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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:47 UTC

Update Date

2022-03-07 02:53:36 UTC

HMDB ID

HMDB0033109

Secondary Accession Numbers

HMDB33109

Metabolite Identification

Common Name

Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate

Description

Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate, also known as methyl 3-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid, belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. Based on a literature review very few articles have been published on Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate.

Structure

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

HMDB0033109
     RDKit          3D
Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.8409   -0.3778   -0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672    0.1681    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432    1.2873    1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -0.3993   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.6982   -1.2240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373    0.5660   -1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848    1.2551   -1.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    0.9325   -1.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1922   -0.0243   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731   -0.3286   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -1.2034    0.7396 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5837    0.3367   -0.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9597    0.1036   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -0.6754    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1906   -0.3927   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718   -0.9432    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616   -2.3288    0.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7170    0.0357    0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9247   -1.2041   -0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6547    1.2232    1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4436    1.3234    1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4509    2.2715    0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7288   -1.1766   -1.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3915    2.0129   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007    1.4368   -1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2776   -0.7018   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0707   -0.1485    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5697    1.0077   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3152   -1.4348    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -0.5811    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5273   -2.7383   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16  4  1  0
 15  6  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv0541 05061306552D          

 17 18  0  0  0  0            999 V2000
    0.0574    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  2  0  0  0  0
 16  3  1  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 17 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033109

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=CC2=C(OC(C2O)C(C)=C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O4/c1-7(2)12-11(14)9-6-8(13(15)16-3)4-5-10(9)17-12/h4-6,11-12,14H,1H2,2-3H3

> <INCHI_KEY>
ZQTUKLOPEQEDKS-UHFFFAOYSA-N

> <FORMULA>
C13H14O4

> <MOLECULAR_WEIGHT>
234.2479

> <EXACT_MASS>
234.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.659852431107225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylate

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.974322038666667

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.98742030029134

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6791023606525677

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
62.178500000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033109
     RDKit          3D
Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.8409   -0.3778   -0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672    0.1681    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432    1.2873    1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -0.3993   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.6982   -1.2240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373    0.5660   -1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848    1.2551   -1.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    0.9325   -1.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1922   -0.0243   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731   -0.3286   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -1.2034    0.7396 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5837    0.3367   -0.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9597    0.1036   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -0.6754    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1906   -0.3927   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718   -0.9432    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616   -2.3288    0.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7170    0.0357    0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9247   -1.2041   -0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6547    1.2232    1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4436    1.3234    1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4509    2.2715    0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7288   -1.1766   -1.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3915    2.0129   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007    1.4368   -1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2776   -0.7018   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0707   -0.1485    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5697    1.0077   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3152   -1.4348    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -0.5811    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5273   -2.7383   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16  4  1  0
 15  6  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  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       0.107   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.846  -1.941   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3   16                                                            
CONECT    4    5    8                                                       
CONECT    5    4   10                                                       
CONECT    6    8    9                                                       
CONECT    7    1    2   12                                                  
CONECT    8    4    6   13                                                  
CONECT    9    6   10   11                                                  
CONECT   10    5    9   17                                                  
CONECT   11    9   12   14                                                  
CONECT   12    7   11   17                                                  
CONECT   13    8   15   16                                                  
CONECT   14   11                                                            
CONECT   15   13                                                            
CONECT   16    3   13                                                       
CONECT   17   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0033109
HETATM    1  C1  UNL     1      -4.841  -0.378  -0.242  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.667   0.168   0.051  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.543   1.287   1.009  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.463  -0.399  -0.634  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.789   0.698  -1.224  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.437   0.566  -1.069  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.585   1.255  -1.723  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.871   0.932  -1.383  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.192  -0.024  -0.443  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.573  -0.329  -0.119  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.819  -1.203   0.740  1.00  0.00           O  
HETATM   12  O3  UNL     1       4.584   0.337  -0.750  1.00  0.00           O  
HETATM   13  C10 UNL     1       5.960   0.104  -0.496  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.150  -0.675   0.173  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.191  -0.393  -0.128  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.472  -0.943   0.384  1.00  0.00           C  
HETATM   17  O4  UNL     1      -1.462  -2.329   0.418  1.00  0.00           O  
HETATM   18  H1  UNL     1      -5.717   0.036   0.256  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.925  -1.204  -0.951  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.655   1.223   1.659  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.444   1.323   1.656  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.451   2.272   0.472  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.729  -1.177  -1.357  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.391   2.013  -2.466  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.701   1.437  -1.860  1.00  0.00           H  
HETATM   26  H9  UNL     1       6.278  -0.702  -1.187  1.00  0.00           H  
HETATM   27  H10 UNL     1       6.071  -0.149   0.560  1.00  0.00           H  
HETATM   28  H11 UNL     1       6.570   1.008  -0.744  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.315  -1.435   0.918  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.748  -0.581   1.372  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.527  -2.738  -0.477  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5   16   23
CONECT    5    6
CONECT    6    7    7   15
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   14
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   26   27   28
CONECT   14   15   15   29
CONECT   15   16
CONECT   16   17   30
CONECT   17   31
END

HMDB0033109
     RDKit          3D
Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate
 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.8409   -0.3778   -0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672    0.1681    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5432    1.2873    1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627   -0.3993   -0.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.6982   -1.2240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4373    0.5660   -1.0693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848    1.2551   -1.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    0.9325   -1.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1922   -0.0243   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5731   -0.3286   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -1.2034    0.7396 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5837    0.3367   -0.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9597    0.1036   -0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -0.6754    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1906   -0.3927   -0.1285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718   -0.9432    0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616   -2.3288    0.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7170    0.0357    0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9247   -1.2041   -0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6547    1.2232    1.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4436    1.3234    1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4509    2.2715    0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7288   -1.1766   -1.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3915    2.0129   -2.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007    1.4368   -1.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2776   -0.7018   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0707   -0.1485    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5697    1.0077   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3152   -1.4348    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7477   -0.5811    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5273   -2.7383   -0.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16  4  1  0
 15  6  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylic acid	Generator
Methyl 3-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid	HMDB

Chemical Formula

C₁₃H₁₄O₄

Average Molecular Weight

234.2479

Monoisotopic Molecular Weight

234.089208936

IUPAC Name

methyl 3-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylate

Traditional Name

methyl 3-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2=C(OC(C2O)C(C)=C)C=C1

InChI Identifier

InChI=1S/C13H14O4/c1-7(2)12-11(14)9-6-8(13(15)16-3)4-5-10(9)17-12/h4-6,11-12,14H,1H2,2-3H3

InChI Key

ZQTUKLOPEQEDKS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Alkyl aryl ether
Benzenoid
Methyl ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033109)
Cytoplasm (HMDB: HMDB0033109)

Source

Exogenous

Exogenous (HMDB: HMDB0033109)

Food

Food (HMDB: HMDB0033109)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033109)

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
Water Solubility	4.4 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.97	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.99	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.18 m³·mol⁻¹	ChemAxon
Polarizability	24.66 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]+	155.413	31661259
DarkChem	[M-H]-	153.71	31661259
DeepCCS	[M+H]+	156.606	30932474
DeepCCS	[M-H]-	154.237	30932474
DeepCCS	[M-2H]-	187.127	30932474
DeepCCS	[M+Na]+	162.688	30932474
AllCCS	[M+H]+	153.3	32859911
AllCCS	[M+H-H2O]+	149.5	32859911
AllCCS	[M+NH4]+	157.0	32859911
AllCCS	[M+Na]+	158.0	32859911
AllCCS	[M-H]-	155.3	32859911
AllCCS	[M+Na-2H]-	155.3	32859911
AllCCS	[M+HCOO]-	155.4	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.	5.56 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6646 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.24 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2235.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	402.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	168.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	109.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	480.8 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	675.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1090.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	426.8 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	1359.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	370.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	411.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	380.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	386.3 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	13.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate	COC(=O)C1=CC2=C(OC(C2O)C(C)=C)C=C1	2741.2	Standard polar	33892256
Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate	COC(=O)C1=CC2=C(OC(C2O)C(C)=C)C=C1	1786.2	Standard non polar	33892256
Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate	COC(=O)C1=CC2=C(OC(C2O)C(C)=C)C=C1	1904.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate,1TMS,isomer #1	C=C(C)C1OC2=CC=C(C(=O)OC)C=C2C1O[Si](C)(C)C	1925.9	Semi standard non polar	33892256
Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate,1TBDMS,isomer #1	C=C(C)C1OC2=CC=C(C(=O)OC)C=C2C1O[Si](C)(C)C(C)(C)C	2149.1	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 - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9550000000-0bdffc4aa5105455dcc6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate GC-MS (1 TMS) - 70eV, Positive	splash10-00bc-9050000000-0e680ee71121714a62b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 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 - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 10V, Positive-QTOF	splash10-000i-0190000000-41943b70d67c8e4ee2f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 20V, Positive-QTOF	splash10-0fgc-6690000000-c71189d6fe74c85ce9ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 40V, Positive-QTOF	splash10-05fr-4900000000-d69be69227c6101c477e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 10V, Negative-QTOF	splash10-001i-0090000000-074bf6ebe578007a6ca7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 20V, Negative-QTOF	splash10-001i-1190000000-08eddf0ee04586a6bb37	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 40V, Negative-QTOF	splash10-03di-3910000000-7b2b8009ccdea462c6d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 10V, Negative-QTOF	splash10-001i-0090000000-517cac6609b86ecea254	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 20V, Negative-QTOF	splash10-005i-0910000000-da1d8f2e5ad9b9239aec	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 40V, Negative-QTOF	splash10-06us-1910000000-3336ce6754395d99fe08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 10V, Positive-QTOF	splash10-000i-0290000000-e09dc1bb565f5364003e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 20V, Positive-QTOF	splash10-0ktr-1970000000-cdd2513f3727e42db5a1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate 40V, Positive-QTOF	splash10-0a4r-9400000000-8ddaea50aa181d2d8ebb	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, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

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

FDB011106

KNApSAcK ID

Not Available

Chemspider ID

35013550

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129835668

PDB ID

Not Available

ChEBI ID

173251

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 Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate (HMDB0033109)

MOL for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D MOL for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D SDF for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D-SDF for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

PDB for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D PDB for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

SMILES for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

INCHI for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

Structure for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D Structure for HMDB0033109 (Methyl (2R*,3S*)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Showing metabocard for Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate (HMDB0033109)

MOL for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D MOL for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D SDF for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D-SDF for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

PDB for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D PDB for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

SMILES for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

INCHI for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

Structure for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)

3D Structure for HMDB0033109 (Methyl (2R,3S)-2,3-dihydro-3-hydroxy-2-isopropenyl-5-benzofurancarboxylate)