NP-MRD: Showing NP-Card for 3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone (NP0026471)

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Record Information

Version

2.0

Created at

2021-06-19 18:20:17 UTC

Updated at

2021-06-29 23:52:01 UTC

NP-MRD ID

NP0026471

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone

Provided By

JEOL Database JEOL Logo

Description

Norlichexanthone 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. 3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone is found in Lecanora iseana, Lecanora reuteri, Penicillium griseofulvum, Senna obtusifolia and Wardomyces anomalus. 3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone was first documented in 2003 (PMID: 14613627). Based on a literature review a small amount of articles have been published on norlichexanthone (PMID: 22061662) (PMID: 21568875) (PMID: 33643823) (PMID: 31874327).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123583D          

 29 31  0  0  0  0            999 V2000
   -0.5877    0.3172   -5.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -0.8326   -4.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -2.1410   -5.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -3.2346   -4.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -4.5111   -4.9841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566   -3.0579   -3.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -1.7681   -2.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -1.7022   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8825   -0.4696   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -0.4561    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    0.7580    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    0.7217    2.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    1.9640    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8007    1.9453   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067    3.1612   -1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.7292   -1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134    0.6777   -2.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.7309   -3.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -0.6546   -3.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455   -0.0330   -6.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    0.9593   -5.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706    0.8981   -5.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217   -2.2947   -6.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139   -4.4889   -5.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -3.9226   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -1.3878    1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    1.6330    2.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    2.9168    1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    2.9946   -2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 17 18  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  9 16  2  0  0  0  0
 14 15  1  0  0  0  0
 13 14  2  0  0  0  0
  7 19  1  0  0  0  0
 14 16  1  0  0  0  0
 19  2  2  0  0  0  0
 11 13  1  0  0  0  0
  2  3  1  0  0  0  0
  9  8  1  0  0  0  0
  3  4  2  0  0  0  0
 16 17  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
 17 19  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
  4  5  1  0  0  0  0
 13 28  1  0  0  0  0
 10 26  1  0  0  0  0
 12 27  1  0  0  0  0
 15 29  1  0  0  0  0
  3 23  1  0  0  0  0
  6 25  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  5 24  1  0  0  0  0
M  END

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -0.5877    0.3172   -5.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -0.8326   -4.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -2.1410   -5.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -3.2346   -4.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -4.5111   -4.9841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566   -3.0579   -3.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -1.7681   -2.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -1.7022   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8825   -0.4696   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -0.4561    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    0.7580    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    0.7217    2.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    1.9640    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8007    1.9453   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067    3.1612   -1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.7292   -1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134    0.6777   -2.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.7309   -3.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -0.6546   -3.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455   -0.0330   -6.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    0.9593   -5.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706    0.8981   -5.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217   -2.2947   -6.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139   -4.4889   -5.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -3.9226   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -1.3878    1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    1.6330    2.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    2.9168    1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    2.9946   -2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 17 18  2  0
 10 11  2  0
 11 12  1  0
  9 16  2  0
 14 15  1  0
 13 14  2  0
  7 19  1  0
 14 16  1  0
 19  2  2  0
 11 13  1  0
  2  3  1  0
  9  8  1  0
  3  4  2  0
 16 17  1  0
  4  6  1  0
  6  7  2  0
 17 19  1  0
  2  1  1  0
  7  8  1  0
  4  5  1  0
 13 28  1  0
 10 26  1  0
 12 27  1  0
 15 29  1  0
  3 23  1  0
  6 25  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 24  1  0
M  END


  Mrv1652306192123583D          

 29 31  0  0  0  0            999 V2000
   -0.5877    0.3172   -5.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -0.8326   -4.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -2.1410   -5.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -3.2346   -4.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -4.5111   -4.9841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566   -3.0579   -3.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -1.7681   -2.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -1.7022   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8825   -0.4696   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -0.4561    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    0.7580    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    0.7217    2.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    1.9640    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8007    1.9453   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067    3.1612   -1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.7292   -1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134    0.6777   -2.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.7309   -3.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -0.6546   -3.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455   -0.0330   -6.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    0.9593   -5.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706    0.8981   -5.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217   -2.2947   -6.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139   -4.4889   -5.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -3.9226   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -1.3878    1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    1.6330    2.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    2.9168    1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    2.9946   -2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0  0  0  0
 17 18  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  9 16  2  0  0  0  0
 14 15  1  0  0  0  0
 13 14  2  0  0  0  0
  7 19  1  0  0  0  0
 14 16  1  0  0  0  0
 19  2  2  0  0  0  0
 11 13  1  0  0  0  0
  2  3  1  0  0  0  0
  9  8  1  0  0  0  0
  3  4  2  0  0  0  0
 16 17  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
 17 19  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
  4  5  1  0  0  0  0
 13 28  1  0  0  0  0
 10 26  1  0  0  0  0
 12 27  1  0  0  0  0
 15 29  1  0  0  0  0
  3 23  1  0  0  0  0
  6 25  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  5 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026471

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O5/c1-6-2-7(15)4-10-12(6)14(18)13-9(17)3-8(16)5-11(13)19-10/h2-5,15-17H,1H3

> <INCHI_KEY>
AQZHBCDRWFMXIN-UHFFFAOYSA-N

> <FORMULA>
C14H10O5

> <MOLECULAR_WEIGHT>
258.229

> <EXACT_MASS>
258.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.490802228086114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,6-trihydroxy-8-methyl-9H-xanthen-9-one

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
3.212365644666666

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.867716859311225

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.2637514723018795

> <JCHEM_PKA_STRONGEST_BASIC>
-3.777689973456758

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
67.8002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norlichexanthone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -0.5877    0.3172   -5.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -0.8326   -4.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -2.1410   -5.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -3.2346   -4.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -4.5111   -4.9841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566   -3.0579   -3.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -1.7681   -2.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -1.7022   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8825   -0.4696   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -0.4561    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    0.7580    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    0.7217    2.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    1.9640    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8007    1.9453   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067    3.1612   -1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.7292   -1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134    0.6777   -2.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.7309   -3.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -0.6546   -3.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455   -0.0330   -6.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    0.9593   -5.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706    0.8981   -5.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217   -2.2947   -6.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139   -4.4889   -5.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -3.9226   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -1.3878    1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    1.6330    2.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    2.9168    1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    2.9946   -2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 17 18  2  0
 10 11  2  0
 11 12  1  0
  9 16  2  0
 14 15  1  0
 13 14  2  0
  7 19  1  0
 14 16  1  0
 19  2  2  0
 11 13  1  0
  2  3  1  0
  9  8  1  0
  3  4  2  0
 16 17  1  0
  4  6  1  0
  6  7  2  0
 17 19  1  0
  2  1  1  0
  7  8  1  0
  4  5  1  0
 13 28  1  0
 10 26  1  0
 12 27  1  0
 15 29  1  0
  3 23  1  0
  6 25  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 24  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      -0.588   0.317  -5.756  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.863  -0.833  -4.825  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.780  -2.141  -5.337  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.026  -3.235  -4.513  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.952  -4.511  -4.984  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.357  -3.058  -3.178  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.444  -1.768  -2.652  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.777  -1.702  -1.320  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.883  -0.470  -0.732  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.224  -0.456   0.622  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.350   0.758   1.291  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.684   0.722   2.612  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.141   1.964   0.631  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.801   1.945  -0.720  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.607   3.161  -1.319  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.671   0.729  -1.404  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.313   0.678  -2.828  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.125   1.731  -3.428  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.200  -0.655  -3.465  0.00  0.00           C+0
HETATM   20  H   UNK     0      -0.346  -0.033  -6.766  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.470   0.959  -5.843  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.271   0.898  -5.404  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.522  -2.295  -6.382  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.714  -4.489  -5.926  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.546  -3.923  -2.547  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.391  -1.388   1.156  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.736   1.633   2.948  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.236   2.917   1.142  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.375   2.995  -2.262  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2   19    3    1                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   24                                                       
CONECT    6    4    7   25                                                  
CONECT    7   19    6    8                                                  
CONECT    8    9    7                                                       
CONECT    9   10   16    8                                                  
CONECT   10    9   11   26                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   27                                                       
CONECT   13   14   11   28                                                  
CONECT   14   15   13   16                                                  
CONECT   15   14   29                                                       
CONECT   16    9   14   17                                                  
CONECT   17   18   16   19                                                  
CONECT   18   17                                                            
CONECT   19    7    2   17                                                  
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26   10                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
CONECT   29   15                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

RDKit          3D

29 31  0  0  0  0  0  0  0  0999 V2000
   -0.5877    0.3172   -5.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -0.8326   -4.8255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7799   -2.1410   -5.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -3.2346   -4.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9521   -4.5111   -4.9841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3566   -3.0579   -3.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4439   -1.7681   -2.6517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -1.7022   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8825   -0.4696   -0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -0.4561    0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    0.7580    1.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    0.7217    2.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1406    1.9640    0.6308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8007    1.9453   -0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067    3.1612   -1.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.7292   -1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3134    0.6777   -2.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251    1.7309   -3.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1997   -0.6546   -3.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3455   -0.0330   -6.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4698    0.9593   -5.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706    0.8981   -5.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217   -2.2947   -6.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7139   -4.4889   -5.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5460   -3.9226   -2.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -1.3878    1.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    1.6330    2.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359    2.9168    1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    2.9946   -2.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 17 18  2  0
 10 11  2  0
 11 12  1  0
  9 16  2  0
 14 15  1  0
 13 14  2  0
  7 19  1  0
 14 16  1  0
 19  2  2  0
 11 13  1  0
  2  3  1  0
  9  8  1  0
  3  4  2  0
 16 17  1  0
  4  6  1  0
  6  7  2  0
 17 19  1  0
  2  1  1  0
  7  8  1  0
  4  5  1  0
 13 28  1  0
 10 26  1  0
 12 27  1  0
 15 29  1  0
  3 23  1  0
  6 25  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 24  1  0
M  END

View in JSmol

Synonyms

Value	Source
1,3,6-Trihydroxy-8-methyl-9H-xanthen-9-one	ChEBI

Chemical Formula

C₁₄H₁₀O₅

Average Mass

258.2290 Da

Monoisotopic Mass

258.05282 Da

IUPAC Name

1,3,6-trihydroxy-8-methyl-9H-xanthen-9-one

Traditional Name

norlichexanthone

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(=O)C3=C(C([H])=C(O[H])C([H])=C3OC2=C1[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C14H10O5/c1-6-2-7(15)4-10-12(6)14(18)13-9(17)3-8(16)5-11(13)19-10/h2-5,15-17H,1H3

InChI Key

AQZHBCDRWFMXIN-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Lecanora iseana	-	KNApSAcK
Lecanora reuteri	-	KNApSAcK
Penicillium griseofulvum	LOTUS Database	35616633
Senna obtusifolia	LOTUS Database	35616633
Wardomyces anomalus	JEOL database	Abdel-Lateff, A., et al, J. Nat. Prod. 66, 706 (2003)

Species Where Detected

Species Name	Source	Reference
Penicillium griseofulvum (a mutant strain)	KNApSAcK Database	22123792

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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Polyol
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:7632 )
xanthones (CHEBI:7632 )
xanthenes (C10087 )

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	2.64	ALOGPS
logP	3.21	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.8 m³·mol⁻¹	ChemAxon
Polarizability	25.49 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

C00002969

Chemspider ID

4444976

KEGG Compound ID

C10087

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

7632

Good Scents ID

Not Available

References

General References

Wang QX, Bao L, Yang XL, Guo H, Yang RN, Ren B, Zhang LX, Dai HQ, Guo LD, Liu HW: Polyketides with antimicrobial activity from the solid culture of an endolichenic fungus Ulocladium sp. Fitoterapia. 2012 Jan;83(1):209-14. doi: 10.1016/j.fitote.2011.10.013. Epub 2011 Oct 28. [PubMed:22061662 ]
Fotie J, Nkengfack AE, Rukunga G, Tolo F, Peter MG, Heydenreich M, Fomum ZT: In-vivo antimalarial activity of some oxygenated xanthones. Ann Trop Med Parasitol. 2003 Oct;97(7):683-8. doi: 10.1179/000349803225002390. [PubMed:14613627 ]
Ikeda M, Kurotobi Y, Namikawa A, Kuranuki S, Matsuura N, Sato M, Igarashi Y, Nakamura T, Oikawa T: Norlichexanthone isolated from fungus P16 promotes the secretion and expression of adiponectin in cultured ST-13 adipocytes. Med Chem. 2011 Jul;7(4):250-6. doi: 10.2174/157340611796150950. [PubMed:21568875 ]
Wang K, Chen Y, Gao S, Wang M, Ge M, Yang Q, Liao M, Xu L, Chen J, Zeng Z, Chen H, Zhang XK, Lin T, Zhou H: Norlichexanthone purified from plant endophyte prevents postmenopausal osteoporosis by targeting ER alpha to inhibit RANKL signaling. Acta Pharm Sin B. 2021 Feb;11(2):442-455. doi: 10.1016/j.apsb.2020.09.012. Epub 2020 Sep 28. [PubMed:33643823 ]
Akinfala TO, Houbraken J, Sulyok M, Adedeji AR, Odebode AC, Krska R, Ezekiel CN: Moulds and their secondary metabolites associated with the fermentation and storage of two cocoa bean hybrids in Nigeria. Int J Food Microbiol. 2020 Mar 2;316:108490. doi: 10.1016/j.ijfoodmicro.2019.108490. Epub 2019 Dec 14. [PubMed:31874327 ]
Abdel-Lateff, A., et al. (2003). Abdel-Lateff, A., et al, J. Nat. Prod. 66, 706 (2003). J. Nat. Prod..

Showing NP-Card for 3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone (NP0026471)

MOL for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)

3D MOL for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)

3D SDF for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)

3D-SDF for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)

PDB for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)

3D PDB for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)

SMILES for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)

INCHI for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)

Structure for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)

3D Structure for NP0026471 (3,6,8-trihydroxy-1-methylxanthone. Norlichexanthone)