NP-MRD: Showing NP-Card for Xanthofulvin (NP0004902)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 02:18:05 UTC

Updated at

2021-07-15 16:50:29 UTC

NP-MRD ID

NP0004902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xanthofulvin

Provided By

NPAtlas

Description

5-Acetyl-7-{[(3Z)-5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene](hydroxy)methyl}-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid belongs to the class of organic compounds known as homoisoflavonoids. These are naturally occurring oxygen heterocycles with a structure based on a 16-carbon skeleton including a chromanone, chromone or chromane system with a benzyl group at position C-3. Xanthofulvin is found in Penicillium. Xanthofulvin was first documented in 2003 (PMID: 14513903). Based on a literature review very few articles have been published on 5-acetyl-7-{[(3Z)-5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene](hydroxy)methyl}-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118093D          

 60 64  0  0  0  0            999 V2000
   -2.5851   -1.4221    4.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769   -2.0790    2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263   -3.1962    2.7619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637   -1.5008    1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -1.7130    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -2.5790    2.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -1.1676    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173   -1.4942   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -2.8458   -0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2076   -0.6053   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    0.8235   -0.4756 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9539    1.5999   -0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569    1.2354   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2605    2.2029   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5526    1.9108   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5395    2.8748   -0.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550    0.6080   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2443    0.3642   -1.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -0.3979   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620   -1.7298   -1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396   -2.7086   -1.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7373   -2.0030   -1.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.0567   -0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6053   -1.0433   -0.6983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7730   -2.2325   -0.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595   -0.3607   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795   -0.1157   -0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210    0.7024   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    1.1711   -2.1461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    0.9490   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    1.7469   -1.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5941    2.3859   -2.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4331    3.1150   -3.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3382    2.3124   -3.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3863    1.9627   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2843    2.7180   -1.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8257    1.3367   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1546    1.5441    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0165    0.5563    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6967    0.3361    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579   -0.4238    1.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -0.6888    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6590   -1.1576    4.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3010   -2.1927    4.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -0.5255    4.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2795   -2.7276    3.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337   -3.5570    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -2.0927    2.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275   -3.3613   -0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.1009    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962    1.1515   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357    3.2178    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    3.8294   -0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8531   -0.3016   -1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2200   -2.7408   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4359    0.0765   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0593    2.7609   -4.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3676    3.2552   -2.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4967    1.1060    1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642    0.0661    1.5864 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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  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  1  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
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 26  2  0  0  0  0
 26 27  1  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
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 31 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42  4  1  0  0  0  0
 24 10  1  0  0  0  0
 42 27  2  0  0  0  0
 23 13  1  0  0  0  0
 40 30  1  0  0  0  0
  1 43  1  0  0  0  0
  1 44  1  0  0  0  0
  1 45  1  0  0  0  0
  6 46  1  0  0  0  0
  6 47  1  0  0  0  0
  6 48  1  0  0  0  0
  9 49  1  0  0  0  0
 11 50  1  0  0  0  0
 11 51  1  0  0  0  0
 14 52  1  0  0  0  0
 16 53  1  0  0  0  0
 18 54  1  0  0  0  0
 22 55  1  0  0  0  0
 26 56  1  0  0  0  0
 34 57  1  0  0  0  0
 36 58  1  0  0  0  0
 38 59  1  0  0  0  0
 39 60  1  0  0  0  0
M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
   -2.5851   -1.4221    4.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769   -2.0790    2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263   -3.1962    2.7619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637   -1.5008    1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -1.7130    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -2.5790    2.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -1.1676    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173   -1.4942   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -2.8458   -0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2076   -0.6053   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    0.8235   -0.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9539    1.5999   -0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569    1.2354   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2605    2.2029   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5526    1.9108   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5395    2.8748   -0.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550    0.6080   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2443    0.3642   -1.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -0.3979   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620   -1.7298   -1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396   -2.7086   -1.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7373   -2.0030   -1.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.0567   -0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6053   -1.0433   -0.6983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7730   -2.2325   -0.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595   -0.3607   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795   -0.1157   -0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210    0.7024   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    1.1711   -2.1461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    0.9490   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    1.7469   -1.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5941    2.3859   -2.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4331    3.1150   -3.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3382    2.3124   -3.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3863    1.9627   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2843    2.7180   -1.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8257    1.3367   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1546    1.5441    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0165    0.5563    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6967    0.3361    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579   -0.4238    1.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -0.6888    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6590   -1.1576    4.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3010   -2.1927    4.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -0.5255    4.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2795   -2.7276    3.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337   -3.5570    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -2.0927    2.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275   -3.3613   -0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.1009    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962    1.1515   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357    3.2178    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    3.8294   -0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8531   -0.3016   -1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2200   -2.7408   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4359    0.0765   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0593    2.7609   -4.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3676    3.2552   -2.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4967    1.1060    1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642    0.0661    1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  2  0
 23 24  1  0
 24 25  2  0
  7 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 31 35  1  0
 35 36  1  0
 35 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  1  0
 42  4  1  0
 24 10  1  0
 42 27  2  0
 23 13  1  0
 40 30  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  6 46  1  0
  6 47  1  0
  6 48  1  0
  9 49  1  0
 11 50  1  0
 11 51  1  0
 14 52  1  0
 16 53  1  0
 18 54  1  0
 22 55  1  0
 26 56  1  0
 34 57  1  0
 36 58  1  0
 38 59  1  0
 39 60  1  0
M  END


  Mrv1652306242118093D          

 60 64  0  0  0  0            999 V2000
   -2.5851   -1.4221    4.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769   -2.0790    2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263   -3.1962    2.7619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637   -1.5008    1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -1.7130    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -2.5790    2.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -1.1676    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173   -1.4942   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -2.8458   -0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2076   -0.6053   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    0.8235   -0.4756 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9539    1.5999   -0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569    1.2354   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2605    2.2029   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5526    1.9108   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5395    2.8748   -0.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550    0.6080   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2443    0.3642   -1.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -0.3979   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620   -1.7298   -1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396   -2.7086   -1.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7373   -2.0030   -1.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.0567   -0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6053   -1.0433   -0.6983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7730   -2.2325   -0.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595   -0.3607   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795   -0.1157   -0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210    0.7024   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    1.1711   -2.1461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    0.9490   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    1.7469   -1.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5941    2.3859   -2.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4331    3.1150   -3.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3382    2.3124   -3.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3863    1.9627   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2843    2.7180   -1.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8257    1.3367   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1546    1.5441    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0165    0.5563    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6967    0.3361    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579   -0.4238    1.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -0.6888    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6590   -1.1576    4.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3010   -2.1927    4.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -0.5255    4.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2795   -2.7276    3.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337   -3.5570    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -2.0927    2.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275   -3.3613   -0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.1009    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962    1.1515   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357    3.2178    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    3.8294   -0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8531   -0.3016   -1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2200   -2.7408   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4359    0.0765   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0593    2.7609   -4.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3676    3.2552   -2.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4967    1.1060    1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642    0.0661    1.5864 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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  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  1  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
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 19 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 26  2  0  0  0  0
 26 27  1  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
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 31 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42  4  1  0  0  0  0
 24 10  1  0  0  0  0
 42 27  2  0  0  0  0
 23 13  1  0  0  0  0
 40 30  1  0  0  0  0
  1 43  1  0  0  0  0
  1 44  1  0  0  0  0
  1 45  1  0  0  0  0
  6 46  1  0  0  0  0
  6 47  1  0  0  0  0
  6 48  1  0  0  0  0
  9 49  1  0  0  0  0
 11 50  1  0  0  0  0
 11 51  1  0  0  0  0
 14 52  1  0  0  0  0
 16 53  1  0  0  0  0
 18 54  1  0  0  0  0
 22 55  1  0  0  0  0
 26 56  1  0  0  0  0
 34 57  1  0  0  0  0
 36 58  1  0  0  0  0
 38 59  1  0  0  0  0
 39 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C2C(=O)C3=C(OC2=C([H])C(O[H])=C1O[H])C(C(=O)C([H])([H])[H])=C(C(=C3[H])C(\O[H])=C1\C(=O)C2=C(C(=O)O[H])C(O[H])=C(O[H])C([H])=C2OC1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H18O14/c1-7-9(21(32)11-6-41-14-4-12(30)24(35)19(27(37)38)17(14)23(11)34)3-10-22(33)18-15(42-26(10)16(7)8(2)29)5-13(31)25(36)20(18)28(39)40/h3-5,30-32,35-36H,6H2,1-2H3,(H,37,38)(H,39,40)/b21-11-

> <INCHI_KEY>
VZJACTNXARYXEM-NHDPSOOVSA-N

> <FORMULA>
C28H18O14

> <MOLECULAR_WEIGHT>
578.438

> <EXACT_MASS>
578.06965526

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
55.77754937438679

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-acetyl-7-{[(3Z)-5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene](hydroxy)methyl}-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
3.0708313873333335

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.33995439911659

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4231377466450006

> <JCHEM_PKA_STRONGEST_BASIC>
-6.582102617734841

> <JCHEM_POLAR_SURFACE_AREA>
245.41999999999996

> <JCHEM_REFRACTIVITY>
141.7412999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-acetyl-7-{[(3Z)-5-carboxy-6,7-dihydroxy-4-oxo-2H-1-benzopyran-3-ylidene](hydroxy)methyl}-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
   -2.5851   -1.4221    4.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769   -2.0790    2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263   -3.1962    2.7619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637   -1.5008    1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -1.7130    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -2.5790    2.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -1.1676    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173   -1.4942   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -2.8458   -0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2076   -0.6053   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    0.8235   -0.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9539    1.5999   -0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569    1.2354   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2605    2.2029   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5526    1.9108   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5395    2.8748   -0.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550    0.6080   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2443    0.3642   -1.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -0.3979   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620   -1.7298   -1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396   -2.7086   -1.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7373   -2.0030   -1.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.0567   -0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6053   -1.0433   -0.6983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7730   -2.2325   -0.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595   -0.3607   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795   -0.1157   -0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210    0.7024   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    1.1711   -2.1461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    0.9490   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    1.7469   -1.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5941    2.3859   -2.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4331    3.1150   -3.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3382    2.3124   -3.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3863    1.9627   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2843    2.7180   -1.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8257    1.3367   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1546    1.5441    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0165    0.5563    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6967    0.3361    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579   -0.4238    1.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -0.6888    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6590   -1.1576    4.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3010   -2.1927    4.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -0.5255    4.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2795   -2.7276    3.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337   -3.5570    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -2.0927    2.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275   -3.3613   -0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.1009    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962    1.1515   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357    3.2178    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    3.8294   -0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8531   -0.3016   -1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2200   -2.7408   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4359    0.0765   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0593    2.7609   -4.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3676    3.2552   -2.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4967    1.1060    1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642    0.0661    1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  2  0
 23 24  1  0
 24 25  2  0
  7 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 31 35  1  0
 35 36  1  0
 35 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  1  0
 42  4  1  0
 24 10  1  0
 42 27  2  0
 23 13  1  0
 40 30  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  6 46  1  0
  6 47  1  0
  6 48  1  0
  9 49  1  0
 11 50  1  0
 11 51  1  0
 14 52  1  0
 16 53  1  0
 18 54  1  0
 22 55  1  0
 26 56  1  0
 34 57  1  0
 36 58  1  0
 38 59  1  0
 39 60  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      -2.585  -1.422   4.199  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.577  -2.079   2.875  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.126  -3.196   2.762  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.964  -1.501   1.686  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.648  -1.713   1.326  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.168  -2.579   2.215  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.071  -1.168   0.204  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.317  -1.494  -0.087  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.729  -2.846  -0.028  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.208  -0.605  -0.400  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.846   0.824  -0.476  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.954   1.600  -0.002  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.257   1.235  -0.270  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.261   2.203  -0.190  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.553   1.911  -0.440  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.540   2.875  -0.359  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.955   0.608  -0.796  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.244   0.364  -1.036  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.971  -0.398  -0.887  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.362  -1.730  -1.260  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.640  -2.709  -1.383  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.737  -2.003  -1.529  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.660  -0.057  -0.622  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.605  -1.043  -0.698  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.773  -2.232  -0.994  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.860  -0.361  -0.607  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.180  -0.116  -0.294  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.921   0.702  -1.150  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.363   1.171  -2.146  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.235   0.949  -0.846  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.044   1.747  -1.641  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.594   2.386  -2.846  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.433   3.115  -3.526  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.338   2.312  -3.381  0.00  0.00           O+0
HETATM   35  C   UNK     0      -6.386   1.963  -1.278  0.00  0.00           C+0
HETATM   36  O   UNK     0      -7.284   2.718  -1.963  0.00  0.00           O+0
HETATM   37  C   UNK     0      -6.826   1.337  -0.102  0.00  0.00           C+0
HETATM   38  O   UNK     0      -8.155   1.544   0.267  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.016   0.556   0.665  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.697   0.336   0.320  0.00  0.00           C+0
HETATM   41  O   UNK     0      -3.958  -0.424   1.089  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.700  -0.689   0.841  0.00  0.00           C+0
HETATM   43  H   UNK     0      -3.659  -1.158   4.417  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.301  -2.193   4.955  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.959  -0.526   4.253  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.280  -2.728   3.200  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.334  -3.557   1.701  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.177  -2.093   2.269  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.528  -3.361  -0.893  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.958   1.101   0.111  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.696   1.151  -1.521  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.936   3.218   0.090  0.00  0.00           H+0
HETATM   53  H   UNK     0       7.404   3.829  -0.120  0.00  0.00           H+0
HETATM   54  H   UNK     0       8.853  -0.302  -1.274  0.00  0.00           H+0
HETATM   55  H   UNK     0       8.220  -2.741  -1.046  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.436   0.077  -1.501  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.059   2.761  -4.244  0.00  0.00           H+0
HETATM   58  H   UNK     0      -7.368   3.255  -2.736  0.00  0.00           H+0
HETATM   59  H   UNK     0      -8.497   1.106   1.105  0.00  0.00           H+0
HETATM   60  H   UNK     0      -6.364   0.066   1.586  0.00  0.00           H+0
CONECT    1    2   43   44   45                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   42                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   46   47   48                                             
CONECT    7    5    8   26                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   49                                                       
CONECT   10    8   11   24                                                  
CONECT   11   10   12   50   51                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15   52                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   53                                                       
CONECT   17   15   18   19                                                  
CONECT   18   17   54                                                       
CONECT   19   17   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   55                                                       
CONECT   23   19   24   13                                                  
CONECT   24   23   25   10                                                  
CONECT   25   24                                                            
CONECT   26    7   27   56                                                  
CONECT   27   26   28   42                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   40                                                  
CONECT   31   30   32   35                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   57                                                       
CONECT   35   31   36   37                                                  
CONECT   36   35   58                                                       
CONECT   37   35   38   39                                                  
CONECT   38   37   59                                                       
CONECT   39   37   40   60                                                  
CONECT   40   39   41   30                                                  
CONECT   41   40   42                                                       
CONECT   42   41    4   27                                                  
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    1                                                            
CONECT   46    6                                                            
CONECT   47    6                                                            
CONECT   48    6                                                            
CONECT   49    9                                                            
CONECT   50   11                                                            
CONECT   51   11                                                            
CONECT   52   14                                                            
CONECT   53   16                                                            
CONECT   54   18                                                            
CONECT   55   22                                                            
CONECT   56   26                                                            
CONECT   57   34                                                            
CONECT   58   36                                                            
CONECT   59   38                                                            
CONECT   60   39                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

RDKit          3D

60 64  0  0  0  0  0  0  0  0999 V2000
   -2.5851   -1.4221    4.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5769   -2.0790    2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1263   -3.1962    2.7619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9637   -1.5008    1.6859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6479   -1.7130    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1684   -2.5790    2.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -1.1676    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3173   -1.4942   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -2.8458   -0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2076   -0.6053   -0.4003 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8456    0.8235   -0.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9539    1.5999   -0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2569    1.2354   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2605    2.2029   -0.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5526    1.9108   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5395    2.8748   -0.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9550    0.6080   -0.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2443    0.3642   -1.0356 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9707   -0.3979   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3620   -1.7298   -1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396   -2.7086   -1.3829 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7373   -2.0030   -1.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6595   -0.0567   -0.6222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6053   -1.0433   -0.6983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7730   -2.2325   -0.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595   -0.3607   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1795   -0.1157   -0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9210    0.7024   -1.1499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    1.1711   -2.1461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2354    0.9490   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0436    1.7469   -1.6408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5941    2.3859   -2.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4331    3.1150   -3.5264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3382    2.3124   -3.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3863    1.9627   -1.2781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2843    2.7180   -1.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8257    1.3367   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1546    1.5441    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0165    0.5563    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6967    0.3361    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579   -0.4238    1.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003   -0.6888    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6590   -1.1576    4.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3010   -2.1927    4.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9590   -0.5255    4.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2795   -2.7276    3.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337   -3.5570    1.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1765   -2.0927    2.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275   -3.3613   -0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.1009    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6962    1.1515   -1.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357    3.2178    0.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4039    3.8294   -0.1201 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8531   -0.3016   -1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2200   -2.7408   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4359    0.0765   -1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0593    2.7609   -4.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3676    3.2552   -2.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4967    1.1060    1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642    0.0661    1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  2  0
 23 24  1  0
 24 25  2  0
  7 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 31 35  1  0
 35 36  1  0
 35 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  1  0
 42  4  1  0
 24 10  1  0
 42 27  2  0
 23 13  1  0
 40 30  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  6 46  1  0
  6 47  1  0
  6 48  1  0
  9 49  1  0
 11 50  1  0
 11 51  1  0
 14 52  1  0
 16 53  1  0
 18 54  1  0
 22 55  1  0
 26 56  1  0
 34 57  1  0
 36 58  1  0
 38 59  1  0
 39 60  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
5-Acetyl-7-{[(3Z)-5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene](hydroxy)methyl}-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate	Generator

Chemical Formula

C₂₈H₁₈O₁₄

Average Mass

578.4380 Da

Monoisotopic Mass

578.06966 Da

IUPAC Name

5-acetyl-7-{[(3Z)-5-carboxy-6,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-ylidene](hydroxy)methyl}-2,3-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid

Traditional Name

5-acetyl-7-{[(3Z)-5-carboxy-6,7-dihydroxy-4-oxo-2H-1-benzopyran-3-ylidene](hydroxy)methyl}-2,3-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C2OC3=CC(O)=C(O)C(C(O)=O)=C3C(=O)C2=CC(\C(O)=C2/COC3=CC(O)=C(O)C(C(O)=O)=C3C2=O)=C1C

InChI Identifier

InChI=1S/C28H18O14/c1-7-9(21(32)11-6-41-14-4-12(30)24(35)19(27(37)38)17(14)23(11)34)3-10-22(33)18-15(42-26(10)16(7)8(2)29)5-13(31)25(36)20(18)28(39)40/h3-5,30-32,35-36H,6H2,1-2H3,(H,37,38)(H,39,40)/b21-11-

InChI Key

VZJACTNXARYXEM-NHDPSOOVSA-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
Penicillium	NPAtlas	14513903

Species Where Detected

Species Name	Source	Reference
Penicillium sp. SPF-3059	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavonoids. These are naturally occurring oxygen heterocycles with a structure based on a 16-carbon skeleton including a chromanone, chromone or chromane system with a benzyl group at position C-3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Not Available

Direct Parent

Homoisoflavonoids

Alternative Parents

Substituents

Homoisoflavonoid
Xanthone
Dibenzopyran
Xanthene
Chromone
Chromane
Benzopyran
Hydroxybenzoic acid
Salicylic acid or derivatives
1-benzopyran
Acetophenone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Pyran
Benzenoid
Vinylogous acid
Heteroaromatic compound
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Enol
Ether
Hydrocarbon derivative
Organic oxygen compound
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	2.11	ALOGPS
logP	3.07	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	1.42	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	245.42 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.74 m³·mol⁻¹	ChemAxon
Polarizability	55.78 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA004924

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00014942

Chemspider ID

8070140

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kumagai K, Hosotani N, Kikuchi K, Kimura T, Saji I: Xanthofulvin, a novel semaphorin inhibitor produced by a strain of Penicillium. J Antibiot (Tokyo). 2003 Jul;56(7):610-6. doi: 10.7164/antibiotics.56.610. [PubMed:14513903 ]

Showing NP-Card for Xanthofulvin (NP0004902)

MOL for NP0004902 (Xanthofulvin)

3D MOL for NP0004902 (Xanthofulvin)

3D SDF for NP0004902 (Xanthofulvin)

3D-SDF for NP0004902 (Xanthofulvin)

PDB for NP0004902 (Xanthofulvin)

3D PDB for NP0004902 (Xanthofulvin)

SMILES for NP0004902 (Xanthofulvin)

INCHI for NP0004902 (Xanthofulvin)

Structure for NP0004902 (Xanthofulvin)

3D Structure for NP0004902 (Xanthofulvin)