Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:25 UTC

Update Date

2022-03-07 02:52:43 UTC

HMDB ID

HMDB0030852

Secondary Accession Numbers

HMDB30852

Metabolite Identification

Common Name

Asperxanthone

Description

Asperxanthone, also known as TMC 256C2 or flavasperone, belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Asperxanthone 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. Based on a literature review a significant number of articles have been published on Asperxanthone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0030852
     RDKit          3D
Asperxanthone
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.2115    0.4613    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3016   -0.6146    0.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9523   -0.3651    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0727   -1.4119    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923   -1.2006    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2320   -2.2265    0.3760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1519   -3.5867    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423    0.1088    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100    1.1711    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989    0.9241    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934    2.4544    0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785    2.7685    0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985    4.0492    0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5758    1.7146    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414    1.8698    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4405    2.9959    0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8175    0.7811    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -0.4669    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -1.6667    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -0.6242    0.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135    0.4032    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    0.0273   -0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9426    1.1707   -0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2562    1.0610    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897   -2.4438    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -3.8617    1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -3.7715   -0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6954   -4.2671    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771    1.7798    0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    3.2995    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456    4.4897    0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8727    0.8671    0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1693   -1.3869    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0493   -2.2789   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094   -2.2239    1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 10  3  1  0
 21 14  2  0
 21  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 17 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
M  END


  Mrv0541 05061305332D          

 21 23  0  0  0  0            999 V2000
    0.6039    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9664    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  2  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 11  2  0  0  0  0
 18 12  1  0  0  0  0
 19  2  1  0  0  0  0
 19 10  1  0  0  0  0
 20  3  1  0  0  0  0
 20 13  1  0  0  0  0
 21  8  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030852

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-8-4-11(17)15-12(18)6-9-5-10(19-2)7-13(20-3)14(9)16(15)21-8/h4-7,18H,1-3H3

> <INCHI_KEY>
ARXPDHLVDOYIPX-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.240617625656768

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-8,10-dimethoxy-2-methyl-4H-benzo[h]chromen-4-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.8921221729999997

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.816314133038201

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.397204320523224

> <JCHEM_PKA_STRONGEST_BASIC>
-4.492396726526867

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
78.46470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030852
     RDKit          3D
Asperxanthone
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.2115    0.4613    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3016   -0.6146    0.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9523   -0.3651    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0727   -1.4119    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923   -1.2006    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2320   -2.2265    0.3760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1519   -3.5867    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423    0.1088    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100    1.1711    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989    0.9241    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934    2.4544    0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785    2.7685    0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985    4.0492    0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5758    1.7146    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414    1.8698    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4405    2.9959    0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8175    0.7811    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -0.4669    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -1.6667    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -0.6242    0.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135    0.4032    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    0.0273   -0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9426    1.1707   -0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2562    1.0610    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897   -2.4438    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -3.8617    1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -3.7715   -0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6954   -4.2671    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771    1.7798    0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    3.2995    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456    4.4897    0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8727    0.8671    0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1693   -1.3869    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0493   -2.2789   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094   -2.2239    1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 10  3  1  0
 21 14  2  0
 21  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 17 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.127   5.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.137   4.414   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.207   5.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.127   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.057   1.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747   0.413   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.057   4.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.517   1.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.827   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.897   1.746   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.207   0.413   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.517   4.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.437   1.746   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.127   0.413   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.437  -0.921   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.367   3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.747   5.747   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.437   4.414   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4    8   11                                                       
CONECT    5    9   10                                                       
CONECT    6    9   12                                                       
CONECT    7   10   13                                                       
CONECT    8    1    4   21                                                  
CONECT    9    5    6   14                                                  
CONECT   10    5    7   19                                                  
CONECT   11    4   15   17                                                  
CONECT   12    6   15   18                                                  
CONECT   13    7   14   20                                                  
CONECT   14    9   13   16                                                  
CONECT   15   11   12   16                                                  
CONECT   16   14   15   21                                                  
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19    2   10                                                       
CONECT   20    3   13                                                       
CONECT   21    8   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0030852
HETATM    1  C1  UNL     1       5.212   0.461   0.033  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.302  -0.615   0.123  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.952  -0.365   0.160  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.073  -1.412   0.248  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.692  -1.201   0.288  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.232  -2.226   0.376  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.152  -3.587   0.433  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.242   0.109   0.236  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.110   1.171   0.148  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.499   0.924   0.110  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.693   2.454   0.096  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.678   2.768   0.131  1.00  0.00           C  
HETATM   13  O3  UNL     1      -1.099   4.049   0.079  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.576   1.715   0.219  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.941   1.870   0.262  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.440   2.996   0.222  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.817   0.781   0.351  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.240  -0.467   0.395  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.116  -1.667   0.491  1.00  0.00           C  
HETATM   20  O5  UNL     1      -1.941  -0.624   0.355  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.113   0.403   0.271  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.199   0.027  -0.239  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.943   1.171  -0.788  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.256   1.061   0.968  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.390  -2.444   0.290  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.512  -3.862   1.445  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.970  -3.772  -0.321  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.695  -4.267   0.210  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.177   1.780   0.040  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.361   3.299   0.027  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.946   4.490   0.088  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.873   0.867   0.386  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.169  -1.387   0.613  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.049  -2.279  -0.443  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.809  -2.224   1.389  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   25
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   26   27   28
CONECT    8    9   21
CONECT    9   10   10   11
CONECT   10   29
CONECT   11   12   12   30
CONECT   12   13   14
CONECT   13   31
CONECT   14   15   21   21
CONECT   15   16   16   17
CONECT   17   18   18   32
CONECT   18   19   20
CONECT   19   33   34   35
CONECT   20   21
END

HMDB0030852
     RDKit          3D
Asperxanthone
 35 37  0  0  0  0  0  0  0  0999 V2000
    5.2115    0.4613    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3016   -0.6146    0.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9523   -0.3651    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0727   -1.4119    0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923   -1.2006    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2320   -2.2265    0.3760 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1519   -3.5867    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423    0.1088    0.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100    1.1711    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4989    0.9241    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6934    2.4544    0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6785    2.7685    0.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0985    4.0492    0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5758    1.7146    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414    1.8698    0.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4405    2.9959    0.2215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8175    0.7811    0.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -0.4669    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -1.6667    0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405   -0.6242    0.3554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135    0.4032    0.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    0.0273   -0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9426    1.1707   -0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2562    1.0610    0.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3897   -2.4438    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -3.8617    1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700   -3.7715   -0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6954   -4.2671    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771    1.7798    0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    3.2995    0.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9456    4.4897    0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8727    0.8671    0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1693   -1.3869    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0493   -2.2789   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094   -2.2239    1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 10  3  1  0
 21 14  2  0
 21  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 17 32  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Antibiotic TMC 256c2	ChEBI
Asperxanthon	ChEBI
TMC 256c2	ChEBI
5-Hydroxy-8,10-dimethoxy-2-methyl-4H-naphtho[1,2-b]pyran-4-one, 9ci	HMDB
Flavasperone	HMDB
Asperxanthone	ChEBI

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

5-hydroxy-8,10-dimethoxy-2-methyl-4H-benzo[h]chromen-4-one

Traditional Name

5-hydroxy-8,10-dimethoxy-2-methylbenzo[h]chromen-4-one

CAS Registry Number

3566-99-2

SMILES

COC1=CC(OC)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C1

InChI Identifier

InChI=1S/C16H14O5/c1-8-4-11(17)15-12(18)6-9-5-10(19-2)7-13(20-3)14(9)16(15)21-8/h4-7,18H,1-3H3

InChI Key

ARXPDHLVDOYIPX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Chromone
2-naphthol
Benzopyran
1-benzopyran
Naphthalene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030852)

Cellular substructure

Membrane (HMDB: HMDB0030852)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030852)

Source

Endogenous

Endogenous (HMDB: HMDB0030852)

Plant

Plant (HMDB: HMDB0030852)

Exogenous

Food

Food (HMDB: HMDB0030852)

Nut

Nuts (FooDB: FOOD00869)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	203 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	2.95	ALOGPS
logP	2.89	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.46 m³·mol⁻¹	ChemAxon
Polarizability	29.24 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	173.551	30932474
DeepCCS	[M-H]-	171.193	30932474
DeepCCS	[M-2H]-	204.08	30932474
DeepCCS	[M+Na]+	179.644	30932474
AllCCS	[M+H]+	163.8	32859911
AllCCS	[M+H-H2O]+	160.0	32859911
AllCCS	[M+NH4]+	167.3	32859911
AllCCS	[M+Na]+	168.3	32859911
AllCCS	[M-H]-	168.1	32859911
AllCCS	[M+Na-2H]-	167.5	32859911
AllCCS	[M+HCOO]-	166.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Asperxanthone	COC1=CC(OC)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C1	4042.7	Standard polar	33892256
Asperxanthone	COC1=CC(OC)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C1	2708.9	Standard non polar	33892256
Asperxanthone	COC1=CC(OC)=C2C(C=C(O)C3=C2OC(C)=CC3=O)=C1	2703.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Asperxanthone,1TMS,isomer #1	COC1=CC(OC)=C2C(=C1)C=C(O[Si](C)(C)C)C1=C2OC(C)=CC1=O	2895.0	Semi standard non polar	33892256
Asperxanthone,1TBDMS,isomer #1	COC1=CC(OC)=C2C(=C1)C=C(O[Si](C)(C)C(C)(C)C)C1=C2OC(C)=CC1=O	3085.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Asperxanthone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g0-0190000000-63920300296fa73fc6f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Asperxanthone GC-MS (1 TMS) - 70eV, Positive	splash10-006x-3039000000-f28c7fa3d08e69eb1ecb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Asperxanthone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 10V, Positive-QTOF	splash10-000i-0090000000-de1606154f2a2faca204	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 20V, Positive-QTOF	splash10-000i-0090000000-bca81911b2811ca93c19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 40V, Positive-QTOF	splash10-014r-1090000000-6090504d235c75f5e350	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 10V, Negative-QTOF	splash10-000i-0090000000-6ce0c2acfdede9a11d51	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 20V, Negative-QTOF	splash10-000i-0090000000-df2ba0a5599ddcef0c61	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 40V, Negative-QTOF	splash10-000i-2290000000-ff5174e06bbefd010cd8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 20V, Positive-QTOF	splash10-000i-0090000000-56020f0820eed7b46084	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 40V, Positive-QTOF	splash10-015j-0190000000-6691e283e1ff3d05dc24	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 10V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 20V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Asperxanthone 40V, Negative-QTOF	splash10-0a4i-1090000000-1fdfc323058c65ba3cb8	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002811

KNApSAcK ID

C00054889

Chemspider ID

4678011

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5748546

PDB ID

Not Available

ChEBI ID

133814

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Asperxanthone (HMDB0030852)

MOL for HMDB0030852 (Asperxanthone)

3D MOL for HMDB0030852 (Asperxanthone)

3D SDF for HMDB0030852 (Asperxanthone)

3D-SDF for HMDB0030852 (Asperxanthone)

PDB for HMDB0030852 (Asperxanthone)

3D PDB for HMDB0030852 (Asperxanthone)

SMILES for HMDB0030852 (Asperxanthone)

INCHI for HMDB0030852 (Asperxanthone)

Structure for HMDB0030852 (Asperxanthone)

3D Structure for HMDB0030852 (Asperxanthone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra