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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:10 UTC

Update Date

2022-03-07 02:53:29 UTC

HMDB ID

HMDB0032838

Secondary Accession Numbers

HMDB32838

Metabolite Identification

Common Name

Dorsteniol

Description

Dorsteniol belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Dorsteniol has been detected, but not quantified in, green vegetables. This could make dorsteniol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dorsteniol.

Structure

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

HMDB0032838
     RDKit          3D
Dorsteniol
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5852   -0.3971    1.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546    0.0530    0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214    1.4360   -0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288   -0.6067   -1.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0615   -0.1725   -0.9064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249   -0.4249    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7215    0.2425    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666    0.1772    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    0.2531    1.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0420    0.1662    0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2659    0.2464    1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980    0.1530    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371   -0.0137   -1.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -0.0930   -1.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394   -0.0813   -1.6605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9415    0.0006   -0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -0.0762   -1.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5262    0.0114   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8408   -0.0308   -1.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775    0.2361    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7019   -0.3741    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214   -1.4497    1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2353    1.8207   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7612   -1.7062   -0.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076   -0.3708   -2.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0647    0.7680   -0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044   -1.5108    0.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -0.3097    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9753    1.2891    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947    0.3839    2.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888    0.3759    2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3810    0.2117    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072   -0.2072   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  6  1  0
 18  8  1  0
 16 10  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 17 33  1  0
M  END


  Mrv0541 05061306442D          

 19 21  0  0  0  0            999 V2000
   -1.4534    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12  5  1  0  0  0  0
 13  3  1  0  0  0  0
 14  1  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 10  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032838

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)(CO)C1CC2=C(O1)C=C1OC(=O)C=CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O5/c1-14(17,7-15)12-5-9-4-8-2-3-13(16)19-10(8)6-11(9)18-12/h2-4,6,12,15,17H,5,7H2,1H3

> <INCHI_KEY>
JWWIYTKCAJCERS-UHFFFAOYSA-N

> <FORMULA>
C14H14O5

> <MOLECULAR_WEIGHT>
262.258

> <EXACT_MASS>
262.084123558

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.538300149954566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1,2-dihydroxypropan-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
1.06

> <JCHEM_LOGP>
0.6854836403333326

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.183858447115256

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.238129356150953

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1037396087825666

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
67.88460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(1,2-dihydroxypropan-2-yl)-2H,3H-furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032838
     RDKit          3D
Dorsteniol
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5852   -0.3971    1.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546    0.0530    0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214    1.4360   -0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288   -0.6067   -1.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0615   -0.1725   -0.9064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249   -0.4249    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7215    0.2425    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666    0.1772    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    0.2531    1.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0420    0.1662    0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2659    0.2464    1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980    0.1530    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371   -0.0137   -1.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -0.0930   -1.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394   -0.0813   -1.6605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9415    0.0006   -0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -0.0762   -1.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5262    0.0114   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8408   -0.0308   -1.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775    0.2361    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7019   -0.3741    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214   -1.4497    1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2353    1.8207   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7612   -1.7062   -0.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076   -0.3708   -2.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0647    0.7680   -0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044   -1.5108    0.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -0.3097    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9753    1.2891    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947    0.3839    2.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888    0.3759    2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3810    0.2117    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072   -0.2072   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  6  1  0
 18  8  1  0
 16 10  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 17 33  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      -2.713   4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.253   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.023   1.509   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.713   1.303   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    3    8                                                       
CONECT    3    2   13                                                       
CONECT    4    8    9                                                       
CONECT    5    9   12                                                       
CONECT    6   10   11                                                       
CONECT    7   14   15                                                       
CONECT    8    2    4   10                                                  
CONECT    9    4    5   11                                                  
CONECT   10    6    8   19                                                  
CONECT   11    6    9   18                                                  
CONECT   12    5   14   18                                                  
CONECT   13    3   16   19                                                  
CONECT   14    1    7   12   17                                             
CONECT   15    7                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   11   12                                                       
CONECT   19   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0032838
HETATM    1  C1  UNL     1      -3.585  -0.397   1.374  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.955   0.053   0.075  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.021   1.436  -0.002  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.729  -0.607  -1.050  1.00  0.00           C  
HETATM    5  O2  UNL     1      -5.061  -0.173  -0.906  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.525  -0.425   0.072  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.721   0.242   1.139  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.667   0.177   0.563  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.909   0.253   1.155  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.042   0.166   0.407  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.266   0.246   1.034  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.398   0.153   0.234  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.237  -0.014  -1.136  1.00  0.00           C  
HETATM   14  O3  UNL     1       6.291  -0.093  -1.818  1.00  0.00           O  
HETATM   15  O4  UNL     1       4.039  -0.081  -1.661  1.00  0.00           O  
HETATM   16  C12 UNL     1       2.941   0.001  -0.955  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.679  -0.076  -1.554  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.526   0.011  -0.800  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.841  -0.031  -1.110  1.00  0.00           O  
HETATM   20  H1  UNL     1      -3.278   0.236   2.232  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.702  -0.374   1.267  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.321  -1.450   1.597  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.235   1.821  -0.487  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.761  -1.706  -0.916  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.308  -0.371  -2.027  1.00  0.00           H  
HETATM   26  H7  UNL     1      -5.065   0.768  -0.621  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.504  -1.511   0.163  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.779  -0.310   2.094  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.975   1.289   1.314  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.995   0.384   2.230  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.389   0.376   2.099  1.00  0.00           H  
HETATM   32  H13 UNL     1       6.381   0.212   0.691  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.607  -0.207  -2.631  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4    6
CONECT    3   23
CONECT    4    5   24   25
CONECT    5   26
CONECT    6    7   19   27
CONECT    7    8   28   29
CONECT    8    9    9   18
CONECT    9   10   30
CONECT   10   11   16   16
CONECT   11   12   12   31
CONECT   12   13   32
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   17
CONECT   17   18   18   33
CONECT   18   19
END

HMDB0032838
     RDKit          3D
Dorsteniol
 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5852   -0.3971    1.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546    0.0530    0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214    1.4360   -0.0021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288   -0.6067   -1.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0615   -0.1725   -0.9064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249   -0.4249    0.0725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7215    0.2425    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6666    0.1772    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    0.2531    1.1545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0420    0.1662    0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2659    0.2464    1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980    0.1530    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2371   -0.0137   -1.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2907   -0.0930   -1.8180 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394   -0.0813   -1.6605 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9415    0.0006   -0.9548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -0.0762   -1.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5262    0.0114   -0.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8408   -0.0308   -1.1105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2775    0.2361    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7019   -0.3741    1.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3214   -1.4497    1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2353    1.8207   -0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7612   -1.7062   -0.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3076   -0.3708   -2.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0647    0.7680   -0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044   -1.5108    0.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -0.3097    2.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9753    1.2891    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947    0.3839    2.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888    0.3759    2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3810    0.2117    0.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6072   -0.2072   -2.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19  6  1  0
 18  8  1  0
 16 10  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₄O₅

Average Molecular Weight

262.258

Monoisotopic Molecular Weight

262.084123558

IUPAC Name

2-(1,2-dihydroxypropan-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

Traditional Name

2-(1,2-dihydroxypropan-2-yl)-2H,3H-furo[3,2-g]chromen-7-one

CAS Registry Number

80794-85-0

SMILES

CC(O)(CO)C1CC2=C(O1)C=C1OC(=O)C=CC1=C2

InChI Identifier

InChI=1S/C14H14O5/c1-14(17,7-15)12-5-9-4-8-2-3-13(16)19-10(8)6-11(9)18-12/h2-4,6,12,15,17H,5,7H2,1H3

InChI Key

JWWIYTKCAJCERS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Benzopyran
1-benzopyran
Coumaran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Tertiary alcohol
1,2-diol
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Primary alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032838)
Cytoplasm (HMDB: HMDB0032838)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032838)

Source

Exogenous

Exogenous (HMDB: HMDB0032838)

Food

Food (HMDB: HMDB0032838)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0032838)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032838)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 - 180 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.26 g/L	ALOGPS
logP	1.06	ALOGPS
logP	0.69	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.88 m³·mol⁻¹	ChemAxon
Polarizability	26.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.786	31661259
DarkChem	[M-H]-	158.977	31661259
DeepCCS	[M+H]+	158.304	30932474
DeepCCS	[M-H]-	155.946	30932474
DeepCCS	[M-2H]-	188.832	30932474
DeepCCS	[M+Na]+	164.397	30932474
AllCCS	[M+H]+	159.5	32859911
AllCCS	[M+H-H2O]+	155.7	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	164.1	32859911
AllCCS	[M-H]-	163.1	32859911
AllCCS	[M+Na-2H]-	162.8	32859911
AllCCS	[M+HCOO]-	162.6	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. Predicted by Afia on May 17, 2022.	4.36 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6154 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.81 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1352.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	289.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	359.6 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	378.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	740.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	304.9 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	1075.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	257.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	250.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	331.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	253.8 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	76.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dorsteniol	CC(O)(CO)C1CC2=C(O1)C=C1OC(=O)C=CC1=C2	3266.2	Standard polar	33892256
Dorsteniol	CC(O)(CO)C1CC2=C(O1)C=C1OC(=O)C=CC1=C2	2376.6	Standard non polar	33892256
Dorsteniol	CC(O)(CO)C1CC2=C(O1)C=C1OC(=O)C=CC1=C2	2571.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dorsteniol,1TMS,isomer #1	CC(CO)(O[Si](C)(C)C)C1CC2=CC3=C(C=C2O1)OC(=O)C=C3	2610.5	Semi standard non polar	33892256
Dorsteniol,1TMS,isomer #2	CC(O)(CO[Si](C)(C)C)C1CC2=CC3=C(C=C2O1)OC(=O)C=C3	2607.1	Semi standard non polar	33892256
Dorsteniol,2TMS,isomer #1	CC(CO[Si](C)(C)C)(O[Si](C)(C)C)C1CC2=CC3=C(C=C2O1)OC(=O)C=C3	2607.7	Semi standard non polar	33892256
Dorsteniol,1TBDMS,isomer #1	CC(CO)(O[Si](C)(C)C(C)(C)C)C1CC2=CC3=C(C=C2O1)OC(=O)C=C3	2842.0	Semi standard non polar	33892256
Dorsteniol,1TBDMS,isomer #2	CC(O)(CO[Si](C)(C)C(C)(C)C)C1CC2=CC3=C(C=C2O1)OC(=O)C=C3	2833.3	Semi standard non polar	33892256
Dorsteniol,2TBDMS,isomer #1	CC(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C1CC2=CC3=C(C=C2O1)OC(=O)C=C3	3085.0	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 - Dorsteniol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0016-7690000000-184ffc0e99853c92d7bb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dorsteniol GC-MS (2 TMS) - 70eV, Positive	splash10-0109-9428000000-307a9e2b1f1ceb5193c4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dorsteniol 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 - Dorsteniol 10V, Positive-QTOF	splash10-03di-1390000000-044d5a9a6c89a75e2e0a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 20V, Positive-QTOF	splash10-01tj-0590000000-2137dc4aaacff03a7871	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 40V, Positive-QTOF	splash10-0059-1900000000-4f4a6132fc20f8163ae2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 10V, Negative-QTOF	splash10-03di-0190000000-a1cfad72a70ed9d096e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 20V, Negative-QTOF	splash10-01s9-1590000000-afdfcf120ed5e8ff092f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 40V, Negative-QTOF	splash10-0ab9-9400000000-d56e71bdb833c43a6086	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 10V, Negative-QTOF	splash10-03di-0090000000-b90e97974ec134cc9c61	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 20V, Negative-QTOF	splash10-03di-2190000000-deaea1534faf0cd240c0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 40V, Negative-QTOF	splash10-000i-0910000000-b42584795630e315a84b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 10V, Positive-QTOF	splash10-03dj-0090000000-41d8a384596f54be1c57	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 20V, Positive-QTOF	splash10-03di-0290000000-c39e2076f7fffab17256	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorsteniol 40V, Positive-QTOF	splash10-05gi-2910000000-d8af5501885d816d5174	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

FDB010815

KNApSAcK ID

Not Available

Chemspider ID

35013502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71438319

PDB ID

Not Available

ChEBI ID

174448

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.. .

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

Dorsteniol → (2-hydroxy-2-{7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl}propoxy)sulfonic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Dorsteniol → 3,4,5-trihydroxy-6-(2-hydroxy-2-{7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl}propoxy)oxane-2-carboxylic acid	details
Dorsteniol → 3,4,5-trihydroxy-6-[(1-hydroxy-2-{7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl}propan-2-yl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for Dorsteniol (HMDB0032838)

MOL for HMDB0032838 (Dorsteniol)

3D MOL for HMDB0032838 (Dorsteniol)

3D SDF for HMDB0032838 (Dorsteniol)

3D-SDF for HMDB0032838 (Dorsteniol)

PDB for HMDB0032838 (Dorsteniol)

3D PDB for HMDB0032838 (Dorsteniol)

SMILES for HMDB0032838 (Dorsteniol)

INCHI for HMDB0032838 (Dorsteniol)

Structure for HMDB0032838 (Dorsteniol)

3D Structure for HMDB0032838 (Dorsteniol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions