NP-MRD: Showing NP-Card for Yamogenin (NP0044750)

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Record Information

Version

2.0

Created at

2022-02-24 21:14:43 UTC

Updated at

2022-02-24 21:14:44 UTC

NP-MRD ID

NP0044750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Yamogenin

Description

Yamogenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, yamogenin is considered to be a sterol lipid molecule. Yamogenin is found in Asparagus tenuifolium, Borassus flabellifer , Urochloa decumbens, Cordyline australis, Cordyline banksii, Dioscorea colletii, Dioscorea collettii, Dioscorea gracillima, Dioscorea hypoglauca , Dioscorea paranensis, Dioscorea parviflora, Dioscorea pyrenaica, Dioscorea tokoro, Smilax aspera , Solanum dulcamara , Solanum incanum, Solanum spirale and Tribulus terrestris . Yamogenin was first documented in 2002 (Farid, et al.). Yamogenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

yamogenin
  Mrv1572001071617182D          

 30 35  0  0  1  0            999 V2000
    7.2076   -4.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319   -3.4645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0648   -3.0857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9311   -2.2716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6640   -1.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2507   -2.4728    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0743   -2.4249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4446   -1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2682   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7215   -2.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5451   -2.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9984   -2.9704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8221   -2.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6282   -3.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8046   -3.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3512   -3.0662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9810   -3.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5276   -3.1142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1573   -3.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3337   -3.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8804   -3.2101    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4351   -3.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -2.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7452   -2.8845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4540   -3.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6399   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -3.1521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3030   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082   -2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2223   -2.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  1  0  0  0
  6 21  1  0  0  0  0
 21 22  1  1  0  0  0
  4 23  1  0  0  0  0
 24 23  1  1  0  0  0
  2 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
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  1  0  0  0  0
M  END

     RDKit          3D

 72 77  0  0  0  0  0  0  0  0999 V2000
   -7.3409    1.3342    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9272    0.7503    0.5940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0239   -0.6945    0.9877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7974   -1.4819    0.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8622   -0.5802   -0.1299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5173   -0.0385   -1.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2890    0.3495    0.7235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1082    0.7710    0.1993 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9367    0.6750    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1728    0.6149    0.2376 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5412    0.3200    0.6961 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9872    1.1642    1.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.8373    2.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2510    0.4566    1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6751    0.1756    1.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5605    0.4670    0.3657 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9406   -0.7025   -0.3003 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0401    1.5215   -0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7036    1.2410   -1.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8536    0.2977   -0.3291 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9912   -1.1138   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4180    0.7314   -0.4983 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8167    0.3916   -1.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249   -0.4574   -1.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376   -0.5423   -0.6634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0535   -1.8887    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -0.2099   -0.8783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6153   -1.3763   -0.5469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8728   -2.2641   -1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3186    2.2618    0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0628    0.6013    0.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6217    1.6104    1.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3612    1.2755    1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1316   -0.7448    2.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9621   -1.1776    0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1148   -2.2877   -0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3145   -1.9742    1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1705    1.1641   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7154    1.9039   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1418    1.7948   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8994    1.5875    1.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1298   -0.1919    1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1445    1.5239   -0.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838   -0.7140    0.9298 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4027    0.8602    2.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8825    2.2406    1.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8282    0.9257    3.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7488   -0.8773    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9407    0.8120    2.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5260    0.8693    0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0433   -1.3965    0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970    2.4760    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8216    1.6975   -1.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8860    0.8342   -2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1439    2.1899   -1.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6308   -1.1028   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4293   -1.7898   -0.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0487   -1.5950   -1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4627    1.8611   -0.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329   -0.0903   -2.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6076    1.3401   -2.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945   -1.5113   -2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -0.1353   -2.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9853   -2.2521   -0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3611   -1.9094    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6696   -2.6381   -0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343    0.1247   -1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3063   -1.9045    0.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1479   -2.0780   -2.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9343   -3.3218   -1.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822   -1.9876   -2.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 28  1  0
 28  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
  9  8  1  0
  5  8  1  1
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2  7  1  0
  7  6  1  0
  5 29  1  0
  6  5  1  0
 26 28  1  0
 26 11  1  0
 23 12  1  0
 21 15  1  0
 30 70  1  0
 30 71  1  0
 30 72  1  0
 29 69  1  1
 28 68  1  6
  9 41  1  6
 10 42  1  0
 10 43  1  0
 11 44  1  6
 12 45  1  1
 13 46  1  0
 13 47  1  0
 14 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  1
 18 52  1  0
 19 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  6
 24 61  1  0
 24 62  1  0
 25 63  1  0
 25 64  1  0
 27 65  1  0
 27 66  1  0
 27 67  1  0
  4 37  1  0
  4 38  1  0
  3 35  1  0
  3 36  1  0
  2 34  1  1
  1 31  1  0
  1 32  1  0
  1 33  1  0
  7 39  1  0
  7 40  1  0
M  END

yamogenin
  Mrv1572001071617182D          

 30 35  0  0  1  0            999 V2000
    7.2076   -4.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319   -3.4645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0648   -3.0857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9311   -2.2716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6640   -1.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2507   -2.4728    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0743   -2.4249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4446   -1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2682   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7215   -2.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5451   -2.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9984   -2.9704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8221   -2.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6282   -3.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8046   -3.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3512   -3.0662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9810   -3.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5276   -3.1142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1573   -3.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3337   -3.8994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8804   -3.2101    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4351   -3.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -2.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7452   -2.8845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4540   -3.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6399   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -3.1521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3030   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082   -2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2223   -2.2464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  1  0  0  0
  6 21  1  0  0  0  0
 21 22  1  1  0  0  0
  4 23  1  0  0  0  0
 24 23  1  1  0  0  0
  2 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
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@]11CC[C@H](C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

> <INCHI_KEY>
WQLVFSAGQJTQCK-CAKNJAFZSA-N

> <FORMULA>
C27H42O3

> <MOLECULAR_WEIGHT>
414.63

> <EXACT_MASS>
414.313395212

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.5168001848525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-en-16'-ol

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
4.927305454

> <ALOGPS_LOGS>
-5.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204289505503816

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3962771891939112

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
120.26589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
yamogenin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: yamogenin                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      13.454  -7.990   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.686  -6.467   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.054  -5.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.805  -4.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.173  -3.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.268  -4.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.805  -4.526   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.497  -3.150   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.034  -3.061   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.880  -4.347   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.418  -4.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.264  -5.545   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.801  -5.455   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      23.573  -6.921   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.035  -7.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.189  -5.724   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.498  -7.100   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.652  -5.813   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.960  -7.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.423  -7.279   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.577  -5.992   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.746  -7.289   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.282  -4.008   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.591  -5.384   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.047  -6.825   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.528  -7.075   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.552  -5.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.032  -6.133   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.095  -4.443   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.615  -4.193   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17   18                                             
CONECT   17   16                                                            
CONECT   18   16    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    3    6   22                                             
CONECT   22   21                                                            
CONECT   23    4   24                                                       
CONECT   24   23    2   25   30                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₃

Average Mass

414.6300 Da

Monoisotopic Mass

414.31340 Da

IUPAC Name

(1'S,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan]-18'-en-16'-ol

Traditional Name

yamogenin

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@]11CC[C@H](C)CO1

InChI Identifier

InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

InChI Key

WQLVFSAGQJTQCK-CAKNJAFZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Asparagus officinalis	FooDB	KNAPSACK
Asparagus tenuifolium	Plant	KNApSAcK
Borassus flabellifer	Plant	KNApSAcK
Brachiaria decumbens	LOTUS Database	35616633
Cordyline australis	LOTUS Database	35616633
Cordyline banksii	LOTUS Database	35616633
Dioscorea colletii	Plant	KNApSAcK
Dioscorea collettii	Plant	KNApSAcK
Dioscorea gracillima	Plant	KNApSAcK
Dioscorea hypoglauca	Plant	KNApSAcK
Dioscorea paranensis	Plant	KNApSAcK
Dioscorea parviflora	Plant	KNApSAcK
Dioscorea pyrenaica	LOTUS Database	35616633
Dioscorea tokoro	Plant	KNApSAcK
Smilax aspera	Plant	KNApSAcK
Solanum dulcamara	Plant	KNApSAcK
Solanum incanum	LOTUS Database	35616633
Solanum spirale	LOTUS Database	35616633
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tribulus terrestris	Plant	KNApSAcK
Trigonella foenum-graecum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Spirostane skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Steroid
Delta-5-steroid
Ketal
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid (CHEBI:10086 )
spirostan (C08918 )
Spirostanols and derivatives (LMST01080045 )

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	4.15	ALOGPS
logP	4.93	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	120.27 m³·mol⁻¹	ChemAxon
Polarizability	50.52 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

C00003597

Chemspider ID

Not Available

KEGG Compound ID

C08918

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Yamogenin

METLIN ID

Not Available

PubChem Compound

441900

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huda Farid, Ernst Haslinger, Olaf Kunert, Christian Wegner, Matthias Hamburger (2002). Huda Farid, Ernst Haslinger, Olaf Kunert, Christian Wegner, Matthias Hamburger. New Steroidal Glycosides from Balanites aegyptiaca. Helvetica 85(4), 1019-1026, 2002. 10.1002/1522-2675(200204)85:4<1019::AID-HLCA1019>3.0.CO;2-S. Helvetica.

Showing NP-Card for Yamogenin (NP0044750)

MOL for NP0044750 (Yamogenin)

3D MOL for NP0044750 (Yamogenin)

3D SDF for NP0044750 (Yamogenin)

3D-SDF for NP0044750 (Yamogenin)

PDB for NP0044750 (Yamogenin)

3D PDB for NP0044750 (Yamogenin)

SMILES for NP0044750 (Yamogenin)

INCHI for NP0044750 (Yamogenin)

Structure for NP0044750 (Yamogenin)

3D Structure for NP0044750 (Yamogenin)