NP-MRD: Showing NP-Card for (1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one (NP0270491)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 16:25:53 UTC

Updated at

2022-09-08 16:25:54 UTC

NP-MRD ID

NP0270491

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one

Description

(1R,2R,5S,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3R)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-one belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. (1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one is found in Silene viridiflora. Based on a literature review very few articles have been published on (1R,2R,5S,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3R)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082218252D          

 38 42  0  0  1  0            999 V2000
    3.0381   -5.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649   -4.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822   -4.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2421   -4.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9312   -3.6726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1302   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586   -4.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -3.8722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4401   -4.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0447   -3.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434   -3.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150   -4.2693    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
    1.9671   -2.5692    0.0000 C   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 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
    6.8898   -0.5288    0.0000 O   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
    7.9534   -1.7902    0.0000 C   0  0  1  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  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  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
    3.2626   -3.5763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 20  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 15 36  1  0  0  0  0
 18 36  1  0  0  0  0
 36 37  1  1  0  0  0
 13 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END

     RDKit          3D

 86 90  0  0  0  0  0  0  0  0999 V2000
   -2.8248   -0.1762   -3.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6433    0.1798   -2.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0174    0.5540   -2.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8165   -0.8800   -1.1978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8346   -0.7047   -0.2361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1246   -1.3706    1.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2634   -1.1654    1.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650   -1.4055    1.4568 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1896   -0.5591    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8735   -2.7751    1.1605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5890   -1.1167    2.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4558    0.2117    3.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925    0.7226   -0.2988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7349    1.5223    0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9863    0.8856   -0.7748 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7225    2.3565   -1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6842    2.6212   -0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2408    1.2672   -0.6152 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2168    0.8955   -1.9594 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5469    0.9937   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2830    1.8191    0.6356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5914    1.4482    1.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3558    2.3318    1.5847 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9669   -0.0063    1.1574 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4182   -0.6468    2.2738 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4514   -0.0895    1.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0646    0.4904    0.0109 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4428    0.6404    0.1161 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6834   -0.4631   -1.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2088   -0.3533   -1.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4105   -0.6854   -0.0669 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5647   -2.1848    0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096   -0.3869   -0.3541 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9994   -1.3051    0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5820   -1.0020   -0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1366    0.4093    0.0555 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1483    0.7388    1.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1689    1.2382   -1.3367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2616    0.6930   -3.6830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905   -1.0882   -3.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4852   -0.4726   -4.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5196    1.3159   -1.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8763    1.0448   -3.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6587   -0.3224   -2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9690   -1.3439   -0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2044   -2.5076    0.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1487   -1.4962    1.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2907   -0.1567    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1104   -1.8437    2.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2442   -0.1685    0.6063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3552   -1.0922   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6237    0.3810    0.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8478   -2.8960    1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6215   -1.2526    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3337   -1.7604    3.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9625    0.3266    3.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8225    1.7117    1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879    2.5304    0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4091    1.0507    1.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9133    0.3575   -1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4720    3.0511   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961    2.5369   -2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6757    3.0850    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2479    3.3084   -1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6543    1.5442   -2.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8601    2.8213    0.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896   -1.4469    2.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8180   -1.1375    1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7560    0.4837    2.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5613    1.4514   -0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5887    1.5523    0.5124 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1773   -0.0729   -2.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0561   -1.4811   -0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8449   -1.0241   -2.1190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    0.6813   -1.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527   -2.3894    0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2233   -2.6807   -0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9982   -2.5325    1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8503   -0.5472   -1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1235   -1.3654    1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2211   -2.3252   -0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685   -1.2903   -1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0266   -1.6753    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3039   -0.0611    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1447    1.7574    1.7819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434    0.6960    1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  6
  8 11  1  0
 11 12  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 38  1  0
 38 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  1
 13  5  1  0
 36 15  1  0
 36 18  1  0
 33 20  1  0
 31 24  1  0
  9 50  1  0
  9 51  1  0
  9 52  1  0
 10 53  1  0
 11 54  1  0
 11 55  1  0
 12 56  1  0
  7 48  1  0
  7 49  1  0
  6 46  1  0
  6 47  1  0
  5 45  1  6
  1 39  1  0
  1 40  1  0
  1 41  1  0
  3 42  1  0
  3 43  1  0
  3 44  1  0
 14 57  1  0
 14 58  1  0
 14 59  1  0
 15 60  1  6
 16 61  1  0
 16 62  1  0
 17 63  1  0
 17 64  1  0
 19 65  1  0
 21 66  1  0
 25 67  1  0
 26 68  1  0
 26 69  1  0
 27 70  1  6
 28 71  1  0
 29 72  1  0
 29 73  1  0
 30 74  1  0
 30 75  1  0
 32 76  1  0
 32 77  1  0
 32 78  1  0
 33 79  1  6
 34 80  1  0
 34 81  1  0
 35 82  1  0
 35 83  1  0
 37 84  1  0
 37 85  1  0
 37 86  1  0
M  END


  Mrv1652309082218252D          

 38 42  0  0  1  0            999 V2000
    3.0381   -5.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0649   -4.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8822   -4.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2421   -4.4368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9312   -3.6726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1302   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586   -4.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424   -3.8722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4401   -4.6731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0447   -3.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434   -3.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6150   -4.2693    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
    1.9671   -2.5692    0.0000 C   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 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
    6.8898   -0.5288    0.0000 O   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
    7.9534   -1.7902    0.0000 C   0  0  1  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  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  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
    3.2626   -3.5763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 20  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 15 36  1  0  0  0  0
 18 36  1  0  0  0  0
 36 37  1  1  0  0  0
 13 38  1  0  0  0  0
  2 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270491

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O8/c1-24(2)37-23(10-11-25(3,34)17-31)28(6,38-24)21-9-14-29(35)20-15-22(33)30(36)16-18(32)7-12-26(30,4)19(20)8-13-27(21,29)5/h15,18-19,21,23,31-32,34-36H,7-14,16-17H2,1-6H3/t18-,19-,21-,23+,25+,26+,27+,28+,29+,30+/m0/s1

> <INCHI_KEY>
MENIOZHCBSKIIJ-CVTIUVKFSA-N

> <FORMULA>
C30H48O8

> <MOLECULAR_WEIGHT>
536.706

> <EXACT_MASS>
536.334918506

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.14338264216258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3R)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_LOGP>
1.5200613316666653

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.60885866638338

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.543442568986816

> <JCHEM_PKA_STRONGEST_BASIC>
-2.733934903659212

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
142.62139999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3R)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       5.671  -9.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.721  -8.171   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.247  -8.382   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.185  -8.282   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.605  -6.856   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.110  -6.487   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.043  -7.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.452  -7.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.821  -8.723   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.084  -5.733   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.948  -6.859   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.015  -7.969   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.672  -4.796   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.861  -0.987   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       6.090  -6.676   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   38                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   15   38                                             
CONECT   14   13                                                            
CONECT   15   13   16   36                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   36                                             
CONECT   19   18                                                            
CONECT   20   18   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   31                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   24   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   20   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   15   18   37                                             
CONECT   37   36                                                            
CONECT   38   13    2                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₈

Average Mass

536.7060 Da

Monoisotopic Mass

536.33492 Da

IUPAC Name

(1R,2R,5S,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3R)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1R,2R,5S,7S,11S,14S,15R)-14-[(4R,5R)-5-[(3R)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H48O8/c1-24(2)37-23(10-11-25(3,34)17-31)28(6,38-24)21-9-14-29(35)20-15-22(33)30(36)16-18(32)7-12-26(30,4)19(20)8-13-27(21,29)5/h15,18-19,21,23,31-32,34-36H,7-14,16-17H2,1-6H3/t18-,19-,21-,23+,25+,26+,27+,28+,29+,30+/m0/s1

InChI Key

MENIOZHCBSKIIJ-CVTIUVKFSA-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
Silene viridiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Trihydroxy bile acid, alcohol, or derivatives
3-hydroxy-delta-7-steroid
3-hydroxysteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-beta-hydroxysteroid
6-oxosteroid
Delta-7-steroid
Ketal
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Meta-dioxolane
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Carbonyl group
Primary alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.52	ChemAxon
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	142.62 m³·mol⁻¹	ChemAxon
Polarizability	60.14 Å³	ChemAxon
Number of Rings	5	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162986588

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one (NP0270491)

MOL for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D MOL for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D SDF for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D-SDF for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

PDB for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D PDB for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

SMILES for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

INCHI for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

Structure for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D Structure for NP0270491 ((1s,3as,5as,7s,9ar,9br,11ar)-1-[(4r,5r)-5-[(3r)-3,4-dihydroxy-3-methylbutyl]-2,2,4-trimethyl-1,3-dioxolan-4-yl]-3a,5a,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)