NP-MRD: Showing NP-Card for (6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione (NP0220164)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 21:23:44 UTC

Updated at

2022-09-05 21:23:45 UTC

NP-MRD ID

NP0220164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione

Description

Cohaerin E belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. (6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione is found in Annulohypoxylon cohaerens. Based on a literature review very few articles have been published on Cohaerin E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052223232D          

 34 37  0  0  1  0            999 V2000
   -5.4971   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7826   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0681   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6392   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -4.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958   -2.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9724   -3.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273   -2.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -1.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -0.8373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -0.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921    0.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4401    0.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    0.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950    1.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020    1.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7991    0.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -0.3227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2892   -1.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5863   -2.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314   -3.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8834   -4.0743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5244   -3.6327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0093   -4.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119   -4.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049   -4.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3082   -4.7277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 25  2  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
    6.9365    2.0219    0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6414    2.5578    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8847    1.4158    1.4169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6331    0.3890    0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8915   -0.7887    0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -1.8734   -0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7868   -1.5681   -1.3291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2504   -0.5473   -2.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -1.3270   -0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -0.1156   -0.9418 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.3971   -0.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8569   -2.3179   -0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7727   -1.1926   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7039   -0.1725   -1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5657    0.9166   -0.8267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5105    0.9160    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164    2.1473    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8974    2.5733    1.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6469    2.0238    2.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7599    3.6948    1.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0311    4.3797    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4534    3.9650   -0.9065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5932    2.8440   -0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0819    2.5210   -2.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204   -0.1066    1.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7489   -1.2706    0.8890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435   -2.3881    1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -3.5790    1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7831   -4.4302    2.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4413   -3.6820   -0.1310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5472   -4.0207   -1.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4027   -4.5353   -0.3391 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518   -3.8146   -0.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8162   -4.4345   -0.9314 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426    1.1070    0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298    1.7813   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6944    2.8365    0.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476    2.9419   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8220    3.3951    1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9252    1.7979    1.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5357    0.9719    2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0743    0.9856   -0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6337    0.0625   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5752   -1.2449    1.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9974   -0.4915    1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1481   -2.7088    0.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5789   -2.2668   -0.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392   -2.5480   -1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3484   -0.3910   -2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    0.4279   -2.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9971   -0.9056   -3.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198   -0.1250   -1.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4172    1.3219    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6271    1.6314    2.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7148    2.9178    3.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2314    4.0453    2.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7038    5.2414    0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6626    4.5019   -1.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130    1.8529   -2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3798   -0.1396    1.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5567   -2.4203    2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369   -4.6159   -0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1629   -4.6606   -1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9499   -3.1064   -1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  6
 30 32  1  0
 32 33  1  0
 33 34  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 33 11  1  0
 23 17  1  0
 30 12  1  0
 26 13  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  6
  8 49  1  0
  8 50  1  0
  8 51  1  0
 14 52  1  0
 25 60  1  0
 27 61  1  0
 31 62  1  0
 31 63  1  0
 31 64  1  0
 19 53  1  0
 19 54  1  0
 19 55  1  0
 20 56  1  0
 21 57  1  0
 22 58  1  0
 24 59  1  0
M  END


  Mrv1652309052223232D          

 34 37  0  0  1  0            999 V2000
   -5.4971   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7826   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0681   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6392   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9247   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2103   -4.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958   -2.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958   -2.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2187   -3.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9724   -3.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273   -2.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -1.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -0.8373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -0.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9921    0.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4401    0.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6331    0.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950    1.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5020    1.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540    1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7991    0.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3511   -0.3227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2892   -1.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5863   -2.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3314   -3.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8834   -4.0743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5244   -3.6327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0093   -4.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119   -4.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049   -4.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3082   -4.7277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 25  2  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0220164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCC(C)C(=O)C1=C2C3=COC(=CC3=CC(=O)[C@]2(C)OC1=O)C1=C(C)C=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O6/c1-5-6-7-8-10-17(3)26(31)24-25-19-15-33-21(23-16(2)11-9-12-20(23)29)13-18(19)14-22(30)28(25,4)34-27(24)32/h9,11-15,17,29H,5-8,10H2,1-4H3/t17?,28-/m0/s1

> <INCHI_KEY>
BNPNEDGQFYVZTE-SNCIIYAQSA-N

> <FORMULA>
C28H30O6

> <MOLECULAR_WEIGHT>
462.542

> <EXACT_MASS>
462.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.79437038513985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

> <JCHEM_LOGP>
5.743631604666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.842489827402876

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.064182062901105

> <JCHEM_PKA_STRONGEST_BASIC>
-5.242189633431766

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
131.7772

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6aR)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.261  -6.263   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.928  -5.493   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.594  -6.263   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.260  -5.493   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.926  -6.263   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.593  -5.493   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.259  -6.263   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.259  -7.803   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.925  -5.493   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.925  -3.953   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.408  -6.263   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.815  -5.637   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.291  -4.172   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.261  -3.028   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.736  -1.563   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.243  -1.243   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.719   0.222   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.688   1.366   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.182   1.046   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.164   2.831   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.670   3.151   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.701   2.007   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.225   0.542   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.255  -0.602   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.273  -2.387   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.797  -3.852   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.828  -4.996   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.352  -6.461   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.382  -7.605   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.846  -6.781   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.751  -8.027   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.076  -8.115   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.569  -7.795   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.575  -8.825   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13   30                                                  
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23                                                            
CONECT   25   16   26                                                       
CONECT   26   25   13   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   12   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   11   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₆

Average Mass

462.5420 Da

Monoisotopic Mass

462.20424 Da

IUPAC Name

(6aR)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)-6H,6aH,8H-furo[2,3-h]isochromene-6,8-dione

Traditional Name

(6aR)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione

CAS Registry Number

Not Available

SMILES

CCCCCCC(C)C(=O)C1=C2C3=COC(=CC3=CC(=O)[C@]2(C)OC1=O)C1=C(C)C=CC=C1O

InChI Identifier

InChI=1S/C28H30O6/c1-5-6-7-8-10-17(3)26(31)24-25-19-15-33-21(23-16(2)11-9-12-20(23)29)13-18(19)14-22(30)28(25,4)34-27(24)32/h9,11-15,17,29H,5-8,10H2,1-4H3/t17?,28-/m0/s1

InChI Key

BNPNEDGQFYVZTE-SNCIIYAQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Annulohypoxylon cohaerens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Alpha-acyloxy ketone
Toluene
Phenol
Monocyclic benzene moiety
2-furanone
Benzenoid
Pyran
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Aldehyde
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	5.74	ChemAxon
pKa (Strongest Acidic)	8.06	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	131.78 m³·mol⁻¹	ChemAxon
Polarizability	50.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00053154

Chemspider ID

9794329

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11619581

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione (NP0220164)

MOL for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)

3D MOL for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)

3D SDF for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)

3D-SDF for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)

PDB for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)

3D PDB for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)

SMILES for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)

INCHI for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)

Structure for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)

3D Structure for NP0220164 ((6ar)-3-(2-hydroxy-6-methylphenyl)-6a-methyl-9-(2-methyloctanoyl)furo[2,3-h]isochromene-6,8-dione)