NP-MRD: Showing NP-Card for n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid (NP0201756)

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Record Information

Version

2.0

Created at

2022-09-04 20:51:32 UTC

Updated at

2022-09-04 20:51:32 UTC

NP-MRD ID

NP0201756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid

Description

N-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzene-1-carboximidic acid belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid is found in Euphorbia milii. N-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzene-1-carboximidic acid is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502522D          

 58 64  0  0  0  0            999 V2000
    2.8954    1.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4052    1.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2142    1.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8755    1.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8487    0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1923   -0.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8299   -1.1403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155   -1.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8731   -2.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057   -2.7287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3455   -0.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072   -1.2553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5568   -2.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447   -2.5341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184   -2.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3503   -0.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6649   -0.4950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5824    0.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -0.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542    0.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1287    1.0554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5472   -0.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217   -1.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231   -1.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9500   -1.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -0.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741    0.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2996    1.0112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0264    1.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7278    0.9671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0519    2.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505    2.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3760    3.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1029    3.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8043    3.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5311    3.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788    2.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4802    2.1819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2070    2.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2325    3.3968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9084    2.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8830    1.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5843    0.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3112    1.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3367    2.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6353    2.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6608    3.3526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9594    3.7870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3877    3.7429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462    1.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547    1.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9627    0.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5813    0.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0824    0.7753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0233    1.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5762    0.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2362    0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2670    1.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 11 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
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 18 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
  2 52  1  0  0  0  0
 16 52  1  0  0  0  0
 52 53  1  0  0  0  0
  6 53  1  0  0  0  0
 53 54  2  0  0  0  0
 50 55  1  0  0  0  0
  5 56  1  0  0  0  0
  4 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 58  1  0  0  0  0
M  END

     RDKit          3D

107113  0  0  0  0  0  0  0  0999 V2000
   -4.6882   -3.9458    0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6633   -2.8757   -0.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6347   -3.1793   -0.7621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759   -1.6325    0.4105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7911   -0.5730    0.2944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2054   -0.2861    1.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1381   -1.2553    2.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7196   -2.5181    2.0680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3756    0.6298    2.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3716    1.7353    2.5398 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1606    2.3373    1.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5544    3.3935    1.2386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5539    1.8607   -0.1612 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7872    2.6801   -1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2030    1.9952   -2.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3711    2.5237   -3.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834    0.5561   -1.8508 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2994   -0.2086   -1.8901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500   -1.2240   -2.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -1.4321   -3.5568 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0652   -2.0799   -2.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0272   -3.0862   -3.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0031   -3.9503   -4.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1719   -3.8810   -3.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2802   -2.8853   -2.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2586   -1.9959   -2.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559   -1.0043   -1.2569 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6704   -1.1574   -1.0715 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8638    2.3121    2.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9808    1.6927    1.8693 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2306    2.0112    2.3600 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8957    0.7331    0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6595   -1.0245    0.8147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9731   -1.6383    1.7330 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8630   -1.6716    0.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9702   -3.0765    0.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0667   -3.8066    0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1212   -3.1901   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0616   -1.8350   -0.5445 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9368   -1.0638   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9769    0.3171   -0.4214 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8829    0.7706   -1.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1311    1.3081    0.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2763    0.4933   -0.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.7538    1.2154    2.5768 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.8436    2.6637    4.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1854    0.8966    3.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1713   -4.8173    0.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9937   -4.2353   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5668   -3.6254    0.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9734   -1.1068   -0.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705   -1.0032    2.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3465   -1.2611    1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -2.5970    2.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7418    0.5914    3.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2178    2.4607    3.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7497    3.7779   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223    1.7078   -3.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9944    3.2806   -3.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4272    2.9752   -2.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946    0.1725   -2.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9519   -3.1696   -4.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8387   -4.6966   -4.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988   -4.5515   -3.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2130   -2.8834   -2.0029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711   -0.5354   -0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7575    2.4627    2.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3886    2.6867    3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5650    0.7244   -0.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1208   -3.5772    1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0238   -4.8778    0.4451 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9939   -3.7418   -0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8803   -1.3102   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9253    1.0323   -2.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4793   -0.0419   -2.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0201756

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2C(C3C=C(CO)C(OC(C)=O)C4(O)C(OC(=O)C5=CC=CC=C5NC(=O)C5=CC=CC(O)=C5NC(=O)C5=CC=CC=C5N(C)C)C(C)=CC14C3=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C45H49N3O10/c1-23-21-44-24(2)19-31-35(43(31,4)5)30(37(44)52)20-26(22-49)39(57-25(3)50)45(44,56)38(23)58-42(55)27-13-8-10-16-32(27)46-41(54)29-15-12-18-34(51)36(29)47-40(53)28-14-9-11-17-33(28)48(6)7/h8-18,20-21,24,30-31,35,38-39,49,51,56H,19,22H2,1-7H3,(H,46,54)(H,47,53)

> <INCHI_KEY>
YDFJPDIIZZEIAJ-UHFFFAOYSA-N

> <FORMULA>
C45H49N3O10

> <MOLECULAR_WEIGHT>
791.898

> <EXACT_MASS>
791.34179479

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
107

> <JCHEM_AVERAGE_POLARIZABILITY>
81.91010307732338

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-{2-[2-(dimethylamino)benzamido]-3-hydroxybenzamido}benzoate

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
5.867341433666667

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.066617632715623

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.119631642786157

> <JCHEM_PKA_STRONGEST_BASIC>
2.094760719533481

> <JCHEM_POLAR_SURFACE_AREA>
191.79999999999998

> <JCHEM_REFRACTIVITY>
220.47689999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-{2-[2-(dimethylamino)benzamido]-3-hydroxybenzamido}benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       5.405   3.727   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.356   2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.867   2.961   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.101   1.978   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.051   0.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.826  -0.664   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.149  -2.129   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.629  -2.588   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.363  -4.105   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.544  -5.093   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.378  -1.656   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.000  -2.343   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.906  -3.880   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.190  -4.730   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.528  -4.567   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.387  -0.067   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.108  -0.924   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.954   0.513   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.645  -0.298   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.288   0.431   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.240   1.970   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.021  -0.380   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.974  -1.919   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.283  -2.730   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.640  -2.002   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.688  -0.462   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.378   0.348   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -2.426   1.888   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -3.783   2.616   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.092   1.805   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.830   4.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.521   4.966   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.569   6.505   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.925   7.234   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.235   6.423   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.591   7.151   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -5.187   4.884   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      -6.496   4.073   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      -7.853   4.801   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -7.901   6.341   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -9.162   3.991   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -9.115   2.451   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -10.424   1.640   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -11.781   2.369   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -11.828   3.908   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -10.519   4.719   0.000  0.00  0.00           C+0
HETATM   47  N   UNK     0     -10.567   6.258   0.000  0.00  0.00           N+0
HETATM   48  C   UNK     0      -9.258   7.069   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -11.924   6.987   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       3.073   2.049   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.582   2.383   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.530   1.091   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       6.685   0.224   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       7.620   1.447   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       1.910   3.059   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      10.409   1.165   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      11.641   0.241   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      11.698   2.007   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   52                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   56                                                  
CONECT    5    4    6   56                                                  
CONECT    6    5    7   53                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17   18   52                                             
CONECT   17   16                                                            
CONECT   18   16   19   50                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   31   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   41   47                                                  
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   18   51   55                                                  
CONECT   51   50   52                                                       
CONECT   52   51    2   16   53                                             
CONECT   53   52    6   54                                                  
CONECT   54   53                                                            
CONECT   55   50                                                            
CONECT   56    5    4   57   58                                             
CONECT   57   56                                                            
CONECT   58   56                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Value	Source
N-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0,.0,]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzene-1-carboximidate	Generator
N-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzene-1-carboximidate	Generator

Chemical Formula

C₄₅H₄₉N₃O₁₀

Average Mass

791.8980 Da

Monoisotopic Mass

791.34179 Da

IUPAC Name

6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-{2-[2-(dimethylamino)benzamido]-3-hydroxybenzamido}benzoate

Traditional Name

6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl 2-{2-[2-(dimethylamino)benzamido]-3-hydroxybenzamido}benzoate

CAS Registry Number

Not Available

SMILES

CC1CC2C(C3C=C(CO)C(OC(C)=O)C4(O)C(OC(=O)C5=CC=CC=C5NC(=O)C5=CC=CC(O)=C5NC(=O)C5=CC=CC=C5N(C)C)C(C)=CC14C3=O)C2(C)C

InChI Identifier

InChI=1S/C45H49N3O10/c1-23-21-44-24(2)19-31-35(43(31,4)5)30(37(44)52)20-26(22-49)39(57-25(3)50)45(44,56)38(23)58-42(55)27-13-8-10-16-32(27)46-41(54)29-15-12-18-34(51)36(29)47-40(53)28-14-9-11-17-33(28)48(6)7/h8-18,20-21,24,30-31,35,38-39,49,51,56H,19,22H2,1-7H3,(H,46,54)(H,47,53)

InChI Key

YDFJPDIIZZEIAJ-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
Euphorbia milii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Ingenane diterpenoid
Benzanilide
Oligoanthrilamide fragment
Aromatic anilide
Anthranilamide
Benzoate ester
Aminobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Dialkylarylamine
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Tertiary alcohol
Vinylogous amide
Secondary carboxylic acid amide
Carboxylic acid ester
Carboxamide group
Amino acid or derivatives
Ketone
Tertiary amine
Carboxylic acid derivative
Alcohol
Organonitrogen compound
Carbonyl group
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.21	ALOGPS
logP	5.87	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	8.12	ChemAxon
pKa (Strongest Basic)	2.09	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	191.8 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	220.48 m³·mol⁻¹	ChemAxon
Polarizability	81.91 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 n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid (NP0201756)

MOL for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)

3D MOL for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)

3D SDF for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)

3D-SDF for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)

PDB for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)

3D PDB for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)

SMILES for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)

INCHI for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)

Structure for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)

3D Structure for NP0201756 (n-[2-({[6-(acetyloxy)-5-hydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-4-yl]oxy}carbonyl)phenyl]-2-({[2-(dimethylamino)phenyl](hydroxy)methylidene}amino)-3-hydroxybenzenecarboximidic acid)