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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:48:01 UTC

Update Date

2021-09-26 23:01:01 UTC

HMDB ID

HMDB0249887

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid

Description

8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid, also known as antimycin, belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Based on a literature review a significant number of articles have been published on 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3h-isochromene-7-carboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249887
     RDKit          3D
8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.2961   -2.2404    0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -0.9286    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876   -0.0314   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143    1.2652   -0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792    2.2908   -0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436    2.0393   -0.7704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    1.0892    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987    0.8779   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756   -0.2520    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -1.1186    1.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    1.5540   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531    2.6770   -1.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855    0.5090   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225    0.7792   -0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362    1.9025   -0.9391 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0880   -0.1865   -0.2776 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -0.6324   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -1.6555    0.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347   -2.8289   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2409   -2.8838    0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977   -2.3014    1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122    3.2465   -1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626    1.4029    1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894   -0.0357   -0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2183    1.7282   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542    0.9059    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9620   -0.6355   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533   -0.9472    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821   -2.1721    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144   -0.8435    1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7336   -0.1306    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0972   -2.4434   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 17  2  1  0
  9  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 16 31  1  0
 18 32  1  0
M  END

  Mrv1652309112108482D          

 18 19  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 16  1  0  0  0  0
  8 17  1  0  0  0  0
  3 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249887

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC=C2C(=O)C(C(O)=O)=C(O)C(C)=C2C1C

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,14H,1-3H3,(H,16,17)

> <INCHI_KEY>
CBGDIJWINPWWJW-UHFFFAOYSA-N

> <FORMULA>
C13H14O5

> <MOLECULAR_WEIGHT>
250.25

> <EXACT_MASS>
250.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.710495688167175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-3,4,5-trimethyl-8-oxo-4,8-dihydro-3H-2-benzopyran-7-carboxylic acid

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
0.8089523660000004

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.507691995617237

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.711233797860997

> <JCHEM_PKA_STRONGEST_BASIC>
-4.79617697814066

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
65.2535

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249887
     RDKit          3D
8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.2961   -2.2404    0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -0.9286    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876   -0.0314   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143    1.2652   -0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792    2.2908   -0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436    2.0393   -0.7704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    1.0892    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987    0.8779   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756   -0.2520    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -1.1186    1.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    1.5540   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531    2.6770   -1.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855    0.5090   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225    0.7792   -0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362    1.9025   -0.9391 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0880   -0.1865   -0.2776 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -0.6324   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -1.6555    0.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347   -2.8289   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2409   -2.8838    0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977   -2.3014    1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122    3.2465   -1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626    1.4029    1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894   -0.0357   -0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2183    1.7282   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542    0.9059    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9620   -0.6355   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533   -0.9472    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821   -2.1721    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144   -0.8435    1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7336   -0.1306    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0972   -2.4434   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 17  2  1  0
  9  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 16 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9                                                            
CONECT   17    8                                                            
CONECT   18    3                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0249887
HETATM    1  C1  UNL     1       0.296  -2.240   0.579  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.762  -0.929   0.134  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.188  -0.031  -0.122  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.314   1.265  -0.566  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.479   2.291  -0.888  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.844   2.039  -0.770  1.00  0.00           O  
HETATM    7  C6  UNL     1      -2.327   1.089   0.148  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.799   0.878  -0.146  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.576  -0.252   0.010  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.198  -1.119   1.028  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.754   1.554  -0.717  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.153   2.677  -1.100  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.686   0.509  -0.412  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.123   0.779  -0.556  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.536   1.902  -0.939  1.00  0.00           O  
HETATM   16  O4  UNL     1       5.088  -0.187  -0.278  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.205  -0.632  -0.020  1.00  0.00           C  
HETATM   18  O5  UNL     1       3.102  -1.655   0.280  1.00  0.00           O  
HETATM   19  H1  UNL     1      -0.235  -2.829  -0.188  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.241  -2.884   0.692  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.098  -2.301   1.605  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.112   3.247  -1.216  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.163   1.403   1.201  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.989  -0.036  -0.736  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.218   1.728  -0.751  1.00  0.00           H  
HETATM   26  H8  UNL     1      -4.354   0.906   0.813  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.962  -0.636  -0.990  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.953  -0.947   2.071  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.282  -2.172   0.695  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.314  -0.843   1.027  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.734  -0.131   0.479  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.097  -2.443  -0.366  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   17
CONECT    3    4    9
CONECT    4    5    5   11
CONECT    5    6   22
CONECT    6    7
CONECT    7    8    9   23
CONECT    8   24   25   26
CONECT    9   10   27
CONECT   10   28   29   30
CONECT   11   12   12   13
CONECT   13   14   17   17
CONECT   14   15   15   16
CONECT   16   31
CONECT   17   18
CONECT   18   32
END

HMDB0249887
     RDKit          3D
8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.2961   -2.2404    0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -0.9286    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876   -0.0314   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3143    1.2652   -0.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4792    2.2908   -0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436    2.0393   -0.7704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3272    1.0892    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987    0.8779   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756   -0.2520    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1978   -1.1186    1.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540    1.5540   -0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531    2.6770   -1.1000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855    0.5090   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1225    0.7792   -0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362    1.9025   -0.9391 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0880   -0.1865   -0.2776 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -0.6324   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -1.6555    0.2797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2347   -2.8289   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2409   -2.8838    0.6922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977   -2.3014    1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1122    3.2465   -1.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626    1.4029    1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9894   -0.0357   -0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2183    1.7282   -0.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542    0.9059    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9620   -0.6355   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9533   -0.9472    2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821   -2.1721    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144   -0.8435    1.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7336   -0.1306    0.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0972   -2.4434   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  2  0
 17 18  1  0
 17  2  1  0
  9  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 16 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylate	Generator
Antimycin	HMDB

Chemical Formula

C₁₃H₁₄O₅

Average Molecular Weight

250.25

Monoisotopic Molecular Weight

250.084123551

IUPAC Name

6-hydroxy-3,4,5-trimethyl-8-oxo-4,8-dihydro-3H-2-benzopyran-7-carboxylic acid

Traditional Name

6-hydroxy-3,4,5-trimethyl-8-oxo-3,4-dihydro-2-benzopyran-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1OC=C2C(=O)C(C(O)=O)=C(O)C(C)=C2C1C

InChI Identifier

InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,14H,1-3H3,(H,16,17)

InChI Key

CBGDIJWINPWWJW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Vinylogous ester
Vinylogous acid
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.24	ALOGPS
logP	0.81	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.25 m³·mol⁻¹	ChemAxon
Polarizability	24.71 Å³	ChemAxon
Number of Rings	2	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]+	154.943	30932474
DeepCCS	[M-H]-	152.585	30932474
DeepCCS	[M-2H]-	185.983	30932474
DeepCCS	[M+Na]+	161.105	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid	CC1OC=C2C(=O)C(C(O)=O)=C(O)C(C)=C2C1C	3403.5	Standard polar	33892256
8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid	CC1OC=C2C(=O)C(C(O)=O)=C(O)C(C)=C2C1C	1749.3	Standard non polar	33892256
8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid	CC1OC=C2C(=O)C(C(O)=O)=C(O)C(C)=C2C1C	2041.7	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 - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dr-1950000000-033eac702afe822040ec	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid 10V, Positive-QTOF	splash10-0ue9-0090000000-719d816638185ee9f2d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid 20V, Positive-QTOF	splash10-001i-0090000000-d12dccba0308bf4d813c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid 40V, Positive-QTOF	splash10-0kml-7980000000-bcd1bee9a6aba3dedf3d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid 10V, Negative-QTOF	splash10-052b-0090000000-7a03f081a2bf74c0fd1c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid 20V, Negative-QTOF	splash10-0a4j-0290000000-af4a3ca81e684a67b86e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid 40V, Negative-QTOF	splash10-000i-1910000000-2c87b5d32929ea1760b3	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29786146

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54682830

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid (HMDB0249887)

MOL for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

3D MOL for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

3D SDF for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

3D-SDF for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

PDB for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

3D PDB for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

SMILES for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

INCHI for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

Structure for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

3D Structure for HMDB0249887 (8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra