NP-MRD: Showing NP-Card for Arthone C (NP0001548)

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Record Information

Version

1.0

Created at

2020-09-15 19:20:19 UTC

Updated at

2021-08-10 02:55:10 UTC

NP-MRD ID

NP0001548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arthone C

Provided By

NPAtlas

Description

Methyl 2,3,8-trihydroxy-6-(hydroxymethyl)-9-oxo-9H-xanthene-1-carboxylate belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Arthone C is found in Arthrinium. Based on a literature review very few articles have been published on methyl 2,3,8-trihydroxy-6-(hydroxymethyl)-9-oxo-9H-xanthene-1-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 36 38  0  0  0  0            999 V2000
   -3.7480   -3.0081   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221   -1.9607   -0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1320   -0.6750    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184   -0.5013    0.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3505    0.5199    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    1.7457    0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3706    1.6962    0.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    2.9328    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    4.1389    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    2.9616    0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    1.8035    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322    1.8433    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.8106   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1477    0.8699   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8975   -0.2599   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771   -0.1899   -0.4606 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9839   -0.3934    0.7824 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -1.4712   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697   -1.5564   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285   -2.7777   -0.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639   -0.4208   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2266   -0.5006   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7632   -1.6107   -0.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846    0.6128    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -3.4069    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3329   -3.8290   -0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6373   -2.6239   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801    2.4517    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    4.1346    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    3.9107    0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    1.8475    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612   -0.9963   -1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.7908   -0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7518   -1.2471    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -2.3769   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -3.2649   -0.6750 H   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  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
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24  5  1  0  0  0  0
 24 11  2  0  0  0  0
 21 13  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  7 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 14 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  0  0  0  0
 18 35  1  0  0  0  0
 20 36  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.7480   -3.0081   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221   -1.9607   -0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1320   -0.6750    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184   -0.5013    0.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3505    0.5199    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    1.7457    0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3706    1.6962    0.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    2.9328    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    4.1389    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    2.9616    0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    1.8035    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322    1.8433    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.8106   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1477    0.8699   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8975   -0.2599   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771   -0.1899   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9839   -0.3934    0.7824 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -1.4712   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697   -1.5564   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285   -2.7777   -0.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639   -0.4208   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2266   -0.5006   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7632   -1.6107   -0.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846    0.6128    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -3.4069    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3329   -3.8290   -0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6373   -2.6239   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801    2.4517    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    4.1346    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    3.9107    0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    1.8475    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612   -0.9963   -1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.7908   -0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7518   -1.2471    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -2.3769   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -3.2649   -0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  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
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  5  1  0
 24 11  2  0
 21 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END


  Mrv1652306242117433D          

 36 38  0  0  0  0            999 V2000
   -3.7480   -3.0081   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221   -1.9607   -0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1320   -0.6750    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184   -0.5013    0.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3505    0.5199    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    1.7457    0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3706    1.6962    0.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    2.9328    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    4.1389    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    2.9616    0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    1.8035    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322    1.8433    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.8106   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1477    0.8699   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8975   -0.2599   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771   -0.1899   -0.4606 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9839   -0.3934    0.7824 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -1.4712   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697   -1.5564   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285   -2.7777   -0.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639   -0.4208   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2266   -0.5006   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7632   -1.6107   -0.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846    0.6128    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -3.4069    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3329   -3.8290   -0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6373   -2.6239   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801    2.4517    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    4.1346    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    3.9107    0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    1.8475    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612   -0.9963   -1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.7908   -0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7518   -1.2471    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -2.3769   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -3.2649   -0.6750 H   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  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
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24  5  1  0  0  0  0
 24 11  2  0  0  0  0
 21 13  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  7 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 14 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  0  0  0  0
 18 35  1  0  0  0  0
 20 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)C3=C(O[H])C([H])=C(C([H])=C3O2)C([H])([H])O[H])C(C(=O)OC([H])([H])[H])=C1O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O8/c1-23-16(22)13-12-10(4-8(19)14(13)20)24-9-3-6(5-17)2-7(18)11(9)15(12)21/h2-4,17-20H,5H2,1H3

> <INCHI_KEY>
MMJCUOJBTFCNHB-UHFFFAOYSA-N

> <FORMULA>
C16H12O8

> <MOLECULAR_WEIGHT>
332.264

> <EXACT_MASS>
332.053217346

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
31.832710293155447

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2,3,8-trihydroxy-6-(hydroxymethyl)-9-oxo-9H-xanthene-1-carboxylate

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
2.585071452

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.304829358552213

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.396510306470365

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9150930483423716

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
81.60019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2,3,8-trihydroxy-6-(hydroxymethyl)-9-oxoxanthene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.7480   -3.0081   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221   -1.9607   -0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1320   -0.6750    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184   -0.5013    0.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3505    0.5199    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    1.7457    0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3706    1.6962    0.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    2.9328    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    4.1389    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    2.9616    0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    1.8035    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322    1.8433    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.8106   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1477    0.8699   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8975   -0.2599   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771   -0.1899   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9839   -0.3934    0.7824 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -1.4712   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697   -1.5564   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285   -2.7777   -0.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639   -0.4208   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2266   -0.5006   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7632   -1.6107   -0.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846    0.6128    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -3.4069    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3329   -3.8290   -0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6373   -2.6239   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801    2.4517    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    4.1346    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    3.9107    0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    1.8475    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612   -0.9963   -1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.7908   -0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7518   -1.2471    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -2.3769   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -3.2649   -0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  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
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  5  1  0
 24 11  2  0
 21 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  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      -3.748  -3.008  -0.334  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.822  -1.961  -0.210  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.132  -0.675   0.041  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.418  -0.501   0.162  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.350   0.520   0.201  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.011   1.746   0.467  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.371   1.696   0.552  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.368   2.933   0.635  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.028   4.139   0.896  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.980   2.962   0.544  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.279   1.804   0.288  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.032   1.843   0.204  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.785   0.811  -0.033  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.148   0.870  -0.117  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.898  -0.260  -0.371  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.377  -0.190  -0.461  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.984  -0.393   0.782  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.285  -1.471  -0.545  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.870  -1.556  -0.463  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.329  -2.778  -0.644  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.164  -0.421  -0.210  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.227  -0.501  -0.129  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.763  -1.611  -0.290  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.985   0.613   0.123  0.00  0.00           C+0
HETATM   25  H   UNK     0      -4.106  -3.407   0.630  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.333  -3.829  -0.988  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.637  -2.624  -0.911  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.980   2.452   0.729  0.00  0.00           H+0
HETATM   29  H   UNK     0      -4.023   4.135   0.964  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.469   3.911   0.678  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.626   1.847   0.026  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.761  -0.996  -1.132  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.671   0.791  -0.849  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.752  -1.247   1.186  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.834  -2.377  -0.746  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.515  -3.265  -0.675  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   28                                                       
CONECT    8    6    9   10                                                  
CONECT    9    8   29                                                       
CONECT   10    8   11   30                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17   32   33                                             
CONECT   17   16   34                                                       
CONECT   18   15   19   35                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   36                                                       
CONECT   21   19   22   13                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5   11                                                  
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    7                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   14                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   20                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
   -3.7480   -3.0081   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8221   -1.9607   -0.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1320   -0.6750    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184   -0.5013    0.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3505    0.5199    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    1.7457    0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3706    1.6962    0.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    2.9328    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0281    4.1389    0.8963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    2.9616    0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792    1.8035    0.2878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322    1.8433    0.2042 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.8106   -0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1477    0.8699   -0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8975   -0.2599   -0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3771   -0.1899   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9839   -0.3934    0.7824 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847   -1.4712   -0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697   -1.5564   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3285   -2.7777   -0.6440 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1639   -0.4208   -0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2266   -0.5006   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7632   -1.6107   -0.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846    0.6128    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1065   -3.4069    0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3329   -3.8290   -0.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6373   -2.6239   -0.9114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801    2.4517    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    4.1346    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    3.9107    0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6260    1.8475    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7612   -0.9963   -1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713    0.7908   -0.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7518   -1.2471    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -2.3769   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154   -3.2649   -0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  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
 16 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  5  1  0
 24 11  2  0
 21 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl 2,3,8-trihydroxy-6-(hydroxymethyl)-9-oxo-9H-xanthene-1-carboxylic acid	Generator

Chemical Formula

C₁₆H₁₂O₈

Average Mass

332.2640 Da

Monoisotopic Mass

332.05322 Da

IUPAC Name

methyl 2,3,8-trihydroxy-6-(hydroxymethyl)-9-oxo-9H-xanthene-1-carboxylate

Traditional Name

methyl 2,3,8-trihydroxy-6-(hydroxymethyl)-9-oxoxanthene-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C(=O)C3=C(O[H])C([H])=C(C([H])=C3O2)C([H])([H])O[H])C(C(=O)OC([H])([H])[H])=C1O[H]

InChI Identifier

InChI=1S/C16H12O8/c1-23-16(22)13-12-10(4-8(19)14(13)20)24-9-3-6(5-17)2-7(18)11(9)15(12)21/h2-4,17-20H,5H2,1H3

InChI Key

MMJCUOJBTFCNHB-UHFFFAOYSA-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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600Mz, DMSO, simulated)	ryan.renslow@pnnl.gov	Not Available	Not Available	2020-09-15	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Arthrinium	NPAtlas	30096887

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Salicylic acid or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Methyl ester
Carboxylic acid ester
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
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	1.48	ALOGPS
logP	2.59	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.4	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.6 m³·mol⁻¹	ChemAxon
Polarizability	31.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA027956

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

71044435

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146684178

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Arthone C (NP0001548)

MOL for NP0001548 (Arthone C)

3D MOL for NP0001548 (Arthone C)

3D SDF for NP0001548 (Arthone C)

3D-SDF for NP0001548 (Arthone C)

PDB for NP0001548 (Arthone C)

3D PDB for NP0001548 (Arthone C)

SMILES for NP0001548 (Arthone C)

INCHI for NP0001548 (Arthone C)

Structure for NP0001548 (Arthone C)

3D Structure for NP0001548 (Arthone C)