NP-MRD: Showing NP-Card for (2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid (NP0238403)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 21:47:52 UTC

Updated at

2022-09-06 21:47:52 UTC

NP-MRD ID

NP0238403

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid

Description

Tsugaric acid B, also known as tsugarate b, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid is found in Ganoderma tsugae. (2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid was first documented in 2008 (PMID: 17655889). Based on a literature review very few articles have been published on Tsugaric acid B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309062223472D          

 38 41  0  0  1  0            999 V2000
   -0.9457   -5.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207   -5.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918   -5.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918   -6.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207   -7.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168   -6.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293   -7.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543   -7.2044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7668   -6.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543   -5.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5918   -6.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7668   -7.9188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4313   -8.6725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6243   -8.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0443   -9.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588   -8.8121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8451   -9.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434   -9.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1565   -8.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9850   -7.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2004   -7.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873   -8.0051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3324   -7.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9412   -8.7699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7696   -7.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5543   -8.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3389   -8.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5104   -9.2798    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2950   -9.5347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4665  -10.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2512  -10.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8535  -10.8937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8973   -9.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5474  -10.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5100  -10.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127   -9.5769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4996  -10.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7150   -9.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12  8  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  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
 12 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  6  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 18 38  1  0  0  0  0
M  END

     RDKit          3D

 90 93  0  0  0  0  0  0  0  0999 V2000
   -7.8248   -0.7077    0.4500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7480    0.5792    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0518    1.3181    0.7603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5588    1.4493    0.2226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8971    2.2315   -1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2731    0.6970    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7967   -0.0525    1.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5041   -0.8087    0.9644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6784   -2.0136    0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1845   -3.1302    0.4102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4210   -1.9801   -1.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4039    0.0839    0.5941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1196    1.1123    1.6678 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4376    2.4024    1.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6023    1.0394    1.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481    0.6158    0.5493 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2556    1.7097   -0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329    0.0887    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5201   -0.7045   -0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5388   -1.0577   -1.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8955   -0.9538   -1.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0807   -0.5588    0.3042 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7021   -1.6897    1.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9090   -1.2935   -0.6457 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8286   -2.6931   -0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3401   -1.3322   -2.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554   -0.2760   -2.4258 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870   -0.3288   -1.5687 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1962    0.9455   -1.6558 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4733    1.1506   -2.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9546    2.5726   -2.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1463    0.1879   -2.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2894   -0.6003   -0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0158    0.4196    0.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7763   -1.9500    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259   -0.3832    0.0939 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4638   -0.2756    1.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1457    0.4740    1.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0559   -1.4558    0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8059   -1.1869    0.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4725    0.9590    1.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8706    2.4075    0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7361    1.0814   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5264    2.2147    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5710    1.5159   -1.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2498    3.1038   -1.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9673    2.4286   -1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3021    0.1074   -0.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4964    1.4932   -0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5061    0.6998    2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5106   -0.6988    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685   -1.2116    2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8822   -2.0947   -1.9065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6716    0.6508   -0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894    0.8383    2.6406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0277    2.7893    2.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722    0.2329    2.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2380    2.0230    2.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7148    1.8497   -1.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461    2.6732    0.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1140    1.6753   -1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -0.3998   -2.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885   -2.0823   -1.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772   -0.2291   -1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744   -1.9366   -1.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095   -1.4575    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4961   -2.6416    0.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3561   -1.8585    2.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3206   -2.8682    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892   -3.4359   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687   -3.0676   -0.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034   -1.2113   -2.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8119   -2.3052   -2.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8648    0.7157   -2.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6746   -0.4566   -3.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3293   -1.0628   -1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2117    3.1831   -2.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9519    2.6687   -2.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9034    2.9601   -1.1018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4880    1.3847    0.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2250   -0.0040    1.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0181    0.6420    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5162   -2.7658   -0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9063   -1.8985    0.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5134   -2.0743    1.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6189    0.6547   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614   -1.2252    2.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398    0.3781    2.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4262    1.5506    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7575    0.4595    2.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 19 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 28 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
 36 37  1  0
 37 38  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 22 12  1  0
 36 24  1  0
 22 16  1  0
 38 18  1  0
  5 45  1  0
  5 46  1  0
  5 47  1  0
  4 44  1  1
  6 48  1  0
  6 49  1  0
  7 50  1  0
  7 51  1  0
  8 52  1  1
 12 54  1  6
 13 55  1  1
 14 56  1  0
 15 57  1  0
 15 58  1  0
 17 59  1  0
 17 60  1  0
 17 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  0
 21 65  1  0
 23 66  1  0
 23 67  1  0
 23 68  1  0
 25 69  1  0
 25 70  1  0
 25 71  1  0
 26 72  1  0
 26 73  1  0
 27 74  1  0
 27 75  1  0
 28 76  1  6
 31 77  1  0
 31 78  1  0
 31 79  1  0
 34 80  1  0
 34 81  1  0
 34 82  1  0
 35 83  1  0
 35 84  1  0
 35 85  1  0
 36 86  1  6
 37 87  1  0
 37 88  1  0
 38 89  1  0
 38 90  1  0
 11 53  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  1 39  1  0
  1 40  1  0
M  END

  Mrv1652309062223472D          

 38 41  0  0  1  0            999 V2000
   -0.9457   -5.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207   -5.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918   -5.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918   -6.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207   -7.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1168   -6.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293   -7.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543   -7.2044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7668   -6.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543   -5.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5918   -6.4899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7668   -7.9188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4313   -8.6725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6243   -8.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0443   -9.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588   -8.8121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8451   -9.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5434   -9.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1565   -8.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9850   -7.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2004   -7.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873   -8.0051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3324   -7.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9412   -8.7699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7696   -7.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5543   -8.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3389   -8.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5104   -9.2798    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2950   -9.5347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4665  -10.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2512  -10.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8535  -10.8937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8973   -9.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5474  -10.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5100  -10.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127   -9.5769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4996  -10.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7150   -9.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12  8  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  2  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
 12 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  6  0  0  0
 19 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 18 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC[C@H]([C@H]1[C@H](O)C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](OC(C)=O)C(C)(C)[C@@H]1CC3)C(O)=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H52O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h20,22,25-28,35H,1,10-18H2,2-9H3,(H,36,37)/t20?,22-,25-,26+,27-,28+,31-,32-,33+/m1/s1

> <INCHI_KEY>
ZCMJUAGNOJTZBJ-MJWPTZKTSA-N

> <FORMULA>
C33H52O5

> <MOLECULAR_WEIGHT>
528.774

> <EXACT_MASS>
528.381474774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
62.172133406911485

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2S,5R,7R,11R,13R,14R,15R)-5-(acetyloxy)-13-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-5,6-dimethylhept-6-enoic acid

> <JCHEM_LOGP>
6.119711318

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.901648297353546

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7736831298168525

> <JCHEM_PKA_STRONGEST_BASIC>
-2.854174423549309

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
150.45610000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2S,5R,7R,11R,13R,14R,15R)-5-(acetyloxy)-13-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-5,6-dimethylhept-6-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.765 -10.781   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.225 -10.781   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.545  -9.447   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.545 -12.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.225 -13.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.085 -12.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.855 -13.448   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.395 -13.448   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.165 -12.114   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.395 -10.781   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       6.705 -12.114   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.165 -14.782   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.538 -16.189   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.032 -16.509   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.683 -17.219   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.016 -16.449   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.177 -17.981   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.481 -16.925   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.626 -15.895   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.305 -14.388   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.841 -13.912   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.696 -14.943   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.220 -13.478   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.090 -16.370   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.770 -14.864   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.235 -15.340   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.699 -15.816   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.019 -17.322   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      15.484 -17.798   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.804 -19.304   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.269 -19.780   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.660 -20.335   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.875 -18.353   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.089 -19.301   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.152 -19.712   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.410 -17.877   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.266 -18.907   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.801 -18.431   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   22                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19   38                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   12   16   23                                             
CONECT   23   22                                                            
CONECT   24   19   25   26   36                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   24   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   18                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
Tsugarate b	Generator

Chemical Formula

C₃₃H₅₂O₅

Average Mass

528.7740 Da

Monoisotopic Mass

528.38147 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(CC[C@H]([C@H]1[C@H](O)C[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](OC(C)=O)C(C)(C)[C@@H]1CC3)C(O)=O)C(C)=C

InChI Identifier

InChI=1S/C33H52O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h20,22,25-28,35H,1,10-18H2,2-9H3,(H,36,37)/t20?,22-,25-,26+,27-,28+,31-,32-,33+/m1/s1

InChI Key

ZCMJUAGNOJTZBJ-MJWPTZKTSA-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
Ganoderma tsugae	LOTUS Database	35616633

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
Monohydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid ester
Steroid acid
14-alpha-methylsteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
Hydroxysteroid
Steroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00058001

Chemspider ID

78441294

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101936600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ko HH, Hung CF, Wang JP, Lin CN: Antiinflammatory triterpenoids and steroids from Ganoderma lucidum and G. tsugae. Phytochemistry. 2008 Jan;69(1):234-9. doi: 10.1016/j.phytochem.2007.06.008. Epub 2007 Jul 25. [PubMed:17655889 ]
LOTUS database [Link]

Showing NP-Card for (2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid (NP0238403)

MOL for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)

3D MOL for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)

3D SDF for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)

3D-SDF for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)

PDB for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)

3D PDB for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)

SMILES for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)

INCHI for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)

Structure for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)

3D Structure for NP0238403 ((2r)-2-[(1r,2r,3ar,5ar,7r,9as,11ar)-7-(acetyloxy)-2-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-5,6-dimethylhept-6-enoic acid)