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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:33:09 UTC

Update Date

2022-03-07 02:55:16 UTC

HMDB ID

HMDB0037314

Secondary Accession Numbers

HMDB37314

Metabolite Identification

Common Name

Norartocarpanone

Description

Norartocarpanone belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, norartocarpanone is considered to be a flavonoid. Norartocarpanone has been detected, but not quantified in, fruits. This could make norartocarpanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Norartocarpanone.

Structure

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

HMDB0037314
     RDKit          3D
Norartocarpanone
 33 35  0  0  0  0  0  0  0  0999 V2000
    1.6754   -2.8227    0.9070 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358   -1.7574    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -1.5395   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803   -0.1720    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269    0.0826    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -1.0376    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1435   -0.9510    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070    0.2967   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0779    0.4111   -0.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9090    1.4089    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    1.3301    0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7687    2.4657    0.1188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867    0.7783   -0.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.5808   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558    1.5987   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296    1.3821   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9168    2.4402   -0.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5429    0.1369   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6562   -0.9204    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1505   -2.1617    0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -0.6952    0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914   -2.3668    0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -1.5163   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3248   -0.1866    1.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940   -2.0412    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7664   -1.8589    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6698   -0.4215   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3378    2.3951   -0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8032    2.6039    0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2736    2.6165   -0.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2237    2.9600    0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6048    0.0072   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8061   -3.0460    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 11  5  1  0
 21 14  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END


  Mrv0541 05061309422D          

 21 23  0  0  0  0            999 V2000
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14  5  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  7  1  0  0  0  0
 17  8  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037314

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O6/c16-7-1-2-9(10(18)3-7)13-6-12(20)15-11(19)4-8(17)5-14(15)21-13/h1-5,13,16-19H,6H2

> <INCHI_KEY>
QBLQLKNOKUHRCH-UHFFFAOYSA-N

> <FORMULA>
C15H12O6

> <MOLECULAR_WEIGHT>
288.2522

> <EXACT_MASS>
288.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
28.133123006983936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
2.5315427286666665

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.99310761379941

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.884122376979166

> <JCHEM_PKA_STRONGEST_BASIC>
-3.86132469771466

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
73.2707

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
steppogenin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037314
     RDKit          3D
Norartocarpanone
 33 35  0  0  0  0  0  0  0  0999 V2000
    1.6754   -2.8227    0.9070 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358   -1.7574    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -1.5395   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803   -0.1720    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269    0.0826    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -1.0376    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1435   -0.9510    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070    0.2967   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0779    0.4111   -0.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9090    1.4089    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    1.3301    0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7687    2.4657    0.1188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867    0.7783   -0.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.5808   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558    1.5987   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296    1.3821   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9168    2.4402   -0.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5429    0.1369   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6562   -0.9204    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1505   -2.1617    0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -0.6952    0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914   -2.3668    0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -1.5163   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3248   -0.1866    1.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940   -2.0412    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7664   -1.8589    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6698   -0.4215   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3378    2.3951   -0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8032    2.6039    0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2736    2.6165   -0.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2237    2.9600    0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6048    0.0072   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8061   -3.0460    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 11  5  1  0
 21 14  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    9                                                       
CONECT    3    7   10                                                       
CONECT    4    8   11                                                       
CONECT    5    8   14                                                       
CONECT    6   12   13                                                       
CONECT    7    1    3   16                                                  
CONECT    8    4    5   17                                                  
CONECT    9    2   10   13                                                  
CONECT   10    3    9   18                                                  
CONECT   11    4   15   19                                                  
CONECT   12    6   15   20                                                  
CONECT   13    6    9   21                                                  
CONECT   14    5   15   21                                                  
CONECT   15   11   12   14                                                  
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0037314
HETATM    1  O1  UNL     1       1.675  -2.823   0.907  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.336  -1.757   0.344  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.072  -1.540  -0.126  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.480  -0.172   0.358  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.927   0.083   0.185  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.767  -1.038   0.167  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.144  -0.951   0.075  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.707   0.297  -0.004  1.00  0.00           C  
HETATM    9  O2  UNL     1      -6.078   0.411  -0.097  1.00  0.00           O  
HETATM   10  C8  UNL     1      -3.909   1.409   0.010  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.506   1.330   0.106  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.769   2.466   0.119  1.00  0.00           O  
HETATM   13  O4  UNL     1       0.387   0.778  -0.152  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.757   0.581  -0.117  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.656   1.599  -0.314  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.030   1.382  -0.278  1.00  0.00           C  
HETATM   17  O5  UNL     1       4.917   2.440  -0.482  1.00  0.00           O  
HETATM   18  C13 UNL     1       4.543   0.137  -0.043  1.00  0.00           C  
HETATM   19  C14 UNL     1       3.656  -0.920   0.163  1.00  0.00           C  
HETATM   20  O6  UNL     1       4.151  -2.162   0.393  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.293  -0.695   0.127  1.00  0.00           C  
HETATM   22  H1  UNL     1      -0.691  -2.367   0.200  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.037  -1.516  -1.257  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.325  -0.187   1.501  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.394  -2.041   0.228  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.766  -1.859   0.071  1.00  0.00           H  
HETATM   27  H6  UNL     1      -6.670  -0.422  -0.105  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.338   2.395  -0.067  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.803   2.604   0.174  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.274   2.617  -0.502  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.224   2.960   0.360  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.605   0.007  -0.024  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.806  -3.046   0.545  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4   22   23
CONECT    4    5   13   24
CONECT    5    6    6   11
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   27
CONECT   10   11   11   28
CONECT   11   12
CONECT   12   29
CONECT   13   14
CONECT   14   15   15   21
CONECT   15   16   30
CONECT   16   17   18   18
CONECT   17   31
CONECT   18   19   32
CONECT   19   20   21   21
CONECT   20   33
END

HMDB0037314
     RDKit          3D
Norartocarpanone
 33 35  0  0  0  0  0  0  0  0999 V2000
    1.6754   -2.8227    0.9070 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3358   -1.7574    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -1.5395   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803   -0.1720    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269    0.0826    0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7666   -1.0376    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1435   -0.9510    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7070    0.2967   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0779    0.4111   -0.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9090    1.4089    0.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    1.3301    0.1061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7687    2.4657    0.1188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3867    0.7783   -0.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566    0.5808   -0.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558    1.5987   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296    1.3821   -0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9168    2.4402   -0.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5429    0.1369   -0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6562   -0.9204    0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1505   -2.1617    0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -0.6952    0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914   -2.3668    0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -1.5163   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3248   -0.1866    1.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940   -2.0412    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7664   -1.8589    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6698   -0.4215   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3378    2.3951   -0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8032    2.6039    0.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2736    2.6165   -0.5024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2237    2.9600    0.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6048    0.0072   -0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8061   -3.0460    0.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21  2  1  0
 11  5  1  0
 21 14  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 15 30  1  0
 17 31  1  0
 18 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₂O₆

Average Molecular Weight

288.2522

Monoisotopic Molecular Weight

288.063388116

IUPAC Name

2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

steppogenin

CAS Registry Number

56486-94-3

SMILES

OC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C15H12O6/c16-7-1-2-9(10(18)3-7)13-6-12(20)15-11(19)4-8(17)5-14(15)21-13/h1-5,13,16-19H,6H2

InChI Key

QBLQLKNOKUHRCH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140533 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	255 - 257 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	824.2 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	0.35 g/L	ALOGPS
logP	2.07	ALOGPS
logP	2.53	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.88	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.27 m³·mol⁻¹	ChemAxon
Polarizability	28.13 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]+	167.997	31661259
DarkChem	[M-H]-	163.993	31661259
DeepCCS	[M+H]+	166.91	30932474
DeepCCS	[M-H]-	164.553	30932474
DeepCCS	[M-2H]-	197.439	30932474
DeepCCS	[M+Na]+	173.004	30932474
AllCCS	[M+H]+	166.4	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.9	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	165.4	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	164.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norartocarpanone	OC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1	4266.3	Standard polar	33892256
Norartocarpanone	OC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1	3013.2	Standard non polar	33892256
Norartocarpanone	OC1=CC(O)=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1	3097.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norartocarpanone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C(O)=C1	2979.2	Semi standard non polar	33892256
Norartocarpanone,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC=C1C1CC(=O)C2=C(O)C=C(O)C=C2O1	2926.9	Semi standard non polar	33892256
Norartocarpanone,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1O)O2	2940.1	Semi standard non polar	33892256
Norartocarpanone,1TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C(=O)CC(C3=CC=C(O)C=C3O)OC2=C1	2971.5	Semi standard non polar	33892256
Norartocarpanone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C(O)=C1	2962.6	Semi standard non polar	33892256
Norartocarpanone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C(O)=C1	2946.8	Semi standard non polar	33892256
Norartocarpanone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C(O[Si](C)(C)C)=C1	2912.9	Semi standard non polar	33892256
Norartocarpanone,2TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=CC=C1C1CC(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C)O1	2917.7	Semi standard non polar	33892256
Norartocarpanone,2TMS,isomer #5	C[Si](C)(C)OC1=CC(O)=C2C(=O)CC(C3=CC=C(O)C=C3O[Si](C)(C)C)OC2=C1	2905.0	Semi standard non polar	33892256
Norartocarpanone,2TMS,isomer #6	C[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C(O)C=C3O)O2)C(O[Si](C)(C)C)=C1	2940.7	Semi standard non polar	33892256
Norartocarpanone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C(O)=C1	2875.7	Semi standard non polar	33892256
Norartocarpanone,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C(O[Si](C)(C)C)=C1	2879.6	Semi standard non polar	33892256
Norartocarpanone,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C(O[Si](C)(C)C)=C1	2886.0	Semi standard non polar	33892256
Norartocarpanone,3TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C(O)C=C3O[Si](C)(C)C)O2)C(O[Si](C)(C)C)=C1	2853.7	Semi standard non polar	33892256
Norartocarpanone,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C(O[Si](C)(C)C)=C1	2920.5	Semi standard non polar	33892256
Norartocarpanone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C(O)=C1	3262.0	Semi standard non polar	33892256
Norartocarpanone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C1CC(=O)C2=C(O)C=C(O)C=C2O1	3204.0	Semi standard non polar	33892256
Norartocarpanone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1O)O2	3225.5	Semi standard non polar	33892256
Norartocarpanone,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)CC(C3=CC=C(O)C=C3O)OC2=C1	3257.3	Semi standard non polar	33892256
Norartocarpanone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O)=C1	3509.3	Semi standard non polar	33892256
Norartocarpanone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O)=C1	3503.7	Semi standard non polar	33892256
Norartocarpanone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C1	3438.5	Semi standard non polar	33892256
Norartocarpanone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C1CC(=O)C2=C(C=C(O)C=C2O[Si](C)(C)C(C)(C)C)O1	3460.2	Semi standard non polar	33892256
Norartocarpanone,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)CC(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)OC2=C1	3421.6	Semi standard non polar	33892256
Norartocarpanone,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C(O)C=C3O)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3491.5	Semi standard non polar	33892256
Norartocarpanone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O)=C1	3626.0	Semi standard non polar	33892256
Norartocarpanone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3601.5	Semi standard non polar	33892256
Norartocarpanone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C(O[Si](C)(C)C(C)(C)C)=C1	3622.0	Semi standard non polar	33892256
Norartocarpanone,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3561.6	Semi standard non polar	33892256
Norartocarpanone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3771.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norartocarpanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0490000000-6b9257ef487bbf5b280b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norartocarpanone GC-MS (4 TMS) - 70eV, Positive	splash10-0imi-2420190000-d69f33ce6070e010921a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norartocarpanone 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 - Norartocarpanone 10V, Positive-QTOF	splash10-000i-0290000000-9910dd0b08a9b6831e76	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 20V, Positive-QTOF	splash10-000i-0980000000-98d5dfe9e50cacc3856b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 40V, Positive-QTOF	splash10-0f79-2910000000-6a49a7db32889325fa51	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 10V, Negative-QTOF	splash10-000i-0090000000-4b19f2e022b00086491d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 20V, Negative-QTOF	splash10-000i-0390000000-7a12ab87af82f880cbee	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 40V, Negative-QTOF	splash10-0pwi-5950000000-e3cc21d16f515f4cd223	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 10V, Positive-QTOF	splash10-000i-0090000000-6ba2690e52ef797ececb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 20V, Positive-QTOF	splash10-0uds-0940000000-cb26dafebd1059de9c9b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 40V, Positive-QTOF	splash10-0udi-0900000000-5ed3e87ec31a61a942ee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 10V, Negative-QTOF	splash10-000i-0090000000-fd96bbe1d8ed2e3ede5b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 20V, Negative-QTOF	splash10-0f79-0980000000-c6bfd4913da1e44ef31d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norartocarpanone 40V, Negative-QTOF	splash10-000i-0900000000-8d4818271eab4b80a22f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016333

KNApSAcK ID

C00008367

Chemspider ID

10221696

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21596130

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1859751

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 Norartocarpanone (HMDB0037314)

MOL for HMDB0037314 (Norartocarpanone)

3D MOL for HMDB0037314 (Norartocarpanone)

3D SDF for HMDB0037314 (Norartocarpanone)

3D-SDF for HMDB0037314 (Norartocarpanone)

PDB for HMDB0037314 (Norartocarpanone)

3D PDB for HMDB0037314 (Norartocarpanone)

SMILES for HMDB0037314 (Norartocarpanone)

INCHI for HMDB0037314 (Norartocarpanone)

Structure for HMDB0037314 (Norartocarpanone)

3D Structure for HMDB0037314 (Norartocarpanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra