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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:56:51 UTC

Update Date

2022-03-07 02:56:35 UTC

HMDB ID

HMDB0040407

Secondary Accession Numbers

HMDB40407

Metabolite Identification

Common Name

(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid

Description

(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid, also known as 2-(7-hydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl)acetate, belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety (S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid has been detected, but not quantified in, green vegetables. This could make (S)-2,3-dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid.

Structure

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

HMDB0040407
     RDKit          3D
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.0422   -0.0517   -0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5672   -0.0195    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -1.1897   -0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4698   -1.1942   -0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0690   -2.2679    0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2093    0.0804    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5651    0.0875    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545   -1.1477    0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -1.8634   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2524   -1.4794   -1.8354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679   -3.0261   -0.6329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1528    1.3527    0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4378    2.5137    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317    3.7510    0.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870    2.4406   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511    1.2244   -0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309    1.1464   -0.3785 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752    0.7516   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541    0.0459    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904   -1.0132   -0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560   -0.1439    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -2.1189   -0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625   -1.0192   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3842   -0.7991    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327   -1.7763    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241   -3.6190    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143    1.3775    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5283    4.5966    0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    3.3607   -0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17  2  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
M  END


  Mrv0541 05061311492D          

 17 18  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  2  1  0  0  0  0
 10  5  1  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 17  6  1  0  0  0  0
 17 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040407

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC(=O)C2=C(O1)C=C(O)C=C2CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O5/c1-6-2-9(14)12-7(4-11(15)16)3-8(13)5-10(12)17-6/h3,5-6,13H,2,4H2,1H3,(H,15,16)

> <INCHI_KEY>
MONKQYHCNQSQHL-UHFFFAOYSA-N

> <FORMULA>
C12H12O5

> <MOLECULAR_WEIGHT>
236.2207

> <EXACT_MASS>
236.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
22.9802656216523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(7-hydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl)acetic acid

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.0623218203333327

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.753988896727877

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.476949155751217

> <JCHEM_PKA_STRONGEST_BASIC>
-4.917870387832259

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
58.771600000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7-hydroxy-2-methyl-4-oxo-2,3-dihydro-1-benzopyran-5-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040407
     RDKit          3D
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.0422   -0.0517   -0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5672   -0.0195    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -1.1897   -0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4698   -1.1942   -0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0690   -2.2679    0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2093    0.0804    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5651    0.0875    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545   -1.1477    0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -1.8634   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2524   -1.4794   -1.8354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679   -3.0261   -0.6329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1528    1.3527    0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4378    2.5137    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317    3.7510    0.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870    2.4406   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511    1.2244   -0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309    1.1464   -0.3785 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752    0.7516   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541    0.0459    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904   -1.0132   -0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560   -0.1439    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -2.1189   -0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625   -1.0192   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3842   -0.7991    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327   -1.7763    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241   -3.6190    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143    1.3775    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5283    4.5966    0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    3.3607   -0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17  2  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6    9                                                       
CONECT    3    7    8                                                       
CONECT    4    7   11                                                       
CONECT    5    8   10                                                       
CONECT    6    1    2   17                                                  
CONECT    7    3    4   12                                                  
CONECT    8    3    5   13                                                  
CONECT    9    2   12   14                                                  
CONECT   10    5   12   17                                                  
CONECT   11    4   15   16                                                  
CONECT   12    7    9   10                                                  
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0040407
HETATM    1  C1  UNL     1       4.042  -0.052  -0.111  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.567  -0.019   0.153  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.864  -1.190  -0.523  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.470  -1.194  -0.013  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.069  -2.268   0.311  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.209   0.080   0.084  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.565   0.088   0.355  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.355  -1.148   0.558  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.636  -1.863  -0.706  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.252  -1.479  -1.835  1.00  0.00           O  
HETATM   11  O3  UNL     1      -3.368  -3.026  -0.633  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.153   1.353   0.432  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.438   2.514   0.253  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.032   3.751   0.332  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.087   2.441  -0.015  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.551   1.224  -0.104  1.00  0.00           C  
HETATM   17  O5  UNL     1       1.931   1.146  -0.378  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.275   0.752  -0.850  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.654   0.046   0.823  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.290  -1.013  -0.631  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.356  -0.144   1.247  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.393  -2.119  -0.277  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.862  -1.019  -1.640  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.384  -0.799   0.890  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.033  -1.776   1.395  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.424  -3.619   0.197  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.214   1.378   0.644  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.528   4.597   0.205  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.491   3.361  -0.161  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   17   21
CONECT    3    4   22   23
CONECT    4    5    5    6
CONECT    6    7    7   16
CONECT    7    8   12
CONECT    8    9   24   25
CONECT    9   10   10   11
CONECT   11   26
CONECT   12   13   13   27
CONECT   13   14   15
CONECT   14   28
CONECT   15   16   16   29
CONECT   16   17
END

HMDB0040407
     RDKit          3D
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid
 29 30  0  0  0  0  0  0  0  0999 V2000
    4.0422   -0.0517   -0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5672   -0.0195    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -1.1897   -0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4698   -1.1942   -0.0127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0690   -2.2679    0.3114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2093    0.0804    0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5651    0.0875    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3545   -1.1477    0.5577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -1.8634   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2524   -1.4794   -1.8354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679   -3.0261   -0.6329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1528    1.3527    0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4378    2.5137    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317    3.7510    0.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0870    2.4406   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511    1.2244   -0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9309    1.1464   -0.3785 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2752    0.7516   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541    0.0459    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904   -1.0132   -0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560   -0.1439    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926   -2.1189   -0.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8625   -1.0192   -1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3842   -0.7991    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0327   -1.7763    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4241   -3.6190    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2143    1.3775    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5283    4.5966    0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    3.3607   -0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17  2  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  8 24  1  0
  8 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetate	Generator
2-(7-Hydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl)acetate	HMDB

Chemical Formula

C₁₂H₁₂O₅

Average Molecular Weight

236.2207

Monoisotopic Molecular Weight

236.068473494

IUPAC Name

2-(7-hydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl)acetic acid

Traditional Name

(7-hydroxy-2-methyl-4-oxo-2,3-dihydro-1-benzopyran-5-yl)acetic acid

CAS Registry Number

94356-37-3

SMILES

CC1CC(=O)C2=C(O1)C=C(O)C=C2CC(O)=O

InChI Identifier

InChI=1S/C12H12O5/c1-6-2-9(14)12-7(4-11(15)16)3-8(13)5-10(12)17-6/h3,5-6,13H,2,4H2,1H3,(H,15,16)

InChI Key

MONKQYHCNQSQHL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ketone
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040407)
Cytoplasm (HMDB: HMDB0040407)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040407)

Source

Exogenous

Exogenous (HMDB: HMDB0040407)

Food

Food (HMDB: HMDB0040407)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0040407)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040407)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	205 - 207 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	36130 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.77 g/L	ALOGPS
logP	1.5	ALOGPS
logP	1.06	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.77 m³·mol⁻¹	ChemAxon
Polarizability	22.98 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
DarkChem	[M+H]+	155.58	31661259
DarkChem	[M-H]-	154.32	31661259
DeepCCS	[M+H]+	154.05	30932474
DeepCCS	[M-H]-	151.68	30932474
DeepCCS	[M-2H]-	184.566	30932474
DeepCCS	[M+Na]+	160.131	30932474
AllCCS	[M+H]+	152.6	32859911
AllCCS	[M+H-H2O]+	148.7	32859911
AllCCS	[M+NH4]+	156.2	32859911
AllCCS	[M+Na]+	157.3	32859911
AllCCS	[M-H]-	153.1	32859911
AllCCS	[M+Na-2H]-	153.1	32859911
AllCCS	[M+HCOO]-	153.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	4.99 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5213 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1580.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	280.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	119.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	76.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	411.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	388.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	110.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	791.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	344.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1205.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	380.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	268.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	225.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid	CC1CC(=O)C2=C(O1)C=C(O)C=C2CC(O)=O	3285.3	Standard polar	33892256
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid	CC1CC(=O)C2=C(O1)C=C(O)C=C2CC(O)=O	2093.8	Standard non polar	33892256
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid	CC1CC(=O)C2=C(O1)C=C(O)C=C2CC(O)=O	2265.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid,1TMS,isomer #1	CC1CC(=O)C2=C(CC(=O)O)C=C(O[Si](C)(C)C)C=C2O1	2172.5	Semi standard non polar	33892256
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid,1TMS,isomer #2	CC1CC(=O)C2=C(CC(=O)O[Si](C)(C)C)C=C(O)C=C2O1	2121.9	Semi standard non polar	33892256
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid,2TMS,isomer #1	CC1CC(=O)C2=C(CC(=O)O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C2O1	2210.1	Semi standard non polar	33892256
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid,1TBDMS,isomer #1	CC1CC(=O)C2=C(CC(=O)O)C=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2441.4	Semi standard non polar	33892256
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid,1TBDMS,isomer #2	CC1CC(=O)C2=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C(O)C=C2O1	2388.6	Semi standard non polar	33892256
(S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid,2TBDMS,isomer #1	CC1CC(=O)C2=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2713.6	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020139

KNApSAcK ID

Not Available

Chemspider ID

514417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

591742

PDB ID

Not Available

ChEBI ID

174213

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1883221

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 (S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid (HMDB0040407)

MOL for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

3D MOL for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

3D SDF for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

3D-SDF for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

PDB for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

3D PDB for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

SMILES for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

INCHI for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

Structure for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

3D Structure for HMDB0040407 ((S)-2,3-Dihydro-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-5-acetic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized