NP-MRD: Showing NP-Card for 17-acetoxyjolkinolide B (NP0032269)

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Record Information

Version

2.0

Created at

2021-06-19 23:06:54 UTC

Updated at

2021-06-30 00:01:21 UTC

NP-MRD ID

NP0032269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-acetoxyjolkinolide B

Provided By

JEOL Database JEOL Logo

Description

17-Acetoxyjolkinolide B, also known as 17-ajb CPD, belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 17-acetoxyjolkinolide B is found in Euphorbia fischeriana. 17-acetoxyjolkinolide B was first documented in 2006 (PMID: 16792421). Based on a literature review very few articles have been published on 17-acetoxyjolkinolide B (PMID: 18566223).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101063D          

 56 61  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202101063D          

 56 61  0  0  0  0            999 V2000
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   -0.3112   -0.0423   -2.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3506   -2.4958   -2.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1201   -3.3579   -2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -2.6642   -0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7336   -4.2417   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078   -3.9461   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391   -3.9398    1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -3.1387    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738   -4.8455    2.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294   -6.1460    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107   -5.9366    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -6.5587    1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -5.0233    3.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097   -4.9938    2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069   -3.2127    3.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110   -2.5602    3.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0541   -2.7281    1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481   -1.2850    2.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4844   -0.0718    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5190   -1.3875    2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453   -0.8059    0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8170   -2.0250   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648    0.0632    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  1  0  0  0
 17 14  1  0  0  0  0
 14 16  1  0  0  0  0
 12 11  1  0  0  0  0
 25  7  1  0  0  0  0
 20 22  1  0  0  0  0
 13 12  1  0  0  0  0
 11 10  1  0  0  0  0
 22 10  1  0  0  0  0
 14 13  1  0  0  0  0
  7  6  2  0  0  0  0
  6 27  1  0  0  0  0
 27 26  1  0  0  0  0
 25 26  1  1  0  0  0
 20 19  1  0  0  0  0
 27 28  2  0  0  0  0
 20 13  1  0  0  0  0
  6  5  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  0  0  0  0
 22 23  1  0  0  0  0
 10  9  1  6  0  0  0
  8  9  1  0  0  0  0
 10  8  1  0  0  0  0
 23 56  1  1  0  0  0
  8  7  1  0  0  0  0
  8 34  1  6  0  0  0
 25 23  1  0  0  0  0
  5  4  1  0  0  0  0
 18 17  1  0  0  0  0
  4  2  1  0  0  0  0
 20 21  1  1  0  0  0
  2  1  1  0  0  0  0
 18 19  1  0  0  0  0
  2  3  2  0  0  0  0
 18 48  1  0  0  0  0
 18 49  1  0  0  0  0
 17 46  1  0  0  0  0
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 19 51  1  0  0  0  0
 13 39  1  6  0  0  0
 12 37  1  0  0  0  0
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 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 22 55  1  6  0  0  0
 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 21 54  1  0  0  0  0
 15 40  1  0  0  0  0
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 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032269

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])C(=O)OC([H])([H])C1=C2[C@@]3([H])O[C@]33C([H])([H])C([H])([H])[C@]4([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@]3([H])[C@@]3([H])O[C@@]23OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O6/c1-11(23)25-10-12-14-16-21(26-16)9-6-13-19(2,3)7-5-8-20(13,4)15(21)17-22(14,27-17)28-18(12)24/h13,15-17H,5-10H2,1-4H3/t13-,15+,16-,17-,20-,21+,22-/m1/s1

> <INCHI_KEY>
GYXLGRPTVRBMFK-OVURXTQHSA-N

> <FORMULA>
C22H28O6

> <MOLECULAR_WEIGHT>
388.46

> <EXACT_MASS>
388.188588622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.2663553850975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,3R,8R,10R,11R,12R,17R)-12,16,16-trimethyl-6-oxo-2,7,9-trioxahexacyclo[9.8.0.0^{1,3}.0^{4,8}.0^{8,10}.0^{12,17}]nonadec-4-en-5-yl]methyl acetate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.0859609426666665

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.042397373150915

> <JCHEM_POLAR_SURFACE_AREA>
77.66

> <JCHEM_REFRACTIVITY>
97.5695

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.04e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,3R,8R,10R,11R,12R,17R)-12,16,16-trimethyl-6-oxo-2,7,9-trioxahexacyclo[9.8.0.0^{1,3}.0^{4,8}.0^{8,10}.0^{12,17}]nonadec-4-en-5-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 61  0  0  0  0  0  0  0  0999 V2000
   -1.5311    5.2552   -4.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9065    4.2293   -3.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0518    3.8787   -3.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908    3.7410   -2.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2192    2.3234   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945    1.1727   -1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143   -0.0420   -2.2676 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6902   -0.8172   -2.8118 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0624   -1.3619   -1.6350 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3728   -2.6506   -1.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -3.2718   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6226   -3.4250    0.3921 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0944   -4.3944    1.5134 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3063   -4.0474    2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -5.8378    0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1123   -4.4501    2.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -3.0817    3.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385   -2.2394    2.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715   -2.0158    0.8515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0593   -1.0288    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9645   -1.3702   -0.3787 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5524   -0.0067   -0.0050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3412    0.6378   -1.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0859    1.2345   -0.6989 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0968    2.4737    0.0087 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766    3.1622   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321    4.2583    0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386    5.6566   -5.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    6.0769   -4.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9185    4.7942   -5.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229    1.9407   -2.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1201   -3.3579   -2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -2.6642   -0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7336   -4.2417   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078   -3.9461   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391   -3.9398    1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -3.1387    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738   -4.8455    2.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294   -6.1460    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107   -5.9366    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -6.5587    1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -5.0233    3.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097   -4.9938    2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069   -3.2127    3.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110   -2.5602    3.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0541   -2.7281    1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481   -1.2850    2.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4844   -0.0718    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5190   -1.3875    2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453   -0.8059    0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8170   -2.0250   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648    0.0632    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  1
 17 14  1  0
 14 16  1  0
 12 11  1  0
 25  7  1  0
 20 22  1  0
 13 12  1  0
 11 10  1  0
 22 10  1  0
 14 13  1  0
  7  6  2  0
  6 27  1  0
 27 26  1  0
 25 26  1  1
 20 19  1  0
 27 28  2  0
 20 13  1  0
  6  5  1  0
 23 24  1  0
 25 24  1  0
 22 23  1  0
 10  9  1  6
  8  9  1  0
 10  8  1  0
 23 56  1  1
  8  7  1  0
  8 34  1  6
 25 23  1  0
  5  4  1  0
 18 17  1  0
  4  2  1  0
 20 21  1  1
  2  1  1  0
 18 19  1  0
  2  3  2  0
 18 48  1  0
 18 49  1  0
 17 46  1  0
 17 47  1  0
 19 50  1  0
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 13 39  1  6
 12 37  1  0
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 11 35  1  0
 11 36  1  0
 22 55  1  6
 21 52  1  0
 21 53  1  0
 21 54  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
  5 32  1  0
  5 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.531   5.255  -4.594  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.907   4.229  -3.570  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.052   3.879  -3.324  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.791   3.741  -2.965  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.068   2.784  -1.939  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.219   2.323  -1.377  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.895   1.173  -1.515  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.614  -0.042  -2.268  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.690  -0.817  -2.812  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.062  -1.362  -1.635  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.373  -2.651  -1.987  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.343  -3.272  -0.798  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.623  -3.425   0.392  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.094  -4.394   1.513  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.306  -4.047   2.054  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.007  -5.838   0.948  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.112  -4.450   2.676  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.548  -3.082   3.174  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.139  -2.239   2.048  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.172  -2.016   0.852  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.059  -1.029   1.289  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.964  -1.370  -0.379  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.552  -0.007  -0.005  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.341   0.638  -1.024  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.086   1.234  -0.699  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.097   2.474   0.009  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.977   3.162  -0.396  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.632   4.258   0.008  0.00  0.00           O+0
HETATM   29  H   UNK     0      -2.439   5.657  -5.054  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.992   6.077  -4.116  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.919   4.794  -5.373  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.623   1.941  -2.366  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.682   3.243  -1.154  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.311  -0.042  -2.833  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.351  -2.496  -2.797  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.120  -3.358  -2.369  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.212  -2.664  -0.526  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.734  -4.242  -1.119  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.508  -3.946  -0.010  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.039  -3.940   1.248  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.323  -3.139   2.654  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.674  -4.846   2.711  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.929  -6.146   0.469  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.811  -5.937   0.212  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.217  -6.559   1.748  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.700  -5.023   3.517  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.010  -4.994   2.350  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.307  -3.213   3.955  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.711  -2.560   3.650  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.054  -2.728   1.690  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.448  -1.285   2.487  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.484  -0.072   1.612  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.519  -1.387   2.138  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.645  -0.806   0.483  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.817  -2.025  -0.607  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.965   0.063   0.989  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   32   33                                             
CONECT    6    7   27    5                                                  
CONECT    7   25    6    8                                                  
CONECT    8    9   10    7   34                                             
CONECT    9   10    8                                                       
CONECT   10   11   22    9    8                                             
CONECT   11   12   10   35   36                                             
CONECT   12   11   13   37   38                                             
CONECT   13   12   14   20   39                                             
CONECT   14   15   17   16   13                                             
CONECT   15   14   40   41   42                                             
CONECT   16   14   43   44   45                                             
CONECT   17   14   18   46   47                                             
CONECT   18   17   19   48   49                                             
CONECT   19   20   18   50   51                                             
CONECT   20   22   19   13   21                                             
CONECT   21   20   52   53   54                                             
CONECT   22   20   10   23   55                                             
CONECT   23   24   22   56   25                                             
CONECT   24   23   25                                                       
CONECT   25    7   26   24   23                                             
CONECT   26   27   25                                                       
CONECT   27    6   26   28                                                  
CONECT   28   27                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    8                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   23                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  122    0
END

RDKit          3D

56 61  0  0  0  0  0  0  0  0999 V2000
   -1.5311    5.2552   -4.5942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9065    4.2293   -3.5699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0518    3.8787   -3.3243 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7908    3.7410   -2.9648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    2.7842   -1.9387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2192    2.3234   -1.3773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945    1.1727   -1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6143   -0.0420   -2.2676 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6902   -0.8172   -2.8118 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0624   -1.3619   -1.6350 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3728   -2.6506   -1.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425   -3.2718   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6226   -3.4250    0.3921 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0944   -4.3944    1.5134 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3063   -4.0474    2.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -5.8378    0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1123   -4.4501    2.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -3.0817    3.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385   -2.2394    2.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1715   -2.0158    0.8515 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0593   -1.0288    1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9645   -1.3702   -0.3787 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5524   -0.0067   -0.0050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3412    0.6378   -1.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0859    1.2345   -0.6989 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0968    2.4737    0.0087 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766    3.1622   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321    4.2583    0.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386    5.6566   -5.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921    6.0769   -4.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9185    4.7942   -5.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6229    1.9407   -2.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6815    3.2426   -1.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3112   -0.0423   -2.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3506   -2.4958   -2.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1201   -3.3579   -2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2115   -2.6642   -0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7336   -4.2417   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078   -3.9461   -0.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391   -3.9398    1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -3.1387    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6738   -4.8455    2.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9294   -6.1460    0.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8107   -5.9366    0.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -6.5587    1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -5.0233    3.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097   -4.9938    2.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3069   -3.2127    3.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110   -2.5602    3.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0541   -2.7281    1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4481   -1.2850    2.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4844   -0.0718    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5190   -1.3875    2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453   -0.8059    0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8170   -2.0250   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9648    0.0632    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  1
 17 14  1  0
 14 16  1  0
 12 11  1  0
 25  7  1  0
 20 22  1  0
 13 12  1  0
 11 10  1  0
 22 10  1  0
 14 13  1  0
  7  6  2  0
  6 27  1  0
 27 26  1  0
 25 26  1  1
 20 19  1  0
 27 28  2  0
 20 13  1  0
  6  5  1  0
 23 24  1  0
 25 24  1  0
 22 23  1  0
 10  9  1  6
  8  9  1  0
 10  8  1  0
 23 56  1  1
  8  7  1  0
  8 34  1  6
 25 23  1  0
  5  4  1  0
 18 17  1  0
  4  2  1  0
 20 21  1  1
  2  1  1  0
 18 19  1  0
  2  3  2  0
 18 48  1  0
 18 49  1  0
 17 46  1  0
 17 47  1  0
 19 50  1  0
 19 51  1  0
 13 39  1  6
 12 37  1  0
 12 38  1  0
 11 35  1  0
 11 36  1  0
 22 55  1  6
 21 52  1  0
 21 53  1  0
 21 54  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
  5 32  1  0
  5 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
17-AJB CPD	MeSH

Chemical Formula

C₂₂H₂₈O₆

Average Mass

388.4600 Da

Monoisotopic Mass

388.18859 Da

IUPAC Name

[(1S,3R,8R,10R,11R,12R,17R)-12,16,16-trimethyl-6-oxo-2,7,9-trioxahexacyclo[9.8.0.0^{1,3}.0^{4,8}.0^{8,10}.0^{12,17}]nonadec-4-en-5-yl]methyl acetate

Traditional Name

[(1S,3R,8R,10R,11R,12R,17R)-12,16,16-trimethyl-6-oxo-2,7,9-trioxahexacyclo[9.8.0.0^{1,3}.0^{4,8}.0^{8,10}.0^{12,17}]nonadec-4-en-5-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])C(=O)OC([H])([H])C1=C2[C@@]3([H])O[C@]33C([H])([H])C([H])([H])[C@]4([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@]3([H])[C@@]3([H])O[C@@]23OC1=O

InChI Identifier

InChI=1S/C22H28O6/c1-11(23)25-10-12-14-16-21(26-16)9-6-13-19(2,3)7-5-8-20(13,4)15(21)17-22(14,27-17)28-18(12)24/h13,15-17H,5-10H2,1-4H3/t13-,15+,16-,17-,20-,21+,22-/m1/s1

InChI Key

GYXLGRPTVRBMFK-OVURXTQHSA-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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia fischeriana	JEOL database	Wang, Y. -B., et al, J. Nat. Prod. 69, 967 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Enol ester epoxide
Oxepane
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.41	ALOGPS
logP	3.09	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.57 m³·mol⁻¹	ChemAxon
Polarizability	41.27 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

9821496

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11646757

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yan SS, Li Y, Wang Y, Shen SS, Gu Y, Wang HB, Qin GW, Yu Q: 17-Acetoxyjolkinolide B irreversibly inhibits IkappaB kinase and induces apoptosis of tumor cells. Mol Cancer Ther. 2008 Jun;7(6):1523-32. doi: 10.1158/1535-7163.MCT-08-0263. [PubMed:18566223 ]
Wang YB, Huang R, Wang HB, Jin HZ, Lou LG, Qin GW: Diterpenoids from the roots of Euphorbia fischeriana. J Nat Prod. 2006 Jun;69(6):967-70. doi: 10.1021/np0600088. [PubMed:16792421 ]
Wang, Y. -B., et al. (2006). Wang, Y. -B., et al, J. Nat. Prod. 69, 967 (2006) . J. Nat. Prod..

Showing NP-Card for 17-acetoxyjolkinolide B (NP0032269)

MOL for NP0032269 (17-acetoxyjolkinolide B)

3D MOL for NP0032269 (17-acetoxyjolkinolide B)

3D SDF for NP0032269 (17-acetoxyjolkinolide B)

3D-SDF for NP0032269 (17-acetoxyjolkinolide B)

PDB for NP0032269 (17-acetoxyjolkinolide B)

3D PDB for NP0032269 (17-acetoxyjolkinolide B)

SMILES for NP0032269 (17-acetoxyjolkinolide B)

INCHI for NP0032269 (17-acetoxyjolkinolide B)

Structure for NP0032269 (17-acetoxyjolkinolide B)

3D Structure for NP0032269 (17-acetoxyjolkinolide B)