NP-MRD: Showing NP-Card for 13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide (NP0028991)

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Record Information

Version

2.0

Created at

2021-06-19 20:43:47 UTC

Updated at

2021-06-29 23:56:05 UTC

NP-MRD ID

NP0028991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide

Provided By

JEOL Database JEOL Logo

Description

13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide is found in Artemisia myriantha. 13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide was first documented in 2002 (Wong, H.-F., et al.). Based on a literature review very few articles have been published on Acetic acid [(9S)-2,4,5,8,9,11aalpha-hexahydro-6,10-dimethyl-9alpha-(tigloyloxy)-2-oxocyclodeca[b]furan]-3-ylmethyl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122433D          

 56 57  0  0  0  0            999 V2000
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    1.5151    2.2616    1.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192122433D          

 56 57  0  0  0  0            999 V2000
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    1.5151    2.2616    1.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5651    1.9753    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    2.8048    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138    4.3522    1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342    2.9993    2.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980    3.5669   -2.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128    2.2518   -3.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655    1.5423   -4.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770    0.4197   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519   -2.8480   -3.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3605   -1.8613   -1.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -2.5371   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0385   -0.2127   -4.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005   -1.7569   -4.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392   -1.9232   -3.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468   -2.8761   -2.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6719   -3.0817   -0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -3.7909    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822   -6.8260   -3.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807   -5.2415   -4.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -5.9004   -3.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187    0.1871   -0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3938    1.1328   -2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    4.1720   -3.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8073    3.1513   -4.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3577    2.8933   -3.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 13  1  0  0  0  0
 11 12  1  0  0  0  0
 26 25  1  0  0  0  0
 22 23  2  0  0  0  0
 15 14  1  0  0  0  0
 16 17  1  0  0  0  0
 14 13  1  0  0  0  0
 17 18  1  0  0  0  0
 15 25  1  0  0  0  0
 18 19  1  0  0  0  0
 27 26  2  0  0  0  0
 19 20  1  0  0  0  0
 11 10  2  0  0  0  0
 19 21  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
  7  5  1  0  0  0  0
  9 10  1  0  0  0  0
  5  3  1  0  0  0  0
 25 24  1  0  0  0  0
  5  6  2  0  0  0  0
 24 22  1  0  0  0  0
  3  2  2  0  0  0  0
 22 16  1  0  0  0  0
  2  1  1  0  0  0  0
 16 15  2  0  0  0  0
  3  4  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
  8 36  1  6  0  0  0
 10 39  1  0  0  0  0
 26 53  1  0  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 25 52  1  1  0  0  0
 28 54  1  0  0  0  0
 28 55  1  0  0  0  0
 28 56  1  0  0  0  0
 12 40  1  0  0  0  0
 12 41  1  0  0  0  0
 12 42  1  0  0  0  0
 17 47  1  0  0  0  0
 17 48  1  0  0  0  0
 20 49  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
  2 32  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
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028991

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(/C(=O)O[C@]1([H])\C(=C([H])/[C@@]2([H])OC(=O)C(=C2C([H])([H])C([H])([H])\C(=C([H])/C1([H])[H])C([H])([H])[H])C([H])([H])OC(=O)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O6/c1-6-14(3)21(24)27-19-10-8-13(2)7-9-17-18(12-26-16(5)23)22(25)28-20(17)11-15(19)4/h6,8,11,19-20H,7,9-10,12H2,1-5H3/b13-8-,14-6+,15-11-/t19-,20+/m0/s1

> <INCHI_KEY>
GLMKCGIRLHWKCY-GVOJNPQGSA-N

> <FORMULA>
C22H28O6

> <MOLECULAR_WEIGHT>
388.46

> <EXACT_MASS>
388.188588622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.03623995154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,11aR)-3-[(acetyloxy)methyl]-6,10-dimethyl-2-oxo-2H,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
3.9350093029999993

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.245546972653507

> <JCHEM_PKA_STRONGEST_BASIC>
-6.466407635130268

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
106.94679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,11aR)-3-[(acetyloxy)methyl]-6,10-dimethyl-2-oxo-4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
    1.5554    1.9934    3.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5151    2.2616    1.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781    2.8089    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8277    3.2639    1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0250    3.6811   -1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8607    2.5095   -2.4644 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.2641    0.3421   -2.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7171   -0.8779   -2.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -2.0961   -2.3919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4433   -1.1340   -3.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804   -1.8479   -2.9737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755   -1.2565   -1.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6068   -3.2095   -0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4900   -3.9153   -1.9317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0223   -5.1662   -1.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8546   -5.8198   -3.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5594   -5.6901   -0.9428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715   -0.9241    0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8210   -1.1513    1.3203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490    0.2453    0.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8408    0.1166   -1.2031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3302    1.1977   -2.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189    2.1977   -2.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3076    3.1547   -3.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    0.9170    3.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7041    2.4834    3.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618    2.3519    3.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5651    1.9753    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    2.8048    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138    4.3522    1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342    2.9993    2.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980    3.5669   -2.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128    2.2518   -3.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655    1.5423   -4.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770    0.4197   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519   -2.8480   -3.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3605   -1.8613   -1.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -2.5371   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0385   -0.2127   -4.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005   -1.7569   -4.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392   -1.9232   -3.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468   -2.8761   -2.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6719   -3.0817   -0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -3.7909    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822   -6.8260   -3.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807   -5.2415   -4.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -5.9004   -3.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187    0.1871   -0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3938    1.1328   -2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    4.1720   -3.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8073    3.1513   -4.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3577    2.8933   -3.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 27  1  0
 27 28  1  0
 11 13  1  0
 11 12  1  0
 26 25  1  0
 22 23  2  0
 15 14  1  0
 16 17  1  0
 14 13  1  0
 17 18  1  0
 15 25  1  0
 18 19  1  0
 27 26  2  0
 19 20  1  0
 11 10  2  0
 19 21  2  0
  8  7  1  0
  9  8  1  0
  7  5  1  0
  9 10  1  0
  5  3  1  0
 25 24  1  0
  5  6  2  0
 24 22  1  0
  3  2  2  0
 22 16  1  0
  2  1  1  0
 16 15  2  0
  3  4  1  0
  9 37  1  0
  9 38  1  0
  8 36  1  6
 10 39  1  0
 26 53  1  0
 14 45  1  0
 14 46  1  0
 13 43  1  0
 13 44  1  0
 25 52  1  1
 28 54  1  0
 28 55  1  0
 28 56  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 17 47  1  0
 17 48  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 33  1  0
  4 34  1  0
  4 35  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       1.555   1.993   3.087  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.515   2.262   1.615  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.478   2.809   0.845  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.828   3.264   1.320  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.264   3.025  -0.623  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.025   3.681  -1.319  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.159   2.379  -1.065  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.861   2.510  -2.464  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.799   1.667  -3.364  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.264   0.342  -2.805  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.717  -0.878  -2.978  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.386  -2.096  -2.392  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.443  -1.134  -3.752  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.680  -1.848  -2.974  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.176  -1.256  -1.680  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.953  -1.875  -0.780  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.607  -3.209  -0.691  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.490  -3.915  -1.932  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.022  -5.166  -1.907  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.855  -5.820  -3.244  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.559  -5.690  -0.943  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.172  -0.924   0.316  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.821  -1.151   1.320  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.549   0.245   0.032  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.841   0.117  -1.203  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.330   1.198  -2.122  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.619   2.198  -2.688  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.308   3.155  -3.631  0.00  0.00           C+0
HETATM   29  H   UNK     0       1.474   0.917   3.267  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.704   2.483   3.570  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.462   2.352   3.577  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.565   1.975   1.163  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.619   2.805   0.717  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.914   4.352   1.233  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.034   2.999   2.359  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.998   3.567  -2.733  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.713   2.252  -3.539  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.365   1.542  -4.363  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.177   0.420  -2.212  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.552  -2.848  -3.170  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.361  -1.861  -1.951  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.767  -2.537  -1.605  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.039  -0.213  -4.181  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.701  -1.757  -4.620  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.539  -1.923  -3.654  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.347  -2.876  -2.785  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.672  -3.082  -0.463  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.130  -3.791   0.108  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.282  -6.826  -3.212  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.381  -5.242  -4.008  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.792  -5.900  -3.487  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.219   0.187  -0.962  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.394   1.133  -2.351  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.281   4.172  -3.227  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.807   3.151  -4.605  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.358   2.893  -3.800  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1   32                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3   33   34   35                                             
CONECT    5    7    3    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8   27    7    9   36                                             
CONECT    9    8   10   37   38                                             
CONECT   10   11    9   39                                                  
CONECT   11   13   12   10                                                  
CONECT   12   11   40   41   42                                             
CONECT   13   11   14   43   44                                             
CONECT   14   15   13   45   46                                             
CONECT   15   14   25   16                                                  
CONECT   16   17   22   15                                                  
CONECT   17   16   18   47   48                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   49   50   51                                             
CONECT   21   19                                                            
CONECT   22   23   24   16                                                  
CONECT   23   22                                                            
CONECT   24   25   22                                                       
CONECT   25   26   15   24   52                                             
CONECT   26   25   27   53                                                  
CONECT   27    8   28   26                                                  
CONECT   28   27   54   55   56                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   12                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   28                                                            
CONECT   55   28                                                            
CONECT   56   28                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  114    0
END

RDKit          3D

56 57  0  0  0  0  0  0  0  0999 V2000
    1.5554    1.9934    3.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5151    2.2616    1.6154 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8408    0.1166   -1.2031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3302    1.1977   -2.1219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189    2.1977   -2.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3076    3.1547   -3.6311 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    0.9170    3.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7041    2.4834    3.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618    2.3519    3.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5651    1.9753    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6186    2.8048    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138    4.3522    1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342    2.9993    2.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9980    3.5669   -2.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128    2.2518   -3.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655    1.5423   -4.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1770    0.4197   -2.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519   -2.8480   -3.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3605   -1.8613   -1.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -2.5371   -1.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0385   -0.2127   -4.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7005   -1.7569   -4.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392   -1.9232   -3.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468   -2.8761   -2.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6719   -3.0817   -0.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -3.7909    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2822   -6.8260   -3.2123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807   -5.2415   -4.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -5.9004   -3.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187    0.1871   -0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3938    1.1328   -2.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    4.1720   -3.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8073    3.1513   -4.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3577    2.8933   -3.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
  8 27  1  0
 27 28  1  0
 11 13  1  0
 11 12  1  0
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 22 23  2  0
 15 14  1  0
 16 17  1  0
 14 13  1  0
 17 18  1  0
 15 25  1  0
 18 19  1  0
 27 26  2  0
 19 20  1  0
 11 10  2  0
 19 21  2  0
  8  7  1  0
  9  8  1  0
  7  5  1  0
  9 10  1  0
  5  3  1  0
 25 24  1  0
  5  6  2  0
 24 22  1  0
  3  2  2  0
 22 16  1  0
  2  1  1  0
 16 15  2  0
  3  4  1  0
  9 37  1  0
  9 38  1  0
  8 36  1  6
 10 39  1  0
 26 53  1  0
 14 45  1  0
 14 46  1  0
 13 43  1  0
 13 44  1  0
 25 52  1  1
 28 54  1  0
 28 55  1  0
 28 56  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 17 47  1  0
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 20 49  1  0
 20 50  1  0
 20 51  1  0
  2 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 33  1  0
  4 34  1  0
  4 35  1  0
M  END

View in JSmol

Synonyms

Value	Source
(9S,11AR)-3-[(acetyloxy)methyl]-6,10-dimethyl-2-oxo-2H,4H,5H,8H,9H,11ah-cyclodeca[b]furan-9-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₂H₂₈O₆

Average Mass

388.4600 Da

Monoisotopic Mass

388.18859 Da

IUPAC Name

(9S,11aR)-3-[(acetyloxy)methyl]-6,10-dimethyl-2-oxo-2H,4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl (2E)-2-methylbut-2-enoate

Traditional Name

(9S,11aR)-3-[(acetyloxy)methyl]-6,10-dimethyl-2-oxo-4H,5H,8H,9H,11aH-cyclodeca[b]furan-9-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/C(=O)O[C@]1([H])\C(=C([H])/[C@@]2([H])OC(=O)C(=C2C([H])([H])C([H])([H])\C(=C([H])/C1([H])[H])C([H])([H])[H])C([H])([H])OC(=O)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H28O6/c1-6-14(3)21(24)27-19-10-8-13(2)7-9-17-18(12-26-16(5)23)22(25)28-20(17)11-15(19)4/h6,8,11,19-20H,7,9-10,12H2,1-5H3/b13-8-,14-6+,15-11-/t19-,20+/m0/s1

InChI Key

GLMKCGIRLHWKCY-GVOJNPQGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Artemisia myriantha	JEOL database	Wong, H.-F., e al, Phytochemistry 59, 529 (2002)

Chemical Taxonomy

Classification

Not classified

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	3.73	ALOGPS
logP	3.94	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.95 m³·mol⁻¹	ChemAxon
Polarizability	42.04 Å³	ChemAxon
Number of Rings	2	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

101182171

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wong, H.-F., et al. (2002). Wong, H.-F., e al, Phytochemistry 59, 529 (2002). Phytochem..

Showing NP-Card for 13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide (NP0028991)

MOL for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)

3D MOL for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)

3D SDF for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)

3D-SDF for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)

PDB for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)

3D PDB for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)

SMILES for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)

INCHI for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)

Structure for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)

3D Structure for NP0028991 (13-acetoxy-3beta-tigloyl-germacra-1(10)E,4E,7(11)-trien-12,6alpha-olide)