NP-MRD: Showing NP-Card for (1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate (NP0178025)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 15:56:50 UTC

Updated at

2022-09-03 15:56:50 UTC

NP-MRD ID

NP0178025

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate

Description

(1R,2R,5R,7S,10R,11R,14R,15R,16R)-5,14-dihydroxy-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-16-yl acetate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate is found in Betula maximowicziana. Based on a literature review very few articles have been published on (1R,2R,5R,7S,10R,11R,14R,15R,16R)-5,14-dihydroxy-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-16-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032217562D          

 38 42  0  0  1  0            999 V2000
    3.3449   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5328   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525    0.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -1.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3100   -4.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9702   -4.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9844   -1.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1127   -2.4737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0532   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420   -1.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3408   -1.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -1.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7846   -1.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771   -1.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139   -2.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553   -0.7028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118   -2.5005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 32 37  1  0  0  0  0
 28 37  1  1  0  0  0
 38 26  1  1  0  0  0
  5 38  1  0  0  0  0
 22 38  1  0  0  0  0
M  END

     RDKit          3D

 92 96  0  0  0  0  0  0  0  0999 V2000
    3.0157   -3.6117    1.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191   -2.5500    1.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6476   -2.3619    2.9594 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5036   -1.7822    0.7768 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510   -0.7681    1.0256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6943   -1.1731    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7352   -0.1342    0.1558 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9616   -0.5543   -0.5816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7479   -1.2103   -1.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -1.6154    0.3034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9694   -2.0520   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7588   -1.0812   -0.9576 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1183   -1.1925   -0.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3450    0.3178   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9233    0.7053    0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1048    1.2082   -1.6837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968    0.6056   -0.7827 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6017    1.7698    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2513    2.2924   -0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922    1.2338   -0.2690 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6321    1.2055   -1.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1535    1.5353    0.7935 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6941    1.5376    2.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327    2.8583    0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8678    2.5973    1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2232    1.1451    1.0281 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5044    0.5349    2.2723 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4264    1.0057    0.1791 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6797    1.6061    0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633    1.5290   -1.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5553    0.8159   -1.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8441   -0.3049   -0.9110 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0815   -1.5696   -1.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5141   -2.7190   -0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2116   -1.2778   -2.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9878   -1.9307   -2.4586 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7600   -0.3533   -0.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9689    0.5719    0.5238 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5909   -4.5499    1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1239   -3.7714    0.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9708   -3.3739    1.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4118   -0.8159    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1243   -2.0124    0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3663   -1.6471   -0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0971    0.0701    1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9476   -0.4885   -2.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.6582   -2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056   -2.0324   -2.0856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9587   -2.5154    0.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5673   -1.3048    1.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204   -3.0059   -0.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5545   -2.3704    0.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833   -1.2913   -2.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2028   -1.6616    0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3695    0.2687    1.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0154    1.8217    0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9726    0.3337    0.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8312    0.8581   -2.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8357    2.2593   -1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2050    1.0893   -1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7039    1.0009   -1.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3490    2.5678   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8002    1.5309    1.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3725    2.8082   -1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9618    3.1599    0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4398    1.5526   -2.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3187    0.2308   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1996    1.9126   -1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8586    0.6251    2.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6890    2.0731    2.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0876    2.1973    2.8556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0395    3.6500    1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5706    3.2628   -0.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    3.2957    0.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7980    2.7888    2.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561    0.3860    2.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4047    1.8598    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4870    2.5514    1.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2036    0.8556    1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5024    1.2863   -1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188    2.6258   -1.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084    1.5092   -1.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916    0.4453   -2.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7390   -0.1303   -0.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5874   -3.0056   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3735   -2.4993    0.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9362   -3.6168   -1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8155   -0.8388   -3.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7922   -2.1755   -2.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8814   -0.4812   -2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9374   -2.9218   -2.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930    0.4578   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  1
 26 38  1  0
 26 28  1  0
 28 29  1  1
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 37  1  0
 32 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
 38  5  1  0
 37 28  1  0
 20  7  1  0
 38 22  1  0
 17  8  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  5 42  1  1
  6 43  1  0
  6 44  1  0
  7 45  1  1
  9 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  0
 10 50  1  0
 11 51  1  0
 11 52  1  0
 12 53  1  6
 13 54  1  0
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 16 59  1  0
 16 60  1  0
 17 61  1  6
 18 62  1  0
 18 63  1  0
 19 64  1  0
 19 65  1  0
 21 66  1  0
 21 67  1  0
 21 68  1  0
 23 69  1  0
 23 70  1  0
 23 71  1  0
 24 72  1  0
 24 73  1  0
 25 74  1  0
 25 75  1  0
 27 76  1  0
 38 92  1  6
 29 77  1  0
 29 78  1  0
 29 79  1  0
 30 80  1  0
 30 81  1  0
 31 82  1  0
 31 83  1  0
 32 84  1  1
 34 85  1  0
 34 86  1  0
 34 87  1  0
 35 88  1  0
 35 89  1  0
 35 90  1  0
 36 91  1  0
M  END


  Mrv1652309032217562D          

 38 42  0  0  1  0            999 V2000
    3.3449   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5328   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525    0.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -1.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812   -1.9614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0934   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3737   -2.8825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1858   -3.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9055   -2.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7176   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5297   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100   -3.3182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6221   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942   -4.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -3.8037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9343   -4.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1221   -4.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418   -3.5132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3100   -4.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297   -3.3680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9702   -4.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249   -2.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9844   -1.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1127   -2.4737    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0532   -3.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420   -1.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3408   -1.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -1.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7846   -1.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771   -1.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139   -2.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5553   -0.7028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118   -2.5005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 32 37  1  0  0  0  0
 28 37  1  1  0  0  0
 38 26  1  1  0  0  0
  5 38  1  0  0  0  0
 22 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@@H](O)C(C)(C)[C@H]3CC[C@@]2(C)[C@]2(C)CC[C@@](O)([C@@H]12)[C@]1(C)CC[C@@H](O1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C32H54O6/c1-19(33)37-20-18-22-28(6)13-11-23(34)26(2,3)21(28)10-14-29(22,7)30(8)16-17-32(36,25(20)30)31(9)15-12-24(38-31)27(4,5)35/h20-25,34-36H,10-18H2,1-9H3/t20-,21-,22-,23-,24-,25+,28+,29-,30-,31+,32-/m1/s1

> <INCHI_KEY>
VFLCKJPVDPYIKP-NHIJABKCSA-N

> <FORMULA>
C32H54O6

> <MOLECULAR_WEIGHT>
534.778

> <EXACT_MASS>
534.392039459

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
61.795032421583194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R,7S,10R,11R,14R,15R,16R)-5,14-dihydroxy-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-16-yl acetate

> <JCHEM_LOGP>
3.9545386690000015

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.374980875308943

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.358093386259377

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8349451352270537

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
146.5772

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,7S,10R,11R,14R,15R,16R)-5,14-dihydroxy-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-16-yl acetate

> <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       6.244  -1.307   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.728  -1.036   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.205   0.413   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.735  -2.213   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.184  -8.144   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.322  -8.817   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.312  -7.735   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.678  -7.823   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.838  -3.353   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.210  -4.618   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.099  -6.154   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.638  -3.138   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.636  -2.274   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.852  -3.219   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.331  -2.791   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.811  -2.363   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.759  -4.270   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.903  -1.312   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.329  -4.668   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   38                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   10   17                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    8   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    7   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   24   38                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   38                                             
CONECT   27   26                                                            
CONECT   28   26   29   30   37                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   32   28                                                       
CONECT   38   26    5   22                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,5R,7S,10R,11R,14R,15R,16R)-5,14-Dihydroxy-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0,.0,]heptadecan-16-yl acetic acid	Generator

Chemical Formula

C₃₂H₅₄O₆

Average Mass

534.7780 Da

Monoisotopic Mass

534.39204 Da

IUPAC Name

(1R,2R,5R,7S,10R,11R,14R,15R,16R)-5,14-dihydroxy-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-16-yl acetate

Traditional Name

(1R,2R,5R,7S,10R,11R,14R,15R,16R)-5,14-dihydroxy-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-16-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@@H](O)C(C)(C)[C@H]3CC[C@@]2(C)[C@]2(C)CC[C@@](O)([C@@H]12)[C@]1(C)CC[C@@H](O1)C(C)(C)O

InChI Identifier

InChI=1S/C32H54O6/c1-19(33)37-20-18-22-28(6)13-11-23(34)26(2,3)21(28)10-14-29(22,7)30(8)16-17-32(36,25(20)30)31(9)15-12-24(38-31)27(4,5)35/h20-25,34-36H,10-18H2,1-9H3/t20-,21-,22-,23-,24-,25+,28+,29-,30-,31+,32-/m1/s1

InChI Key

VFLCKJPVDPYIKP-NHIJABKCSA-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
Betula maximowicziana	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid ester
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
17-hydroxysteroid
14-alpha-methylsteroid
Steroid
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Hydrocarbon derivative
Alcohol
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
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	3.95	ChemAxon
pKa (Strongest Acidic)	13.36	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	146.58 m³·mol⁻¹	ChemAxon
Polarizability	61.8 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

162897551

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate (NP0178025)

MOL for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D MOL for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D SDF for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D-SDF for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

PDB for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D PDB for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

SMILES for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

INCHI for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

Structure for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)

3D Structure for NP0178025 ((1r,3ar,3br,5as,7r,9ar,9br,11r,11ar)-1,7-dihydroxy-1-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydrocyclopenta[a]phenanthren-11-yl acetate)