NP-MRD: Showing NP-Card for Ingenol-3,4:5,20-diacetonide (NP0139066)

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Record Information

Version

1.0

Created at

2022-06-29 19:38:01 UTC

Updated at

2022-06-29 19:38:01 UTC

NP-MRD ID

NP0139066

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ingenol-3,4:5,20-diacetonide

Description

3,6,6,11,11,18,18,21-Octamethyl-5,7,10,12-tetraoxahexacyclo[14.5.1.0¹,⁸.0⁴,⁸.0⁹,¹⁴.0¹⁷,¹⁹]Docosa-2,14-dien-22-one belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. 3,6,6,11,11,18,18,21-Octamethyl-5,7,10,12-tetraoxahexacyclo[14.5.1.0¹,⁸.0⁴,⁸.0⁹,¹⁴.0¹⁷,¹⁹]Docosa-2,14-dien-22-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171516302D          

 31 36  0  0  0  0            999 V2000
    1.9637    1.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1784    0.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7249   -0.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5362   -0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7780   -1.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818   -2.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4488   -2.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740   -2.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629   -3.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1733   -2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -3.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917   -2.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1015   -1.6548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126   -1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -1.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082   -0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654   -1.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113   -0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902   -0.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4293    0.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5844    0.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480   -0.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673   -0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8806   -0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8757   -1.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.3133    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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 28  1  0  0  0  0
  5 29  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

 67 72  0  0  0  0  0  0  0  0999 V2000
   -1.9789   -3.8921   -1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636   -2.6548   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1064   -2.5878   -0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4695   -1.1550   -0.2143 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1622   -0.8617    1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2104   -1.7234    1.9292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7842    0.4739    1.3652 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8145    1.5885    1.3894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1509    1.8429    0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4975    3.2886    0.5210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680    3.3439    0.7555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5232    2.6367   -0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144    2.7658    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3029    3.3716   -1.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433    1.3086   -0.2916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8972    0.9669   -0.3274 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8193   -0.4778   -0.0797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2790   -0.6721    1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5631   -1.1511    1.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -2.5431    1.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5661   -0.2501    1.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9516   -1.2481   -0.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668   -1.2954   -0.8726 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8310    0.6909    0.3177 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4095   -0.7314    0.0331 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7846   -1.1392   -1.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191   -0.8005   -1.3947 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9339   -1.6573   -2.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2288    0.3921    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109    0.4259    1.7190 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1063    0.9715   -0.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0496   -3.7057   -0.9608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6368   -4.3252   -1.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6846   -4.6431   -0.2249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282   -3.4690   -0.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2891    0.4264    2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    2.2803    2.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0263    3.8481    1.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2129    3.7316   -0.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6167    2.0942   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3685    3.8090   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891    2.5642    1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3864    2.9574   -1.9805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1839    3.1598   -2.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1364    4.4502   -1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830    1.1717   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5504   -3.1075    1.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0096   -2.4779    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7698   -3.1161    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4641   -0.0708    1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1138    0.6994    2.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9135   -0.7683    2.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881   -0.9847   -1.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4579    1.2773   -0.5377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671   -1.4967    0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760   -2.2270   -1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3124   -0.6241   -2.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1761    0.2329   -1.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608   -1.4670   -3.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980   -2.7104   -2.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -1.3237   -3.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8533   -0.5920    2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9767    0.7204    1.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3982    1.1258    2.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4361    1.9966   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4944    1.0440   -1.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9516    0.2929   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
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 23  2  1  0
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  5  6  2  0
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 29 30  1  0
 29 31  1  0
  4 27  1  0
 29 25  1  0
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 16  9  1  0
 23 17  1  0
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 28 59  1  0
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 26 57  1  0
 25 55  1  1
 24 54  1  6
  7 36  1  1
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 10 38  1  0
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 13 40  1  0
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 13 42  1  0
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 20 47  1  0
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 21 52  1  0
 23 53  1  6
  1 32  1  0
  1 33  1  0
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  3 35  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  0
 31 66  1  0
 31 67  1  0
M  END


  Mrv1533004171516302D          

 31 36  0  0  0  0            999 V2000
    1.9637    1.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1784    0.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7249   -0.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5362   -0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7780   -1.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2818   -2.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4488   -2.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740   -2.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3629   -3.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1733   -2.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -3.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8917   -2.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1015   -1.6548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9126   -1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -1.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082   -0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7654   -1.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113   -0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3902   -0.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4293    0.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5844    0.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7480   -0.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673   -0.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8806   -0.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261   -0.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8757   -1.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.3133    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
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 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
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 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  2  0  0  0  0
 23 28  1  0  0  0  0
  5 29  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139066

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC2C(C3C=C4COC(C)(C)OC4C45OC(C)(C)OC4C(C)=CC15C3=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O5/c1-13-11-25-14(2)9-17-18(22(17,3)4)16(19(25)27)10-15-12-28-23(5,6)30-21(15)26(25)20(13)29-24(7,8)31-26/h10-11,14,16-18,20-21H,9,12H2,1-8H3

> <INCHI_KEY>
JOKBBQPBIIZMJV-UHFFFAOYSA-N

> <FORMULA>
C26H36O5

> <MOLECULAR_WEIGHT>
428.569

> <EXACT_MASS>
428.256274259

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.2411149634363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,6,11,11,18,18,21-octamethyl-5,7,10,12-tetraoxahexacyclo[14.5.1.0¹,⁸.0⁴,⁸.0⁹,¹⁴.0¹⁷,¹⁹]docosa-2,14-dien-22-one

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
3.6975172576666666

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.548156570421622

> <JCHEM_PKA_STRONGEST_BASIC>
-3.796416395791821

> <JCHEM_POLAR_SURFACE_AREA>
53.99

> <JCHEM_REFRACTIVITY>
118.4409

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,6,11,11,18,18,21-octamethyl-5,7,10,12-tetraoxahexacyclo[14.5.1.0¹,⁸.0⁴,⁸.0⁹,¹⁴.0¹⁷,¹⁹]docosa-2,14-dien-22-one

> <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       3.666   2.273   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.373   0.905   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.933   1.092   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.953  -0.102   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.601  -1.601   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.186  -2.461   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.259  -3.788   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.704  -3.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.191  -5.430   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.677  -5.711   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.324  -4.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.302  -5.730   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.664  -3.784   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.189  -3.089   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.704  -2.807   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.744  -1.144   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.465  -2.170   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.949  -1.567   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.429  -3.030   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.448  -1.215   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.728  -0.051   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.801   0.167   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.488   1.538   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.958   1.230   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.263  -0.324   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.232  -1.372   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.377  -0.342   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.818   2.924   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.075  -1.156   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.101  -2.305   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.505  -0.585   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6   29                                                  
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15   17   22   25                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24    2   16   26                                             
CONECT   26   25    6   27                                                  
CONECT   27   26                                                            
CONECT   28   23                                                            
CONECT   29    5    4   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₅

Average Mass

428.5690 Da

Monoisotopic Mass

428.25627 Da

IUPAC Name

3,6,6,11,11,18,18,21-octamethyl-5,7,10,12-tetraoxahexacyclo[14.5.1.0¹,⁸.0⁴,⁸.0⁹,¹⁴.0¹⁷,¹⁹]docosa-2,14-dien-22-one

Traditional Name

3,6,6,11,11,18,18,21-octamethyl-5,7,10,12-tetraoxahexacyclo[14.5.1.0¹,⁸.0⁴,⁸.0⁹,¹⁴.0¹⁷,¹⁹]docosa-2,14-dien-22-one

CAS Registry Number

Not Available

SMILES

CC1CC2C(C3C=C4COC(C)(C)OC4C45OC(C)(C)OC4C(C)=CC15C3=O)C2(C)C

InChI Identifier

InChI=1S/C26H36O5/c1-13-11-25-14(2)9-17-18(22(17,3)4)16(19(25)27)10-15-12-28-23(5,6)30-21(15)26(25)20(13)29-24(7,8)31-26/h10-11,14,16-18,20-21H,9,12H2,1-8H3

InChI Key

JOKBBQPBIIZMJV-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Meta-dioxane
Meta-dioxolane
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	4.29	ALOGPS
logP	3.7	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	15.55	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	118.44 m³·mol⁻¹	ChemAxon
Polarizability	47.24 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157081

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ingenol-3,4:5,20-diacetonide (NP0139066)

MOL for NP0139066 (Ingenol-3,4:5,20-diacetonide)

3D MOL for NP0139066 (Ingenol-3,4:5,20-diacetonide)

3D SDF for NP0139066 (Ingenol-3,4:5,20-diacetonide)

3D-SDF for NP0139066 (Ingenol-3,4:5,20-diacetonide)

PDB for NP0139066 (Ingenol-3,4:5,20-diacetonide)

3D PDB for NP0139066 (Ingenol-3,4:5,20-diacetonide)

SMILES for NP0139066 (Ingenol-3,4:5,20-diacetonide)

INCHI for NP0139066 (Ingenol-3,4:5,20-diacetonide)

Structure for NP0139066 (Ingenol-3,4:5,20-diacetonide)

3D Structure for NP0139066 (Ingenol-3,4:5,20-diacetonide)