NP-MRD: Showing NP-Card for 1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione (NP0009722)

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Record Information

Version

2.0

Created at

2021-01-05 19:18:02 UTC

Updated at

2021-07-15 17:04:04 UTC

NP-MRD ID

NP0009722

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione

Provided By

NPAtlas

Description

(-)-Microdiplodiasolol 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 (-)-microdiplodiasolol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione is found in Microdiplodia sp. Based on a literature review very few articles have been published on (-)-microdiplodiasolol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106523D          

 39 41  0  0  0  0            999 V2000
   -3.0904    2.5466   -0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160    1.7554    0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675    0.3958    0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4558   -0.5208    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1049   -1.9322    0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9419   -2.8049    0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7140   -2.3327    0.9129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3011   -3.3985    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485   -1.1821    0.7996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5520   -0.6789    2.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5424   -1.6130    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.7184   -0.2435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5470   -0.5298    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841   -0.7635    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -2.0467    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151    0.2969    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3432    1.5758   -0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889    2.7382   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    1.8049   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678    0.7842   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    0.9915   -0.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -0.0506   -0.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3670   -0.4927   -1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407    2.5494   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304    3.5990   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    2.2787   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618   -0.2122    1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -2.7122    1.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368   -4.0521    0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.5359    2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596   -2.8600    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8708    0.0922    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933    3.1181    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7611    3.5070   -0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889    2.3657   -0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377    2.8459   -0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -1.0204   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -1.1750   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214    0.3872   -2.1477 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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22  3  1  0  0  0  0
 22  9  1  0  0  0  0
 20 13  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
  7 28  1  1  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 18 35  1  0  0  0  0
 19 36  1  0  0  0  0
 23 37  1  0  0  0  0
 23 38  1  0  0  0  0
 23 39  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.0904    2.5466   -0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160    1.7554    0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675    0.3958    0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4558   -0.5208    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1049   -1.9322    0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9419   -2.8049    0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7140   -2.3327    0.9129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3011   -3.3985    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485   -1.1821    0.7996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5520   -0.6789    2.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5424   -1.6130    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.7184   -0.2435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5470   -0.5298    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841   -0.7635    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -2.0467    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151    0.2969    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3432    1.5758   -0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889    2.7382   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    1.8049   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678    0.7842   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    0.9915   -0.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -0.0506   -0.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3670   -0.4927   -1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407    2.5494   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304    3.5990   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    2.2787   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618   -0.2122    1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -2.7122    1.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368   -4.0521    0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.5359    2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596   -2.8600    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8708    0.0922    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933    3.1181    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7611    3.5070   -0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889    2.3657   -0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377    2.8459   -0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -1.0204   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -1.1750   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214    0.3872   -2.1477 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  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  3  1  0
 22  9  1  0
 20 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  1
  8 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
M  END


  Mrv1652306242106523D          

 39 41  0  0  0  0            999 V2000
   -3.0904    2.5466   -0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160    1.7554    0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675    0.3958    0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4558   -0.5208    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1049   -1.9322    0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9419   -2.8049    0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7140   -2.3327    0.9129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3011   -3.3985    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485   -1.1821    0.7996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5520   -0.6789    2.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5424   -1.6130    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.7184   -0.2435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5470   -0.5298    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841   -0.7635    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -2.0467    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151    0.2969    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3432    1.5758   -0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889    2.7382   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    1.8049   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678    0.7842   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    0.9915   -0.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -0.0506   -0.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3670   -0.4927   -1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407    2.5494   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304    3.5990   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    2.2787   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618   -0.2122    1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -2.7122    1.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368   -4.0521    0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.5359    2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596   -2.8600    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8708    0.0922    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933    3.1181    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7611    3.5070   -0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889    2.3657   -0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377    2.8459   -0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -1.0204   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -1.1750   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214    0.3872   -2.1477 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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22  3  1  0  0  0  0
 22  9  1  0  0  0  0
 20 13  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
  7 28  1  1  0  0  0
  8 29  1  0  0  0  0
 10 30  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  0  0  0  0
 18 33  1  0  0  0  0
 18 34  1  0  0  0  0
 18 35  1  0  0  0  0
 19 36  1  0  0  0  0
 23 37  1  0  0  0  0
 23 38  1  0  0  0  0
 23 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009722

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(O[C@@]3(C(OC([H])([H])[H])=C([H])C(=O)[C@@]([H])(O[H])[C@@]3(O[H])C2=O)C([H])([H])[H])=C([H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O7/c1-7-4-8(17)12-10(5-7)23-15(2)11(22-3)6-9(18)13(19)16(15,21)14(12)20/h4-6,13,17,19,21H,1-3H3/t13-,15-,16-/m1/s1

> <INCHI_KEY>
SIUXYUWNLUKHJD-FVQBIDKESA-N

> <FORMULA>
C16H16O7

> <MOLECULAR_WEIGHT>
320.297

> <EXACT_MASS>
320.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.015613550779864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aS,9aS)-1,8,9a-trihydroxy-4-methoxy-4a,6-dimethyl-2,4a,9,9a-tetrahydro-1H-xanthene-2,9-dione

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
1.0247406153333343

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.17587049072888

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.699264045210796

> <JCHEM_PKA_STRONGEST_BASIC>
-4.126215047901316

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
79.84909999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,9aS)-1,8,9a-trihydroxy-4-methoxy-4a,6-dimethyl-1H-xanthene-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -3.0904    2.5466   -0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160    1.7554    0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675    0.3958    0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4558   -0.5208    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1049   -1.9322    0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9419   -2.8049    0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7140   -2.3327    0.9129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3011   -3.3985    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485   -1.1821    0.7996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5520   -0.6789    2.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5424   -1.6130    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.7184   -0.2435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5470   -0.5298    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841   -0.7635    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -2.0467    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151    0.2969    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3432    1.5758   -0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889    2.7382   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    1.8049   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678    0.7842   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    0.9915   -0.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -0.0506   -0.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3670   -0.4927   -1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407    2.5494   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304    3.5990   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    2.2787   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618   -0.2122    1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -2.7122    1.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368   -4.0521    0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.5359    2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596   -2.8600    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8708    0.0922    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933    3.1181    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7611    3.5070   -0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889    2.3657   -0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377    2.8459   -0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -1.0204   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -1.1750   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214    0.3872   -2.1477 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
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  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  2  0
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 13 14  2  0
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 16 17  2  0
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 22  3  1  0
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  1 24  1  0
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  1 26  1  0
  4 27  1  0
  7 28  1  1
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 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  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      -3.090   2.547  -0.705  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.916   1.755   0.446  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.567   0.396   0.368  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.456  -0.521   0.691  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.105  -1.932   0.615  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.942  -2.805   0.306  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.714  -2.333   0.913  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.301  -3.398   0.128  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.749  -1.182   0.800  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.552  -0.679   2.084  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.542  -1.613   0.180  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.830  -2.718  -0.244  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.547  -0.530   0.095  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.884  -0.764   0.120  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.369  -2.047   0.232  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.815   0.297   0.033  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.343   1.576  -0.075  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.289   2.738  -0.170  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.985   1.805  -0.098  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.068   0.784  -0.016  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.291   0.992  -0.038  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.234  -0.051  -0.066  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.367  -0.493  -1.513  0.00  0.00           C+0
HETATM   24  H   UNK     0      -2.141   2.549  -1.265  0.00  0.00           H+0
HETATM   25  H   UNK     0      -3.230   3.599  -0.342  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.963   2.279  -1.306  0.00  0.00           H+0
HETATM   27  H   UNK     0      -4.462  -0.212   1.016  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.744  -2.712   1.977  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.837  -4.052   0.693  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.388  -0.536   2.304  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.860  -2.860   0.320  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.871   0.092   0.053  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.493   3.118   0.837  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.761   3.507  -0.771  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.189   2.366  -0.667  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.638   2.846  -0.186  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.462  -1.020  -1.876  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.228  -1.175  -1.664  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.521   0.387  -2.148  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   28                                             
CONECT    8    7   29                                                       
CONECT    9    7   10   11   22                                             
CONECT   10    9   30                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14   31                                                       
CONECT   16   14   17   32                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   33   34   35                                             
CONECT   19   17   20   36                                                  
CONECT   20   19   21   13                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23    3    9                                             
CONECT   23   22   37   38   39                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    4                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30   10                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
CONECT   33   18                                                            
CONECT   34   18                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   23                                                            
CONECT   38   23                                                            
CONECT   39   23                                                            
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
   -3.0904    2.5466   -0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9160    1.7554    0.4457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675    0.3958    0.3680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4558   -0.5208    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1049   -1.9322    0.6145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9419   -2.8049    0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7140   -2.3327    0.9129 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3011   -3.3985    0.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7485   -1.1821    0.7996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5520   -0.6789    2.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5424   -1.6130    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300   -2.7184   -0.2435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5470   -0.5298    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8841   -0.7635    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -2.0467    0.2324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8151    0.2969    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3432    1.5758   -0.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2889    2.7382   -0.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9850    1.8049   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678    0.7842   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    0.9915   -0.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -0.0506   -0.0656 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3670   -0.4927   -1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1407    2.5494   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304    3.5990   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    2.2787   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618   -0.2122    1.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7438   -2.7122    1.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8368   -4.0521    0.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3883   -0.5359    2.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596   -2.8600    0.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8708    0.0922    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933    3.1181    0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7611    3.5070   -0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889    2.3657   -0.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6377    2.8459   -0.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622   -1.0204   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2283   -1.1750   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5214    0.3872   -2.1477 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  2  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 22  3  1  0
 22  9  1  0
 20 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  1
  8 29  1  0
 10 30  1  0
 15 31  1  0
 16 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₇

Average Mass

320.2970 Da

Monoisotopic Mass

320.08960 Da

IUPAC Name

(1S,4aS,9aS)-1,8,9a-trihydroxy-4-methoxy-4a,6-dimethyl-2,4a,9,9a-tetrahydro-1H-xanthene-2,9-dione

Traditional Name

(1S,4aS,9aS)-1,8,9a-trihydroxy-4-methoxy-4a,6-dimethyl-1H-xanthene-2,9-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)[C@@H](O)[C@@]2(O)C(=O)C3=C(O[C@]12C)C=C(C)C=C3O

InChI Identifier

InChI=1S/C16H16O7/c1-7-4-8(17)12-10(5-7)23-15(2)11(22-3)6-9(18)13(19)16(15,21)14(12)20/h4-6,13,17,19,21H,1-3H3/t13-,15-,16-/m1/s1

InChI Key

SIUXYUWNLUKHJD-FVQBIDKESA-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
Microdiplodia sp.	NPAtlas	21244021

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
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Cyclohexenone
Benzenoid
Vinylogous ester
Vinylogous acid
Tertiary alcohol
1,2-diol
Ketone
Cyclic ketone
Secondary alcohol
Ether
Oxacycle
Polyol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:68285 )
enol ether (CHEBI:68285 )
xanthones (CHEBI:68285 )

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	1.59	ALOGPS
logP	1.02	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.85 m³·mol⁻¹	ChemAxon
Polarizability	31.02 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

NPA015783

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26347792

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52937072

PDB ID

Not Available

ChEBI ID

68285

Good Scents ID

Not Available

References

General References

Showing NP-Card for 1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione (NP0009722)

MOL for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)

3D MOL for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)

3D SDF for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)

3D-SDF for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)

PDB for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)

3D PDB for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)

SMILES for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)

INCHI for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)

Structure for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)

3D Structure for NP0009722 (1,8,8a-trihydroxy-5-methoxy-3,5a-dimethyl-5a,8a-dihydro-1H-xanthene-7,9-dione)