NP-MRD: Showing NP-Card for methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate (NP0256923)

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Record Information

Version

2.0

Created at

2022-09-07 21:54:30 UTC

Updated at

2022-09-07 21:54:30 UTC

NP-MRD ID

NP0256923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate

Description

Methyl 2,5,6-trihydroxy-2-methyl-6-{4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl}heptanoate belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group. methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate is found in Rhaponticum carthamoides. Based on a literature review very few articles have been published on methyl 2,5,6-trihydroxy-2-methyl-6-{4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl}heptanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072223542D          

 38 41  0  0  0  0            999 V2000
   -2.2261   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089   -4.7563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025   -4.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134   -3.3408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1981   -5.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276   -3.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556   -3.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2132   -3.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -2.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  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  0  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  0  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  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  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  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 15 37  1  0  0  0  0
 18 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END

     RDKit          3D

 82 85  0  0  0  0  0  0  0  0999 V2000
    8.7482   -0.7431    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5708   -0.1825   -0.4320 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5924   -0.9149   -1.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7801   -2.1601   -1.2066 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4057   -0.2045   -1.5795 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8715    0.7609   -2.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5671   -1.1335   -2.1920 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6735    0.5500   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2005   -0.3614    0.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4891    0.2393    1.7388 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3046    1.1788    2.3827 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908    0.7463    1.5457 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6038    1.1844    2.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1563    1.8865    0.7541 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2720   -0.2820    0.8697 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2208   -1.5973    1.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0691   -2.2350    1.1087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9390   -1.0797    1.1849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2434   -0.7634    2.4919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2155   -1.0838    0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6023   -2.0532   -0.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8680   -1.9564   -1.0341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2798   -2.9336   -1.7075 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0174   -1.1823   -0.8857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5975   -0.0215   -2.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9028    0.7799   -2.3901 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9290    1.5583   -3.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1581    1.1256   -0.3512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7823    1.5782   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    0.1863    0.1533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3422   -0.1575    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9968    0.1770    0.6817 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1522    1.3957    0.3444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631    1.2681    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1132    0.0353    0.5137 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3217   -0.2110   -0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7492   -1.8458    0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6039   -0.2996   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8283   -0.4337    1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426    1.0989   -3.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6537    0.2295   -3.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3944    1.6178   -2.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471   -1.2442   -3.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8200    1.0330   -0.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147    1.3765   -0.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1471   -0.8238    1.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029   -1.2474    0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4012   -0.5856    2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0432    2.1010    2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0800    0.4296    3.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4959    1.4822    3.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0410    2.1424    2.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928    1.7652   -0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -0.5551   -0.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1763   -1.4523    2.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0082   -2.2974    1.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2979   -3.0558    1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960   -2.7085    0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9974   -1.4386    3.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355   -2.9056   -0.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1147   -1.8349   -1.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7218    0.6244   -2.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6672   -0.7990   -3.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7163    0.0172   -2.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8595    1.5876   -3.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2736    2.6020   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8919    0.8715   -0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9463    2.1777    0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588    2.0768   -0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6177    0.7763    1.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2612   -0.6116    0.9270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7883   -0.8421    1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0540    0.2231    1.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    1.6428   -0.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6254    2.2570    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2701    2.2213    0.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0233    1.1320    2.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1465   -1.1418   -1.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001    0.6242   -1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3625   -0.1605   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  6
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  6
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
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 21 22  1  0
 22 23  2  0
 22 24  1  0
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 24 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  1
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  6
 37 15  1  0
 37 18  1  0
 34 20  1  0
 32 24  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  6 42  1  0
  6 43  1  0
  6 44  1  0
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  8 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
 10 50  1  1
 11 51  1  0
 13 52  1  0
 13 53  1  0
 13 54  1  0
 14 55  1  0
 15 56  1  6
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 16 58  1  0
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 17 60  1  0
 19 61  1  0
 21 62  1  0
 25 63  1  0
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 31 70  1  0
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 33 72  1  0
 33 73  1  0
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 34 75  1  1
 35 76  1  0
 35 77  1  0
 36 78  1  0
 36 79  1  0
 38 80  1  0
 38 81  1  0
 38 82  1  0
M  END


  Mrv1652309072223542D          

 38 41  0  0  0  0            999 V2000
   -2.2261   -4.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4089   -4.7563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025   -4.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2134   -3.3408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1981   -5.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276   -3.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320   -4.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556   -3.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -4.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2132   -3.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -2.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  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  0  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  0  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  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2049   -3.1969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  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  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 20 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 15 37  1  0  0  0  0
 18 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(C)(O)CCC(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4(O)CC(O)C(O)CC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O10/c1-23-9-6-15-16(12-21(32)28(37)14-18(30)17(29)13-24(15,28)2)27(23,36)11-7-19(23)26(4,35)20(31)8-10-25(3,34)22(33)38-5/h12,15,17-20,29-31,34-37H,6-11,13-14H2,1-5H3

> <INCHI_KEY>
HJFRJOLPKVDZSE-UHFFFAOYSA-N

> <FORMULA>
C28H44O10

> <MOLECULAR_WEIGHT>
540.65

> <EXACT_MASS>
540.293447617

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.27706762861442

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2,5,6-trihydroxy-2-methyl-6-{4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl}heptanoate

> <JCHEM_LOGP>
-0.6389090793333342

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.768737622829597

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.23561550851039

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1574315713505037

> <JCHEM_POLAR_SURFACE_AREA>
184.98

> <JCHEM_REFRACTIVITY>
136.48749999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2,5,6-trihydroxy-2-methyl-6-{4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl}heptanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.155  -8.668   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.630  -8.878   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.685  -7.663   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.265  -6.236   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.370  -9.399   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.051  -6.348   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.366  -8.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.998  -6.808   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.566  -4.918   0.000  0.00  0.00           O+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  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   37                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   37                                             
CONECT   19   18                                                            
CONECT   20   18   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   32                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   24   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   20   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   15   18   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2,5,6-trihydroxy-2-methyl-6-{4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0,.0,]heptadec-9-en-14-yl}heptanoic acid	Generator

Chemical Formula

C₂₈H₄₄O₁₀

Average Mass

540.6500 Da

Monoisotopic Mass

540.29345 Da

IUPAC Name

methyl 2,5,6-trihydroxy-2-methyl-6-{4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl}heptanoate

Traditional Name

methyl 2,5,6-trihydroxy-2-methyl-6-{4,5,7,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl}heptanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(C)(O)CCC(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4(O)CC(O)C(O)CC4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H44O10/c1-23-9-6-15-16(12-21(32)28(37)14-18(30)17(29)13-24(15,28)2)27(23,36)11-7-19(23)26(4,35)20(31)8-10-25(3,34)22(33)38-5/h12,15,17-20,29-31,34-37H,6-11,13-14H2,1-5H3

InChI Key

HJFRJOLPKVDZSE-UHFFFAOYSA-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
Rhaponticum carthamoides	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Hydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Hexahydroxy bile acid, alcohol, or derivatives
25-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
6-oxosteroid
Oxosteroid
2-hydroxysteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Delta-7-steroid
Cyclohexenone
Cyclic alcohol
Methyl ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	-0.64	ChemAxon
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	184.98 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	136.49 m³·mol⁻¹	ChemAxon
Polarizability	57.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162967024

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate (NP0256923)

MOL for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)

3D MOL for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)

3D SDF for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)

3D-SDF for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)

PDB for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)

3D PDB for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)

SMILES for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)

INCHI for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)

Structure for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)

3D Structure for NP0256923 (methyl 6-{3a,5a,7,8-tetrahydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2,5,6-trihydroxy-2-methylheptanoate)