NP-MRD: Showing NP-Card for Melleolide K (NP0003257)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2020-12-09 00:32:26 UTC

Updated at

2021-07-15 16:45:56 UTC

NP-MRD ID

NP0003257

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Melleolide K

Provided By

NPAtlas

Description

(2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups. Melleolide K is found in Armillaria mellea , Armillariella and Armillariella mellea (Vahl. ex Fr.) Karst . It was first documented in 2000 (PMID: 10805573). Based on a literature review very few articles have been published on (2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate (PMID: 21376582) (PMID: 25524590).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 57 60  0  0  0  0            999 V2000
   -2.1841   -0.0814   -1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331   -0.1063   -1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5783   -0.4273   -2.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0381   -0.8125   -3.8830 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9201   -0.4528   -1.9838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8375   -0.7810   -2.9748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3020   -0.1468   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3498    0.1857    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8569    0.4709    1.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046    0.2105    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    0.5434    0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    0.8304    2.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    0.5749    0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729    0.9082    1.7252 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2844    1.9825    1.2802 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3559    0.9246    1.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5399    1.3494    1.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.5771   -0.2703 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0213    1.1482   -0.7205 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9770    0.0168   -0.9225 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3574    0.2572   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539   -0.3157   -2.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975   -1.1735   -0.2952 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8412   -0.8768   -0.5413 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9345   -1.7266    0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3216   -1.3583    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -2.3049    1.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -3.4800    1.4938 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4932   -0.0267    1.8745 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8436   -0.1634    3.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294    0.9562   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -0.4027   -2.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6090   -0.8406   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8332   -0.8121   -2.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3528   -0.1595   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3918    0.7178    2.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    1.1391    2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.7420    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0105    2.4899    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550    0.8001    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882    1.1898    3.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6432    2.4614    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8695    0.9579   -0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8669    1.6312   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    1.9493   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3775    1.2434    0.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1402    0.3263   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.5114    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992    0.4084   -2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684   -1.3099   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -0.4354   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5357   -1.3474    0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6037   -2.1084   -0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6776   -1.0209   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -2.7446   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.0951    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388   -0.9706    3.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
 10  2  1  0  0  0  0
 29 14  1  0  0  0  0
 29 16  1  0  0  0  0
 24 18  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  6 34  1  0  0  0  0
  7 35  1  0  0  0  0
  9 36  1  0  0  0  0
 14 37  1  1  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 17 40  1  0  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 18 43  1  6  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 21 46  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 22 51  1  0  0  0  0
 23 52  1  0  0  0  0
 23 53  1  0  0  0  0
 24 54  1  6  0  0  0
 25 55  1  0  0  0  0
 27 56  1  0  0  0  0
 30 57  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -2.1841   -0.0814   -1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331   -0.1063   -1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5783   -0.4273   -2.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0381   -0.8125   -3.8830 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9201   -0.4528   -1.9838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8375   -0.7810   -2.9748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3020   -0.1468   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3498    0.1857    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8569    0.4709    1.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046    0.2105    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    0.5434    0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    0.8304    2.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    0.5749    0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729    0.9082    1.7252 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2844    1.9825    1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559    0.9246    1.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5399    1.3494    1.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.5771   -0.2703 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0213    1.1482   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9770    0.0168   -0.9225 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3574    0.2572   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539   -0.3157   -2.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975   -1.1735   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412   -0.8768   -0.5413 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9345   -1.7266    0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3216   -1.3583    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -2.3049    1.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -3.4800    1.4938 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4932   -0.0267    1.8745 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8436   -0.1634    3.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294    0.9562   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -0.4027   -2.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6090   -0.8406   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8332   -0.8121   -2.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3528   -0.1595   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3918    0.7178    2.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    1.1391    2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.7420    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0105    2.4899    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550    0.8001    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882    1.1898    3.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6432    2.4614    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8695    0.9579   -0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8669    1.6312   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    1.9493   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3775    1.2434    0.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1402    0.3263   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.5114    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992    0.4084   -2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684   -1.3099   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -0.4354   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5357   -1.3474    0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6037   -2.1084   -0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6776   -1.0209   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -2.7446   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.0951    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388   -0.9706    3.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 26 29  1  0
 29 30  1  1
 10  2  1  0
 29 14  1  0
 29 16  1  0
 24 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 14 37  1  1
 15 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  6
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  6
 25 55  1  0
 27 56  1  0
 30 57  1  0
M  END


  Mrv1652306242117463D          

 57 60  0  0  0  0            999 V2000
   -2.1841   -0.0814   -1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331   -0.1063   -1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5783   -0.4273   -2.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0381   -0.8125   -3.8830 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9201   -0.4528   -1.9838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8375   -0.7810   -2.9748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3020   -0.1468   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3498    0.1857    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8569    0.4709    1.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046    0.2105    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    0.5434    0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    0.8304    2.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    0.5749    0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729    0.9082    1.7252 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2844    1.9825    1.2802 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3559    0.9246    1.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5399    1.3494    1.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.5771   -0.2703 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0213    1.1482   -0.7205 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9770    0.0168   -0.9225 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3574    0.2572   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539   -0.3157   -2.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975   -1.1735   -0.2952 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8412   -0.8768   -0.5413 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9345   -1.7266    0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3216   -1.3583    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -2.3049    1.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -3.4800    1.4938 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4932   -0.0267    1.8745 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8436   -0.1634    3.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294    0.9562   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -0.4027   -2.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6090   -0.8406   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8332   -0.8121   -2.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3528   -0.1595   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3918    0.7178    2.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    1.1391    2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.7420    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0105    2.4899    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550    0.8001    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882    1.1898    3.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6432    2.4614    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8695    0.9579   -0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8669    1.6312   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    1.9493   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3775    1.2434    0.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1402    0.3263   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.5114    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992    0.4084   -2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684   -1.3099   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -0.4354   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5357   -1.3474    0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6037   -2.1084   -0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6776   -1.0209   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -2.7446   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.0951    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388   -0.9706    3.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
 10  2  1  0  0  0  0
 29 14  1  0  0  0  0
 29 16  1  0  0  0  0
 24 18  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  6 34  1  0  0  0  0
  7 35  1  0  0  0  0
  9 36  1  0  0  0  0
 14 37  1  1  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 17 40  1  0  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 18 43  1  6  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 21 46  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 22 51  1  0  0  0  0
 23 52  1  0  0  0  0
 23 53  1  0  0  0  0
 24 54  1  6  0  0  0
 25 55  1  0  0  0  0
 27 56  1  0  0  0  0
 30 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C(C(=O)O[C@]2([H])C([H])([H])[C@]3(C([H])([H])[H])[C@@]4([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[C@@]4([H])C([H])=C(C([H])=O)[C@]23O[H])C(=C1Cl)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H27ClO6/c1-11-18(15(26)6-16(27)19(11)24)20(28)30-17-9-22(4)14-8-21(2,3)7-12(14)5-13(10-25)23(17,22)29/h5-6,10,12,14,17,26-27,29H,7-9H2,1-4H3/t12-,14+,17-,22-,23+/m1/s1

> <INCHI_KEY>
UHFQTECWVLYLBG-PPUVGZBRSA-N

> <FORMULA>
C23H27ClO6

> <MOLECULAR_WEIGHT>
434.91

> <EXACT_MASS>
434.1496163

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.87327764651432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
4.7115738920000005

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.02485799749977

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.208684618370319

> <JCHEM_PKA_STRONGEST_BASIC>
-3.762219145840386

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
112.85159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -2.1841   -0.0814   -1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331   -0.1063   -1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5783   -0.4273   -2.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0381   -0.8125   -3.8830 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9201   -0.4528   -1.9838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8375   -0.7810   -2.9748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3020   -0.1468   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3498    0.1857    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8569    0.4709    1.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046    0.2105    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    0.5434    0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    0.8304    2.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    0.5749    0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729    0.9082    1.7252 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2844    1.9825    1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559    0.9246    1.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5399    1.3494    1.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.5771   -0.2703 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0213    1.1482   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9770    0.0168   -0.9225 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3574    0.2572   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539   -0.3157   -2.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975   -1.1735   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412   -0.8768   -0.5413 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9345   -1.7266    0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3216   -1.3583    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -2.3049    1.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -3.4800    1.4938 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4932   -0.0267    1.8745 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8436   -0.1634    3.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294    0.9562   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -0.4027   -2.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6090   -0.8406   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8332   -0.8121   -2.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3528   -0.1595   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3918    0.7178    2.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    1.1391    2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.7420    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0105    2.4899    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550    0.8001    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882    1.1898    3.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6432    2.4614    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8695    0.9579   -0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8669    1.6312   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    1.9493   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3775    1.2434    0.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1402    0.3263   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.5114    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992    0.4084   -2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684   -1.3099   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -0.4354   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5357   -1.3474    0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6037   -2.1084   -0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6776   -1.0209   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -2.7446   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.0951    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388   -0.9706    3.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 26 29  1  0
 29 30  1  1
 10  2  1  0
 29 14  1  0
 29 16  1  0
 24 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 14 37  1  1
 15 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  6
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  6
 25 55  1  0
 27 56  1  0
 30 57  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.184  -0.081  -1.627  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.633  -0.106  -1.310  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.578  -0.427  -2.266  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      -4.038  -0.813  -3.883  0.00  0.00          Cl+0
HETATM    5  C   UNK     0      -5.920  -0.453  -1.984  0.00  0.00           C+0
HETATM    6  O   UNK     0      -6.838  -0.781  -2.975  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.302  -0.147  -0.710  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.350   0.186   0.288  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.857   0.471   1.520  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.005   0.211   0.003  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.990   0.543   0.986  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.290   0.830   2.165  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.621   0.575   0.724  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.673   0.908   1.725  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.284   1.982   1.280  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.356   0.925   1.139  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.540   1.349   2.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.705   0.577  -0.270  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.021   1.148  -0.721  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.977   0.017  -0.923  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.357   0.257  -0.378  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.154  -0.316  -2.410  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.297  -1.174  -0.295  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.841  -0.877  -0.541  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.935  -1.727   0.216  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.322  -1.358   1.304  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.561  -2.305   1.968  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.735  -3.480   1.494  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.493  -0.027   1.875  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.844  -0.163   3.248  0.00  0.00           O+0
HETATM   31  H   UNK     0      -1.829   0.956  -1.509  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.104  -0.403  -2.710  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.609  -0.841  -1.059  0.00  0.00           H+0
HETATM   34  H   UNK     0      -7.833  -0.812  -2.807  0.00  0.00           H+0
HETATM   35  H   UNK     0      -7.353  -0.160  -0.464  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.392   0.718   2.329  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.122   1.139   2.713  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.456   2.742   2.080  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.011   2.490   0.331  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.455   0.800   1.802  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.288   1.190   3.088  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.643   2.461   1.895  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.870   0.958  -0.923  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.867   1.631  -1.720  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.392   1.949  -0.049  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.378   1.243   0.126  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.140   0.326  -1.182  0.00  0.00           H+0
HETATM   48  H   UNK     0       5.639  -0.511   0.366  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.799   0.408  -2.919  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.668  -1.310  -2.420  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.175  -0.435  -2.912  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.536  -1.347   0.751  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.604  -2.108  -0.848  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.678  -1.021  -1.649  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.763  -2.745  -0.166  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.108  -2.095   2.866  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.439  -0.971   3.349  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5   34                                                       
CONECT    7    5    8   35                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   36                                                       
CONECT   10    8   11    2                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   29   37                                             
CONECT   15   14   16   38   39                                             
CONECT   16   15   17   18   29                                             
CONECT   17   16   40   41   42                                             
CONECT   18   16   19   24   43                                             
CONECT   19   18   20   44   45                                             
CONECT   20   19   21   22   23                                             
CONECT   21   20   46   47   48                                             
CONECT   22   20   49   50   51                                             
CONECT   23   20   24   52   53                                             
CONECT   24   23   25   18   54                                             
CONECT   25   24   26   55                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28   56                                                  
CONECT   28   27                                                            
CONECT   29   26   30   14   16                                             
CONECT   30   29   57                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    9                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   17                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   21                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   22                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   27                                                            
CONECT   57   30                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

RDKit          3D

57 60  0  0  0  0  0  0  0  0999 V2000
   -2.1841   -0.0814   -1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331   -0.1063   -1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5783   -0.4273   -2.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0381   -0.8125   -3.8830 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9201   -0.4528   -1.9838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8375   -0.7810   -2.9748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3020   -0.1468   -0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3498    0.1857    0.2881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8569    0.4709    1.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0046    0.2105    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    0.5434    0.9862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    0.8304    2.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    0.5749    0.7242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6729    0.9082    1.7252 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2844    1.9825    1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559    0.9246    1.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5399    1.3494    1.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.5771   -0.2703 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0213    1.1482   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9770    0.0168   -0.9225 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3574    0.2572   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539   -0.3157   -2.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2975   -1.1735   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412   -0.8768   -0.5413 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9345   -1.7266    0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3216   -1.3583    1.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -2.3049    1.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351   -3.4800    1.4938 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4932   -0.0267    1.8745 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8436   -0.1634    3.2475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294    0.9562   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -0.4027   -2.7104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6090   -0.8406   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8332   -0.8121   -2.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3528   -0.1595   -0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3918    0.7178    2.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    1.1391    2.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4558    2.7420    2.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0105    2.4899    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550    0.8001    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2882    1.1898    3.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6432    2.4614    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8695    0.9579   -0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8669    1.6312   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    1.9493   -0.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3775    1.2434    0.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1402    0.3263   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.5114    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992    0.4084   -2.9187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684   -1.3099   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1748   -0.4354   -2.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5357   -1.3474    0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6037   -2.1084   -0.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6776   -1.0209   -1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7630   -2.7446   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.0951    2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388   -0.9706    3.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 26 29  1  0
 29 30  1  1
 10  2  1  0
 29 14  1  0
 29 16  1  0
 24 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  0
 14 37  1  1
 15 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  6
 19 44  1  0
 19 45  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  6
 25 55  1  0
 27 56  1  0
 30 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,2AS,4as,7as,7BR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoic acid	Generator
Melleolide-K	MeSH

Chemical Formula

C₂₃H₂₇ClO₆

Average Mass

434.9100 Da

Monoisotopic Mass

434.14962 Da

IUPAC Name

(2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

Traditional Name

(2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

CAS Registry Number

Not Available

SMILES

CC1=C(C(=O)O[C@@H]2C[C@]3(C)[C@H]4CC(C)(C)C[C@H]4C=C(C=O)[C@]23O)C(O)=CC(O)=C1Cl

InChI Identifier

InChI=1S/C23H27ClO6/c1-11-18(15(26)6-16(27)19(11)24)20(28)30-17-9-22(4)14-8-21(2,3)7-12(14)5-13(10-25)23(17,22)29/h5-6,10,12,14,17,26-27,29H,7-9H2,1-4H3/t12-,14+,17-,22-,23+/m1/s1

InChI Key

UHFQTECWVLYLBG-PPUVGZBRSA-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
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Armillaria mellea	Fungi	KNApSAcK
Armillariella	NPAtlas	10805573
Armillariella mellea (Vahl. ex Fr.) Karst	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Hexacarboxylic acids and derivatives

Direct Parent

Hexacarboxylic acids and derivatives

Alternative Parents

Substituents

Hexacarboxylic acid or derivatives
Para-terphenyl
Terphenyl
Biphenyl
Phenol ester
Phenoxy compound
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Hydroxy acid
Benzenoid
Carboxylic acid ester
Secondary alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:65698 )
acetate ester (CHEBI:65698 )
para-terphenyl (CHEBI:65698 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.09	ALOGPS
logP	4.71	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.85 m³·mol⁻¹	ChemAxon
Polarizability	44.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA001668

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8086475

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9910824

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Momose I, Sekizawa R, Hosokawa N, Iinuma H, Matsui S, Nakamura H, Naganawa H, Hamada M, Takeuchi T: Melleolides K, L and M, new melleolides from Armillariella mellea. J Antibiot (Tokyo). 2000 Feb;53(2):137-43. doi: 10.7164/antibiotics.53.137. [PubMed:10805573 ]
Bohnert M, Miethbauer S, Dahse HM, Ziemen J, Nett M, Hoffmeister D: In vitro cytotoxicity of melleolide antibiotics: structural and mechanistic aspects. Bioorg Med Chem Lett. 2011 Apr 1;21(7):2003-6. doi: 10.1016/j.bmcl.2011.02.026. Epub 2011 Feb 12. [PubMed:21376582 ]
Kobori H, Sekiya A, Suzuki T, Choi JH, Hirai H, Kawagishi H: Bioactive sesquiterpene aryl esters from the culture broth of Armillaria sp. J Nat Prod. 2015 Jan 23;78(1):163-7. doi: 10.1021/np500322t. Epub 2014 Dec 19. [PubMed:25524590 ]

Showing NP-Card for Melleolide K (NP0003257)

MOL for NP0003257 (Melleolide K)

3D MOL for NP0003257 (Melleolide K)

3D SDF for NP0003257 (Melleolide K)

3D-SDF for NP0003257 (Melleolide K)

PDB for NP0003257 (Melleolide K)

3D PDB for NP0003257 (Melleolide K)

SMILES for NP0003257 (Melleolide K)

INCHI for NP0003257 (Melleolide K)

Structure for NP0003257 (Melleolide K)

3D Structure for NP0003257 (Melleolide K)