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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:06:48 UTC

Update Date

2022-03-07 02:54:45 UTC

HMDB ID

HMDB0036045

Secondary Accession Numbers

HMDB36045

Metabolite Identification

Common Name

O-Formyloreadone

Description

O-Formyloreadone 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. O-Formyloreadone 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 O-formyloreadone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on O-Formyloreadone.

Structure

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

HMDB0036045
     RDKit          3D
O-Formyloreadone
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.8997    1.2499   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686    0.2436   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2491   -0.6437   -0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4812    0.9314    0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740    1.3229    1.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    1.2603    1.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    2.2362    0.7618 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2489   -0.1333    0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5982   -0.2056   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6846   -1.5739   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967   -1.9494   -1.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979   -0.9717   -1.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813   -0.6312   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9561   -2.1177   -0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0512   -1.4657    1.1496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.1614    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5800    0.6566    1.9618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306    1.7200    2.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3455    1.9241    1.3253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    0.7828   -2.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763    1.6284   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6370    2.0622   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549   -1.5912   -0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -0.8331   -1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2068   -0.1389   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0190    1.8744    0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2541    0.3213    1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866    2.2837    2.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174    0.5426    2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243   -0.7247    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    0.5694   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6728   -2.9128   -1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -0.0925   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286   -1.4115   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2213   -1.6284    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -1.8616   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -3.1845    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312    0.2227    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512    2.4001    3.0149 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
  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
 17 18  1  0
 18 19  2  0
 13  2  1  0
 13  8  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
M  END


  Mrv0541 02241207462D          

 19 21  0  0  0  0            999 V2000
   -1.4567   -1.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6187   -0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0516   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2948    0.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1329   -2.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6470   -1.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -2.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1329    1.0922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4044    0.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4044    0.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425   -0.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -1.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7284   -1.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948   -1.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1329   -0.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6187    0.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    1.3355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1612    2.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8896    2.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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 11  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036045

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-15(2)6-5-11(17)13-10(15)4-3-9-7-18-14(12(9)13)19-8-16/h3,8,10,12-14H,4-7H2,1-2H3

> <INCHI_KEY>
MIBOGOAYMHICPV-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.92797815745061

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,6-dimethyl-9-oxo-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-1-yl formate

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.9351955509999987

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.409558877833238

> <JCHEM_PKA_STRONGEST_BASIC>
-4.352981792481527

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
69.6036

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,6-dimethyl-9-oxo-1H,3H,5H,5aH,7H,8H,9aH,9bH-naphtho[1,2-c]furan-1-yl formate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036045
     RDKit          3D
O-Formyloreadone
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.8997    1.2499   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686    0.2436   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2491   -0.6437   -0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4812    0.9314    0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740    1.3229    1.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    1.2603    1.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    2.2362    0.7618 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2489   -0.1333    0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5982   -0.2056   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6846   -1.5739   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967   -1.9494   -1.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979   -0.9717   -1.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813   -0.6312   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9561   -2.1177   -0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0512   -1.4657    1.1496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.1614    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5800    0.6566    1.9618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306    1.7200    2.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3455    1.9241    1.3253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    0.7828   -2.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763    1.6284   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6370    2.0622   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549   -1.5912   -0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -0.8331   -1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2068   -0.1389   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0190    1.8744    0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2541    0.3213    1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866    2.2837    2.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174    0.5426    2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243   -0.7247    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    0.5694   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6728   -2.9128   -1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -0.0925   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286   -1.4115   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2213   -1.6284    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -1.8616   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -3.1845    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312    0.2227    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512    2.4001    3.0149 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
  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
 17 18  1  0
 18 19  2  0
 13  2  1  0
 13  8  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  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      -2.719  -2.946   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.022  -1.586   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.963  -0.529   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.417   0.981   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.115  -4.910   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.208  -3.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.152  -4.760   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.115   2.039   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.755   1.586   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.755   0.074   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.453  -0.981   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.152  -2.493   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.360  -2.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.417  -1.888   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.115  -0.378   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.022   0.831   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.453   2.493   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.301   4.003   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.661   4.910   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3                                                            
CONECT    5    6                                                            
CONECT    6    1    5    7   12                                             
CONECT    7    6                                                            
CONECT    8    9   16                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   15                                                  
CONECT   11    3   10   12                                                  
CONECT   12    6   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16    8   15                                                       
CONECT   17    9   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0036045
HETATM    1  C1  UNL     1      -1.900   1.250  -1.478  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.069   0.244  -0.350  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.249  -0.644  -0.781  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.481   0.931   0.901  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.374   1.323   1.813  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.098   1.260   1.011  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.551   2.236   0.762  1.00  0.00           O  
HETATM    8  C7  UNL     1       0.249  -0.133   0.575  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.598  -0.206  -0.080  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.685  -1.574  -0.665  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.697  -1.949  -1.450  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.398  -0.972  -1.666  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.881  -0.631  -0.247  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.956  -2.118  -0.114  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.051  -1.466   1.150  1.00  0.00           O  
HETATM   16  C14 UNL     1       2.765  -0.161   0.831  1.00  0.00           C  
HETATM   17  O3  UNL     1       2.580   0.657   1.962  1.00  0.00           O  
HETATM   18  C15 UNL     1       3.431   1.720   2.162  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.346   1.924   1.325  1.00  0.00           O  
HETATM   20  H1  UNL     1      -2.195   0.783  -2.450  1.00  0.00           H  
HETATM   21  H2  UNL     1      -0.876   1.628  -1.505  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.637   2.062  -1.289  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.155  -1.591  -0.214  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.229  -0.833  -1.870  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.207  -0.139  -0.517  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.019   1.874   0.604  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.254   0.321   1.438  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.487   2.284   2.311  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.317   0.543   2.625  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.324  -0.725   1.533  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.666   0.569  -0.889  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.673  -2.913  -1.916  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.034  -0.092  -2.200  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.229  -1.412  -2.252  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.221  -1.628   0.162  1.00  0.00           H  
HETATM   36  H17 UNL     1       3.834  -1.862  -0.728  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.922  -3.184   0.106  1.00  0.00           H  
HETATM   38  H19 UNL     1       3.631   0.223   0.246  1.00  0.00           H  
HETATM   39  H20 UNL     1       3.351   2.400   3.015  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4   13
CONECT    3   23   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7    7    8
CONECT    8    9   13   30
CONECT    9   10   16   31
CONECT   10   11   11   14
CONECT   11   12   32
CONECT   12   13   33   34
CONECT   13   35
CONECT   14   15   36   37
CONECT   15   16
CONECT   16   17   38
CONECT   17   18
CONECT   18   19   19   39
END

HMDB0036045
     RDKit          3D
O-Formyloreadone
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.8997    1.2499   -1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686    0.2436   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2491   -0.6437   -0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4812    0.9314    0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740    1.3229    1.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980    1.2603    1.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5510    2.2362    0.7618 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2489   -0.1333    0.5745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5982   -0.2056   -0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6846   -1.5739   -0.6655 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967   -1.9494   -1.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979   -0.9717   -1.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8813   -0.6312   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9561   -2.1177   -0.1141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0512   -1.4657    1.1496 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.1614    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5800    0.6566    1.9618 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4306    1.7200    2.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3455    1.9241    1.3253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    0.7828   -2.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8763    1.6284   -1.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6370    2.0622   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549   -1.5912   -0.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2289   -0.8331   -1.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2068   -0.1389   -0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0190    1.8744    0.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2541    0.3213    1.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4866    2.2837    2.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174    0.5426    2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243   -0.7247    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6659    0.5694   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6728   -2.9128   -1.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -0.0925   -2.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286   -1.4115   -2.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2213   -1.6284    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -1.8616   -0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -3.1845    0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312    0.2227    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512    2.4001    3.0149 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
  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
 17 18  1  0
 18 19  2  0
 13  2  1  0
 13  8  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 18 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,6-Dimethyl-9-oxo-1H,3H,5H,5ah,6H,7H,8H,9H,9ah,9BH-naphtho[1,2-c]furan-1-yl formic acid	HMDB

Chemical Formula

C₁₅H₂₀O₄

Average Molecular Weight

264.3169

Monoisotopic Molecular Weight

264.136159128

IUPAC Name

6,6-dimethyl-9-oxo-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-1-yl formate

Traditional Name

6,6-dimethyl-9-oxo-1H,3H,5H,5aH,7H,8H,9aH,9bH-naphtho[1,2-c]furan-1-yl formate

CAS Registry Number

Not Available

SMILES

CC1(C)CCC(=O)C2C3C(OC=O)OCC3=CCC12

InChI Identifier

InChI=1S/C15H20O4/c1-15(2)6-5-11(17)13-10(15)4-3-9-7-18-14(12(9)13)19-8-16/h3,8,10,12-14H,4-7H2,1-2H3

InChI Key

MIBOGOAYMHICPV-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
Tetrahydrofuran
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
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: HMDB0036045)
Cytoplasm (HMDB: HMDB0036045)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036045)

Source

Exogenous

Exogenous (HMDB: HMDB0036045)

Food

Food (HMDB: HMDB0036045)

Plant (HMDB: HMDB0036045)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036045)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.37 g/L	ALOGPS
logP	2.03	ALOGPS
logP	1.94	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	18.41	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.6 m³·mol⁻¹	ChemAxon
Polarizability	27.93 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]+	161.939	31661259
DarkChem	[M-H]-	158.916	31661259
DeepCCS	[M-2H]-	190.822	30932474
DeepCCS	[M+Na]+	166.388	30932474
AllCCS	[M+H]+	160.8	32859911
AllCCS	[M+H-H2O]+	157.3	32859911
AllCCS	[M+NH4]+	164.1	32859911
AllCCS	[M+Na]+	165.1	32859911
AllCCS	[M-H]-	166.3	32859911
AllCCS	[M+Na-2H]-	166.2	32859911
AllCCS	[M+HCOO]-	166.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.16 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8473 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.12 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2153.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	310.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	175.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	127.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	453.7 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	573.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	87.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1055.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	393.3 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	1217.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	320.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	293.9 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	14.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Formyloreadone	CC1(C)CCC(=O)C2C3C(OC=O)OCC3=CCC12	2948.2	Standard polar	33892256
O-Formyloreadone	CC1(C)CCC(=O)C2C3C(OC=O)OCC3=CCC12	2002.7	Standard non polar	33892256
O-Formyloreadone	CC1(C)CCC(=O)C2C3C(OC=O)OCC3=CCC12	2114.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Formyloreadone,1TMS,isomer #1	CC1(C)CCC(O[Si](C)(C)C)=C2C3C(=CCC21)COC3OC=O	2185.3	Semi standard non polar	33892256
O-Formyloreadone,1TMS,isomer #1	CC1(C)CCC(O[Si](C)(C)C)=C2C3C(=CCC21)COC3OC=O	2051.9	Standard non polar	33892256
O-Formyloreadone,1TMS,isomer #2	CC1(C)CC=C(O[Si](C)(C)C)C2C3C(=CCC21)COC3OC=O	2135.1	Semi standard non polar	33892256
O-Formyloreadone,1TMS,isomer #2	CC1(C)CC=C(O[Si](C)(C)C)C2C3C(=CCC21)COC3OC=O	1994.6	Standard non polar	33892256
O-Formyloreadone,1TBDMS,isomer #1	CC1(C)CCC(O[Si](C)(C)C(C)(C)C)=C2C3C(=CCC21)COC3OC=O	2455.3	Semi standard non polar	33892256
O-Formyloreadone,1TBDMS,isomer #1	CC1(C)CCC(O[Si](C)(C)C(C)(C)C)=C2C3C(=CCC21)COC3OC=O	2297.4	Standard non polar	33892256
O-Formyloreadone,1TBDMS,isomer #2	CC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C2C3C(=CCC21)COC3OC=O	2375.8	Semi standard non polar	33892256
O-Formyloreadone,1TBDMS,isomer #2	CC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C2C3C(=CCC21)COC3OC=O	2185.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-Formyloreadone GC-MS (Non-derivatized) - 70eV, Positive	splash10-009i-2890000000-6026b8a4bd5ac12db301	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Formyloreadone 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 - O-Formyloreadone 10V, Positive-QTOF	splash10-014i-2190000000-76cc9a732ce474a99f83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 20V, Positive-QTOF	splash10-014s-5970000000-ab4cda431239f46423ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 40V, Positive-QTOF	splash10-0101-8910000000-3dacbb1b732937910091	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 10V, Negative-QTOF	splash10-03di-0090000000-ae7eb75236231647cf1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 20V, Negative-QTOF	splash10-03dr-2390000000-7aed213d52f7f4bbdf7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 40V, Negative-QTOF	splash10-007c-8930000000-7bc42adf25f3c1203516	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 10V, Positive-QTOF	splash10-014i-0290000000-f16149990fd9e1995317	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 20V, Positive-QTOF	splash10-014i-1490000000-9fc6aeca226aa9a8beab	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 40V, Positive-QTOF	splash10-00fr-4910000000-9b43db5801c7c77d94c7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 10V, Negative-QTOF	splash10-014i-0090000000-db2b6069f7767bee9988	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 20V, Negative-QTOF	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Formyloreadone 40V, Negative-QTOF	splash10-0076-4950000000-7379a65d108689453f83	2021-09-24	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

FDB014867

KNApSAcK ID

Not Available

Chemspider ID

35014079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14433042

PDB ID

Not Available

ChEBI ID

174477

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for O-Formyloreadone (HMDB0036045)

MOL for HMDB0036045 (O-Formyloreadone)

3D MOL for HMDB0036045 (O-Formyloreadone)

3D SDF for HMDB0036045 (O-Formyloreadone)

3D-SDF for HMDB0036045 (O-Formyloreadone)

PDB for HMDB0036045 (O-Formyloreadone)

3D PDB for HMDB0036045 (O-Formyloreadone)

SMILES for HMDB0036045 (O-Formyloreadone)

INCHI for HMDB0036045 (O-Formyloreadone)

Structure for HMDB0036045 (O-Formyloreadone)

3D Structure for HMDB0036045 (O-Formyloreadone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra