NP-MRD: Showing NP-Card for 14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate (NP0203177)

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Record Information

Version

1.0

Created at

2022-09-04 22:34:22 UTC

Updated at

2022-09-04 22:34:23 UTC

NP-MRD ID

NP0203177

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate

Description

13-(Acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-14-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate is found in Beesia calthifolia. 13-(Acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-14-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171502342D          

 51 57  0  0  0  0            999 V2000
    7.9138    1.3828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1379    1.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9927    2.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5072    1.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0216    0.1240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7223   -0.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4498    0.0776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6955   -1.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5743    3.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032    2.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3076    3.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5053    4.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    4.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6390    3.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7637    4.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991    5.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0630    5.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4643    4.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7271    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392    1.8451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0711    2.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7908    3.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3226    3.8824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786    3.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6983    4.1728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653    2.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  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  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 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
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 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
 32 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 41  1  0  0  0  0
 20 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
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 43 50  1  0  0  0  0
 50 51  1  0  0  0  0
M  END

     RDKit          3D

113119  0  0  0  0  0  0  0  0999 V2000
   -1.5559   -4.3594   -3.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5326   -3.9286   -2.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1930   -4.7845   -1.4782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8580   -2.6646   -1.9203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8512   -2.2251   -0.6309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2904   -2.0331   -0.0734 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0734   -2.8976   -0.8384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8274   -3.9484   -0.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5928   -4.7502   -1.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8253   -4.1728    0.8523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730   -0.5520   -0.2971 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6426   -0.0135    0.5509 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9333   -0.7994    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6244   -0.1439    2.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8254    0.7876    2.3488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4040    1.9186    1.3995 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4355    2.9621    1.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7798    2.4714    0.7379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7059    3.6210    2.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9863    4.0247    0.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9275    1.2955    0.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3016    0.1273   -0.5234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2734    0.5905   -1.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975   -0.3602   -2.9211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9653    1.3783    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959    1.6522    0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629    0.8858   -0.6750 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2014    1.5883   -1.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.0991   -0.4816 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3510    1.9593    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8132    2.2248    0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6446    0.9843    0.2534 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9350    1.3883    0.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8109    0.9274    1.0470 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3662    1.9991    1.7013 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9547    1.6317    2.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7686    0.3626    2.7440 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0161   -0.6988    3.1804 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1468    0.2437    1.2781 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8256    1.3879    0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8838    0.0324    0.4790 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5084   -1.3121    0.5260 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0987    0.3491   -0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351    1.3733   -2.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8840   -0.8422   -1.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6749   -0.1466   -0.6970 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2197   -0.9373   -1.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -1.2760   -1.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229   -0.5927   -0.6618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2496   -0.9449   -0.2407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1843   -1.0474    1.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366   -5.0857   -3.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465   -3.4743   -4.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4963   -4.8735   -4.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4945   -3.0921    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3786   -2.3275    0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8453   -5.0779   -2.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0452   -5.6559   -0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3188   -4.1176   -1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1103   -0.6076   -1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0790   -1.6600    0.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7951   -1.2553   -0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7958   -0.1484    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8305    0.2942    2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8933   -1.1853    2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7634    1.1173    3.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7618    0.3140    2.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5031    2.3631    1.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5093    3.3030    0.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1162    1.6651    1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7402    2.1606   -0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6409    4.2061    2.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9028    4.3612    2.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8339    2.8712    3.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8052    3.6078   -0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2604    1.1843   -2.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5681    1.3758   -2.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8672   -0.3306   -3.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    2.2761   -0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3903    1.5196    1.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0747    1.4710    1.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2528    2.7449    0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993    2.6980   -1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4902    0.3331    1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3354   -1.5252    2.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7688   -0.6777    1.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1779    1.9117    1.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1026    0.2905   -0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5373    2.2693   -1.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5533   -1.0140   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7795   -1.7266   -0.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7181   -2.3790   -1.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9  8  1  0
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 51111  1  0
 51112  1  0
 51113  1  0
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 47106  1  0
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 11 60  1  6
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 32 89  1  1
 34 90  1  1
 36 91  1  0
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 37 93  1  1
 38 94  1  0
 39 95  1  1
 40 96  1  0
 41 97  1  6
 42 98  1  0
 44 99  1  0
 44100  1  0
 44101  1  0
 45102  1  0
 45103  1  0
 45104  1  0
M  END


  Mrv1533004171502342D          

 51 57  0  0  0  0            999 V2000
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    6.9927    2.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2411    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5743    3.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032    2.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3076    3.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3282    4.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6983    4.1728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653    2.9114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  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  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 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
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 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
 32 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 41  1  0  0  0  0
 20 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
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 43 50  1  0  0  0  0
 50 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203177

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(OC(C)=O)C2(C)C3CCC4C5(CC35CCC2(CO)C1C1(C)CCC(O1)C(C)(C)O)CCC(OC1OCC(O)C(O)C1O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C39H62O12/c1-20(41)48-29-30(35(7)13-11-26(51-35)34(5,6)46)39(19-40)16-15-38-18-37(38)14-12-25(50-32-28(45)27(44)22(43)17-47-32)33(3,4)23(37)9-10-24(38)36(39,8)31(29)49-21(2)42/h22-32,40,43-46H,9-19H2,1-8H3

> <INCHI_KEY>
AOEKSLVHJZEURZ-UHFFFAOYSA-N

> <FORMULA>
C39H62O12

> <MOLECULAR_WEIGHT>
722.913

> <EXACT_MASS>
722.424127436

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
78.86550252874282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
1.4505409293333322

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.35005498761814

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.242014500803354

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7680396549683115

> <JCHEM_POLAR_SURFACE_AREA>
181.44

> <JCHEM_REFRACTIVITY>
181.85950000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate

> <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      14.773   2.581   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.324   3.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.053   4.620   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.147   2.112   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.374   0.232   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.682  -0.581   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.040   0.145   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      10.632  -2.121   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.539   6.825   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.326   4.263   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.908   6.143   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.277   7.638   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.813   7.749   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.393   6.323   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.625   9.057   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.438  10.365   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.318   9.870   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.933   8.244   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -1.357   3.715   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.873   3.444   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -3.866   4.621   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -3.343   6.070   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -4.335   7.247   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -1.827   6.341   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -1.304   7.789   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -0.834   5.164   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       0.682   5.435   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13   28                                             
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   42                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16   24   25                                             
CONECT   24   23   25                                                       
CONECT   25   24   13   23   26                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   11   29   31                                             
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28    5   32                                                  
CONECT   32   31   33   34   37                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36   32                                                       
CONECT   38   36   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   38                                                            
CONECT   42   20   43                                                       
CONECT   43   42   44   50                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   43   51                                                  
CONECT   51   50                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  114    0
END

View in JSmol

Synonyms

Value	Source
13-(Acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0,.0,.0,]octadecan-14-yl acetic acid	Generator
13-(Acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-14-yl acetic acid	Generator

Chemical Formula

C₃₉H₆₂O₁₂

Average Mass

722.9130 Da

Monoisotopic Mass

722.42413 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(OC(C)=O)C2(C)C3CCC4C5(CC35CCC2(CO)C1C1(C)CCC(O1)C(C)(C)O)CCC(OC1OCC(O)C(O)C1O)C4(C)C

InChI Identifier

InChI=1S/C39H62O12/c1-20(41)48-29-30(35(7)13-11-26(51-35)34(5,6)46)39(19-40)16-15-38-18-37(38)14-12-25(50-32-28(45)27(44)22(43)17-47-32)33(3,4)23(37)9-10-24(38)36(39,8)31(29)49-21(2)42/h22-32,40,43-46H,9-19H2,1-8H3

InChI Key

AOEKSLVHJZEURZ-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
Beesia calthifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Triterpene saponin
Triterpene glycoside
Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
Steroid ester
18-hydroxysteroid
Hydroxysteroid
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Dialkyl ether
Ether
Polyol
Organic oxide
Carbonyl group
Alcohol
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
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	2.69	ALOGPS
logP	1.45	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	181.86 m³·mol⁻¹	ChemAxon
Polarizability	78.87 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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

73817236

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate (NP0203177)

MOL for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)

3D MOL for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)

3D SDF for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)

3D-SDF for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)

PDB for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)

3D PDB for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)

SMILES for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)

INCHI for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)

Structure for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)

3D Structure for NP0203177 (14-(acetyloxy)-16-(hydroxymethyl)-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12-trimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-13-yl acetate)