NP-MRD: Showing NP-Card for methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate (NP0155750)

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Record Information

Version

2.0

Created at

2022-09-02 12:51:43 UTC

Updated at

2022-09-02 12:51:43 UTC

NP-MRD ID

NP0155750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate

Description

Methyl 3,4-dihydroxy-6-({13-hydroxy-2,15-dimethyl-12-oxo-14-[4-oxo-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-13-en-5-yl}oxy)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate is found in Pandaros acanthifolium. Methyl 3,4-dihydroxy-6-({13-hydroxy-2,15-dimethyl-12-oxo-14-[4-oxo-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-13-en-5-yl}oxy)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512532D          

 57 62  0  0  0  0            999 V2000
    8.0178   -3.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2981   -2.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7663   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.2555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0463    1.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0469   -2.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3921   -0.4543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8858    0.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2094   -0.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875    0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6996    1.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2314    0.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0435    0.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5754    0.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2951   -0.7535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3238    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1360    1.5742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7920    2.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0723    2.8356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9799    1.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4481    2.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    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  2  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
  7  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 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
 12 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
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 21 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
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  4  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 26 39  1  0  0  0  0
 14 40  1  0  0  0  0
  9 40  1  0  0  0  0
  7 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 45 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 43 52  1  0  0  0  0
 52 53  1  0  0  0  0
 41 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
  5 56  1  0  0  0  0
 56 57  1  0  0  0  0
M  END

     RDKit          3D

121126  0  0  0  0  0  0  0  0999 V2000
   10.8156    1.9737   -2.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7854    0.5876   -2.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6788    0.0544   -1.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4436    0.7907   -1.7394 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4607    1.9978   -2.1767 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1320    0.3286   -1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9891    0.3982    0.2352 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3342    1.7730    0.7827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6503   -0.0767    0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4935   -1.1278    1.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5182   -1.9477    2.0473 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0864   -1.3361    1.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4601   -2.3712    2.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5529    0.0856    1.6757 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1003    0.0349    1.6749 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3782    1.2789    2.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0412    0.7640    2.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4649   -0.3728    1.8726 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9728   -0.3744    1.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5814    0.8037    1.2359 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8009    0.5604    0.6277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691    1.1928    1.1891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5981    1.8205    0.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7545    2.4242    0.6210 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5584    2.7118   -0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7005    3.2737   -0.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1731    2.4196   -1.8827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0091    2.7335   -2.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5365    1.7811    1.6779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.1172    2.7401    2.5434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7911    0.8340    2.5753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6069    0.0607    3.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7906    0.0724    1.7456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4645   -0.5351    0.7061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1734   -1.8592    0.4985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7136   -2.1083   -0.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5255   -1.5560   -1.7630 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1643   -2.1658   -3.0986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8289   -1.8749   -3.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9817   -1.5937   -1.5324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5747   -0.3269   -1.7785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4667   -2.1645   -0.2490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.5091   -3.0952   -0.4250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4136   -2.7143    0.6614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7808   -2.6919    1.9992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6888    1.5416    0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6053    0.7423   -0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0254   -0.3276    0.4301 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5256   -1.6565   -0.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171   -0.4814    0.3919 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1958   -0.0253   -0.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931   -0.1017   -0.8063 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3029    0.4564    0.4484 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2702    1.9862    0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8065   -1.3479   -1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9336   -2.3125   -2.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2535   -1.8477   -1.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5687    2.6872   -1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8481    2.2489   -3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1687    2.1585   -3.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.7284    0.0456   -2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9192   -0.6586   -1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    0.9900   -1.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7456   -0.2790    0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3340    1.7798    1.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4421    2.5401   -0.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6096    2.0360    1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5236   -2.9109    1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9865    0.6817    2.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8488   -0.7480    2.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1548    1.9887    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0081    1.7319    2.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6596    1.5743    2.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2992    0.3483    3.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306   -1.3105    2.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2282   -0.3860    3.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329   -1.3549    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8378    1.5320    2.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6409    1.8106    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4490    3.4484    1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7428    2.0576   -3.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0755    2.4739   -2.7462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9574    3.7962   -3.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3951    1.2193    1.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6253    2.8313    3.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1693    1.4929    3.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0215   -0.6335    3.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1379   -0.6092    2.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4243   -2.2621    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2150   -0.4721   -1.8373 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171512532D          

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M  END
> <DATABASE_ID>
NP0155750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1OC(OC2CCC3(C)C(CCC4C5C(=O)C(O)=C(C(C)CC(=O)C(=CC)C(C)C)C5(C)CCC34)C2)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H64O15/c1-8-22(18(2)3)25(44)15-19(4)27-30(46)31(47)28-23-10-9-20-16-21(11-13-41(20,5)24(23)12-14-42(27,28)6)54-40-37(34(50)33(49)36(56-40)38(52)53-7)57-39-35(51)32(48)29(45)26(17-43)55-39/h8,18-21,23-24,26,28-29,32-37,39-40,43,45-46,48-51H,9-17H2,1-7H3

> <INCHI_KEY>
VTSZVHKWOJSFCM-UHFFFAOYSA-N

> <FORMULA>
C42H64O15

> <MOLECULAR_WEIGHT>
808.959

> <EXACT_MASS>
808.424521361

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
121

> <JCHEM_AVERAGE_POLARIZABILITY>
87.08800084986014

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3,4-dihydroxy-6-({13-hydroxy-2,15-dimethyl-12-oxo-14-[4-oxo-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-yl}oxy)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.6139481736666665

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.064128668997709

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20646706512273

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083576687361

> <JCHEM_POLAR_SURFACE_AREA>
238.96999999999997

> <JCHEM_REFRACTIVITY>
203.38380000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,4-dihydroxy-6-{[13-hydroxy-14-(5-isopropyl-4-oxohept-5-en-2-yl)-2,15-dimethyl-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      14.967  -6.565   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.490  -5.117   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.497  -3.939   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.981  -4.210   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.028  -1.314   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.820   3.618   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.558  -2.907   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.088  -3.912   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.018  -2.275   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.963  -3.490   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.383  -4.917   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.599  -0.848   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.653   0.368   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.124  -0.637   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      16.590   1.854   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      18.106   2.125   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      19.099   0.948   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      20.615   1.219   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      21.607   0.042   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      21.084  -1.407   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      21.138   2.667   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      22.654   2.939   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      20.145   3.845   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      20.668   5.293   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      18.629   3.574   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      17.636   4.751   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   56                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   41                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   40                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15   40                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   17   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   39                                                  
CONECT   27   26   21   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   26                                                            
CONECT   40   14    9                                                       
CONECT   41    7   42   54                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   52                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   48                                                  
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   45   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   43   53                                                  
CONECT   53   52                                                            
CONECT   54   41   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54    5   57                                                  
CONECT   57   56                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3,4-dihydroxy-6-({13-hydroxy-2,15-dimethyl-12-oxo-14-[4-oxo-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0,.0,]heptadec-13-en-5-yl}oxy)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid	Generator
Methyl 3,4-dihydroxy-6-({13-hydroxy-2,15-dimethyl-12-oxo-14-[4-oxo-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-yl}oxy)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid	Generator

Chemical Formula

C₄₂H₆₄O₁₅

Average Mass

808.9590 Da

Monoisotopic Mass

808.42452 Da

IUPAC Name

methyl 3,4-dihydroxy-6-({13-hydroxy-2,15-dimethyl-12-oxo-14-[4-oxo-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-yl}oxy)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate

Traditional Name

methyl 3,4-dihydroxy-6-{[13-hydroxy-14-(5-isopropyl-4-oxohept-5-en-2-yl)-2,15-dimethyl-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1OC(OC2CCC3(C)C(CCC4C5C(=O)C(O)=C(C(C)CC(=O)C(=CC)C(C)C)C5(C)CCC34)C2)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O

InChI Identifier

InChI=1S/C42H64O15/c1-8-22(18(2)3)25(44)15-19(4)27-30(46)31(47)28-23-10-9-20-16-21(11-13-41(20,5)24(23)12-14-42(27,28)6)54-40-37(34(50)33(49)36(56-40)38(52)53-7)57-39-35(51)32(48)29(45)26(17-43)55-39/h8,18-21,23-24,26,28-29,32-37,39-40,43,45-46,48-51H,9-17H2,1-7H3

InChI Key

VTSZVHKWOJSFCM-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
Pandaros acanthifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroid glucuronide conjugates

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
Steroid-glucuronide-skeleton
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
23-oxosteroid
Bile acid, alcohol, or derivatives
Hydroxysteroid
15-oxosteroid
Oxosteroid
16-hydroxysteroid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Pyran
Hydroxy acid
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Oxane
Acryloyl-group
Enone
Methyl ester
Alpha,beta-unsaturated ketone
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Enol
Polyol
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Carbonyl group
Organic oxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.51	ALOGPS
logP	2.61	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	238.97 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	203.38 m³·mol⁻¹	ChemAxon
Polarizability	87.09 Å³	ChemAxon
Number of Rings	6	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

75254291

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate (NP0155750)

MOL for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)

3D MOL for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)

3D SDF for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)

3D-SDF for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)

PDB for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)

3D PDB for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)

SMILES for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)

INCHI for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)

Structure for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)

3D Structure for NP0155750 (methyl 3,4-dihydroxy-6-{[2-hydroxy-1-(5-isopropyl-4-oxohept-5-en-2-yl)-9a,11a-dimethyl-3-oxo-3ah,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylate)