NP-MRD: Showing NP-Card for (1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one (NP0214889)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-09-05 14:18:52 UTC

Updated at

2022-09-05 14:18:52 UTC

NP-MRD ID

NP0214889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one

Description

Ganodermanondiol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. It was first documented in 2006 (PMID: 16428083). Based on a literature review a significant number of articles have been published on Ganodermanondiol (PMID: 33691545) (PMID: 33358767) (PMID: 31749435) (PMID: 28912878) (PMID: 28099150) (PMID: 27801787).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052216182D          

 33 36  0  0  1  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -4.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660   -4.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -3.7114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351   -0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   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  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11  2  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 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
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 11 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 81 84  0  0  0  0  0  0  0  0999 V2000
    2.7624    0.0220   -2.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780    0.2219   -1.2267 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6535   -0.9950   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9822   -0.9716    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9562    0.0257    1.2502 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6997    1.3476    1.0696 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3747   -0.2311    0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8026   -1.6506    1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2703    0.6948    1.5705 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5437    0.0870   -0.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8610    0.7570   -0.4698 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4570    2.1723   -0.9728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2071    2.4355   -0.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1858    1.1320    0.4675 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1550    1.0182    1.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6490    0.8671    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5157    1.8315    0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9437    1.5438    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3013    0.1859   -0.3391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7869    0.0693   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3640    1.4620   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5058   -0.8804   -1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0148   -0.2427    1.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7802    0.4623    1.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2948   -1.3939    1.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8295   -1.3941    1.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4886   -0.9360    0.1741 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4919   -2.1256   -0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0350   -0.5351    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1261   -1.4872    0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3507   -1.1877    0.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5234    0.1370   -0.4564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2414    0.1443   -1.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7952   -0.2261   -3.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581   -0.8349   -2.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    0.9786   -3.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7857    1.0305   -1.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5893   -1.2281   -1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0148   -1.8749   -0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994   -1.9855    1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0453   -0.8601    1.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0255   -0.1233    2.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3586    1.8217    0.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3326   -2.4011    0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9032   -1.7307    1.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5589   -1.8101    2.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2699    0.2624    1.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7845    0.9562    2.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3499    1.6553    1.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1647   -0.5926   -0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1590    0.9319    0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2701    2.8872   -0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2931    2.1977   -2.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256    3.1813    0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950    2.8528   -0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0513    0.4957    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1992    2.0689    2.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792    0.5512    2.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1997    2.8452    0.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627    2.3296   -0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4616    1.6350    1.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1530    0.2184   -1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4825    1.3187   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0411    1.7758   -1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2260    2.1773    0.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5858   -0.5229   -1.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1823   -0.9078   -2.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6396   -1.8964   -0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8041   -2.3279    1.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4224   -1.3458    2.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4561   -2.4341    1.6673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144   -0.7969    2.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6117   -2.1089   -1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3425   -3.0415   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4320   -2.2984   -1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -2.5170    0.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8124   -2.0390   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6613   -1.2519    1.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2631    0.5539   -2.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6115   -0.8951   -1.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2044    0.7393   -1.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  6
 32 11  1  0
 32 14  1  0
 29 16  1  0
 27 19  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  6
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  1
  6 43  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
  9 49  1  0
 10 50  1  0
 11 51  1  1
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 15 56  1  0
 15 57  1  0
 15 58  1  0
 17 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  6
 21 63  1  0
 21 64  1  0
 21 65  1  0
 22 66  1  0
 22 67  1  0
 22 68  1  0
 25 69  1  0
 25 70  1  0
 26 71  1  0
 26 72  1  0
 28 73  1  0
 28 74  1  0
 28 75  1  0
 30 76  1  0
 31 77  1  0
 31 78  1  0
 33 79  1  0
 33 80  1  0
 33 81  1  0
M  END


  Mrv1652309052216182D          

 33 36  0  0  1  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5916   -4.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660   -4.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -3.7114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351   -0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   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  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 11  2  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 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
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 11 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0214889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC[C@H](O)C(C)(C)O)[C@H]1CC[C@@]2(C)C3=CCC4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-19(9-12-25(32)27(4,5)33)20-13-17-30(8)22-10-11-23-26(2,3)24(31)15-16-28(23,6)21(22)14-18-29(20,30)7/h10,14,19-20,23,25,32-33H,9,11-13,15-18H2,1-8H3/t19-,20-,23?,25+,28-,29-,30+/m1/s1

> <INCHI_KEY>
AAJIHHYEPHRIET-JNAHJFNHSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.90457454705527

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,11R,14R,15R)-14-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-5-one

> <JCHEM_LOGP>
5.767839759333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.325091178549847

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.849642066659626

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0890278698803355

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
137.1866

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,11R,14R,15R)-14-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.206  -5.231   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.104  -9.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.057  -8.818   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.375  -6.928   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    2   12   32                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   32                                             
CONECT   15   14                                                            
CONECT   16   14   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   16   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   11   14   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7110 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

(2S,11R,14R,15R)-14-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-5-one

Traditional Name

(2S,11R,14R,15R)-14-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-5-one

CAS Registry Number

Not Available

SMILES

C[C@H](CC[C@H](O)C(C)(C)O)[C@H]1CC[C@@]2(C)C3=CCC4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C

InChI Identifier

InChI=1S/C30H48O3/c1-19(9-12-25(32)27(4,5)33)20-13-17-30(8)22-10-11-23-26(2,3)24(31)15-16-28(23,6)21(22)14-18-29(20,30)7/h10,14,19-20,23,25,32-33H,9,11-13,15-18H2,1-8H3/t19-,20-,23?,25+,28-,29-,30+/m1/s1

InChI Key

AAJIHHYEPHRIET-JNAHJFNHSA-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

Not Available

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
25-hydroxysteroid
24-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
Cholane-skeleton
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
14-alpha-methylsteroid
Oxosteroid
3-oxosteroid
3-oxo-delta-7-steroid
Steroid
Delta-7-steroid
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Ketone
1,2-diol
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
logP	5.77	ChemAxon
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.19 m³·mol⁻¹	ChemAxon
Polarizability	55.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00023866

Chemspider ID

8429051

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10253565

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu M, Shen CE, Lin QF, Zhong JY, Zhou YF, Liu BC, Xu JH, Zhang ZQ, Li P: Sterols and triterpenoids from Ganoderma lucidum and their reversal activities of tumor multidrug resistance. Nat Prod Res. 2021 Mar 10:1-4. doi: 10.1080/14786419.2021.1878514. [PubMed:33691545 ]
Li B, Lee DS, Kang Y, Yao NQ, An RB, Kim YC: Corrigendum to "Protective effect of ganodermanondiol isolated from the Lingzhi mushroom against tert-butyl hydroperoxide-induced hepatotoxicity through Nrf2-mediated antioxidant enzymes" [Food Chem. Toxicol. 53 (2013) 317-324]. Food Chem Toxicol. 2021 Mar;149:111939. doi: 10.1016/j.fct.2020.111939. Epub 2020 Dec 25. [PubMed:33358767 ]
Li P, Liu L, Huang S, Zhang Y, Xu J, Zhang Z: Anti-cancer Effects of a Neutral Triterpene Fraction from Ganoderma lucidum and its Active Constituents on SW620 Human Colorectal Cancer Cells. Anticancer Agents Med Chem. 2020;20(2):237-244. doi: 10.2174/1871520619666191015102442. [PubMed:31749435 ]
Zheng DS, Chen LS: Triterpenoids from Ganoderma lucidum inhibit the activation of EBV antigens as telomerase inhibitors. Exp Ther Med. 2017 Oct;14(4):3273-3278. doi: 10.3892/etm.2017.4883. Epub 2017 Aug 3. [PubMed:28912878 ]
Dai J, Miller MA, Everetts NJ, Wang X, Li P, Li Y, Xu JH, Yao G: Elimination of quiescent slow-cycling cells via reducing quiescence depth by natural compounds purified from Ganoderma lucidum. Oncotarget. 2017 Feb 21;8(8):13770-13781. doi: 10.18632/oncotarget.14634. [PubMed:28099150 ]
Kim JW, Kim HI, Kim JH, Kwon OC, Son ES, Lee CS, Park YJ: Effects of Ganodermanondiol, a New Melanogenesis Inhibitor from the Medicinal Mushroom Ganoderma lucidum. Int J Mol Sci. 2016 Oct 27;17(11). pii: ijms17111798. doi: 10.3390/ijms17111798. [PubMed:27801787 ]
Mendoza G, Suarez-Medellin J, Espinoza C, Ramos-Ligonio A, Fernandez JJ, Norte M, Trigos A: Isolation and Characterization of Bioactive Metabolites from Fruiting Bodies and Mycelial Culture of Ganoderma oerstedii (Higher Basidiomycetes) from Mexico. Int J Med Mushrooms. 2015;17(6):501-9. doi: 10.1615/intjmedmushrooms.v17.i6.10. [PubMed:26349508 ]
Li B, Lee DS, Kang Y, Yao NQ, An RB, Kim YC: Protective effect of ganodermanondiol isolated from the Lingzhi mushroom against tert-butyl hydroperoxide-induced hepatotoxicity through Nrf2-mediated antioxidant enzymes. Food Chem Toxicol. 2013 Mar;53:317-24. doi: 10.1016/j.fct.2012.12.016. Epub 2012 Dec 21. [PubMed:23266269 ]
Li P, Deng YP, Wei XX, Xu JH: Triterpenoids from Ganoderma lucidum and their cytotoxic activities. Nat Prod Res. 2013;27(1):17-22. doi: 10.1080/14786419.2011.652961. Epub 2012 Jan 20. [PubMed:22263904 ]
Bae SY, Yim JH, Lee HK, Pyo S: RETRACTED: Activation of murine peritoneal macrophages by sulfated exopolysaccharide from marine microalga Gyrodinium impudicum (strain KG03): involvement of the NF-kappa B and JNK pathway. Int Immunopharmacol. 2006 Mar;6(3):473-84. doi: 10.1016/j.intimp.2005.09.009. Epub 2005 Oct 17. [PubMed:16428083 ]
LOTUS database [Link]

Showing NP-Card for (1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one (NP0214889)

MOL for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)

3D MOL for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)

3D SDF for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)

3D-SDF for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)

PDB for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)

3D PDB for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)

SMILES for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)

INCHI for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)

Structure for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)

3D Structure for NP0214889 ((1r,3ar,9as,11ar)-1-[(2r,5s)-5,6-dihydroxy-6-methylheptan-2-yl]-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-7-one)