NP-MRD: Showing NP-Card for 2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid (NP0006452)

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Record Information

Version

2.0

Created at

2020-12-09 03:28:05 UTC

Updated at

2021-07-15 16:54:50 UTC

NP-MRD ID

NP0006452

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid

Provided By

NPAtlas

Description

2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid is found in Xylaria. Based on a literature review very few articles have been published on 2,5-dihydroxy-8-methoxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

 35 37  0  0  0  0            999 V2000
   -2.2477   -3.6149    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -2.5700    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -1.2272    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.7842    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939    0.5595    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960    1.0179    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640    1.4790    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948    2.8290    0.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433    1.0802    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127    1.9790    0.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506    1.6144   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    2.6018   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5415    2.2472   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317    0.9281   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    0.5569   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795   -0.1121   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505   -1.4617   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7953   -2.4908    0.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -1.6572   -0.0585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    0.2882   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -0.6763    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -1.9061    0.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -0.2635    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -3.3610    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -4.0578   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933   -4.4627    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835   -1.4957    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2257    0.7675   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2532    0.6239    1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7264    2.1181    0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9099    3.5661    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    3.6388   -0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    2.9873   -0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693    1.2583   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2925   -1.9996    0.8179 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
  4  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23  3  1  0  0  0  0
 23  9  2  0  0  0  0
 20 11  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  4 27  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  8 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  0  0  0  0
 15 34  1  0  0  0  0
 19 35  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.2477   -3.6149    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -2.5700    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -1.2272    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.7842    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939    0.5595    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960    1.0179    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640    1.4790    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948    2.8290    0.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433    1.0802    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127    1.9790    0.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506    1.6144   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    2.6018   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5415    2.2472   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317    0.9281   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    0.5569   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795   -0.1121   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505   -1.4617   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7953   -2.4908    0.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -1.6572   -0.0585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    0.2882   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -0.6763    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -1.9061    0.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -0.2635    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -3.3610    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -4.0578   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933   -4.4627    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835   -1.4957    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2257    0.7675   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2532    0.6239    1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7264    2.1181    0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9099    3.5661    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    3.6388   -0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    2.9873   -0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693    1.2583   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2925   -1.9996    0.8179 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23  3  1  0
 23  9  2  0
 20 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 19 35  1  0
M  END


  Mrv1652306242118273D          

 35 37  0  0  0  0            999 V2000
   -2.2477   -3.6149    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -2.5700    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -1.2272    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.7842    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939    0.5595    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960    1.0179    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640    1.4790    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948    2.8290    0.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433    1.0802    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127    1.9790    0.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506    1.6144   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    2.6018   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5415    2.2472   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317    0.9281   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    0.5569   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795   -0.1121   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505   -1.4617   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7953   -2.4908    0.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -1.6572   -0.0585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    0.2882   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -0.6763    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -1.9061    0.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -0.2635    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -3.3610    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -4.0578   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933   -4.4627    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835   -1.4957    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2257    0.7675   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2532    0.6239    1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7264    2.1181    0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9099    3.5661    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    3.6388   -0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    2.9873   -0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693    1.2583   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2925   -1.9996    0.8179 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
  4  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23  3  1  0  0  0  0
 23  9  2  0  0  0  0
 20 11  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  4 27  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
  6 30  1  0  0  0  0
  8 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 33  1  0  0  0  0
 15 34  1  0  0  0  0
 19 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006452

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C2C(=O)C3=C(OC2=C([H])C([H])=C1O[H])C(O[H])=C(C([H])=C3OC([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-6-5-9(22-2)12-14(19)11-8(23-15(12)13(6)18)4-3-7(17)10(11)16(20)21/h3-5,17-18H,1-2H3,(H,20,21)

> <INCHI_KEY>
WNNZOICLHAOLHA-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.265

> <EXACT_MASS>
316.058302726

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.949775751280473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dihydroxy-8-methoxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
3.0158426086666665

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.819753346819551

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6292109249883922

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7620660850492906

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
79.53869999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dihydroxy-8-methoxy-6-methyl-9-oxoxanthene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.2477   -3.6149    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -2.5700    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -1.2272    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.7842    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939    0.5595    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960    1.0179    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640    1.4790    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948    2.8290    0.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433    1.0802    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127    1.9790    0.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506    1.6144   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    2.6018   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5415    2.2472   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317    0.9281   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    0.5569   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795   -0.1121   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505   -1.4617   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7953   -2.4908    0.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -1.6572   -0.0585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    0.2882   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -0.6763    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -1.9061    0.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -0.2635    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -3.3610    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -4.0578   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933   -4.4627    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835   -1.4957    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2257    0.7675   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2532    0.6239    1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7264    2.1181    0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9099    3.5661    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    3.6388   -0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    2.9873   -0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693    1.2583   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2925   -1.9996    0.8179 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
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  9 10  1  0
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 14 15  1  0
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 17 18  2  0
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 16 20  2  0
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 21 23  1  0
 23  3  1  0
 23  9  2  0
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  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 19 35  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      -2.248  -3.615   0.169  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.325  -2.570   0.125  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.666  -1.227   0.110  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.971  -0.784   0.137  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.294   0.560   0.122  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.696   1.018   0.151  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.264   1.479   0.077  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.595   2.829   0.062  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.943   1.080   0.049  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.013   1.979   0.008  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.251   1.614  -0.020  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.225   2.602  -0.064  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.542   2.247  -0.093  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.932   0.928  -0.080  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.263   0.557  -0.109  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.979  -0.112  -0.035  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.450  -1.462  -0.024  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.795  -2.491   0.013  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.875  -1.657  -0.059  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.655   0.288  -0.007  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.672  -0.676   0.037  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.882  -1.906   0.054  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.671  -0.264   0.066  0.00  0.00           C+0
HETATM   24  H   UNK     0      -3.182  -3.361   0.738  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.481  -4.058  -0.823  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.793  -4.463   0.761  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.784  -1.496   0.172  0.00  0.00           H+0
HETATM   28  H   UNK     0      -5.226   0.768  -0.798  0.00  0.00           H+0
HETATM   29  H   UNK     0      -5.253   0.624   1.032  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.726   2.118   0.239  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.910   3.566   0.030  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.913   3.639  -0.074  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.343   2.987  -0.128  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.969   1.258  -0.141  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.293  -2.000   0.818  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   28   29   30                                             
CONECT    7    5    8    9                                                  
CONECT    8    7   31                                                       
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   32                                                  
CONECT   13   12   14   33                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   34                                                       
CONECT   16   14   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   35                                                       
CONECT   20   16   21   11                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    3    9                                                  
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    4                                                            
CONECT   28    6                                                            
CONECT   29    6                                                            
CONECT   30    6                                                            
CONECT   31    8                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   15                                                            
CONECT   35   19                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
   -2.2477   -3.6149    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3248   -2.5700    0.1251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658   -1.2272    0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.7842    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939    0.5595    0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960    1.0179    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2640    1.4790    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948    2.8290    0.0620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433    1.0802    0.0490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0127    1.9790    0.0077 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2506    1.6144   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    2.6018   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5415    2.2472   -0.0930 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9317    0.9281   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2631    0.5569   -0.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795   -0.1121   -0.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505   -1.4617   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7953   -2.4908    0.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749   -1.6572   -0.0585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6546    0.2882   -0.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6723   -0.6763    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8821   -1.9061    0.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -0.2635    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -3.3610    0.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810   -4.0578   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933   -4.4627    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835   -1.4957    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2257    0.7675   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2532    0.6239    1.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7264    2.1181    0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9099    3.5661    0.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    3.6388   -0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    2.9873   -0.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9693    1.2583   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2925   -1.9996    0.8179 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
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
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 14 16  1  0
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 21 23  1  0
 23  3  1  0
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 20 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 19 35  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,5-Dihydroxy-8-methoxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate	Generator
2,5-Dihydroxy-8-methoxy-6-methyl-9-oxo-9H-xanthene -1-carboxylate	Generator

Chemical Formula

C₁₆H₁₂O₇

Average Mass

316.2650 Da

Monoisotopic Mass

316.05830 Da

IUPAC Name

2,5-dihydroxy-8-methoxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid

Traditional Name

2,5-dihydroxy-8-methoxy-6-methyl-9-oxoxanthene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C3=C(OC2=C(O)C(C)=C1)C=CC(O)=C3C(O)=O

InChI Identifier

InChI=1S/C16H12O7/c1-6-5-9(22-2)12-14(19)11-8(23-15(12)13(6)18)4-3-7(17)10(11)16(20)21/h3-5,17-18H,1-2H3,(H,20,21)

InChI Key

WNNZOICLHAOLHA-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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xylaria	NPAtlas	16826555

Chemical Taxonomy

Description

This compound 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
Hydroxybenzoic acid
Salicylic acid or derivatives
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
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	2.17	ALOGPS
logP	3.02	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	1.63	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.54 m³·mol⁻¹	ChemAxon
Polarizability	30.95 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

NPA010937

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21378323

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90750926

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid (NP0006452)

MOL for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)

3D MOL for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)

3D SDF for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)

3D-SDF for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)

PDB for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)

3D PDB for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)

SMILES for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)

INCHI for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)

Structure for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)

3D Structure for NP0006452 (2,5‐dihydroxy‐8‐methoxy‐6‐methyl‐9‐oxo‐9H‐xanthene ‐1‐carboxylic acid)