NP-MRD: Showing NP-Card for ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione (NP0026538)

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Record Information

Version

2.0

Created at

2021-06-19 18:23:12 UTC

Updated at

2021-06-29 23:52:08 UTC

NP-MRD ID

NP0026538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione

Provided By

JEOL Database JEOL Logo

Description

CHEMBL456865 is also known as dakdd CPD. ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione is found in Croton kongensis. ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione was first documented in 2003 (Thongtan, J., et al.). Based on a literature review very few articles have been published on CHEMBL456865.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120233D          

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     RDKit          3D

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M  END


  Mrv1652306192120233D          

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    0.4979   -0.2164   -4.8050 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6998    0.1672   -3.9069 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5915    1.1788   -4.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5547   -1.1133   -3.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751    0.6530   -2.4957 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3191    1.0955   -1.5174 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7482    0.0309   -0.4669 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7862    0.5783    0.3714 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0456    0.5277   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177    1.1007    0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3534    0.0916   -1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214   -3.6456    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0333    1.5716    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6541    0.9296   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7470   -2.5854   -3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761   -3.5353   -1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0965   -3.2080   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256    3.8244   -2.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024    3.2385   -3.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276    3.4732   -2.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307    2.0921   -3.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    0.4271   -3.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    0.5452   -5.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026    1.7658   -5.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -1.1046   -4.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -0.5031   -5.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    0.7725   -5.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182    1.3990   -4.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    2.1249   -4.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0168   -1.8797   -3.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -0.9031   -3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8138   -1.5496   -4.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521   -0.2590   -2.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030    1.4202   -2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    1.9939   -0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1132   -0.8768   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7829    2.1522    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0299    1.0343    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819    0.5299    1.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0  0  0  0
  2  1  2  3  0  0  0
 24 25  1  0  0  0  0
 14  9  1  0  0  0  0
 21 24  1  0  0  0  0
  9  8  1  0  0  0  0
 25 26  1  0  0  0  0
  9 10  1  0  0  0  0
 26  5  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  2  0  0  0  0
 11 12  1  0  0  0  0
 16 18  1  0  0  0  0
 11 13  2  0  0  0  0
 21 22  1  6  0  0  0
 19 20  1  0  0  0  0
 24 56  1  1  0  0  0
 24 16  1  0  0  0  0
  7 34  1  1  0  0  0
 19 18  1  0  0  0  0
 26 27  1  0  0  0  0
  5  3  1  0  0  0  0
 16 17  1  6  0  0  0
  3  2  1  0  0  0  0
 14 15  2  0  0  0  0
  2  7  1  0  0  0  0
 21 23  1  0  0  0  0
  7  6  1  0  0  0  0
 27 28  1  0  0  0  0
 16 14  1  0  0  0  0
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  3  4  2  0  0  0  0
 28 30  2  0  0  0  0
  7  8  1  0  0  0  0
 19 46  1  0  0  0  0
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 18 45  1  0  0  0  0
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 26 59  1  6  0  0  0
  6 33  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  9 37  1  6  0  0  0
  8 35  1  0  0  0  0
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 22 50  1  0  0  0  0
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 23 53  1  0  0  0  0
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 23 55  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 29 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C(=O)C2=C([H])[C@@]1([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])C(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])[C@@]2([H])OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-13-16-10-17(21(13)27)18(29-14(2)25)12-20-23(4,5)8-7-9-24(20,6)22(28)19(11-16)30-15(3)26/h10,16,18-20H,1,7-9,11-12H2,2-6H3/t16-,18+,19-,20+,24+/m0/s1

> <INCHI_KEY>
REDVWPQXGVFYQX-AYQBYMDZSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.75932091386998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4R,9R,11S,13R)-11-(acetyloxy)-5,5,9-trimethyl-14-methylidene-10,15-dioxotricyclo[11.2.1.0^{4,9}]hexadec-1(16)-en-2-yl acetate

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
3.934097174666665

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.97199238181958

> <JCHEM_PKA_STRONGEST_BASIC>
-6.293155792491216

> <JCHEM_POLAR_SURFACE_AREA>
86.74000000000001

> <JCHEM_REFRACTIVITY>
111.2258

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4R,9R,11S,13R)-11-(acetyloxy)-5,5,9-trimethyl-14-methylidene-10,15-dioxotricyclo[11.2.1.0^{4,9}]hexadec-1(16)-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -0.9189   -2.6442    1.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -1.5745    1.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4331   -0.1225    1.6377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6711    0.4965    0.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6577    0.5985   -0.6198 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3700   -0.6733   -1.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166   -1.5363   -1.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9729   -2.7947   -2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5603   -1.3107   -0.9539 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5547   -1.1133   -3.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751    0.6530   -2.4957 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3191    1.0955   -1.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7862    0.5783    0.3714 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0177    1.1007    0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3534    0.0916   -1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8395    1.4970    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7470   -2.5854   -3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761   -3.5353   -1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8307    2.0921   -3.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    0.4271   -3.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    0.5452   -5.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026    1.7658   -5.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -1.1046   -4.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -0.5031   -5.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    0.7725   -5.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182    1.3990   -4.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    2.1249   -4.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0168   -1.8797   -3.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -0.9031   -3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8138   -1.5496   -4.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521   -0.2590   -2.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030    1.4202   -2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    1.9939   -0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1132   -0.8768   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7829    2.1522    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0299    1.0343    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819    0.5299    1.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
  2  1  2  3
 24 25  1  0
 14  9  1  0
 21 24  1  0
  9  8  1  0
 25 26  1  0
  9 10  1  0
 26  5  1  0
 10 11  1  0
  6  5  2  0
 11 12  1  0
 16 18  1  0
 11 13  2  0
 21 22  1  6
 19 20  1  0
 24 56  1  1
 24 16  1  0
  7 34  1  1
 19 18  1  0
 26 27  1  0
  5  3  1  0
 16 17  1  6
  3  2  1  0
 14 15  2  0
  2  7  1  0
 21 23  1  0
  7  6  1  0
 27 28  1  0
 16 14  1  0
 28 29  1  0
  3  4  2  0
 28 30  2  0
  7  8  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 18 44  1  0
 18 45  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  6
  6 33  1  0
  1 31  1  0
  1 32  1  0
  9 37  1  6
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  8 36  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 22 50  1  0
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 17 41  1  0
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 23 53  1  0
 23 54  1  0
 23 55  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.919  -2.644   1.713  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.214  -1.575   1.330  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.010  -1.655   0.487  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.422  -2.643  -0.088  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.605  -0.305   0.430  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.839   0.512   1.169  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.433  -0.123   1.638  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.671   0.497   0.936  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.658   0.599  -0.620  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.370  -0.673  -1.202  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.417  -1.536  -1.320  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.973  -2.795  -2.001  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.560  -1.311  -0.954  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.724   1.741  -1.122  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.548   2.733  -0.401  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.042   1.672  -2.536  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.403   3.120  -2.882  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.109   1.274  -3.588  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.533   0.894  -4.945  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.498  -0.216  -4.805  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.700   0.167  -3.907  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.591   1.179  -4.659  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.555  -1.113  -3.733  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.175   0.653  -2.496  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.319   1.095  -1.517  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.748   0.031  -0.467  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.786   0.578   0.371  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.046   0.528  -0.138  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.018   1.101   0.847  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.353   0.092  -1.237  0.00  0.00           O+0
HETATM   31  H   UNK     0      -0.621  -3.646   1.413  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.802  -2.546   2.335  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.033   1.572   1.294  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.525   0.009   2.723  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.546  -0.098   1.230  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.839   1.497   1.356  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.654   0.930  -0.946  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.747  -2.585  -3.049  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.776  -3.535  -1.950  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.097  -3.208  -1.497  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.426   3.824  -2.729  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.702   3.239  -3.923  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.228   3.473  -2.258  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.831   2.092  -3.719  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.710   0.427  -3.252  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.348   0.545  -5.591  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.103   1.766  -5.446  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.001  -1.105  -4.392  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.847  -0.503  -5.805  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.893   0.773  -5.633  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.518   1.399  -4.122  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.095   2.125  -4.864  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.017  -1.880  -3.164  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.496  -0.903  -3.217  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.814  -1.550  -4.705  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.752  -0.259  -2.065  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.203   1.420  -2.071  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.029   1.994  -0.961  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.113  -0.877  -0.958  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.783   2.152   1.030  0.00  0.00           H+0
HETATM   61  H   UNK     0       7.030   1.034   0.438  0.00  0.00           H+0
HETATM   62  H   UNK     0       5.982   0.530   1.778  0.00  0.00           H+0
CONECT    1    2   31   32                                                  
CONECT    2    1    3    7                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5   26    6    3                                                  
CONECT    6    5    7   33                                                  
CONECT    7   34    2    6    8                                             
CONECT    8    9    7   35   36                                             
CONECT    9   14    8   10   37                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   38   39   40                                             
CONECT   13   11                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   18   24   17   14                                             
CONECT   17   16   41   42   43                                             
CONECT   18   16   19   44   45                                             
CONECT   19   20   18   46   47                                             
CONECT   20   21   19   48   49                                             
CONECT   21   20   24   22   23                                             
CONECT   22   21   50   51   52                                             
CONECT   23   21   53   54   55                                             
CONECT   24   25   21   56   16                                             
CONECT   25   24   26   57   58                                             
CONECT   26   25    5   27   59                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28   60   61   62                                             
CONECT   30   28                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    6                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   17                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   22                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  128    0
END

RDKit          3D

62 64  0  0  0  0  0  0  0  0999 V2000
   -0.9189   -2.6442    1.7131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2142   -1.5745    1.3302 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100   -1.6547    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4222   -2.6434   -0.0881 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6052   -0.3054    0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390    0.5120    1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331   -0.1225    1.6377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6711    0.4965    0.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6577    0.5985   -0.6198 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3700   -0.6733   -1.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166   -1.5363   -1.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9729   -2.7947   -2.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5603   -1.3107   -0.9539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7240    1.7409   -1.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475    2.7328   -0.4005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418    1.6722   -2.5360 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4025    3.1201   -2.8823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1094    1.2745   -3.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333    0.8936   -4.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4979   -0.2164   -4.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6998    0.1672   -3.9069 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5915    1.1788   -4.6587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5547   -1.1133   -3.7331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751    0.6530   -2.4957 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3191    1.0955   -1.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7482    0.0309   -0.4669 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7862    0.5783    0.3714 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0456    0.5277   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0177    1.1007    0.8471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3534    0.0916   -1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6214   -3.6456    1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8023   -2.5461    2.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0333    1.5716    1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246    0.0091    2.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464   -0.0977    1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8395    1.4970    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541    0.9296   -0.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7470   -2.5854   -3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7761   -3.5353   -1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0965   -3.2080   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4256    3.8244   -2.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024    3.2385   -3.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276    3.4732   -2.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307    2.0921   -3.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099    0.4271   -3.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    0.5452   -5.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026    1.7658   -5.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0006   -1.1046   -4.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8474   -0.5031   -5.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    0.7725   -5.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182    1.3990   -4.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0948    2.1249   -4.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0168   -1.8797   -3.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4962   -0.9031   -3.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8138   -1.5496   -4.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7521   -0.2590   -2.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030    1.4202   -2.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    1.9939   -0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1132   -0.8768   -0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7829    2.1522    1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0299    1.0343    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9819    0.5299    1.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
  2  1  2  3
 24 25  1  0
 14  9  1  0
 21 24  1  0
  9  8  1  0
 25 26  1  0
  9 10  1  0
 26  5  1  0
 10 11  1  0
  6  5  2  0
 11 12  1  0
 16 18  1  0
 11 13  2  0
 21 22  1  6
 19 20  1  0
 24 56  1  1
 24 16  1  0
  7 34  1  1
 19 18  1  0
 26 27  1  0
  5  3  1  0
 16 17  1  6
  3  2  1  0
 14 15  2  0
  2  7  1  0
 21 23  1  0
  7  6  1  0
 27 28  1  0
 16 14  1  0
 28 29  1  0
  3  4  2  0
 28 30  2  0
  7  8  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 18 44  1  0
 18 45  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  6
  6 33  1  0
  1 31  1  0
  1 32  1  0
  9 37  1  6
  8 35  1  0
  8 36  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
ent-8,9-Seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione	MeSH
DAKDD CPD	MeSH

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

(2R,4R,9R,11S,13R)-11-(acetyloxy)-5,5,9-trimethyl-14-methylidene-10,15-dioxotricyclo[11.2.1.0^{4,9}]hexadec-1(16)-en-2-yl acetate

Traditional Name

(2R,4R,9R,11S,13R)-11-(acetyloxy)-5,5,9-trimethyl-14-methylidene-10,15-dioxotricyclo[11.2.1.0^{4,9}]hexadec-1(16)-en-2-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1C(=O)C2=C([H])[C@@]1([H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])C(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])[C@@]2([H])OC(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C24H32O6/c1-13-16-10-17(21(13)27)18(29-14(2)25)12-20-23(4,5)8-7-9-24(20,6)22(28)19(11-16)30-15(3)26/h10,16,18-20H,1,7-9,11-12H2,2-6H3/t16-,18+,19-,20+,24+/m0/s1

InChI Key

REDVWPQXGVFYQX-AYQBYMDZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Croton kongensis	JEOL database	Thongtan, J., et al, J. Nat. Prod. 66, 868 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-acyloxy ketones

Alternative Parents

Substituents

Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	2.5	ALOGPS
logP	3.93	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	16.97	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	86.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.23 m³·mol⁻¹	ChemAxon
Polarizability	43.76 Å³	ChemAxon
Number of Rings	3	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

2279986

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3010860

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Thongtan, J., et al. (2003). Thongtan, J., et al, J. Nat. Prod. 66, 868 (2003). J. Nat. Prod..

Showing NP-Card for ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione (NP0026538)

MOL for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)

3D MOL for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)

3D SDF for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)

3D-SDF for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)

PDB for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)

3D PDB for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)

SMILES for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)

INCHI for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)

Structure for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)

3D Structure for NP0026538 (ent-8,9-seco-7alpha,11beta-diacetoxykaura-8(14),16-dien-9,15-dione)