NP-MRD: Showing NP-Card for (3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one (NP0225683)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 04:28:36 UTC

Updated at

2022-09-06 04:28:36 UTC

NP-MRD ID

NP0225683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one

Description

CHEMBL3632950 belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. (3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one is found in Alisma plantago-aquatica. Based on a literature review very few articles have been published on CHEMBL3632950.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062206282D          

 34 37  0  0  1  0            999 V2000
    0.1539   -3.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492   -0.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0872   -0.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9830   -0.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.3186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3066    0.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -0.4315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7456   -1.1957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411    0.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4474    0.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5924   -0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2897    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1814   -3.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  1  0  0  0
  2 34  1  0  0  0  0
  7 34  1  0  0  0  0
M  END

     RDKit          3D

 80 83  0  0  0  0  0  0  0  0999 V2000
   -6.8042   -0.5176    1.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1534   -0.3549    0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8176    0.1129   -0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1537    0.2635   -1.8971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8785    0.4693   -2.9035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6537    0.1758   -2.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0758    0.3321   -0.6117 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6160    1.6699   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6029    0.3568   -0.5773 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8965   -0.3549   -1.6985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3243    0.0888   -2.9735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4297   -0.0600   -1.6620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1717    0.1102   -0.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447   -0.0219    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6282   -0.3991   -0.8383 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9986   -1.8122   -0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249    0.6663   -0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    0.9798    0.3126 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2648    2.1195   -0.1017 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4883    0.0192    0.8234 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0190   -1.1858    1.2867 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7378   -0.1711    0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6959   -1.1350   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4283    1.0852   -0.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6638   -0.7578    0.9760 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5181    0.2851    1.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505   -0.1080    1.9963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6668    0.4692    0.8564 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7701    1.9559    1.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820   -0.2071    0.6841 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7033   -1.7036    0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160   -0.0408    1.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -0.9130    1.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7317   -0.7306    0.2384 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6465   -1.5475    2.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5337    0.2745    2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9268   -0.4288    1.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8677    0.3875   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3931    1.0759   -2.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4313   -0.7811   -2.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3809    2.1064   -0.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8193    2.4372   -0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0952    1.5827    0.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    1.4381   -0.6656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0611   -1.4453   -1.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9548    1.0160   -3.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0823   -0.9206   -2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1854    0.8273   -2.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1769   -0.3550   -1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2987   -2.4382   -1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7701   -2.2284    0.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865   -2.0634   -1.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0661    1.6154   -1.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    0.5225   -1.7211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518    1.3964    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6382    2.8984   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8949    0.5017    1.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5882   -1.9534    1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2692   -0.7396   -2.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7870   -1.3225   -1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3373   -2.1464   -0.8082 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5211    0.8542   -0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0372    1.4204   -1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4963    1.8762    0.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6099   -1.7269    0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143    1.3789    1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2855   -0.2962    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1017   -1.1930    2.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341    0.4053    2.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1804    2.2878    1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8222    2.2844    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3553    2.5302    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -2.0954    1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4940   -2.2690    0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7584   -1.8950    0.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1417    0.9852    2.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4000   -0.5036    2.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7962   -0.7725    2.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638   -1.9818    1.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7658   -1.6851   -0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 10  1  0
 10 11  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  1
  7  6  1  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 34  1  0
 34 33  1  0
 33 32  1  0
 32 30  1  0
 30 31  1  6
 30 28  1  0
 28 29  1  1
 28 27  1  0
 27 26  1  0
 26 14  1  0
 28 13  1  0
 30  9  1  0
 34  7  1  0
 16 50  1  0
 16 51  1  0
 16 52  1  0
 15 49  1  6
 17 53  1  0
 17 54  1  0
 18 55  1  1
 19 56  1  0
 20 57  1  1
 21 58  1  0
 23 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 12 47  1  0
 12 48  1  0
 10 45  1  6
 11 46  1  0
  9 44  1  6
  8 41  1  0
  8 42  1  0
  8 43  1  0
  6 39  1  0
  6 40  1  0
  3 38  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 34 80  1  6
 33 78  1  0
 33 79  1  0
 32 76  1  0
 32 77  1  0
 31 73  1  0
 31 74  1  0
 31 75  1  0
 29 70  1  0
 29 71  1  0
 29 72  1  0
 27 68  1  0
 27 69  1  0
 26 66  1  0
 26 67  1  0
M  END


  Mrv1652309062206282D          

 34 37  0  0  1  0            999 V2000
    0.1539   -3.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492   -0.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0872   -0.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9830   -0.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -0.3186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3066    0.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -0.4315    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7456   -1.1957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411    0.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4474    0.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5924   -0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2897    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850   -3.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1814   -3.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  9 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  1  0  0  0
  2 34  1  0  0  0  0
  7 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](C[C@H](O)[C@@H](O)C(C)(C)O)C1=C2C[C@H](O)[C@H]3[C@@]4(C)CC(=O)C=C(C)[C@@H]4CC[C@]3(C)[C@@]2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O5/c1-16(13-23(32)25(33)26(3,4)34)19-8-10-28(6)21(19)14-22(31)24-27(5)15-18(30)12-17(2)20(27)9-11-29(24,28)7/h12,16,20,22-25,31-34H,8-11,13-15H2,1-7H3/t16-,20+,22+,23+,24+,25-,27+,28+,29+/m1/s1

> <INCHI_KEY>
DCYOPZMJKBYLCO-QJDZRUNDSA-N

> <FORMULA>
C29H46O5

> <MOLECULAR_WEIGHT>
474.682

> <EXACT_MASS>
474.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.146335564539726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,7S,10S,11R,17S)-17-hydroxy-2,6,10,11-tetramethyl-14-[(2R,4S,5R)-4,5,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,14-dien-4-one

> <JCHEM_LOGP>
2.8882771929999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.67992005178527

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.026905346420481

> <JCHEM_PKA_STRONGEST_BASIC>
-0.290837093930696

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
135.32380000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,7S,10S,11R,17S)-17-hydroxy-2,6,10,11-tetramethyl-14-[(2R,4S,5R)-4,5,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,14-dien-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.287  -6.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.652  -1.495   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.896  -0.682   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.302  -0.173   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.407  -1.811   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.353  -0.595   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.772   0.832   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.878  -0.805   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.458  -2.232   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.823   0.410   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.769   1.626   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.039  -0.535   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.608   1.356   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.505  -5.709   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.939  -5.912   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   34                                             
CONECT    8    7                                                            
CONECT    9    7   10   30                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   14   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   13   29   30                                             
CONECT   29   28                                                            
CONECT   30   28    9   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₆O₅

Average Mass

474.6820 Da

Monoisotopic Mass

474.33452 Da

IUPAC Name

(1S,2S,7S,10S,11R,17S)-17-hydroxy-2,6,10,11-tetramethyl-14-[(2R,4S,5R)-4,5,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,14-dien-4-one

Traditional Name

(1S,2S,7S,10S,11R,17S)-17-hydroxy-2,6,10,11-tetramethyl-14-[(2R,4S,5R)-4,5,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-5,14-dien-4-one

CAS Registry Number

Not Available

SMILES

C[C@H](C[C@H](O)[C@@H](O)C(C)(C)O)C1=C2C[C@H](O)[C@H]3[C@@]4(C)CC(=O)C=C(C)[C@@H]4CC[C@]3(C)[C@@]2(C)CC1

InChI Identifier

InChI=1S/C29H46O5/c1-16(13-23(32)25(33)26(3,4)34)19-8-10-28(6)21(19)14-22(31)24-27(5)15-18(30)12-17(2)20(27)9-11-29(24,28)7/h12,16,20,22-25,31-34H,8-11,13-15H2,1-7H3/t16-,20+,22+,23+,24+,25-,27+,28+,29+/m1/s1

InChI Key

DCYOPZMJKBYLCO-QJDZRUNDSA-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
Alisma plantago-aquatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

25-hydroxysteroid
24-hydroxysteroid
23-hydroxysteroid
Hydroxysteroid
Oxosteroid
2-oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Polyol
Carbonyl group
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	2.89	ChemAxon
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	-0.29	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.32 m³·mol⁻¹	ChemAxon
Polarizability	55.15 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

58914093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122194870

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one (NP0225683)

MOL for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)

3D MOL for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)

3D SDF for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)

3D-SDF for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)

PDB for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)

3D PDB for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)

SMILES for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)

INCHI for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)

Structure for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)

3D Structure for NP0225683 ((3ar,3bs,5as,9as,9bs,10s)-10-hydroxy-3a,3b,6,9a-tetramethyl-1-[(2r,4s,5r)-4,5,6-trihydroxy-6-methylheptan-2-yl]-2h,3h,4h,5h,5ah,9h,9bh,10h,11h-cyclopenta[a]phenanthren-8-one)