NP-MRD: Showing NP-Card for Xenovulene A (NP0022375)

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Record Information

Version

1.0

Created at

2021-01-06 07:34:08 UTC

Updated at

2021-07-15 17:38:52 UTC

NP-MRD ID

NP0022375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xenovulene A

Provided By

NPAtlas

Description

Xenovulene A is found in Acremonium and Acremonium strictum. It was first documented in 1995 (PMID: 7649852).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105353D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242105353D          

 56 59  0  0  0  0            999 V2000
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   -4.6253   -0.7507   -1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915   -1.5697   -2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030   -1.5712   -1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -2.3373    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -0.7675    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4308   -1.2750    3.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843    0.2309    2.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1194   -1.3828    2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807   -3.4072   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0312    1.4795    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0622    2.5601   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0522    1.0416   -2.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.3079    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4592    0.3584    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377    0.6807   -0.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    1.7358    2.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499    2.8144    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317    1.4929    1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6136    3.1109    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26  2  1  0  0  0  0
 24 11  1  0  0  0  0
 23 14  1  0  0  0  0
 23 19  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  3 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
  6 35  1  0  0  0  0
  7 36  1  0  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
  8 39  1  0  0  0  0
  9 40  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 12 45  1  0  0  0  0
 16 46  1  0  0  0  0
 19 47  1  1  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 22 50  1  1  0  0  0
 23 51  1  1  0  0  0
 24 52  1  6  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 26 55  1  0  0  0  0
 26 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2O[C@]3(C([H])([H])[H])C([H])([H])\C([H])=C([H])/C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])\C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])[C@@]3([H])[C@]3([H])OC([H])([H])[C@]([H])(C1=O)[C@]23[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O4/c1-13-6-7-15-19-16-14(12-25-19)17(23)18(24)20(16)26-22(15,4)10-5-9-21(2,3)11-8-13/h5,8-9,14-16,19,24H,6-7,10-12H2,1-4H3/b9-5-,13-8-/t14-,15-,16-,19-,22+/m0/s1

> <INCHI_KEY>
WDFUVZRTUNQXHC-JSDSTTSESA-N

> <FORMULA>
C22H30O4

> <MOLECULAR_WEIGHT>
358.478

> <EXACT_MASS>
358.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.91468129948345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5Z,9Z,12R,17R,20S)-15-hydroxy-5,8,8,12-tetramethyl-13,19-dioxatetracyclo[12.5.1.0^{2,12}.0^{17,20}]icosa-5,9,14-trien-16-one

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
3.1601038439999987

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.249226007016357

> <JCHEM_PKA_STRONGEST_BASIC>
-4.088369491853777

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
104.55189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5Z,9Z,12R,17R,20S)-15-hydroxy-5,8,8,12-tetramethyl-13,19-dioxatetracyclo[12.5.1.0^{2,12}.0^{17,20}]icosa-5,9,14-trien-16-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
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   -1.7628    1.8208   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0578   -1.4473   -1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526   -1.4487   -0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7652   -0.6002    1.0093 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2121   -0.7181    2.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271   -1.4133    0.2285 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8891   -0.9529   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085   -1.4358   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306   -2.6378   -1.3703 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232   -0.4664   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2366   -0.7109   -0.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3968    0.8205   -0.3066 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7062    1.5095   -1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3539    1.3906   -1.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    1.3035    0.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2310    0.3811    0.5544 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7557    0.7602    0.4303 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0652    1.8346    1.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4022    2.0116    0.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1064    3.0014   -1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556    1.9614   -2.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6365    3.4779   -1.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9268    0.8898   -1.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284    0.2879    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5809    0.4327   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4449   -2.8016    0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111   -2.5446   -1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3589   -1.8008   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6253   -0.7507   -1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915   -1.5697   -2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030   -1.5712   -1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -2.3373    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -0.7675    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4308   -1.2750    3.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843    0.2309    2.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1194   -1.3828    2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807   -3.4072   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0312    1.4795    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0622    2.5601   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0522    1.0416   -2.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.3079    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4592    0.3584    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377    0.6807   -0.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    1.7358    2.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499    2.8144    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317    1.4929    1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6136    3.1109    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26  2  1  0
 24 11  1  0
 23 14  1  0
 23 19  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 12 43  1  0
 12 44  1  0
 12 45  1  0
 16 46  1  0
 19 47  1  1
 20 48  1  0
 20 49  1  0
 22 50  1  1
 23 51  1  1
 24 52  1  6
 25 53  1  0
 25 54  1  0
 26 55  1  0
 26 56  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.049   2.598  -1.466  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.763   1.821  -0.417  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.699   0.987  -0.764  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.505   0.141   0.129  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.292  -1.290  -0.326  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.436  -2.283   0.795  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.435  -1.593  -1.289  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.058  -1.447  -1.120  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.853  -1.449  -0.586  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.615  -1.296   0.830  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.765  -0.600   1.009  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.212  -0.718   2.433  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.627  -1.413   0.229  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.889  -0.953  -0.033  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.909  -1.436  -0.709  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.931  -2.638  -1.370  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.023  -0.466  -0.638  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.237  -0.711  -0.824  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.397   0.821  -0.307  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.706   1.510  -1.431  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.354   1.391  -1.260  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.145   1.304   0.111  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.231   0.381   0.554  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.756   0.760   0.430  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.065   1.835   1.190  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.402   2.012   0.971  0.00  0.00           C+0
HETATM   27  H   UNK     0      -0.106   3.001  -1.048  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.756   1.961  -2.340  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.637   3.478  -1.801  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.927   0.890  -1.835  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.428   0.288   1.190  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.581   0.433  -0.088  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.717  -3.127   0.733  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.430  -1.794   1.811  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.445  -2.802   0.791  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.211  -2.545  -1.813  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.359  -1.801  -0.684  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.625  -0.751  -1.976  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.091  -1.570  -2.199  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.003  -1.571  -1.248  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.524  -2.337   1.270  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.302  -0.768   1.452  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.431  -1.275   3.036  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.484   0.231   2.926  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.119  -1.383   2.553  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.481  -3.407  -0.988  0.00  0.00           H+0
HETATM   47  H   UNK     0       5.031   1.480   0.310  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.062   2.560  -1.471  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.052   1.042  -2.391  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.323   2.308   0.523  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.459   0.358   1.612  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.238   0.681  -0.576  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.316   1.736   2.269  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.550   2.814   0.899  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.932   1.493   1.750  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.614   3.111   1.191  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   26                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5   31   32                                             
CONECT    5    4    6    7    8                                             
CONECT    6    5   33   34   35                                             
CONECT    7    5   36   37   38                                             
CONECT    8    5    9   39                                                  
CONECT    9    8   10   40                                                  
CONECT   10    9   11   41   42                                             
CONECT   11   10   12   13   24                                             
CONECT   12   11   43   44   45                                             
CONECT   13   11   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   46                                                       
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   23   47                                             
CONECT   20   19   21   48   49                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24   50                                             
CONECT   23   22   14   19   51                                             
CONECT   24   22   25   11   52                                             
CONECT   25   24   26   53   54                                             
CONECT   26   25    2   55   56                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   16                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  118    0
END

RDKit          3D

56 59  0  0  0  0  0  0  0  0999 V2000
   -1.0490    2.5981   -1.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628    1.8208   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6986    0.9871   -0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5051    0.1406    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2920   -1.2897   -0.3263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4360   -2.2831    0.7946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4348   -1.5925   -1.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0578   -1.4473   -1.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8526   -1.4487   -0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152   -1.2963    0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652   -0.6002    1.0093 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2121   -0.7181    2.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6271   -1.4133    0.2285 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8891   -0.9529   -0.0328 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9085   -1.4358   -0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9306   -2.6378   -1.3703 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232   -0.4664   -0.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2366   -0.7109   -0.8235 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3968    0.8205   -0.3066 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7062    1.5095   -1.4309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3539    1.3906   -1.2598 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450    1.3035    0.1114 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2310    0.3811    0.5544 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7557    0.7602    0.4303 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0652    1.8346    1.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4022    2.0116    0.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1064    3.0014   -1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556    1.9614   -2.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6365    3.4779   -1.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9268    0.8898   -1.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284    0.2879    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5809    0.4327   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171   -3.1272    0.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4298   -1.7941    1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4449   -2.8016    0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2111   -2.5446   -1.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3589   -1.8008   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6253   -0.7507   -1.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0915   -1.5697   -2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030   -1.5712   -1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5239   -2.3373    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -0.7675    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4308   -1.2750    3.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843    0.2309    2.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1194   -1.3828    2.5532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807   -3.4072   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0312    1.4795    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0622    2.5601   -1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0522    1.0416   -2.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.3079    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4592    0.3584    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377    0.6807   -0.5762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3161    1.7358    2.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499    2.8144    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317    1.4929    1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6136    3.1109    1.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26  2  1  0
 24 11  1  0
 23 14  1  0
 23 19  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 12 43  1  0
 12 44  1  0
 12 45  1  0
 16 46  1  0
 19 47  1  1
 20 48  1  0
 20 49  1  0
 22 50  1  1
 23 51  1  1
 24 52  1  6
 25 53  1  0
 25 54  1  0
 26 55  1  0
 26 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₄

Average Mass

358.4780 Da

Monoisotopic Mass

358.21441 Da

IUPAC Name

(1S,2S,5Z,9Z,12R,17R,20S)-15-hydroxy-5,8,8,12-tetramethyl-13,19-dioxatetracyclo[12.5.1.0^{2,12}.0^{17,20}]icosa-5,9,14-trien-16-one

Traditional Name

(1S,2S,5Z,9Z,12R,17R,20S)-15-hydroxy-5,8,8,12-tetramethyl-13,19-dioxatetracyclo[12.5.1.0^{2,12}.0^{17,20}]icosa-5,9,14-trien-16-one

CAS Registry Number

Not Available

SMILES

C\C1=C\CC(C)(C)\C=C/C[C@@]2(C)OC3=C(O)C(=O)[C@H]4CO[C@H]([C@@H]34)[C@@H]2CC1

InChI Identifier

InChI=1S/C22H30O4/c1-13-6-7-15-19-16-14(12-25-19)17(23)18(24)20(16)26-22(15,4)10-5-9-21(2,3)11-8-13/h5,8-9,14-16,19,24H,6-7,10-12H2,1-4H3/b9-5-,13-8-/t14-,15-,16-,19-,22+/m0/s1

InChI Key

WDFUVZRTUNQXHC-JSDSTTSESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acremonium	NPAtlas	7649852
Acremonium strictum	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Vinylogous ester
Tetrahydrofuran
Ketone
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.08	ALOGPS
logP	3.16	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.25	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	104.55 m³·mol⁻¹	ChemAxon
Polarizability	39.91 Å³	ChemAxon
Number of Rings	4	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

NPAtlas ID

NPA007151

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58168780

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ainsworth AM, Chicarelli-Robinson MI, Copp BR, Fauth U, Hylands PJ, Holloway JA, Latif M, O'Beirne GB, Porter N, Renno DV, et al.: Xenovulene A, a novel GABA-benzodiazepine receptor binding compound produced by Acremonium strictum. J Antibiot (Tokyo). 1995 Jul;48(7):568-73. doi: 10.7164/antibiotics.48.568. [PubMed:7649852 ]

Showing NP-Card for Xenovulene A (NP0022375)

MOL for NP0022375 (Xenovulene A)

3D MOL for NP0022375 (Xenovulene A)

3D SDF for NP0022375 (Xenovulene A)

3D-SDF for NP0022375 (Xenovulene A)

PDB for NP0022375 (Xenovulene A)

3D PDB for NP0022375 (Xenovulene A)

SMILES for NP0022375 (Xenovulene A)

INCHI for NP0022375 (Xenovulene A)

Structure for NP0022375 (Xenovulene A)

3D Structure for NP0022375 (Xenovulene A)