NP-MRD: Showing NP-Card for 8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone (NP0028636)

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Record Information

Version

2.0

Created at

2021-06-19 20:28:12 UTC

Updated at

2021-06-29 23:55:32 UTC

NP-MRD ID

NP0028636

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone

Provided By

JEOL Database JEOL Logo

Description

8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone is found in Leiothrix curvifolia. 8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone was first documented in 2001 (Santos, L. C., et al.). Based on a literature review very few articles have been published on methyl 3,8-dihydroxy-4,6-dimethoxy-9-oxo-9H-xanthene-1-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122283D          

 39 41  0  0  0  0            999 V2000
    1.6842   -0.8981   -5.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -0.6492   -4.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1317   -1.7662   -3.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686   -2.9210   -4.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -1.3738   -2.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -1.7533   -3.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486   -1.3752   -2.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5951   -1.7358   -3.0147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.6460   -1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3584   -0.3275   -0.7555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3449   -0.6039    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -0.2500   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097    0.5362    0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    0.9564    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    1.7802    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    2.2509    2.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    3.0470    3.2864 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7512    3.5596    3.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8586    1.8883    1.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297    1.0644    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390    0.7449   -0.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129    0.6015   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446   -0.2623   -1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5873   -0.6538   -1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -0.6362   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.3657   -4.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605   -1.5247   -6.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245    0.0622   -5.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4068   -2.3260   -4.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2232   -1.3360   -2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3677   -0.8553    0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487    0.2891    1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -1.4552    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    2.0617    2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743    4.2017    3.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    2.7496    4.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849    4.1740    4.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8248    2.2251    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730    0.1361   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 22 20  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
  7  9  2  0  0  0  0
 23 24  2  0  0  0  0
 25 23  1  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 20 21  1  0  0  0  0
 13 14  1  0  0  0  0
  5  3  1  0  0  0  0
 22 23  1  0  0  0  0
  3  4  2  0  0  0  0
 22 14  1  0  0  0  0
  3  2  1  0  0  0  0
  9 12  1  0  0  0  0
 16 17  1  0  0  0  0
 25  5  1  0  0  0  0
 17 18  1  0  0  0  0
 25 12  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  6 29  1  0  0  0  0
 15 34  1  0  0  0  0
 19 38  1  0  0  0  0
  8 30  1  0  0  0  0
 21 39  1  0  0  0  0
 18 35  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    1.6842   -0.8981   -5.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -0.6492   -4.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1317   -1.7662   -3.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686   -2.9210   -4.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -1.3738   -2.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -1.7533   -3.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486   -1.3752   -2.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5951   -1.7358   -3.0147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.6460   -1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3584   -0.3275   -0.7555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3449   -0.6039    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -0.2500   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097    0.5362    0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    0.9564    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    1.7802    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    2.2509    2.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    3.0470    3.2864 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7512    3.5596    3.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8586    1.8883    1.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297    1.0644    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390    0.7449   -0.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129    0.6015   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446   -0.2623   -1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5873   -0.6538   -1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -0.6362   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.3657   -4.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605   -1.5247   -6.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245    0.0622   -5.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4068   -2.3260   -4.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2232   -1.3360   -2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3677   -0.8553    0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487    0.2891    1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -1.4552    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    2.0617    2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743    4.2017    3.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    2.7496    4.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849    4.1740    4.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8248    2.2251    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730    0.1361   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0
 22 20  2  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 19 20  1  0
  7  9  2  0
 23 24  2  0
 25 23  1  0
  7  8  1  0
 12 13  1  0
 20 21  1  0
 13 14  1  0
  5  3  1  0
 22 23  1  0
  3  4  2  0
 22 14  1  0
  3  2  1  0
  9 12  1  0
 16 17  1  0
 25  5  1  0
 17 18  1  0
 25 12  2  0
  9 10  1  0
 10 11  1  0
  6  7  1  0
  2  1  1  0
  6 29  1  0
 15 34  1  0
 19 38  1  0
  8 30  1  0
 21 39  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END


  Mrv1652306192122283D          

 39 41  0  0  0  0            999 V2000
    1.6842   -0.8981   -5.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -0.6492   -4.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1317   -1.7662   -3.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686   -2.9210   -4.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -1.3738   -2.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -1.7533   -3.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486   -1.3752   -2.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5951   -1.7358   -3.0147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.6460   -1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3584   -0.3275   -0.7555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3449   -0.6039    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -0.2500   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097    0.5362    0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    0.9564    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    1.7802    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    2.2509    2.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    3.0470    3.2864 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7512    3.5596    3.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8586    1.8883    1.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297    1.0644    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390    0.7449   -0.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129    0.6015   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446   -0.2623   -1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5873   -0.6538   -1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -0.6362   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.3657   -4.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605   -1.5247   -6.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245    0.0622   -5.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4068   -2.3260   -4.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2232   -1.3360   -2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3677   -0.8553    0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487    0.2891    1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -1.4552    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    2.0617    2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743    4.2017    3.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    2.7496    4.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849    4.1740    4.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8248    2.2251    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730    0.1361   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 22 20  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
  7  9  2  0  0  0  0
 23 24  2  0  0  0  0
 25 23  1  0  0  0  0
  7  8  1  0  0  0  0
 12 13  1  0  0  0  0
 20 21  1  0  0  0  0
 13 14  1  0  0  0  0
  5  3  1  0  0  0  0
 22 23  1  0  0  0  0
  3  4  2  0  0  0  0
 22 14  1  0  0  0  0
  3  2  1  0  0  0  0
  9 12  1  0  0  0  0
 16 17  1  0  0  0  0
 25  5  1  0  0  0  0
 17 18  1  0  0  0  0
 25 12  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  1  0  0  0  0
  6 29  1  0  0  0  0
 15 34  1  0  0  0  0
 19 38  1  0  0  0  0
  8 30  1  0  0  0  0
 21 39  1  0  0  0  0
 18 35  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 11 31  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028636

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C2=C(C(=O)C3=C(O[H])C([H])=C(OC([H])([H])[H])C([H])=C3O2)C(=C1[H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O8/c1-22-7-4-9(18)13-11(5-7)25-16-12(14(13)20)8(17(21)24-3)6-10(19)15(16)23-2/h4-6,18-19H,1-3H3

> <INCHI_KEY>
YOKTYPRIGTVGHQ-UHFFFAOYSA-N

> <FORMULA>
C17H14O8

> <MOLECULAR_WEIGHT>
346.291

> <EXACT_MASS>
346.068867411

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.741817840317196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3,8-dihydroxy-4,6-dimethoxy-9-oxo-9H-xanthene-1-carboxylate

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
2.6906440096666664

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.433490662909982

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.697368067012692

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7597650621197434

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
85.72979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,8-dihydroxy-4,6-dimethoxy-9-oxoxanthene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    1.6842   -0.8981   -5.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -0.6492   -4.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1317   -1.7662   -3.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686   -2.9210   -4.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -1.3738   -2.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -1.7533   -3.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486   -1.3752   -2.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5951   -1.7358   -3.0147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.6460   -1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3584   -0.3275   -0.7555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3449   -0.6039    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -0.2500   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097    0.5362    0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    0.9564    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    1.7802    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    2.2509    2.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    3.0470    3.2864 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7512    3.5596    3.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8586    1.8883    1.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297    1.0644    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390    0.7449   -0.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129    0.6015   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446   -0.2623   -1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5873   -0.6538   -1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -0.6362   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.3657   -4.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605   -1.5247   -6.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245    0.0622   -5.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4068   -2.3260   -4.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2232   -1.3360   -2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3677   -0.8553    0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487    0.2891    1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -1.4552    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    2.0617    2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743    4.2017    3.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    2.7496    4.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849    4.1740    4.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8248    2.2251    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730    0.1361   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0
 22 20  2  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 19 20  1  0
  7  9  2  0
 23 24  2  0
 25 23  1  0
  7  8  1  0
 12 13  1  0
 20 21  1  0
 13 14  1  0
  5  3  1  0
 22 23  1  0
  3  4  2  0
 22 14  1  0
  3  2  1  0
  9 12  1  0
 16 17  1  0
 25  5  1  0
 17 18  1  0
 25 12  2  0
  9 10  1  0
 10 11  1  0
  6  7  1  0
  2  1  1  0
  6 29  1  0
 15 34  1  0
 19 38  1  0
  8 30  1  0
 21 39  1  0
 18 35  1  0
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 18 37  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.684  -0.898  -5.321  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.593  -0.649  -4.435  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.132  -1.766  -3.824  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.469  -2.921  -4.014  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.977  -1.374  -2.944  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.259  -1.753  -3.353  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.349  -1.375  -2.586  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.595  -1.736  -3.015  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.190  -0.646  -1.403  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.358  -0.328  -0.756  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.345  -0.604   0.645  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.904  -0.250  -1.002  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.810   0.536   0.122  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.576   0.956   0.541  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.549   1.780   1.669  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.665   2.251   2.181  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.545   3.047   3.286  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.751   3.560   3.842  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.859   1.888   1.557  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.830   1.064   0.431  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.039   0.745  -0.127  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.613   0.602  -0.080  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.545  -0.262  -1.262  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.587  -0.654  -1.773  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.792  -0.636  -1.764  0.00  0.00           C+0
HETATM   26  H   UNK     0       2.517  -1.366  -4.786  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.361  -1.525  -6.158  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.025   0.062  -5.718  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.407  -2.326  -4.266  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.223  -1.336  -2.381  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.368  -0.855   0.943  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.049   0.289   1.203  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.704  -1.455   0.902  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.479   2.062   2.157  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.274   4.202   3.126  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.398   2.750   4.195  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.485   4.174   4.708  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.825   2.225   1.918  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.873   0.136  -0.883  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3   25                                                  
CONECT    6    5    7   29                                                  
CONECT    7    9    8    6                                                  
CONECT    8    7   30                                                       
CONECT    9    7   12   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   31   32   33                                             
CONECT   12   13    9   25                                                  
CONECT   13   12   14                                                       
CONECT   14   15   13   22                                                  
CONECT   15   14   16   34                                                  
CONECT   16   15   19   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   35   36   37                                             
CONECT   19   16   20   38                                                  
CONECT   20   22   19   21                                                  
CONECT   21   20   39                                                       
CONECT   22   20   23   14                                                  
CONECT   23   24   25   22                                                  
CONECT   24   23                                                            
CONECT   25   23    5   12                                                  
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    6                                                            
CONECT   30    8                                                            
CONECT   31   11                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   15                                                            
CONECT   35   18                                                            
CONECT   36   18                                                            
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   21                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
    1.6842   -0.8981   -5.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -0.6492   -4.4352 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1317   -1.7662   -3.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686   -2.9210   -4.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767   -1.3738   -2.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588   -1.7533   -3.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3486   -1.3752   -2.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5951   -1.7358   -3.0147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.6460   -1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3584   -0.3275   -0.7555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3449   -0.6039    0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044   -0.2500   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097    0.5362    0.1218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757    0.9564    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    1.7802    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    2.2509    2.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    3.0470    3.2864 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7512    3.5596    3.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8586    1.8883    1.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297    1.0644    0.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390    0.7449   -0.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6129    0.6015   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5446   -0.2623   -1.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5873   -0.6538   -1.7725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916   -0.6362   -1.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.3657   -4.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605   -1.5247   -6.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0245    0.0622   -5.7177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4068   -2.3260   -4.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2232   -1.3360   -2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3677   -0.8553    0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487    0.2891    1.2030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7041   -1.4552    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    2.0617    2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2743    4.2017    3.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    2.7496    4.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849    4.1740    4.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8248    2.2251    1.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730    0.1361   -0.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0
 22 20  2  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 19 20  1  0
  7  9  2  0
 23 24  2  0
 25 23  1  0
  7  8  1  0
 12 13  1  0
 20 21  1  0
 13 14  1  0
  5  3  1  0
 22 23  1  0
  3  4  2  0
 22 14  1  0
  3  2  1  0
  9 12  1  0
 16 17  1  0
 25  5  1  0
 17 18  1  0
 25 12  2  0
  9 10  1  0
 10 11  1  0
  6  7  1  0
  2  1  1  0
  6 29  1  0
 15 34  1  0
 19 38  1  0
  8 30  1  0
 21 39  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl 3,8-dihydroxy-4,6-dimethoxy-9-oxo-9H-xanthene-1-carboxylic acid	Generator
3,8-Dihydroxy-4,6-dimethoxy-9-oxo-9H-xanthene-1-carboxylate methyl ester	Generator

Chemical Formula

C₁₇H₁₄O₈

Average Mass

346.2910 Da

Monoisotopic Mass

346.06887 Da

IUPAC Name

methyl 3,8-dihydroxy-4,6-dimethoxy-9-oxo-9H-xanthene-1-carboxylate

Traditional Name

methyl 3,8-dihydroxy-4,6-dimethoxy-9-oxoxanthene-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C2=C(C(=O)C3=C(O[H])C([H])=C(OC([H])([H])[H])C([H])=C3O2)C(=C1[H])C(=O)OC([H])([H])[H]

InChI Identifier

InChI=1S/C17H14O8/c1-22-7-4-9(18)13-11(5-7)25-16-12(14(13)20)8(17(21)24-3)6-10(19)15(16)23-2/h4-6,18-19H,1-3H3

InChI Key

YOKTYPRIGTVGHQ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Leiothrix curvifolia	JEOL database	Santos, L. C., et al, Phytochemistry 56, 853 (2001)

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
Gallic acid or derivatives
Chromone
P-methoxybenzoic acid or derivatives
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	2.75	ALOGPS
logP	2.69	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.7	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.73 m³·mol⁻¹	ChemAxon
Polarizability	33.74 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4481796

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5324260

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Santos, L. C., et al. (2001). Santos, L. C., et al, Phytochemistry 56, 853 (2001). Phytochem..

Showing NP-Card for 8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone (NP0028636)

MOL for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)

3D MOL for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)

3D SDF for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)

3D-SDF for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)

PDB for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)

3D PDB for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)

SMILES for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)

INCHI for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)

Structure for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)

3D Structure for NP0028636 (8-carboxymethyl-1,6-dihydroxy-3,5-dimethoxyxanthone)