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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:34:04 UTC

Update Date

2021-09-26 22:52:07 UTC

HMDB ID

HMDB0244406

Secondary Accession Numbers

None

Metabolite Identification

Common Name

8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one

Description

columbianetin belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Based on a literature review a significant number of articles have been published on columbianetin. This compound has been identified in human blood as reported by (PMID: 31557052 ). 8,9-dihydro-8-(1-hydroxy-1-methylethyl)-2h-furo[2,3-h]1-benzopyran-2-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0250408
     RDKit          3D
Columbianetin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.9222   -0.2977    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8647    0.4655   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5204   -0.1934   -1.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2567    1.7722   -0.3872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6147    0.4897    0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    1.1690    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    0.1878    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464   -0.9768    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664   -2.0457    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3104   -1.9242    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.7626    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147   -0.6498   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6801    0.5434   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650    1.5718   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    2.6509   -1.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4963    1.4344   -0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130    0.3025   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.8640    0.8624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9321    0.1504    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9041   -1.3553    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289   -0.3389    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1104   -1.1372   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    0.4442   -2.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4504   -0.5174   -1.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678    2.0860    0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    0.9585    1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2047    2.0995    0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942    1.3509   -1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730   -2.9965    1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9889   -2.7553    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185   -1.5118    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7362    0.6500   -0.8333 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  8 18  1  0
 18  5  1  0
 17  7  1  0
 17 11  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
M  END


  Mrv1533004171519132D          

 18 20  0  0  0  0            999 V2000
    5.0626    1.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267    1.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7959    0.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 12 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244406

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(O)C1CC2=C(O1)C=CC1=C2OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O4/c1-14(2,16)11-7-9-10(17-11)5-3-8-4-6-12(15)18-13(8)9/h3-6,11,16H,7H2,1-2H3

> <INCHI_KEY>
YRAQEMCYCSSHJG-UHFFFAOYSA-N

> <FORMULA>
C14H14O4

> <MOLECULAR_WEIGHT>
246.262

> <EXACT_MASS>
246.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.419761396302324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(2-hydroxypropan-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.7323936069999994

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.296670429286753

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1064363542299747

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
66.34090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-columbianetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250408
     RDKit          3D
Columbianetin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.9222   -0.2977    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8647    0.4655   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5204   -0.1934   -1.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2567    1.7722   -0.3872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6147    0.4897    0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    1.1690    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    0.1878    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464   -0.9768    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664   -2.0457    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3104   -1.9242    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.7626    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147   -0.6498   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6801    0.5434   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650    1.5718   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    2.6509   -1.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4963    1.4344   -0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130    0.3025   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.8640    0.8624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9321    0.1504    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9041   -1.3553    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289   -0.3389    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1104   -1.1372   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    0.4442   -2.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4504   -0.5174   -1.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678    2.0860    0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    0.9585    1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2047    2.0995    0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942    1.3509   -1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730   -2.9965    1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9889   -2.7553    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185   -1.5118    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7362    0.6500   -0.8333 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  8 18  1  0
 18  5  1  0
 17  7  1  0
 17 11  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       9.450   3.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.141   2.271   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.330   3.580   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.952   0.962   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.719  -0.076   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.289   3.388   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.062   2.127   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    7   12                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0244406
HETATM    1  C1  UNL     1      -3.543   1.523  -0.089  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.844   0.242   0.321  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.796  -0.909  -0.032  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.587   0.208   1.688  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.587   0.013  -0.465  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.469   0.948  -0.095  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.753   0.085  -0.027  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.311  -1.217  -0.044  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.204  -2.267   0.008  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.568  -2.012   0.078  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.029  -0.728   0.096  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.383  -0.476   0.165  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.805   0.834   0.181  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.824   1.805   0.125  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.218   3.016   0.139  1.00  0.00           O  
HETATM   16  O3  UNL     1       2.544   1.526   0.059  1.00  0.00           O  
HETATM   17  C14 UNL     1       2.099   0.303   0.042  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.070  -1.256  -0.116  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.022   2.050  -0.898  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.594   1.343  -0.417  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.634   2.205   0.800  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.841  -0.652   0.204  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.717  -1.011  -1.149  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.413  -1.793   0.498  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.916  -0.635   2.058  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.835   0.026  -1.539  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.672   1.431   0.883  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.278   1.695  -0.902  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.893  -3.302  -0.003  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.258  -2.829   0.118  1.00  0.00           H  
HETATM   31  H13 UNL     1       5.090  -1.288   0.206  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.838   1.119   0.233  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    5
CONECT    3   22   23   24
CONECT    4   25
CONECT    5    6   18   26
CONECT    6    7   27   28
CONECT    7    8    8   17
CONECT    8    9   18
CONECT    9   10   10   29
CONECT   10   11   30
CONECT   11   12   17   17
CONECT   12   13   13   31
CONECT   13   14   32
CONECT   14   15   15   16
CONECT   16   17
END

HMDB0250408
     RDKit          3D
Columbianetin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.9222   -0.2977    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8647    0.4655   -0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5204   -0.1934   -1.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2567    1.7722   -0.3872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6147    0.4897    0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4721    1.1690    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6648    0.1878    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464   -0.9768    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9664   -2.0457    0.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3104   -1.9242    0.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.7626    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2147   -0.6498   -0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6801    0.5434   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7650    1.5718   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361    2.6509   -1.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4963    1.4344   -0.5707 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130    0.3025   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.8640    0.8624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9321    0.1504    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9041   -1.3553    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289   -0.3389    1.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1104   -1.1372   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546    0.4442   -2.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4504   -0.5174   -1.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8678    2.0860    0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    0.9585    1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2047    2.0995    0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942    1.3509   -1.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5730   -2.9965    1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9889   -2.7553    0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8185   -1.5118    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7362    0.6500   -0.8333 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
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  8 18  1  0
 18  5  1  0
 17  7  1  0
 17 11  2  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Columbianetin	ChEBI
8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-H]1-benzopyran-2-one	ChEBI
Columbianetin	MeSH
Columbianetin, (S)-isomer	MeSH
Columbianetin, (+-)-isomer	MeSH

Chemical Formula

C₁₄H₁₄O₄

Average Molecular Weight

246.262

Monoisotopic Molecular Weight

246.089208931

IUPAC Name

8-(2-hydroxypropan-2-yl)-2H,8H,9H-furo[2,3-h]chromen-2-one

Traditional Name

(+-)-columbianetin

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CC2=C(O1)C=CC1=C2OC(=O)C=C1

InChI Identifier

InChI=1S/C14H14O4/c1-14(2,16)11-7-9-10(17-11)5-3-8-4-6-12(15)18-13(8)9/h3-6,11,16H,7H2,1-2H3

InChI Key

YRAQEMCYCSSHJG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Angular furanocoumarins

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:59948 )
furanocoumarin (CHEBI:59948 )
a small molecule (CPD-9799 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.93	ALOGPS
logP	1.73	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	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	1	ChemAxon
Refractivity	66.34 m³·mol⁻¹	ChemAxon
Polarizability	25.42 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
DeepCCS	[M+H]+	161.005	30932474
DeepCCS	[M-H]-	158.647	30932474
DeepCCS	[M-2H]-	191.533	30932474
DeepCCS	[M+Na]+	167.098	30932474
AllCCS	[M+H]+	155.3	32859911
AllCCS	[M+H-H2O]+	151.6	32859911
AllCCS	[M+NH4]+	158.7	32859911
AllCCS	[M+Na]+	159.7	32859911
AllCCS	[M-H]-	158.6	32859911
AllCCS	[M+Na-2H]-	158.2	32859911
AllCCS	[M+HCOO]-	157.9	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=C(C=CC3=C2OC(=O)C=C3)O1	2349.0	Semi standard non polar	33892256
8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=C(C=CC3=C2OC(=O)C=C3)O1	2244.7	Standard non polar	33892256
8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one,1TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1CC2=C(C=CC3=C2OC(=O)C=C3)O1	2760.7	Standard polar	33892256
8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(C=CC3=C2OC(=O)C=C3)O1	2577.3	Semi standard non polar	33892256
8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(C=CC3=C2OC(=O)C=C3)O1	2472.0	Standard non polar	33892256
8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one,1TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1CC2=C(C=CC3=C2OC(=O)C=C3)O1	2824.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9670000000-6e729f9d0a0d0858740f	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 20V, Negative-QTOF	splash10-004i-3960000000-ed68f426dfe9e8b92665	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 40V, Positive-QTOF	splash10-0f6y-5900000000-76a11dea8bd823a9ba49	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 10V, Positive-QTOF	splash10-00kb-0790000000-4e37695c17fbe0c71349	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 20V, Positive-QTOF	splash10-00or-0920000000-f906b3d0640cac1620ce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 10V, Negative-QTOF	splash10-0002-0490000000-e16af364f7a5167057f3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 40V, Negative-QTOF	splash10-03kc-5930000000-aa6ce177fce87e9aef06	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 10V, Positive-QTOF	splash10-0002-0090000000-e0c7625ab84225b2cbab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 20V, Positive-QTOF	splash10-00kb-0190000000-cc99d0793f5e157d59c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 40V, Positive-QTOF	splash10-0pbc-3930000000-6e63b31ef50f39619bb0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 10V, Negative-QTOF	splash10-0002-0090000000-4a890656b917e493d11c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 20V, Negative-QTOF	splash10-000b-0690000000-d96c057886c419f8387f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one 40V, Negative-QTOF	splash10-0a4i-0900000000-a6d8fcf7cd10e5e9cc6d	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00002459

Chemspider ID

132991

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

59948

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one (HMDB0244406)

MOL for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

3D MOL for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

3D SDF for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

3D-SDF for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

PDB for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

3D PDB for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

SMILES for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

INCHI for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

Structure for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

3D Structure for HMDB0244406 (8,9-Dihydro-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]1-benzopyran-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra