NP-MRD: Showing NP-Card for 3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one (NP0299382)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 11:10:52 UTC

Updated at

2022-09-10 11:10:52 UTC

NP-MRD ID

NP0299382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one

Description

4,5,11,17-Tetrahydroxy-14-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-one belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. 3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one is found in Tapinella atrotomentosa. Based on a literature review very few articles have been published on 4,5,11,17-tetrahydroxy-14-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102213102D          

 36 40  0  0  0  0            999 V2000
    1.7472   -6.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2536   -5.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -4.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2914   -4.1030    0.0000 O   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
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -2.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2132   -3.6472    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
    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
    5.7686   -3.6325    0.0000 O   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
    3.0708   -5.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8881   -5.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580   -6.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1837   -4.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  9 31  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
M  END

     RDKit          3D

 80 84  0  0  0  0  0  0  0  0999 V2000
   -5.0862    1.4374    1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6930    0.1730    0.6735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8768   -0.9373    0.1701 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9295   -1.3235    1.2799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5374   -1.1912   -0.0559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3760   -0.3191   -0.4376 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2577   -0.4317   -1.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4394    0.9922   -0.1362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1395   -0.9065    0.1921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3419   -0.9214    1.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -0.7413    2.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171   -0.9507    1.1382 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9059   -2.3177    0.8314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -0.5036    1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8553    0.0492    2.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395    0.4509    2.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6559    1.4384    2.7346 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1359   -0.3161    1.2302 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4622    0.3848    1.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4191    1.5772    0.1347 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6583    1.7104   -0.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3932    1.3973   -0.9937 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8671    1.9503   -2.1772 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2353   -0.0742   -1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4696   -0.7491   -0.0588 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9193   -2.2360   -0.1968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0221   -0.7140   -0.1228 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3250    0.2429   -1.0608 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7822    0.2534   -2.3500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8717   -0.2624   -1.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1113   -0.1699    0.0629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0251    1.2555    0.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7706    0.5174   -0.3673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8200    1.4295    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5084   -0.7725   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2396    1.1102   -1.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2753    1.3698    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8802    2.1491    0.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8952    2.0009    1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2982   -0.2105    1.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5996   -1.8070   -0.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2675   -2.2373   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9401    0.5403   -2.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2627   -0.6386   -2.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6049   -1.2692   -2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8443    1.5439   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   -1.9618   -0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781   -1.8758    2.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912   -0.0848    1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -1.5467    3.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1538    0.2253    2.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8583   -2.5217   -0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2883    0.2050    3.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4460   -1.2121    1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7818    0.7190    2.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1909   -0.3826    0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2305    2.5280    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7407    2.5665   -0.9816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5141    1.9519   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9761    2.9147   -2.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2939   -0.4889   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9563   -0.4089   -2.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7083   -2.5118   -1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0114   -2.2601   -0.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3566   -2.8642    0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786   -1.7231   -0.5419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2240    1.2642   -0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4597   -0.5715   -2.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8603   -1.2352   -1.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4118    0.4607   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2895    1.8686   -0.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9551    1.6870    0.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083    1.3843    1.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4495    2.4450    0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6784    1.4387   -0.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2205    0.9387    1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5316   -0.5682   -1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9918   -1.3753   -1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5768   -1.3897    0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7075    0.4114   -1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  6
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  1
  2 33  1  0
 33 34  1  0
 33 35  1  0
 33 36  1  0
  5  3  1  0
 31  9  1  0
 31 12  1  0
 27 14  1  0
 25 18  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  1
  3 41  1  6
  5 42  1  6
  7 43  1  0
  7 44  1  0
  7 45  1  0
  8 46  1  0
  9 47  1  6
 10 48  1  0
 10 49  1  0
 11 50  1  0
 11 51  1  0
 13 52  1  0
 15 53  1  0
 18 54  1  1
 19 55  1  0
 19 56  1  0
 20 57  1  1
 21 58  1  0
 22 59  1  1
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 27 66  1  6
 28 67  1  1
 29 68  1  0
 30 69  1  0
 30 70  1  0
 32 71  1  0
 32 72  1  0
 32 73  1  0
 34 74  1  0
 34 75  1  0
 34 76  1  0
 35 77  1  0
 35 78  1  0
 35 79  1  0
 36 80  1  0
M  END


  Mrv1652309102213102D          

 36 40  0  0  0  0            999 V2000
    1.7472   -6.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2536   -5.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -4.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2914   -4.1030    0.0000 O   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
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -2.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2132   -3.6472    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
    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
    5.7686   -3.6325    0.0000 O   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
    3.0708   -5.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8881   -5.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9580   -6.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1837   -4.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  9 31  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299382

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1OC1C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3C(O)CC12C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O8/c1-13(24(2,3)33)22-23(36-22)27(6,34)20-7-8-28(35)15-10-16(29)14-9-17(30)18(31)11-25(14,4)21(15)19(32)12-26(20,28)5/h10,13-14,17-23,30-35H,7-9,11-12H2,1-6H3

> <INCHI_KEY>
XBKREFDHEBPCKQ-UHFFFAOYSA-N

> <FORMULA>
C28H44O8

> <MOLECULAR_WEIGHT>
508.652

> <EXACT_MASS>
508.303618377

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.466037652074945

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,11,17-tetrahydroxy-14-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_LOGP>
-0.20557307366666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.750742526677215

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.289001191847806

> <JCHEM_PKA_STRONGEST_BASIC>
-2.80269706345094

> <JCHEM_POLAR_SURFACE_AREA>
150.98

> <JCHEM_REFRACTIVITY>
132.69250000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,5,11,17-tetrahydroxy-14-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       3.262 -11.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.207 -10.031   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.626  -8.604   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.411  -7.659   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.566  -4.918   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.998  -6.808   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.768  -6.781   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.732 -10.241   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.258 -10.452   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.522 -11.767   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.943  -8.716   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3    5                                                       
CONECT    5    4    3    6                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   31                                             
CONECT   13   12                                                            
CONECT   14   12   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   14   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30    9   12   32                                             
CONECT   32   31                                                            
CONECT   33    2   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₄O₈

Average Mass

508.6520 Da

Monoisotopic Mass

508.30362 Da

IUPAC Name

4,5,11,17-tetrahydroxy-14-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

4,5,11,17-tetrahydroxy-14-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

CC(C1OC1C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3C(O)CC12C)C(C)(C)O

InChI Identifier

InChI=1S/C28H44O8/c1-13(24(2,3)33)22-23(36-22)27(6,34)20-7-8-28(35)15-10-16(29)14-9-17(30)18(31)11-25(14,4)21(15)19(32)12-26(20,28)5/h10,13-14,17-23,30-35H,7-9,11-12H2,1-6H3

InChI Key

XBKREFDHEBPCKQ-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
Tapinella atrotomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Ecdysteroid
20-hydroxysteroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
2-hydroxysteroid
14-hydroxysteroid
6-oxosteroid
11-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-7-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Oxacycle
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
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	-0.21	ChemAxon
pKa (Strongest Acidic)	13.29	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	150.98 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.69 m³·mol⁻¹	ChemAxon
Polarizability	55.47 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

85448014

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one (NP0299382)

MOL for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D MOL for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D SDF for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D-SDF for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

PDB for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D PDB for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

SMILES for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

INCHI for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

Structure for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)

3D Structure for NP0299382 (3a,7,8,10-tetrahydroxy-1-{1-hydroxy-1-[3-(3-hydroxy-3-methylbutan-2-yl)oxiran-2-yl]ethyl}-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one)