 Da

Monoisotopic Mass

494.26684 Da

IUPAC Name

(1R,2R,5S,10S,11R,14R,15S,16R)-14-acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1R,2R,5S,10S,11R,14R,15S,16R)-14-acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)[C@@H]1CC[C@@]2(O)[C@]1(C)[C@@H](C[C@@H]1[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21O)OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H38O6/c1-19(31)23-13-16-30(35)28(23,3)25(36-26(33)10-9-20-7-5-4-6-8-20)18-24-27(2)14-12-22(32)17-21(27)11-15-29(24,30)34/h4-11,22-25,32,34-35H,12-18H2,1-3H3/b10-9+/t22-,23-,24+,25+,27-,28-,29-,30+/m0/s1

InChI Key

JSEOJMNUDFVEQJ-HWEYXPBISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Araujia sericifera	Plant	KNApSAcK
Asclepias tuberosa	Plant	KNApSAcK
Cynanchum caudatum Max.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
Steroid ester
3-hydroxy-delta-5-steroid
3-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
Delta-5-steroid
Cinnamic acid or derivatives
Cinnamic acid ester
Styrene
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.17	ALOGPS
logP	3.3	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.01	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.67 m³·mol⁻¹	ChemAxon
Polarizability	54.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031879

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

12310793

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Komarnytsky S, Esposito D, Rathinasabapathy T, Poulev A, Raskin I: Effects of pregnane glycosides on food intake depend on stimulation of the melanocortin pathway and BDNF in an animal model. J Agric Food Chem. 2013 Feb 27;61(8):1841-9. doi: 10.1021/jf3033649. Epub 2013 Feb 17. [PubMed:23308358 ]
Warashina T, Noro T: Acylated-oxypregnane glycosides from the roots of Asclepias syriaca. Chem Pharm Bull (Tokyo). 2009 Feb;57(2):177-84. doi: 10.1248/cpb.57.177. [PubMed:19182408 ]
Warashina T, Noro T: Acylated-oxypregnane glycosides from the roots of Araujia sericifera. Chem Pharm Bull (Tokyo). 2003 Sep;51(9):1036-45. doi: 10.1248/cpb.51.1036. [PubMed:12951444 ]

Showing NP-Card for Ikemagenin (NP0072147)

MOL for NP0072147 (Ikemagenin)

3D MOL for NP0072147 (Ikemagenin)

3D SDF for NP0072147 (Ikemagenin)

3D-SDF for NP0072147 (Ikemagenin)

PDB for NP0072147 (Ikemagenin)

3D PDB for NP0072147 (Ikemagenin)

SMILES for NP0072147 (Ikemagenin)

INCHI for NP0072147 (Ikemagenin)

Structure for NP0072147 (Ikemagenin)

3D Structure for NP0072147 (Ikemagenin)