NP-MRD: Showing NP-Card for nodulisporacid A (E-isomer) (NP0037645)

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Record Information

Version

1.0

Created at

2021-06-20 20:31:21 UTC

Updated at

2021-06-30 00:09:57 UTC

NP-MRD ID

NP0037645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nodulisporacid A (E-isomer)

Provided By

JEOL Database JEOL Logo

Description

2-[(2R)-4-[(2E,5S)-5-methyl-5-[(2R)-2-methylbutyl]-2,5-dihydrofuran-2-ylidene]-3,5-dioxooxolan-2-yl]acetic acid belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. nodulisporacid A (E-isomer) is found in Nodulisporium sp. It was first documented in 2008 (Kasettrathat, C., et al.). Based on a literature review very few articles have been published on 2-[(2R)-4-[(2E,5S)-5-methyl-5-[(2R)-2-methylbutyl]-2,5-dihydrofuran-2-ylidene]-3,5-dioxooxolan-2-yl]acetic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122313D          

 42 43  0  0  0  0            999 V2000
   -4.8694    3.2582   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1874    3.0380    0.2013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7734    2.4208    0.0953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8323    3.3560   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    2.1248    1.5255 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1683    1.0237    1.6655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7225    0.9167    3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6147   -0.3102    1.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7798   -0.7250    0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2344    0.2721    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    0.2452   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961   -0.8214   -1.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975   -1.8626   -1.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7148   -0.4342   -2.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1914    0.8741   -2.0901 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6625    0.8424   -1.7135 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9248    0.0918   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1357   -0.5943    0.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1986    0.2295   -0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    1.2968   -0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    2.3363   -0.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019    1.3476    0.8800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    4.0415   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9069    3.5722   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8794    2.3377   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1424    3.9910    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259    2.3690    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    1.4827   -0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    3.5037   -1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737    4.3386   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    2.9576   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926    1.8372    2.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    3.0626    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    0.6452    3.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016    1.8678    3.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709    0.1693    3.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754   -0.8529    1.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8555   -1.6598   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    1.5357   -2.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210    1.8687   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    0.3575   -2.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507   -0.2953    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  0  0  0  0
 14 12  1  0  0  0  0
 16 17  1  0  0  0  0
 12 11  1  0  0  0  0
 17 19  1  0  0  0  0
 10  9  1  0  0  0  0
 17 18  2  0  0  0  0
 11 10  2  0  0  0  0
 20 21  2  0  0  0  0
 11 20  1  0  0  0  0
 12 13  2  0  0  0  0
  6  7  1  1  0  0  0
 20 15  1  0  0  0  0
  6  5  1  0  0  0  0
  9  8  2  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  3  2  1  0  0  0  0
  6 22  1  0  0  0  0
  2  1  1  0  0  0  0
 22 10  1  0  0  0  0
  3  4  1  0  0  0  0
 15 39  1  6  0  0  0
  9 38  1  0  0  0  0
  8 37  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 19 42  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  3 28  1  6  0  0  0
  2 26  1  0  0  0  0
  2 27  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
M  END

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -4.8694    3.2582   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1874    3.0380    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7734    2.4208    0.0953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8323    3.3560   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    2.1248    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1683    1.0237    1.6655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7225    0.9167    3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6147   -0.3102    1.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7798   -0.7250    0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2344    0.2721    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    0.2452   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961   -0.8214   -1.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975   -1.8626   -1.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7148   -0.4342   -2.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1914    0.8741   -2.0901 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6625    0.8424   -1.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9248    0.0918   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1357   -0.5943    0.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1986    0.2295   -0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    1.2968   -0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    2.3363   -0.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019    1.3476    0.8800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    4.0415   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9069    3.5722   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8794    2.3377   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1424    3.9910    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259    2.3690    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    1.4827   -0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    3.5037   -1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737    4.3386   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    2.9576   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926    1.8372    2.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    3.0626    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    0.6452    3.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016    1.8678    3.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709    0.1693    3.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754   -0.8529    1.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8555   -1.6598   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    1.5357   -2.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210    1.8687   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    0.3575   -2.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507   -0.2953    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 15 16  1  0
 14 12  1  0
 16 17  1  0
 12 11  1  0
 17 19  1  0
 10  9  1  0
 17 18  2  0
 11 10  2  0
 20 21  2  0
 11 20  1  0
 12 13  2  0
  6  7  1  1
 20 15  1  0
  6  5  1  0
  9  8  2  0
  5  3  1  0
  8  6  1  0
  3  2  1  0
  6 22  1  0
  2  1  1  0
 22 10  1  0
  3  4  1  0
 15 39  1  6
  9 38  1  0
  8 37  1  0
 16 40  1  0
 16 41  1  0
 19 42  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  5 32  1  0
  5 33  1  0
  3 28  1  6
  2 26  1  0
  2 27  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
M  END


  Mrv1652306202122313D          

 42 43  0  0  0  0            999 V2000
   -4.8694    3.2582   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1874    3.0380    0.2013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7734    2.4208    0.0953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8323    3.3560   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    2.1248    1.5255 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1683    1.0237    1.6655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7225    0.9167    3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6147   -0.3102    1.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7798   -0.7250    0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2344    0.2721    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    0.2452   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961   -0.8214   -1.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975   -1.8626   -1.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7148   -0.4342   -2.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1914    0.8741   -2.0901 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6625    0.8424   -1.7135 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9248    0.0918   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1357   -0.5943    0.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1986    0.2295   -0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    1.2968   -0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    2.3363   -0.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019    1.3476    0.8800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    4.0415   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9069    3.5722   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8794    2.3377   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1424    3.9910    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259    2.3690    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    1.4827   -0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    3.5037   -1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737    4.3386   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    2.9576   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926    1.8372    2.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    3.0626    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    0.6452    3.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016    1.8678    3.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709    0.1693    3.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754   -0.8529    1.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8555   -1.6598   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    1.5357   -2.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210    1.8687   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    0.3575   -2.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507   -0.2953    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  0  0  0  0
 14 12  1  0  0  0  0
 16 17  1  0  0  0  0
 12 11  1  0  0  0  0
 17 19  1  0  0  0  0
 10  9  1  0  0  0  0
 17 18  2  0  0  0  0
 11 10  2  0  0  0  0
 20 21  2  0  0  0  0
 11 20  1  0  0  0  0
 12 13  2  0  0  0  0
  6  7  1  1  0  0  0
 20 15  1  0  0  0  0
  6  5  1  0  0  0  0
  9  8  2  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  3  2  1  0  0  0  0
  6 22  1  0  0  0  0
  2  1  1  0  0  0  0
 22 10  1  0  0  0  0
  3  4  1  0  0  0  0
 15 39  1  6  0  0  0
  9 38  1  0  0  0  0
  8 37  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 19 42  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  3 28  1  6  0  0  0
  2 26  1  0  0  0  0
  2 27  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0037645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@]1([H])OC(=O)\C(=C2\O[C@@](C([H])=C2[H])(C([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O6/c1-4-9(2)8-16(3)6-5-10(22-16)13-14(19)11(7-12(17)18)21-15(13)20/h5-6,9,11H,4,7-8H2,1-3H3,(H,17,18)/b13-10+/t9-,11-,16-/m1/s1

> <INCHI_KEY>
PJLKMFDHUJBABS-IXWOKTEQSA-N

> <FORMULA>
C16H20O6

> <MOLECULAR_WEIGHT>
308.33

> <EXACT_MASS>
308.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.354680734374444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2R)-4-[(2E,5S)-5-methyl-5-[(2R)-2-methylbutyl]-2,5-dihydrofuran-2-ylidene]-3,5-dioxooxolan-2-yl]acetic acid

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
2.446792232666666

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.670511602417548

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.835296605724682

> <JCHEM_PKA_STRONGEST_BASIC>
-4.91924957115163

> <JCHEM_POLAR_SURFACE_AREA>
89.90000000000002

> <JCHEM_REFRACTIVITY>
79.1367

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R)-4-[(2E,5S)-5-methyl-5-[(2R)-2-methylbutyl]furan-2-ylidene]-3,5-dioxooxolan-2-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -4.8694    3.2582   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1874    3.0380    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7734    2.4208    0.0953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8323    3.3560   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    2.1248    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1683    1.0237    1.6655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7225    0.9167    3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6147   -0.3102    1.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7798   -0.7250    0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2344    0.2721    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    0.2452   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961   -0.8214   -1.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975   -1.8626   -1.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7148   -0.4342   -2.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1914    0.8741   -2.0901 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6625    0.8424   -1.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9248    0.0918   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1357   -0.5943    0.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1986    0.2295   -0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    1.2968   -0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    2.3363   -0.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019    1.3476    0.8800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    4.0415   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9069    3.5722   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8794    2.3377   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1424    3.9910    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259    2.3690    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    1.4827   -0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    3.5037   -1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737    4.3386   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    2.9576   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926    1.8372    2.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    3.0626    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    0.6452    3.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016    1.8678    3.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709    0.1693    3.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754   -0.8529    1.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8555   -1.6598   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    1.5357   -2.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210    1.8687   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    0.3575   -2.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507   -0.2953    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 15 16  1  0
 14 12  1  0
 16 17  1  0
 12 11  1  0
 17 19  1  0
 10  9  1  0
 17 18  2  0
 11 10  2  0
 20 21  2  0
 11 20  1  0
 12 13  2  0
  6  7  1  1
 20 15  1  0
  6  5  1  0
  9  8  2  0
  5  3  1  0
  8  6  1  0
  3  2  1  0
  6 22  1  0
  2  1  1  0
 22 10  1  0
  3  4  1  0
 15 39  1  6
  9 38  1  0
  8 37  1  0
 16 40  1  0
 16 41  1  0
 19 42  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  5 32  1  0
  5 33  1  0
  3 28  1  6
  2 26  1  0
  2 27  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.869   3.258  -1.142  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.187   3.038   0.201  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.773   2.421   0.095  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.832   3.356  -0.673  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.246   2.125   1.526  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.168   1.024   1.666  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.723   0.917   3.129  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.615  -0.310   1.158  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.780  -0.725   0.209  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.234   0.272   0.024  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.264   0.245  -0.829  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.596  -0.821  -1.785  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.998  -1.863  -1.979  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.715  -0.434  -2.477  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.191   0.874  -2.090  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.662   0.842  -1.714  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.925   0.092  -0.439  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.136  -0.594   0.186  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.199   0.230  -0.026  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.276   1.297  -0.980  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.377   2.336  -0.351  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.002   1.348   0.880  0.00  0.00           O+0
HETATM   23  H   UNK     0      -4.374   4.042  -1.723  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.907   3.572  -0.988  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.879   2.338  -1.734  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.142   3.991   0.743  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.826   2.369   0.792  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.863   1.483  -0.464  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.175   3.504  -1.702  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.774   4.339  -0.193  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.819   2.958  -0.742  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.093   1.837   2.164  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.853   3.063   1.942  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.554   0.645   3.788  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.302   1.868   3.475  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.071   0.169   3.251  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.475  -0.853   1.519  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.856  -1.660  -0.327  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.034   1.536  -2.949  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.021   1.869  -1.575  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.240   0.358  -2.508  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.251  -0.295   0.801  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    3    1   26   27                                             
CONECT    3    5    2    4   28                                             
CONECT    4    3   29   30   31                                             
CONECT    5    6    3   32   33                                             
CONECT    6    7    5    8   22                                             
CONECT    7    6   34   35   36                                             
CONECT    8    9    6   37                                                  
CONECT    9   10    8   38                                                  
CONECT   10    9   11   22                                                  
CONECT   11   12   10   20                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15   12                                                       
CONECT   15   14   16   20   39                                             
CONECT   16   15   17   40   41                                             
CONECT   17   16   19   18                                                  
CONECT   18   17                                                            
CONECT   19   17   42                                                       
CONECT   20   21   11   15                                                  
CONECT   21   20                                                            
CONECT   22    6   10                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    2                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   19                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

RDKit          3D

42 43  0  0  0  0  0  0  0  0999 V2000
   -4.8694    3.2582   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1874    3.0380    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7734    2.4208    0.0953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8323    3.3560   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462    2.1248    1.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1683    1.0237    1.6655 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7225    0.9167    3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6147   -0.3102    1.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7798   -0.7250    0.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2344    0.2721    0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    0.2452   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5961   -0.8214   -1.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975   -1.8626   -1.9792 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7148   -0.4342   -2.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1914    0.8741   -2.0901 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6625    0.8424   -1.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9248    0.0918   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1357   -0.5943    0.1863 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1986    0.2295   -0.0260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755    1.2968   -0.9802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    2.3363   -0.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0019    1.3476    0.8800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    4.0415   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9069    3.5722   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8794    2.3377   -1.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1424    3.9910    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8259    2.3690    0.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    1.4827   -0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1750    3.5037   -1.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737    4.3386   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    2.9576   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926    1.8372    2.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    3.0626    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5543    0.6452    3.7879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3016    1.8678    3.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709    0.1693    3.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4754   -0.8529    1.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8555   -1.6598   -0.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0335    1.5357   -2.9491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0210    1.8687   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403    0.3575   -2.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2507   -0.2953    0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 15 16  1  0
 14 12  1  0
 16 17  1  0
 12 11  1  0
 17 19  1  0
 10  9  1  0
 17 18  2  0
 11 10  2  0
 20 21  2  0
 11 20  1  0
 12 13  2  0
  6  7  1  1
 20 15  1  0
  6  5  1  0
  9  8  2  0
  5  3  1  0
  8  6  1  0
  3  2  1  0
  6 22  1  0
  2  1  1  0
 22 10  1  0
  3  4  1  0
 15 39  1  6
  9 38  1  0
  8 37  1  0
 16 40  1  0
 16 41  1  0
 19 42  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
  5 32  1  0
  5 33  1  0
  3 28  1  6
  2 26  1  0
  2 27  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
2-[(2R)-4-[(2E,5S)-5-Methyl-5-[(2R)-2-methylbutyl]-2,5-dihydrofuran-2-ylidene]-3,5-dioxooxolan-2-yl]acetate	Generator

Chemical Formula

C₁₆H₂₀O₆

Average Mass

308.3300 Da

Monoisotopic Mass

308.12599 Da

IUPAC Name

2-[(2R)-4-[(2E,5S)-5-methyl-5-[(2R)-2-methylbutyl]-2,5-dihydrofuran-2-ylidene]-3,5-dioxooxolan-2-yl]acetic acid

Traditional Name

[(2R)-4-[(2E,5S)-5-methyl-5-[(2R)-2-methylbutyl]furan-2-ylidene]-3,5-dioxooxolan-2-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C([H])([H])[C@@]1([H])OC(=O)\C(=C2\O[C@@](C([H])=C2[H])(C([H])([H])[H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C1=O

InChI Identifier

InChI=1S/C16H20O6/c1-4-9(2)8-16(3)6-5-10(22-16)13-14(19)11(7-12(17)18)21-15(13)20/h5-6,9,11H,4,7-8H2,1-3H3,(H,17,18)/b13-10+/t9-,11-,16-/m1/s1

InChI Key

PJLKMFDHUJBABS-IXWOKTEQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nodulisporium sp.	JEOL database	Kasettrathat, C., et al, Phytochem. 69, 2621 (2008)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.45	ALOGPS
logP	2.45	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.84	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.14 m³·mol⁻¹	ChemAxon
Polarizability	31.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76764279

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kasettrathat, C., et al. (2008). Kasettrathat, C., et al, Phytochem. 69, 2621 (2008). Phytochem..

Showing NP-Card for nodulisporacid A (E-isomer) (NP0037645)

MOL for NP0037645 (nodulisporacid A (E-isomer))

3D MOL for NP0037645 (nodulisporacid A (E-isomer))

3D SDF for NP0037645 (nodulisporacid A (E-isomer))

3D-SDF for NP0037645 (nodulisporacid A (E-isomer))

PDB for NP0037645 (nodulisporacid A (E-isomer))

3D PDB for NP0037645 (nodulisporacid A (E-isomer))

SMILES for NP0037645 (nodulisporacid A (E-isomer))

INCHI for NP0037645 (nodulisporacid A (E-isomer))

Structure for NP0037645 (nodulisporacid A (E-isomer))

3D Structure for NP0037645 (nodulisporacid A (E-isomer))