NP-MRD: Showing NP-Card for (1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one (NP0172040)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 08:49:18 UTC

Updated at

2022-09-03 08:49:18 UTC

NP-MRD ID

NP0172040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one

Description

Inokosterone belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group. (1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one is found in Polypodium virginianum and Polypodium vulgare. (1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one was first documented in 2020 (PMID: 32574970). Based on a literature review a small amount of articles have been published on Inokosterone (PMID: 35204097) (PMID: 34432202) (PMID: 31838797) (PMID: 35853303).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032210492D          

 34 37  0  0  1  0            999 V2000
   -0.3962   -3.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 C   0  0  2  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
   -1.4089   -4.7563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.3306    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
    2.0556   -3.7922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2132   -3.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -2.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  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 O   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
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  2  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
    7.9534   -1.7902    0.0000 C   0  0  2  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  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   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  2  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  1  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  1  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  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  6  0  0  0
 12  9  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 17  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 12 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END

     RDKit          3D

 78 81  0  0  0  0  0  0  0  0999 V2000
   -7.3812   -0.9775   -0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2952    0.1638    0.3285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.4674    1.0864    0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3913    1.5455   -1.2346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0004    0.9613    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8686    0.0003    0.3893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    0.7025    0.2303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5119    1.1593   -1.0795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.3586    0.4742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5804   -0.7482    1.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7686   -1.3994   -0.3873 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171    0.2357    0.1454 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0770    0.6835   -1.2823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3912    0.5845   -1.7316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -0.6265   -0.9867 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3468   -1.7277   -1.7561 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -0.8175   -0.8792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234   -1.3791   -1.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609   -1.5525   -1.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9150   -2.5829   -2.1994 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0577   -0.4342   -1.1087 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5266   -0.6105   -0.9020 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0772    0.7719   -0.6115 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2046    0.7200    0.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0759    1.7795   -0.1987 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7453    2.6376   -1.2785 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8468    1.3227    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4535   -0.1068    0.2370 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2329   -0.9245    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366   -0.4240    0.3259 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1917    0.5866    1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9316   -0.0903    1.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0964   -0.6108    0.3481 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1663   -2.0725    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0056   -1.9418   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9245   -0.7835   -1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4721   -1.1852   -0.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3313   -0.1872    1.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4118    1.9911    0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4163    0.5612    0.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8214    0.8239   -1.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9932    1.8431    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9466    1.3183   -0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9646   -0.5393    1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9693   -0.7974   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4433    1.5025    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7135    2.1192   -1.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9222   -1.7992    1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3674   -0.1549    2.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701   -0.5296    2.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1374   -1.1206   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070    1.1682    0.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119    1.7614   -1.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6217    0.0213   -1.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4235    0.3799   -2.8420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433    1.4964   -1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3546   -1.4726   -2.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3769   -1.7144   -2.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9724    0.4878   -1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8306   -1.2896   -0.1100 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9393   -1.0399   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5114    1.1182   -1.5999 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8307    1.4482    0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6050    2.4797    0.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8738    3.0555   -1.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0267    2.0294    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267    1.4449    1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1480   -0.4364    1.6115 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2933   -1.9829    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5465   -0.8941    2.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -1.3419    1.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0106    1.5181    0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7563    0.8218    2.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2076   -0.8850    2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621    0.6640    2.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4180   -2.3259    1.6514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483   -2.5620    0.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7913   -2.5682   -0.1517 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  1
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  1
 33 12  1  0
 33 15  1  0
 30 17  1  0
 28 21  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  3 39  1  0
  3 40  1  0
  4 41  1  0
  5 42  1  0
  5 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  1
  8 47  1  0
 10 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 12 52  1  1
 13 53  1  0
 13 54  1  0
 14 55  1  0
 14 56  1  0
 16 57  1  0
 18 58  1  0
 21 59  1  6
 22 60  1  0
 22 61  1  0
 23 62  1  6
 24 63  1  0
 25 64  1  1
 26 65  1  0
 27 66  1  0
 27 67  1  0
 29 68  1  0
 29 69  1  0
 29 70  1  0
 30 71  1  1
 31 72  1  0
 31 73  1  0
 32 74  1  0
 32 75  1  0
 34 76  1  0
 34 77  1  0
 34 78  1  0
M  END


  Mrv1652309032210492D          

 34 37  0  0  1  0            999 V2000
   -0.3962   -3.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 C   0  0  2  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
   -1.4089   -4.7563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.3306    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
    2.0556   -3.7922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2132   -3.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -2.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  2  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 O   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
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  2  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
    7.9534   -1.7902    0.0000 C   0  0  2  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  1  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   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  2  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  1  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  1  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  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  6  0  0  0
 12  9  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 17  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 12 33  1  0  0  0  0
 15 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0172040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CO)CC[C@H](O)[C@@](C)(O)[C@@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@H](O)[C@@H](O)C[C@@]4(C)[C@H]3CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O7/c1-15(14-28)5-6-23(32)26(4,33)22-8-10-27(34)17-11-19(29)18-12-20(30)21(31)13-24(18,2)16(17)7-9-25(22,27)3/h11,15-16,18,20-23,28,30-34H,5-10,12-14H2,1-4H3/t15-,16-,18-,20-,21-,22+,23-,24-,25-,26-,27+/m0/s1

> <INCHI_KEY>
JQNVCUBPURTQPQ-LWTFCORNSA-N

> <FORMULA>
C27H44O7

> <MOLECULAR_WEIGHT>
480.642

> <EXACT_MASS>
480.308703757

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.68517564441252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4S,5S,7R,11S,14R,15S)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2S,3S,6S)-2,3,7-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
0.7222520029999986

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.743284513630485

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.261540005037546

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7410503055976183

> <JCHEM_POLAR_SURFACE_AREA>
138.45000000000002

> <JCHEM_REFRACTIVITY>
128.89139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,5S,7R,11S,14R,15S)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2S,3S,6S)-2,3,7-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.740  -6.447   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.104  -9.089   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.630  -8.878   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.366  -8.084   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.998  -6.808   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.566  -4.918   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.854  -2.164   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  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   33                                             
CONECT   16   15                                                            
CONECT   17   15   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   21   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   17   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   12   15   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₇

Average Mass

480.6420 Da

Monoisotopic Mass

480.30870 Da

IUPAC Name

(1R,2S,4S,5S,7R,11S,14R,15S)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2S,3S,6S)-2,3,7-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1R,2S,4S,5S,7R,11S,14R,15S)-4,5,11-trihydroxy-2,15-dimethyl-14-[(2S,3S,6S)-2,3,7-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

C[C@H](CO)CC[C@H](O)[C@@](C)(O)[C@@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@H](O)[C@@H](O)C[C@@]4(C)[C@H]3CC[C@@]12C

InChI Identifier

InChI=1S/C27H44O7/c1-15(14-28)5-6-23(32)26(4,33)22-8-10-27(34)17-11-19(29)18-12-20(30)21(31)13-24(18,2)16(17)7-9-25(22,27)3/h11,15-16,18,20-23,28,30-34H,5-10,12-14H2,1-4H3/t15-,16-,18-,20-,21-,22+,23-,24-,25-,26-,27+/m0/s1

InChI Key

JQNVCUBPURTQPQ-LWTFCORNSA-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
Polypodium virginianum	LOTUS Database	35616633
Polypodium vulgare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Hydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Hexahydroxy bile acid, alcohol, or derivatives
26-hydroxysteroid
Ecdysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
6-oxosteroid
3-alpha-hydroxysteroid
Oxosteroid
Hydroxysteroid
14-hydroxysteroid
2-hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Fatty alcohol
Cyclohexenone
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	1.25	ALOGPS
logP	0.72	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	128.89 m³·mol⁻¹	ChemAxon
Polarizability	53.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's 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

C00003655

Chemspider ID

34946050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91900472

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Y, Liu Q, Chen D, Matsuura A, Xiang L, Qi J: Inokosterone from Gentiana rigescens Franch Extends the Longevity of Yeast and Mammalian Cells via Antioxidative Stress and Mitophagy Induction. Antioxidants (Basel). 2022 Jan 23;11(2). pii: antiox11020214. doi: 10.3390/antiox11020214. [PubMed:35204097 ]
Mo JH, Xie HK, Zhou YM, Ng SB, Li SX, Wang L: Inokosterone Is A Potential Drug Target of Estrogen Receptor 1 in Rheumatoid Arthritis Patients: Analysis from Active Ingredient of Cyathula Officinalis. Chin J Integr Med. 2021 Oct;27(10):767-773. doi: 10.1007/s11655-021-3492-5. Epub 2021 Aug 25. [PubMed:34432202 ]
Wang S, Zeng M, Li B, Kan Y, Zhang B, Zheng X, Feng W: Raw and salt-processed Achyranthes bidentata attenuate LPS-induced acute kidney injury by inhibiting ROS and apoptosis via an estrogen-like pathway. Biomed Pharmacother. 2020 Sep;129:110403. doi: 10.1016/j.biopha.2020.110403. Epub 2020 Jun 20. [PubMed:32574970 ]
Lee CW, Lee DY: Metabolomic Investigation on Fermentation Products of Achyranthes japonica Nakai by Lactobacillus plantarum. J Microbiol Biotechnol. 2020 Mar 28;30(3):378-381. doi: 10.4014/jmb.1910.10057. [PubMed:31838797 ]
Jia W, Wang K, Zhang S, Lu W, Du A, Li J, Ji L, Xu H: Integrating network pharmacology and in vivo experimental validation to reveal the alleviation of mailuoning oral liquid on non-alcoholic fatty liver disease. Phytomedicine. 2022 Sep;104:154326. doi: 10.1016/j.phymed.2022.154326. Epub 2022 Jul 6. [PubMed:35853303 ]
LOTUS database [Link]

Showing NP-Card for (1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one (NP0172040)

MOL for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D MOL for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D SDF for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D-SDF for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

PDB for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D PDB for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

SMILES for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

INCHI for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

Structure for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D Structure for NP0172040 ((1r,3as,5ar,7s,8s,9as,9br,11as)-3a,7,8-trihydroxy-9a,11a-dimethyl-1-[(2s,3s,6s)-2,3,7-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)