NP-MRD: Showing NP-Card for Asperolide C (NP0010613)

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Record Information

Version

2.0

Created at

2021-01-05 20:04:30 UTC

Updated at

2021-07-15 17:06:35 UTC

NP-MRD ID

NP0010613

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Asperolide C

Provided By

NPAtlas

Description

(3AS,5aR,6S,9aS,9bR)-3a-(hydroxymethyl)-6,9a-dimethyl-2-oxo-dodecahydronaphtho[2,1-b]furan-6-carboxylic acid 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. Asperolide C is found in Aspergillus. Based on a literature review very few articles have been published on (3aS,5aR,6S,9aS,9bR)-3a-(hydroxymethyl)-6,9a-dimethyl-2-oxo-dodecahydronaphtho[2,1-b]furan-6-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107393D          

 45 47  0  0  0  0            999 V2000
    2.7451   -0.5734   -1.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073   -0.1152   -0.1437 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7292    1.1827    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3642    1.2728    1.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    2.2853   -0.6283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936   -1.1520    0.8886 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2059   -2.0422    1.1797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0175   -1.3060    1.5899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1894    0.0254    0.8723 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2916    1.0941    1.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253    0.2327    0.5715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1214    1.6330    0.8848 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3171    1.7399    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2487    2.5910    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2879    0.7299   -0.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0551   -0.0097   -0.8215 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5127   -1.4340   -1.0815 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4435   -1.7263   -0.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698    0.5331   -1.8834 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1988    0.9437   -1.3974 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6371   -0.0553   -0.3807 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7220   -1.0504   -1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    0.2989   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607   -1.2760   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742    2.5067   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -0.7063    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105   -1.8390    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647   -2.7188    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147   -2.6939    2.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9004   -1.9558    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795   -1.1490    2.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650    1.4869    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995    1.9834    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0160    0.7099    2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -0.4386    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5290    1.6868    1.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3724    2.4087    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7256   -2.1685   -1.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0483   -1.4280   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1122   -2.4483    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -0.2486   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    1.4232   -2.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875    0.8452   -2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    1.9885   -1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888   -1.0665   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21  2  1  0  0  0  0
 21  9  1  0  0  0  0
 16 11  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  5 25  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
 10 32  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 11 35  1  1  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 18 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 21 45  1  6  0  0  0
M  END

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
    2.7451   -0.5734   -1.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073   -0.1152   -0.1437 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7292    1.1827    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3642    1.2728    1.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    2.2853   -0.6283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936   -1.1520    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2059   -2.0422    1.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -1.3060    1.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894    0.0254    0.8723 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2916    1.0941    1.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253    0.2327    0.5715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1214    1.6330    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171    1.7399    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2487    2.5910    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2879    0.7299   -0.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0551   -0.0097   -0.8215 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5127   -1.4340   -1.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1988    0.9437   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -0.0553   -0.3807 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7220   -1.0504   -1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    0.2989   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607   -1.2760   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742    2.5067   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -0.7063    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105   -1.8390    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647   -2.7188    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147   -2.6939    2.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9004   -1.9558    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5650    1.4869    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995    1.9834    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0160    0.7099    2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -0.4386    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5290    1.6868    1.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3724    2.4087    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7256   -2.1685   -1.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0483   -1.4280   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1122   -2.4483    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -0.2486   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    1.4232   -2.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875    0.8452   -2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    1.9885   -1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888   -1.0665   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
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 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  6
 17 18  1  0
 16 19  1  0
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 21  9  1  0
 16 11  1  0
  1 22  1  0
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 11 35  1  1
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 17 38  1  0
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 18 40  1  0
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 20 43  1  0
 20 44  1  0
 21 45  1  6
M  END


  Mrv1652306242107393D          

 45 47  0  0  0  0            999 V2000
    2.7451   -0.5734   -1.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073   -0.1152   -0.1437 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7292    1.1827    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3642    1.2728    1.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    2.2853   -0.6283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936   -1.1520    0.8886 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.0175   -1.3060    1.5899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1894    0.0254    0.8723 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2916    1.0941    1.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3171    1.7399    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2487    2.5910    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2879    0.7299   -0.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5127   -1.4340   -1.0815 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.1988    0.9437   -1.3974 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6371   -0.0553   -0.3807 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7220   -1.0504   -1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    0.2989   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607   -1.2760   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 16 19  1  0  0  0  0
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 21  9  1  0  0  0  0
 16 11  1  0  0  0  0
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  6 27  1  0  0  0  0
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  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
 10 32  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 11 35  1  1  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 18 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 21 45  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0010613

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O5/c1-14-5-3-6-15(2,13(19)20)10(14)4-7-16(9-17)11(14)8-12(18)21-16/h10-11,17H,3-9H2,1-2H3,(H,19,20)/t10-,11-,14+,15+,16-/m1/s1

> <INCHI_KEY>
QQXUVFDWBIAEDS-AKUOKLNBSA-N

> <FORMULA>
C16H24O5

> <MOLECULAR_WEIGHT>
296.363

> <EXACT_MASS>
296.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.400471633242482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,5aR,6S,9aS,9bR)-3a-(hydroxymethyl)-6,9a-dimethyl-2-oxo-dodecahydronaphtho[2,1-b]furan-6-carboxylic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.7463865709999993

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.333280816070289

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.335114153784416

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0904235013528414

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
74.41619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asperolide C

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
    2.7451   -0.5734   -1.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073   -0.1152   -0.1437 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7292    1.1827    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3642    1.2728    1.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    2.2853   -0.6283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936   -1.1520    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2059   -2.0422    1.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -1.3060    1.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894    0.0254    0.8723 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2916    1.0941    1.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253    0.2327    0.5715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1214    1.6330    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171    1.7399    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2487    2.5910    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2879    0.7299   -0.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0551   -0.0097   -0.8215 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5127   -1.4340   -1.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435   -1.7263   -0.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698    0.5331   -1.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988    0.9437   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -0.0553   -0.3807 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7220   -1.0504   -1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    0.2989   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607   -1.2760   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742    2.5067   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -0.7063    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105   -1.8390    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647   -2.7188    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147   -2.6939    2.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9004   -1.9558    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795   -1.1490    2.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650    1.4869    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995    1.9834    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0160    0.7099    2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -0.4386    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5290    1.6868    1.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3724    2.4087    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7256   -2.1685   -1.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0483   -1.4280   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1122   -2.4483    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -0.2486   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    1.4232   -2.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875    0.8452   -2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    1.9885   -1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888   -1.0665   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  6
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
 21  9  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  1
 12 36  1  0
 12 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  6
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       2.745  -0.573  -1.466  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.107  -0.115  -0.144  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.729   1.183   0.171  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.364   1.273   1.254  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.663   2.285  -0.628  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.394  -1.152   0.889  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.206  -2.042   1.180  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.018  -1.306   1.590  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.189   0.025   0.872  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.292   1.094   1.827  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.625   0.233   0.572  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.121   1.633   0.885  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.317   1.740   0.005  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.249   2.591   0.033  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.288   0.730  -0.909  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.055  -0.010  -0.822  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.513  -1.434  -1.081  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.443  -1.726  -0.058  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.170   0.533  -1.883  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.199   0.944  -1.397  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.637  -0.055  -0.381  0.00  0.00           C+0
HETATM   22  H   UNK     0       3.722  -1.050  -1.211  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.984   0.299  -2.101  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.061  -1.276  -1.984  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.274   2.507  -1.401  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.808  -0.706   1.841  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.211  -1.839   0.540  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.065  -2.719   0.319  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.515  -2.694   2.048  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.900  -1.956   1.355  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.080  -1.149   2.703  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.565   1.487   2.451  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.700   1.983   1.316  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.016   0.710   2.575  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.247  -0.439   1.237  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.529   1.687   1.938  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.372   2.409   0.698  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.726  -2.168  -1.078  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.048  -1.428  -2.051  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.112  -2.448   0.516  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.065  -0.249  -2.681  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.591   1.423  -2.418  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.888   0.845  -2.279  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.257   1.988  -1.073  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.389  -1.067  -0.828  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3    6   21                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3   25                                                       
CONECT    6    2    7   26   27                                             
CONECT    7    6    8   28   29                                             
CONECT    8    7    9   30   31                                             
CONECT    9    8   10   11   21                                             
CONECT   10    9   32   33   34                                             
CONECT   11    9   12   16   35                                             
CONECT   12   11   13   36   37                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   19   11                                             
CONECT   17   16   18   38   39                                             
CONECT   18   17   40                                                       
CONECT   19   16   20   41   42                                             
CONECT   20   19   21   43   44                                             
CONECT   21   20    2    9   45                                             
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    8                                                            
CONECT   32   10                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   11                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   17                                                            
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   94    0
END

RDKit          3D

45 47  0  0  0  0  0  0  0  0999 V2000
    2.7451   -0.5734   -1.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1073   -0.1152   -0.1437 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7292    1.1827    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3642    1.2728    1.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    2.2853   -0.6283 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936   -1.1520    0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2059   -2.0422    1.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -1.3060    1.5899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1894    0.0254    0.8723 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2916    1.0941    1.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253    0.2327    0.5715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1214    1.6330    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3171    1.7399    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2487    2.5910    0.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2879    0.7299   -0.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0551   -0.0097   -0.8215 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5127   -1.4340   -1.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4435   -1.7263   -0.0583 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1698    0.5331   -1.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988    0.9437   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6371   -0.0553   -0.3807 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7220   -1.0504   -1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839    0.2989   -2.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0607   -1.2760   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742    2.5067   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -0.7063    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105   -1.8390    0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647   -2.7188    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5147   -2.6939    2.0483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9004   -1.9558    1.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0795   -1.1490    2.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5650    1.4869    2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995    1.9834    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0160    0.7099    2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465   -0.4386    1.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5290    1.6868    1.9378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3724    2.4087    0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7256   -2.1685   -1.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0483   -1.4280   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1122   -2.4483    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -0.2486   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5906    1.4232   -2.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875    0.8452   -2.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567    1.9885   -1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888   -1.0665   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  6
 17 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
 21  9  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  1
 12 36  1  0
 12 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  6
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3AS,5ar,6S,9as,9BR)-3a-(hydroxymethyl)-6,9a-dimethyl-2-oxo-dodecahydronaphtho[2,1-b]furan-6-carboxylate	Generator

Chemical Formula

C₁₆H₂₄O₅

Average Mass

296.3630 Da

Monoisotopic Mass

296.16237 Da

IUPAC Name

(3aS,5aR,6S,9aS,9bR)-3a-(hydroxymethyl)-6,9a-dimethyl-2-oxo-dodecahydronaphtho[2,1-b]furan-6-carboxylic acid

Traditional Name

asperolide C

CAS Registry Number

Not Available

SMILES

C[C@]12CCC[C@@](C)([C@@H]1CC[C@]1(CO)OC(=O)C[C@H]21)C(O)=O

InChI Identifier

InChI=1S/C16H24O5/c1-14-5-3-6-15(2,13(19)20)10(14)4-7-16(9-17)11(14)8-12(18)21-16/h10-11,17H,3-9H2,1-2H3,(H,19,20)/t10-,11-,14+,15+,16-/m1/s1

InChI Key

QQXUVFDWBIAEDS-AKUOKLNBSA-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	NPAtlas	22283451

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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Primary 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	1.63	ALOGPS
logP	1.75	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.42 m³·mol⁻¹	ChemAxon
Polarizability	30.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA003461

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29214725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57331842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Asperolide C (NP0010613)

MOL for NP0010613 (Asperolide C)

3D MOL for NP0010613 (Asperolide C)

3D SDF for NP0010613 (Asperolide C)

3D-SDF for NP0010613 (Asperolide C)

PDB for NP0010613 (Asperolide C)

3D PDB for NP0010613 (Asperolide C)

SMILES for NP0010613 (Asperolide C)

INCHI for NP0010613 (Asperolide C)

Structure for NP0010613 (Asperolide C)

3D Structure for NP0010613 (Asperolide C)