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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:06:51 UTC

Update Date

2022-03-07 02:54:45 UTC

HMDB ID

HMDB0036046

Secondary Accession Numbers

HMDB36046

Metabolite Identification

Common Name

Dehydrooreadone

Description

Dehydrooreadone belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Dehydrooreadone has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make dehydrooreadone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dehydrooreadone.

Structure

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

HMDB0036046
     RDKit          3D
Dehydrooreadone
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.0575    0.8457    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -0.0278    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4086   -1.1717   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113   -0.5994    1.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721   -0.1945    2.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996    0.9033    1.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    1.6321    2.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    1.1656    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102    0.5880   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001   -0.7472   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5476   -1.0639   -1.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -0.0128   -1.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    0.7483   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -1.4809   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6161   -0.5122    0.1141 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198    0.3720    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4102    1.4987    1.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6201    1.0110   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6938    0.2730    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7710    1.8270    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137   -0.8075   -1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690   -1.8878   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0658   -1.7355    0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -1.4161    1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823   -0.6241    3.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550    2.2749    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947    1.2575   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -2.0644   -2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706   -0.3574   -2.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030    0.7511   -2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3362    1.6699   -0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879   -2.3323    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3421   -1.8368   -1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689   -0.1849    1.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    2.2390    0.4684 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 13  2  1  0
 13  8  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
M  END


  Mrv0541 02241215122D          

 17 19  0  0  0  0            999 V2000
   -1.4571   -0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -0.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519    0.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2952    1.1329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1332   -2.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6474   -1.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -1.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    2.0232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4041    1.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1325    1.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6183    1.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4041    0.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1325    0.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2945   -0.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7280   -0.9709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0810   -0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429    0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 17  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 16  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036046

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)C=CC(=O)C2C3C(O)OCC3=CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O3/c1-14(2)6-5-10(15)12-9(14)4-3-8-7-17-13(16)11(8)12/h3,5-6,9,11-13,16H,4,7H2,1-2H3

> <INCHI_KEY>
RBUVATMDYDGAJH-UHFFFAOYSA-N

> <FORMULA>
C14H18O3

> <MOLECULAR_WEIGHT>
234.2909

> <EXACT_MASS>
234.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.331774865485347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-6,6-dimethyl-1H,3H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-c]furan-9-one

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.5405923383333333

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.277806555195944

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.09022033727487

> <JCHEM_PKA_STRONGEST_BASIC>
-4.071536962536848

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
66.0359

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-6,6-dimethyl-1H,3H,5H,5aH,9aH,9bH-naphtho[1,2-c]furan-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036046
     RDKit          3D
Dehydrooreadone
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.0575    0.8457    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -0.0278    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4086   -1.1717   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113   -0.5994    1.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721   -0.1945    2.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996    0.9033    1.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    1.6321    2.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    1.1656    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102    0.5880   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001   -0.7472   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5476   -1.0639   -1.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -0.0128   -1.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    0.7483   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -1.4809   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6161   -0.5122    0.1141 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198    0.3720    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4102    1.4987    1.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6201    1.0110   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6938    0.2730    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7710    1.8270    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137   -0.8075   -1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690   -1.8878   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0658   -1.7355    0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -1.4161    1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823   -0.6241    3.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550    2.2749    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947    1.2575   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -2.0644   -2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706   -0.3574   -2.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030    0.7511   -2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3362    1.6699   -0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879   -2.3323    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3421   -1.8368   -1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689   -0.1849    1.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    2.2390    0.4684 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 13  2  1  0
 13  8  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.720  -1.812   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.021  -0.453   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.964   0.603   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.418   2.115   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.115  -3.777   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.208  -2.417   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.151  -3.626   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.453   3.777   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.754   2.719   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.114   3.172   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.021   1.963   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.754   1.208   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.114   0.755   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.416  -0.755   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.359  -1.812   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.151  -1.360   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.453   0.150   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    1    5    7   16                                             
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10   13                                                       
CONECT   12    9   13   17                                                  
CONECT   13   11   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16    6   15   17                                                  
CONECT   17    3   12   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0036046
HETATM    1  C1  UNL     1      -3.057   0.846   0.501  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.827  -0.028   0.186  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.409  -1.172  -0.639  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.411  -0.599   1.461  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.372  -0.194   2.171  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.400   0.903   1.622  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.061   1.632   2.408  1.00  0.00           O  
HETATM    8  C7  UNL     1       0.411   1.166   0.154  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.710   0.588  -0.362  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.600  -0.747  -0.931  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.548  -1.064  -1.655  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.471  -0.013  -1.841  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.799   0.748  -0.563  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.842  -1.481  -0.501  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.616  -0.512   0.114  1.00  0.00           O  
HETATM   16  C14 UNL     1       2.720   0.372   0.735  1.00  0.00           C  
HETATM   17  O3  UNL     1       3.410   1.499   1.094  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.620   1.011  -0.457  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.694   0.273   1.192  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.771   1.827   0.884  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.114  -0.807  -1.414  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.669  -1.888  -0.983  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.066  -1.736   0.090  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.994  -1.416   1.863  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.082  -0.624   3.102  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.555   2.275   0.071  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.195   1.257  -1.115  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.488  -2.064  -2.068  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.371  -0.357  -2.366  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.003   0.751  -2.531  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.336   1.670  -0.956  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.588  -2.332   0.126  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.342  -1.837  -1.442  1.00  0.00           H  
HETATM   34  H17 UNL     1       2.269  -0.185   1.580  1.00  0.00           H  
HETATM   35  H18 UNL     1       3.313   2.239   0.468  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   13
CONECT    3   21   22   23
CONECT    4    5    5   24
CONECT    5    6   25
CONECT    6    7    7    8
CONECT    8    9   13   26
CONECT    9   10   16   27
CONECT   10   11   11   14
CONECT   11   12   28
CONECT   12   13   29   30
CONECT   13   31
CONECT   14   15   32   33
CONECT   15   16
CONECT   16   17   34
CONECT   17   35
END

HMDB0036046
     RDKit          3D
Dehydrooreadone
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.0575    0.8457    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8271   -0.0278    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4086   -1.1717   -0.6386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113   -0.5994    1.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721   -0.1945    2.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3996    0.9033    1.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    1.6321    2.4083 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4111    1.1656    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102    0.5880   -0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6001   -0.7472   -0.9308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5476   -1.0639   -1.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708   -0.0128   -1.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    0.7483   -0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -1.4809   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6161   -0.5122    0.1141 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198    0.3720    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4102    1.4987    1.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6201    1.0110   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6938    0.2730    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7710    1.8270    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1137   -0.8075   -1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6690   -1.8878   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0658   -1.7355    0.0900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941   -1.4161    1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0823   -0.6241    3.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550    2.2749    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1947    1.2575   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876   -2.0644   -2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706   -0.3574   -2.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030    0.7511   -2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3362    1.6699   -0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5879   -2.3323    0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3421   -1.8368   -1.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2689   -0.1849    1.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    2.2390    0.4684 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 13  2  1  0
 13  8  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈O₃

Average Molecular Weight

234.2909

Monoisotopic Molecular Weight

234.125594442

IUPAC Name

1-hydroxy-6,6-dimethyl-1H,3H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-c]furan-9-one

Traditional Name

1-hydroxy-6,6-dimethyl-1H,3H,5H,5aH,9aH,9bH-naphtho[1,2-c]furan-9-one

CAS Registry Number

124869-07-4

SMILES

CC1(C)C=CC(=O)C2C3C(O)OCC3=CCC12

InChI Identifier

InChI=1S/C14H18O3/c1-14(2)6-5-10(15)12-9(14)4-3-8-7-17-13(16)11(8)12/h3,5-6,9,11-13,16H,4,7H2,1-2H3

InChI Key

RBUVATMDYDGAJH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Cyclohexenone
Tetrahydrofuran
Ketone
Hemiacetal
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036046)
Cytoplasm (HMDB: HMDB0036046)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036046)

Source

Exogenous

Food

Food (HMDB: HMDB0036046)

Plant (HMDB: HMDB0036046)

Not Available

Nutrient (HMDB: HMDB0036046)

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	29150 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.64 g/L	ALOGPS
logP	1.12	ALOGPS
logP	1.54	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.04 m³·mol⁻¹	ChemAxon
Polarizability	25.33 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]+	153.63	31661259
DarkChem	[M-H]-	149.564	31661259
DeepCCS	[M-2H]-	184.54	30932474
DeepCCS	[M+Na]+	159.988	30932474
AllCCS	[M+H]+	152.2	32859911
AllCCS	[M+H-H2O]+	148.2	32859911
AllCCS	[M+NH4]+	155.8	32859911
AllCCS	[M+Na]+	156.9	32859911
AllCCS	[M-H]-	158.4	32859911
AllCCS	[M+Na-2H]-	158.4	32859911
AllCCS	[M+HCOO]-	158.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydrooreadone	CC1(C)C=CC(=O)C2C3C(O)OCC3=CCC12	3041.5	Standard polar	33892256
Dehydrooreadone	CC1(C)C=CC(=O)C2C3C(O)OCC3=CCC12	1875.2	Standard non polar	33892256
Dehydrooreadone	CC1(C)C=CC(=O)C2C3C(O)OCC3=CCC12	2025.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydrooreadone,1TMS,isomer #1	CC1(C)C=CC(=O)C2C3C(=CCC21)COC3O[Si](C)(C)C	2104.9	Semi standard non polar	33892256
Dehydrooreadone,1TMS,isomer #2	CC1(C)C=CC(O[Si](C)(C)C)=C2C3C(=CCC21)COC3O	2103.9	Semi standard non polar	33892256
Dehydrooreadone,2TMS,isomer #1	CC1(C)C=CC(O[Si](C)(C)C)=C2C3C(=CCC21)COC3O[Si](C)(C)C	2162.0	Semi standard non polar	33892256
Dehydrooreadone,2TMS,isomer #1	CC1(C)C=CC(O[Si](C)(C)C)=C2C3C(=CCC21)COC3O[Si](C)(C)C	2053.4	Standard non polar	33892256
Dehydrooreadone,1TBDMS,isomer #1	CC1(C)C=CC(=O)C2C3C(=CCC21)COC3O[Si](C)(C)C(C)(C)C	2379.0	Semi standard non polar	33892256
Dehydrooreadone,1TBDMS,isomer #2	CC1(C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C3C(=CCC21)COC3O	2377.6	Semi standard non polar	33892256
Dehydrooreadone,2TBDMS,isomer #1	CC1(C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C3C(=CCC21)COC3O[Si](C)(C)C(C)(C)C	2660.7	Semi standard non polar	33892256
Dehydrooreadone,2TBDMS,isomer #1	CC1(C)C=CC(O[Si](C)(C)C(C)(C)C)=C2C3C(=CCC21)COC3O[Si](C)(C)C(C)(C)C	2591.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrooreadone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4960000000-38fa483c5785b9a1a52d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrooreadone GC-MS (1 TMS) - 70eV, Positive	splash10-00g0-5950000000-9258f59dce16bfd22c67	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrooreadone 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 - Dehydrooreadone 10V, Positive-QTOF	splash10-000i-0390000000-547abf8373d40bd16b10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 20V, Positive-QTOF	splash10-00kr-2950000000-c4e6047e8afff9b52c43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 40V, Positive-QTOF	splash10-0gb9-9700000000-979cc32734a8f5b8e1c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 10V, Negative-QTOF	splash10-001i-0190000000-38202aa3e5bf9cfc315f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 20V, Negative-QTOF	splash10-0019-0980000000-e1ab36400fc1368335e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 40V, Negative-QTOF	splash10-00dr-1910000000-e031253bbe95aa3e1188	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 10V, Negative-QTOF	splash10-001i-0090000000-c6b812d37e42c36494c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 20V, Negative-QTOF	splash10-001i-0190000000-8061bd0fe13ae48d079c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 40V, Negative-QTOF	splash10-00xr-2920000000-f6a71806c5f485c1351d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 10V, Positive-QTOF	splash10-014r-0190000000-62ca8c424672957ceae7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 20V, Positive-QTOF	splash10-014r-1890000000-d2006d8257e7e57df90f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrooreadone 40V, Positive-QTOF	splash10-062i-4930000000-b5e7b69726a06b97f7bd	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014868

KNApSAcK ID

C00020324

Chemspider ID

35014080

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14433063

PDB ID

Not Available

ChEBI ID

168620

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1853341

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 Dehydrooreadone (HMDB0036046)

MOL for HMDB0036046 (Dehydrooreadone)

3D MOL for HMDB0036046 (Dehydrooreadone)

3D SDF for HMDB0036046 (Dehydrooreadone)

3D-SDF for HMDB0036046 (Dehydrooreadone)

PDB for HMDB0036046 (Dehydrooreadone)

3D PDB for HMDB0036046 (Dehydrooreadone)

SMILES for HMDB0036046 (Dehydrooreadone)

INCHI for HMDB0036046 (Dehydrooreadone)

Structure for HMDB0036046 (Dehydrooreadone)

3D Structure for HMDB0036046 (Dehydrooreadone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra