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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:05 UTC

Update Date

2022-03-07 02:52:34 UTC

HMDB ID

HMDB0030486

Secondary Accession Numbers

HMDB30486

Metabolite Identification

Common Name

(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran

Description

(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 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 (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran.

Structure

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

HMDB0030486
     RDKit          3D
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.4751    0.2032   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455   -0.3886    0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -0.7166    1.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3294   -0.7381    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.0308    1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1296   -0.0456    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659    0.0059    0.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2490   -0.0195   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730    0.0404    0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6216    0.1154    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8990    0.0356   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0131   -0.0382   -1.4747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9013   -0.1015   -1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8672   -0.1334   -2.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -0.1569   -1.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4300   -0.1276   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -0.1675   -1.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0603    0.4486   -1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026    0.4424   -0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945   -1.5687    2.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658    0.1683    2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4376   -0.9075    1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1239   -1.8121    0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7754    1.0121    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788   -0.5539    2.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3274    0.0705    1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731    1.0323    0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5822   -0.7043    0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7933   -0.5853   -1.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6477   -0.1927   -3.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858   -0.2215   -2.8993 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
  8 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17  4  1  0
 16  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
  5 24  1  0
  5 25  1  0
  7 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
M  END


  Mrv0541 05061305152D          

 17 18  0  0  0  0            999 V2000
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 12  7  1  0  0  0  0
 13  5  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030486

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CC2=CC(C(=O)CO)=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O4/c1-7(2)12-4-8-3-9(11(16)6-14)10(15)5-13(8)17-12/h3,5,12,14-15H,1,4,6H2,2H3

> <INCHI_KEY>
DSPWIGNSRMCMGP-UHFFFAOYSA-N

> <FORMULA>
C13H14O4

> <MOLECULAR_WEIGHT>
234.2479

> <EXACT_MASS>
234.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.3897666927676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1-[6-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethan-1-one

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.9766753726666666

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.87093845986885

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.16793604921118

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3440491713765823

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
63.03160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-1-[6-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030486
     RDKit          3D
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.4751    0.2032   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455   -0.3886    0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -0.7166    1.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3294   -0.7381    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.0308    1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1296   -0.0456    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659    0.0059    0.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2490   -0.0195   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730    0.0404    0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6216    0.1154    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8990    0.0356   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0131   -0.0382   -1.4747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9013   -0.1015   -1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8672   -0.1334   -2.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -0.1569   -1.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4300   -0.1276   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -0.1675   -1.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0603    0.4486   -1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026    0.4424   -0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945   -1.5687    2.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658    0.1683    2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4376   -0.9075    1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1239   -1.8121    0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7754    1.0121    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788   -0.5539    2.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3274    0.0705    1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731    1.0323    0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5822   -0.7043    0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7933   -0.5853   -1.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6477   -0.1927   -3.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858   -0.2215   -2.8993 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
  8 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17  4  1  0
 16  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
  5 24  1  0
  5 25  1  0
  7 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 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      -1.090  -2.636   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.090   0.031   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.259   0.237   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.591   1.777   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8    9                                                       
CONECT    4    8   12                                                       
CONECT    5   10   13                                                       
CONECT    6   11   14                                                       
CONECT    7    1    2   12                                                  
CONECT    8    3    4   13                                                  
CONECT    9    3   10   11                                                  
CONECT   10    5    9   15                                                  
CONECT   11    6    9   16                                                  
CONECT   12    4    7   17                                                  
CONECT   13    5    8   17                                                  
CONECT   14    6                                                            
CONECT   15   10                                                            
CONECT   16   11                                                            
CONECT   17   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0030486
HETATM    1  C1  UNL     1       4.475   0.203  -0.526  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.746  -0.389   0.403  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.349  -0.717   1.719  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.329  -0.738   0.170  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.450  -0.031   1.175  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.130  -0.046   0.440  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.166   0.006   0.840  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.249  -0.020  -0.047  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.573   0.040   0.492  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.622   0.115   1.806  1.00  0.00           O  
HETATM   11  C10 UNL     1      -4.899   0.036  -0.123  1.00  0.00           C  
HETATM   12  O2  UNL     1      -5.013  -0.038  -1.475  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.901  -0.102  -1.369  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.867  -0.133  -2.326  1.00  0.00           O  
HETATM   15  C12 UNL     1      -0.580  -0.157  -1.826  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.430  -0.128  -0.898  1.00  0.00           C  
HETATM   17  O4  UNL     1       1.832  -0.167  -1.038  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.060   0.449  -1.481  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.503   0.442  -0.320  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.794  -1.569   2.173  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.166   0.168   2.385  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.438  -0.908   1.657  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.124  -1.812   0.239  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.775   1.012   1.244  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.379  -0.554   2.140  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.327   0.070   1.925  1.00  0.00           H  
HETATM   27  H10 UNL     1      -5.373   1.032   0.174  1.00  0.00           H  
HETATM   28  H11 UNL     1      -5.582  -0.704   0.397  1.00  0.00           H  
HETATM   29  H12 UNL     1      -5.793  -0.585  -1.757  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.648  -0.193  -3.295  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.386  -0.221  -2.899  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5   17   23
CONECT    5    6   24   25
CONECT    6    7    7   16
CONECT    7    8   26
CONECT    8    9   13   13
CONECT    9   10   10   11
CONECT   11   12   27   28
CONECT   12   29
CONECT   13   14   15
CONECT   14   30
CONECT   15   16   16   31
CONECT   16   17
END

HMDB0030486
     RDKit          3D
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.4751    0.2032   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455   -0.3886    0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -0.7166    1.7188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3294   -0.7381    0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4501   -0.0308    1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1296   -0.0456    0.4401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1659    0.0059    0.8399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2490   -0.0195   -0.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730    0.0404    0.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6216    0.1154    1.8065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8990    0.0356   -0.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0131   -0.0382   -1.4747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9013   -0.1015   -1.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8672   -0.1334   -2.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797   -0.1569   -1.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4300   -0.1276   -0.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8324   -0.1675   -1.0376 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0603    0.4486   -1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026    0.4424   -0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945   -1.5687    2.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1658    0.1683    2.3845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4376   -0.9075    1.6566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1239   -1.8121    0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7754    1.0121    1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3788   -0.5539    2.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3274    0.0705    1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731    1.0323    0.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5822   -0.7043    0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7933   -0.5853   -1.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6477   -0.1927   -3.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858   -0.2215   -2.8993 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  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
  8 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17  4  1  0
 16  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
  5 24  1  0
  5 25  1  0
  7 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄O₄

Average Molecular Weight

234.2479

Monoisotopic Molecular Weight

234.089208936

IUPAC Name

2-hydroxy-1-[6-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethan-1-one

Traditional Name

2-hydroxy-1-[6-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethanone

CAS Registry Number

83218-05-7

SMILES

CC(=C)C1CC2=CC(C(=O)CO)=C(O)C=C2O1

InChI Identifier

InChI=1S/C13H14O4/c1-7(2)12-4-8-3-9(11(16)6-14)10(15)5-13(8)17-12/h3,5,12,14-15H,1,4,6H2,2H3

InChI Key

DSPWIGNSRMCMGP-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
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Alpha-hydroxy ketone
Vinylogous acid
Ketone
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Primary alcohol
Organic oxygen 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: HMDB0030486)
Cytoplasm (HMDB: HMDB0030486)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030486)

Source

Endogenous

Endogenous (HMDB: HMDB0030486)

Exogenous

Food

Food (HMDB: HMDB0030486)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0030486)

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
Water Solubility	1.5 g/L	ALOGPS
logP	1.24	ALOGPS
logP	1.98	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	10.17	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.03 m³·mol⁻¹	ChemAxon
Polarizability	24.39 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]+	155.286	31661259
DarkChem	[M-H]-	153.863	31661259
DeepCCS	[M+H]+	152.849	30932474
DeepCCS	[M-H]-	150.491	30932474
DeepCCS	[M-2H]-	183.925	30932474
DeepCCS	[M+Na]+	158.942	30932474
AllCCS	[M+H]+	152.9	32859911
AllCCS	[M+H-H2O]+	149.0	32859911
AllCCS	[M+NH4]+	156.6	32859911
AllCCS	[M+Na]+	157.6	32859911
AllCCS	[M-H]-	155.1	32859911
AllCCS	[M+Na-2H]-	155.2	32859911
AllCCS	[M+HCOO]-	155.3	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.	5.01 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8941 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.29 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1982.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	370.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	518.3 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	662.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	69.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1066.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	445.6 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	1414.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	338.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	212.2 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	24.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran	CC(=C)C1CC2=CC(C(=O)CO)=C(O)C=C2O1	3003.1	Standard polar	33892256
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran	CC(=C)C1CC2=CC(C(=O)CO)=C(O)C=C2O1	1971.3	Standard non polar	33892256
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran	CC(=C)C1CC2=CC(C(=O)CO)=C(O)C=C2O1	2100.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran,1TMS,isomer #1	C=C(C)C1CC2=CC(C(=O)CO[Si](C)(C)C)=C(O)C=C2O1	2074.6	Semi standard non polar	33892256
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran,1TMS,isomer #2	C=C(C)C1CC2=CC(C(=O)CO)=C(O[Si](C)(C)C)C=C2O1	2101.4	Semi standard non polar	33892256
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran,2TMS,isomer #1	C=C(C)C1CC2=CC(C(=O)CO[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2O1	2153.3	Semi standard non polar	33892256
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran,1TBDMS,isomer #1	C=C(C)C1CC2=CC(C(=O)CO[Si](C)(C)C(C)(C)C)=C(O)C=C2O1	2295.1	Semi standard non polar	33892256
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran,1TBDMS,isomer #2	C=C(C)C1CC2=CC(C(=O)CO)=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2331.7	Semi standard non polar	33892256
(S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran,2TBDMS,isomer #1	C=C(C)C1CC2=CC(C(=O)CO[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2590.4	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 - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-5690000000-aa55b689f8d08f6e61fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran GC-MS (2 TMS) - 70eV, Positive	splash10-0jb9-9854000000-17ce820ed6ce8a881089	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 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 - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 10V, Positive-QTOF	splash10-000i-0290000000-2af591ca2a2af05a4775	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 20V, Positive-QTOF	splash10-0ap0-9480000000-f2cac873a63d559afe8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 40V, Positive-QTOF	splash10-0a4i-5900000000-9014f84edf05a5e25a32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 10V, Negative-QTOF	splash10-001i-1190000000-51f98d6daccc68387d69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 20V, Negative-QTOF	splash10-0pc0-7590000000-a558a547364e1333baed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 40V, Negative-QTOF	splash10-0a4i-4900000000-d1d2a6d4cb8de47a7fb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 10V, Negative-QTOF	splash10-0fsi-0090000000-53a058108b407e42a2dc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 20V, Negative-QTOF	splash10-014i-0890000000-ac38e5e67e60eb2077c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 40V, Negative-QTOF	splash10-05aj-0900000000-0261fa45133e44eed68a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 10V, Positive-QTOF	splash10-014r-0090000000-2dd17c7a2e548a3b99f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 20V, Positive-QTOF	splash10-0i29-0690000000-83d4ee70148dcd241715	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran 40V, Positive-QTOF	splash10-0j7r-2910000000-d610e2812f47b6e6266f	2021-09-22	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

FDB002355

KNApSAcK ID

C00054237

Chemspider ID

35013208

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751030

PDB ID

Not Available

ChEBI ID

168100

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 (S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran (HMDB0030486)

MOL for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

3D MOL for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

3D SDF for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

3D-SDF for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

PDB for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

3D PDB for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

SMILES for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

INCHI for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

Structure for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

3D Structure for HMDB0030486 ((S)-2,3-Dihydro-6-hydroxy-5-(hydroxyacetyl)-2-isopropenylbenzofuran)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra