NP-MRD: Showing NP-Card for Asperterpene F (NP0018678)

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Record Information

Version

2.0

Created at

2021-01-06 03:19:50 UTC

Updated at

2021-07-15 17:28:52 UTC

NP-MRD ID

NP0018678

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperterpene F

Provided By

NPAtlas

Description

(1S,2R,5S,7S,10S,11S,16R,18S)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadecane-3,6,14,17-tetrone belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Asperterpene F is found in Aspergillus terreus. Based on a literature review very few articles have been published on (1S,2R,5S,7S,10S,11S,16R,18S)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-4-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadecane-3,6,14,17-tetrone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104373D          

 62 65  0  0  0  0            999 V2000
    2.1192   -2.9693    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843   -1.7004    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5399   -1.2220    1.3058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2678   -0.4523    0.3252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6654   -0.1666    0.7670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7508    0.4347    2.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -1.4803    0.8430 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8409   -1.9823   -0.5175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9068   -1.0377   -0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8147   -1.4108   -1.6869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7703    0.3794   -0.5512 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1264    1.2288   -1.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5146    2.8112   -0.8504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244    0.7441   -0.1338 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.2695    2.5098   -1.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5276   -1.2595   -1.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9966    1.5357    2.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4048   -1.2015    1.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -2.2338    1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2240    0.6315   -2.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1299    1.7278   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
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 19 21  1  0  0  0  0
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  1 31  1  0  0  0  0
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 30 60  1  0  0  0  0
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M  END

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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   -3.9068   -1.0377   -0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8147   -1.4108   -1.6869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7703    0.3794   -0.5512 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242104373D          

 62 65  0  0  0  0            999 V2000
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    3.5801   -2.3598   -1.5357 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9966    1.5357    2.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4048   -1.2015    1.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -2.2338    1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2757   -2.9993   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -2.1000   -1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140    2.0562   -1.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240    0.6315   -2.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1299    1.7278   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3396    1.0884    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4632   -0.1371    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4896    1.5379    0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2454    1.5059   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500    3.4356   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7700    2.3123    0.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686    1.3337    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415    2.5211    0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119   -0.2988   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6540   -0.4898   -2.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0630   -1.2649   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6451   -0.1059   -1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9840    0.5681   -0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -0.6556    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -0.0820    1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220    0.9640    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  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
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29  2  1  0  0  0  0
 19  4  1  0  0  0  0
 29 21  1  0  0  0  0
 14  5  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  6  0  0  0
  6 36  1  0  0  0  0
  6 37  1  0  0  0  0
  6 38  1  0  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
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  8 42  1  0  0  0  0
 12 43  1  0  0  0  0
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 13 47  1  0  0  0  0
 13 48  1  0  0  0  0
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 25 56  1  6  0  0  0
 26 57  1  0  0  0  0
 26 58  1  0  0  0  0
 26 59  1  0  0  0  0
 30 60  1  0  0  0  0
 30 61  1  0  0  0  0
 30 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0018678

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=O)[C@@]2([H])C(C(=O)C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]2([H])C([H])([H])C(=C([H])[H])[C@]3(C(=O)[C@@]([H])(OC(=O)[C@]3([H])[C@@]12C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-11-10-13-22(5)9-8-14(25)21(3,4)16(22)15(26)19(28)24(13,7)17-20(29)30-12(2)18(27)23(11,17)6/h12-13,16-17,19,28H,1,8-10H2,2-7H3/t12-,13-,16-,17-,19+,22-,23+,24-/m0/s1

> <INCHI_KEY>
OJCUHOMXXINHDN-ZKRXJUSPSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.514

> <EXACT_MASS>
416.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
43.69748515680209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,7S,10S,11S,16R,18S)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-4-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadecane-3,6,14,17-tetrone

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
3.234268778666668

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.876350744870003

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.924883472808947

> <JCHEM_PKA_STRONGEST_BASIC>
-3.706427969839088

> <JCHEM_POLAR_SURFACE_AREA>
97.74000000000001

> <JCHEM_REFRACTIVITY>
108.83449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7S,10S,11S,16R,18S)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-4-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadecane-3,6,14,17-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 65  0  0  0  0  0  0  0  0999 V2000
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    3.8220    0.9640    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  6
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  1
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 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  1
 29  2  1  0
 19  4  1  0
 29 21  1  0
 14  5  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  6
  6 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 12 43  1  0
 12 44  1  0
 12 45  1  0
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 13 47  1  0
 13 48  1  0
 14 49  1  1
 17 50  1  6
 18 51  1  0
 20 52  1  0
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 20 54  1  0
 21 55  1  6
 25 56  1  6
 26 57  1  0
 26 58  1  0
 26 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  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       2.119  -2.969   0.703  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.784  -1.700   0.638  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.540  -1.222   1.306  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.268  -0.452   0.325  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.665  -0.167   0.767  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.751   0.435   2.159  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.437  -1.480   0.843  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.841  -1.982  -0.518  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.907  -1.038  -0.992  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.815  -1.411  -1.687  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.770   0.379  -0.551  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.126   1.229  -1.782  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.784   0.722   0.524  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.386   0.742  -0.161  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.562   0.808  -1.424  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.918   0.349  -2.471  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.246   1.512  -1.221  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.515   2.811  -0.850  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.524   0.744  -0.134  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.845   1.728   0.935  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.767   0.273  -0.795  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.629   1.332  -1.342  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.269   2.510  -1.606  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.959   1.045  -1.603  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.497  -0.255  -1.651  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.827  -0.269  -0.984  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.528  -1.260  -1.098  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.580  -2.360  -1.536  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.614  -0.721  -0.056  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.515  -0.061   0.975  0.00  0.00           C+0
HETATM   31  H   UNK     0       2.974  -3.439   0.276  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.453  -3.652   1.260  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.843  -0.650   2.209  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.027  -2.121   1.705  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.361  -1.110  -0.592  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.884   0.246   2.787  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.997   1.536   2.090  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.629   0.012   2.734  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.405  -1.202   1.360  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.982  -2.234   1.480  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.276  -2.999  -0.355  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.024  -2.100  -1.226  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.414   2.056  -1.924  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.224   0.632  -2.692  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.130   1.728  -1.642  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.340   1.088   1.450  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.463  -0.137   0.750  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.490   1.538   0.186  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.409   1.793   0.219  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.245   1.506  -2.191  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.450   3.436  -1.616  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.770   2.312   0.652  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.069   1.334   1.924  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.042   2.521   0.964  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.412  -0.299  -1.714  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.654  -0.490  -2.733  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.063  -1.265  -0.549  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.645  -0.106  -1.748  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.984   0.568  -0.258  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.441  -0.656   1.102  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.025  -0.082   1.993  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.822   0.964   0.706  0.00  0.00           H+0
CONECT    1    2   31   32                                                  
CONECT    2    1    3   29                                                  
CONECT    3    2    4   33   34                                             
CONECT    4    3    5   19   35                                             
CONECT    5    4    6    7   14                                             
CONECT    6    5   36   37   38                                             
CONECT    7    5    8   39   40                                             
CONECT    8    7    9   41   42                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11   43   44   45                                             
CONECT   13   11   46   47   48                                             
CONECT   14   11   15    5   49                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   50                                             
CONECT   18   17   51                                                       
CONECT   19   17   20   21    4                                             
CONECT   20   19   52   53   54                                             
CONECT   21   19   22   29   55                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27   56                                             
CONECT   26   25   57   58   59                                             
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30    2   21                                             
CONECT   30   29   60   61   62                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    6                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   20                                                            
CONECT   53   20                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   30                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  130    0
END

RDKit          3D

62 65  0  0  0  0  0  0  0  0999 V2000
    2.1192   -2.9693    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843   -1.7004    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5399   -1.2220    1.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2678   -0.4523    0.3252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6654   -0.1666    0.7670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7508    0.4347    2.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4367   -1.4803    0.8430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8409   -1.9823   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9068   -1.0377   -0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8147   -1.4108   -1.6869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7703    0.3794   -0.5512 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1264    1.2288   -1.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7842    0.7221    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3865    0.7418   -0.1612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5618    0.8077   -1.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9178    0.3488   -2.4713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2455    1.5120   -1.2211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5146    2.8112   -0.8504 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244    0.7441   -0.1338 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8452    1.7277    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7668    0.2733   -0.7949 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6287    1.3322   -1.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695    2.5098   -1.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595    1.0451   -1.6034 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4968   -0.2550   -1.6514 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8268   -0.2692   -0.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276   -1.2595   -1.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801   -2.3598   -1.5357 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6141   -0.7206   -0.0557 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5149   -0.0608    0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9737   -3.4388    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4528   -3.6520    1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8427   -0.6499    2.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -2.1212    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -1.1099   -0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8836    0.2455    2.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9966    1.5357    2.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6291    0.0120    2.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4048   -1.2015    1.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -2.2338    1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2757   -2.9993   -0.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241   -2.1000   -1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4140    2.0562   -1.9236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2240    0.6315   -2.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1299    1.7278   -1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3396    1.0884    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4632   -0.1371    0.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4896    1.5379    0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090    1.7927    0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454    1.5059   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500    3.4356   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7700    2.3123    0.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686    1.3337    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415    2.5211    0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4119   -0.2988   -1.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6540   -0.4898   -2.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0630   -1.2649   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6451   -0.1059   -1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9840    0.5681   -0.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -0.6556    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -0.0820    1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220    0.9640    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  6
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  1
 29  2  1  0
 19  4  1  0
 29 21  1  0
 14  5  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  6
  6 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 12 43  1  0
 12 44  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  1
 17 50  1  6
 18 51  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  6
 25 56  1  6
 26 57  1  0
 26 58  1  0
 26 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5140 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

(1S,2R,5S,7S,10S,11S,16R,18S)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-4-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadecane-3,6,14,17-tetrone

Traditional Name

(1S,2R,5S,7S,10S,11S,16R,18S)-18-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-4-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadecane-3,6,14,17-tetrone

CAS Registry Number

Not Available

SMILES

C[C@@H]1OC(=O)[C@@H]2[C@@]3(C)[C@H](O)C(=O)[C@H]4C(C)(C)C(=O)CC[C@@]4(C)[C@@H]3CC(=C)[C@@]2(C)C1=O

InChI Identifier

InChI=1S/C24H32O6/c1-11-10-13-22(5)9-8-14(25)21(3,4)16(22)15(26)19(28)24(13,7)17-20(29)30-12(2)18(27)23(11,17)6/h12-13,16-17,19,28H,1,8-10H2,2-7H3/t12-,13-,16-,17-,19+,22-,23+,24-/m0/s1

InChI Key

OJCUHOMXXINHDN-ZKRXJUSPSA-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
Aspergillus terreus	NPAtlas	30207465

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five 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

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Alpha-acyloxy ketone
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.48	ALOGPS
logP	3.23	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.92	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.74 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	108.83 m³·mol⁻¹	ChemAxon
Polarizability	43.7 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

NPA022780

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439133

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590113

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Asperterpene F (NP0018678)

MOL for NP0018678 (Asperterpene F)

3D MOL for NP0018678 (Asperterpene F)

3D SDF for NP0018678 (Asperterpene F)

3D-SDF for NP0018678 (Asperterpene F)

PDB for NP0018678 (Asperterpene F)

3D PDB for NP0018678 (Asperterpene F)

SMILES for NP0018678 (Asperterpene F)

INCHI for NP0018678 (Asperterpene F)

Structure for NP0018678 (Asperterpene F)

3D Structure for NP0018678 (Asperterpene F)