NP-MRD: Showing NP-Card for 17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate (NP0156998)

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Record Information

Version

2.0

Created at

2022-09-02 14:17:36 UTC

Updated at

2022-09-02 14:17:37 UTC

NP-MRD ID

NP0156998

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate

Description

17-(Acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]Hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids. 17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate is found in Veratrum viride. 17-(Acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]Hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171517402D          

 54 60  0  0  0  0            999 V2000
    1.9295    6.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3071    5.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8606    4.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365    4.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2381    3.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622    3.8910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916    3.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1692    2.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932    2.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4397    3.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3708    1.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9243    1.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3018    0.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    0.2631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5034   -0.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275   -0.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7050   -1.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7740    0.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964    0.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    0.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1948    1.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2634    2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9147    2.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1003    1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4881    0.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7014    0.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2790    0.0895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7197    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481    1.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4565    0.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0161   -0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940   -0.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0117    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614   -0.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696    1.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333    1.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1854    2.5007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0737    3.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7258    3.8235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100    3.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2470    2.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4105    3.0421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8905    1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227    1.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797    2.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587    0.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264   -0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5918   -1.0381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6287   -0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4364    0.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8210   -0.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4310    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9987   -0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6656    0.9284    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 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
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 26 43  1  0  0  0  0
 43 44  1  0  0  0  0
  8 44  1  0  0  0  0
 24 44  1  0  0  0  0
 44 45  1  0  0  0  0
 30 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
M  END

     RDKit          3D

115121  0  0  0  0  0  0  0  0999 V2000
   -0.2038    6.5010    1.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195    5.0568    0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528    4.3814    1.8343 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6715    5.1350    1.6073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089    2.9794    1.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072    2.1065    2.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481    2.4903    0.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2921    1.1589   -0.0243 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7212    0.8233   -0.3116 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2480    1.4675   -1.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8269   -0.6570   -0.5262 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5902   -1.3968   -0.0876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8143   -2.8731   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9670   -3.3415    0.2912 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570   -4.7515    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1666   -5.1701    1.2427 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5368   -6.6241    1.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3419   -4.2496    1.2342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4129   -3.3723    0.0091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1326   -2.6943   -0.3256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0765   -1.2441    0.1070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0319   -1.2076    1.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1588   -0.5219   -0.4015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072   -0.9310   -0.8847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1668   -1.2281   -0.0619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8199   -0.2548   -0.6033 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7798    0.1312    0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6616   -0.1181    1.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9250    0.5593    3.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2755   -1.8153    2.8420 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7058   -0.4393    1.5195 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3179   -1.7817    0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896   -1.9684   -1.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029   -0.7976   -1.6650 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0736   -1.2878   -2.9008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6450    0.3620   -1.8081 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0609    1.6170   -2.3302 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2837    1.9381   -3.6596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506    3.0270   -4.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500    3.3056   -5.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3812    3.7732   -3.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5785    1.7852   -2.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3187    3.1626   -1.8345 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3949    0.5832   -1.0929 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.5824    6.6762    2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0407    0.6054    0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3440    1.0880    0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4414    0.8544   -2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9323   -0.8653   -1.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333   -1.3898    1.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9197   -2.9331   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109   -3.4284   -0.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401   -5.3409    0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5883   -4.9435   -0.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6385   -5.0230    2.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8884   -7.2521    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804   -7.0094    0.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5784   -6.8251    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4345   -3.6293    2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2641   -4.8982    1.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7771   -3.9632   -0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7118   -0.4162   -0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7150    2.0838    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3063    1.9373    2.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4041    0.3120    4.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4242   -0.1556    3.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3525   -1.6612    3.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9658   -2.4672    3.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8253   -1.3485    1.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6511   -1.8695    0.9485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1017   -2.5767    0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8475   -2.8853   -1.0028 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2768   -0.7311   -3.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6032    0.1438   -2.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5577    2.4614   -1.7563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2048    3.7153   -5.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 53  8  1  0
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 48110  1  0
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 36 94  1  0
 37 95  1  1
 38 96  1  0
 38 97  1  0
 38 98  1  0
 39 99  1  0
M  END


  Mrv1533004171517402D          

 54 60  0  0  0  0            999 V2000
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   -0.0117    0.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6614   -0.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696    1.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1854    2.5007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8905    1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7227    1.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797    2.5057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4364    0.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8210   -0.8571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9987   -0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6656    0.9284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  5  7  1  0  0  0  0
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 11 21  1  0  0  0  0
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 24 25  1  0  0  0  0
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 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
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 32 33  1  0  0  0  0
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 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 26 43  1  0  0  0  0
 43 44  1  0  0  0  0
  8 44  1  0  0  0  0
 24 44  1  0  0  0  0
 44 45  1  0  0  0  0
 30 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 49 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156998

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1C(O)C2C(CN3CC(C)CCC3C2(C)O)C2CC34OC5(O)C(C(OC(C)=O)C(O)C3C12O)C4(C)CCC5OC(=O)C(C)(O)C(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C39H61NO14/c1-9-18(3)32(45)53-31-26(43)25-21(16-40-15-17(2)10-11-23(40)36(25,8)48)22-14-37-29(38(22,31)49)27(44)28(51-20(5)42)30-34(37,6)13-12-24(39(30,50)54-37)52-33(46)35(7,47)19(4)41/h17-19,21-31,41,43-44,47-50H,9-16H2,1-8H3

> <INCHI_KEY>
IBCBICITVADEJG-UHFFFAOYSA-N

> <FORMULA>
C39H61NO14

> <MOLECULAR_WEIGHT>
767.91

> <EXACT_MASS>
767.409205648

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
115

> <JCHEM_AVERAGE_POLARIZABILITY>
82.3999452893645

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
0.24515651499999838

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.70435837523122

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.745746686954492

> <JCHEM_PKA_STRONGEST_BASIC>
7.971029416522561

> <JCHEM_POLAR_SURFACE_AREA>
232.97999999999996

> <JCHEM_REFRACTIVITY>
187.10790000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate

> <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       3.602  11.371   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.307  10.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.473   8.707   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.935   8.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.178   7.337   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.716   7.263   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.344   6.042   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.049   4.673   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.587   4.599   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.421   5.894   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.292   3.230   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.459   1.935   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.163   0.565   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       7.702   0.491   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       8.406  -0.878   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.945  -0.952   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.649  -2.322   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.778   0.342   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.073   1.712   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.535   1.786   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.830   3.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.958   4.690   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.174   3.907   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.920   2.009   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.778   0.928   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.309   1.574   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.521   0.167   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.343   1.140   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.396   2.679   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.719   0.297   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.897  -1.043   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.362  -0.852   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.022   0.767   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.235  -0.123   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.063   2.191   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.996   3.725   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.213   4.668   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.004   6.194   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.222   7.137   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.579   6.776   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.461   4.169   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       0.766   5.679   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       1.662   3.168   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.216   3.378   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       2.389   4.677   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -4.216   0.656   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -5.276  -0.461   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -4.838  -1.938   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -6.774  -0.102   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -6.415   1.395   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -7.133  -1.600   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -8.271   0.257   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -9.331  -0.861   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -8.709   1.733   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   44                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20   11   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   12   25   44                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33   43                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30   35                                             
CONECT   29   28                                                            
CONECT   30   28   31   46                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   26   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   28   36                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   36   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   26   44                                                  
CONECT   44   43    8   24   45                                             
CONECT   45   44                                                            
CONECT   46   30   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51   52                                             
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   49   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  120    0
END

View in JSmol

Synonyms

Value	Source
17-(Acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0,.0,.0,.0,.0,]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoic acid	Generator
17-(Acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoic acid	Generator

Chemical Formula

C₃₉H₆₁NO₁₄

Average Mass

767.9100 Da

Monoisotopic Mass

767.40921 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1C(O)C2C(CN3CC(C)CCC3C2(C)O)C2CC34OC5(O)C(C(OC(C)=O)C(O)C3C12O)C4(C)CCC5OC(=O)C(C)(O)C(C)O

InChI Identifier

InChI=1S/C39H61NO14/c1-9-18(3)32(45)53-31-26(43)25-21(16-40-15-17(2)10-11-23(40)36(25,8)48)22-14-37-29(38(22,31)49)27(44)28(51-20(5)42)30-34(37,6)13-12-24(39(30,50)54-37)52-33(46)35(7,47)19(4)41/h17-19,21-31,41,43-44,47-50H,9-16H2,1-8H3

InChI Key

IBCBICITVADEJG-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
Veratrum viride	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Cerveratrum-type alkaloids

Alternative Parents

Substituents

Cerveratrum-type alkaloid
Azasteroid
Quinolizidine
Alkaloid or derivatives
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Oxepane
Hydroxy acid
Fatty acyl
Piperidine
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Hemiacetal
Tertiary aliphatic amine
Secondary alcohol
Tertiary amine
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Polyol
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organooxygen compound
Alcohol
Organic nitrogen compound
Organic oxygen 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	1.46	ALOGPS
logP	0.25	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	10.75	ChemAxon
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	232.98 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	187.11 m³·mol⁻¹	ChemAxon
Polarizability	82.4 Å³	ChemAxon
Number of Rings	7	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate (NP0156998)

MOL for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)

3D MOL for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)

3D SDF for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)

3D-SDF for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)

PDB for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)

3D PDB for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)

SMILES for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)

INCHI for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)

Structure for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)

3D Structure for NP0156998 (17-(acetyloxy)-10,12,14,16,23-pentahydroxy-6,10,19-trimethyl-13-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-22-yl 2,3-dihydroxy-2-methylbutanoate)