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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2019-10-11 16:15:47 UTC

Update Date

2022-03-07 03:18:19 UTC

HMDB ID

HMDB0240547

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Naringenin 7-sulfate

Description

Naringenin 7-sulfate 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. Based on a literature review very few articles have been published on Naringenin 7-sulfate.

Structure

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

HMDB0240547
     RDKit          3D
Naringenin 7-sulfate
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.3650   -0.9165    3.0477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740   -1.1665    1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9668   -2.2041    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909   -1.7703   -0.2823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3299   -0.7093   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -0.0072   -1.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    0.9847   -1.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2848    1.3369   -0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2534    2.3461   -0.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0650    0.6580    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991   -0.3518    0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0922   -1.3105   -0.9211 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402   -0.5381   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157    0.1680   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605    0.9481   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862    1.6104   -1.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    0.9680   -1.5556 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.2217    0.5572   -3.0004 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3055    1.9875   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5971   -0.3687   -0.6309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7288    1.0268    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    0.3482    1.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7148    0.3978    3.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8392   -0.4360    1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8452   -2.5522    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893   -3.1085    1.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5937   -2.6814   -0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -0.2862   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6950    1.5218   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2103    2.0715   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6519    0.9074    1.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414   -0.8753    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006    0.0741   -2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1240   -1.1853   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.6244    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    0.9311    3.6980 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
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24  2  1  0
 11  5  1  0
 24 13  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  6
  6 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
M  END


  Mrv1652310111918152D          

 25 27  0  0  1  0            999 V2000
    5.0013   -1.2375    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
    6.4302   -0.4125    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
    5.0013   -0.4125    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
    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  1  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
    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
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  1  0  0  0
 14  6  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  9  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 22 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 10  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  2  0  0  0  0
 24 21  2  0  0  0  0
 24 23  1  0  0  0  0
 13 25  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0240547

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O8S/c16-9-3-1-8(2-4-9)13-7-12(18)15-11(17)5-10(6-14(15)22-13)23-24(19,20)21/h1-6,13,16-17H,7H2,(H,19,20,21)/t13-/m0/s1

> <INCHI_KEY>
LCXKYLMSILXZFG-ZDUSSCGKSA-N

> <FORMULA>
C15H12O8S

> <MOLECULAR_WEIGHT>
352.31

> <EXACT_MASS>
352.02528852

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
32.65064665825194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.42

> <JCHEM_LOGP>
2.3597947039999996

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.197726676092547

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.414352328225105

> <JCHEM_PKA_STRONGEST_BASIC>
-4.955325823130645

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
81.2816

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240547
     RDKit          3D
Naringenin 7-sulfate
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.3650   -0.9165    3.0477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740   -1.1665    1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9668   -2.2041    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909   -1.7703   -0.2823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3299   -0.7093   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -0.0072   -1.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    0.9847   -1.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2848    1.3369   -0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2534    2.3461   -0.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0650    0.6580    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991   -0.3518    0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0922   -1.3105   -0.9211 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402   -0.5381   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157    0.1680   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605    0.9481   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862    1.6104   -1.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    0.9680   -1.5556 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.2217    0.5572   -3.0004 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3055    1.9875   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5971   -0.3687   -0.6309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7288    1.0268    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    0.3482    1.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7148    0.3978    3.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8392   -0.4360    1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8452   -2.5522    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893   -3.1085    1.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5937   -2.6814   -0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -0.2862   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6950    1.5218   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2103    2.0715   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6519    0.9074    1.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414   -0.8753    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006    0.0741   -2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1240   -1.1853   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.6244    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    0.9311    3.6980 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
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24  2  1  0
 11  5  1  0
 24 13  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  6
  6 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
M  END

HEADER    PROTEIN                                 11-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-19         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   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      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   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       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM   25  H   UNK     0       8.002  -1.540   0.000  0.00  0.00           H+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   11                                                       
CONECT    6   10   14                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   13                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   23                                                  
CONECT   11    5   15   17                                                  
CONECT   12    7   15   18                                                  
CONECT   13    7    8   22   25                                             
CONECT   14    6   15   22                                                  
CONECT   15   11   12   14                                                  
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   24                                                            
CONECT   20   24                                                            
CONECT   21   24                                                            
CONECT   22   13   14                                                       
CONECT   23   10   24                                                       
CONECT   24   19   20   21   23                                             
CONECT   25   13                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0240547
HETATM    1  O1  UNL     1      -0.365  -0.916   3.048  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.174  -1.167   1.837  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.967  -2.204   1.138  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.291  -1.770  -0.282  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.330  -0.709  -0.320  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.570  -0.007  -1.504  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.518   0.985  -1.590  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.285   1.337  -0.501  1.00  0.00           C  
HETATM    9  O2  UNL     1      -5.253   2.346  -0.579  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.065   0.658   0.676  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.099  -0.352   0.763  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.092  -1.310  -0.921  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.840  -0.538  -0.282  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.816   0.168  -0.969  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.761   0.948  -0.356  1.00  0.00           C  
HETATM   16  O4  UNL     1       3.686   1.610  -1.111  1.00  0.00           O  
HETATM   17  S1  UNL     1       5.193   0.968  -1.556  1.00  0.00           S  
HETATM   18  O5  UNL     1       5.222   0.557  -3.000  1.00  0.00           O  
HETATM   19  O6  UNL     1       6.305   1.988  -1.367  1.00  0.00           O  
HETATM   20  O7  UNL     1       5.597  -0.369  -0.631  1.00  0.00           O  
HETATM   21  C13 UNL     1       2.729   1.027   1.018  1.00  0.00           C  
HETATM   22  C14 UNL     1       1.784   0.348   1.751  1.00  0.00           C  
HETATM   23  O8  UNL     1       1.715   0.398   3.129  1.00  0.00           O  
HETATM   24  C15 UNL     1       0.839  -0.436   1.086  1.00  0.00           C  
HETATM   25  H1  UNL     1      -1.845  -2.552   1.703  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.289  -3.109   1.101  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.594  -2.681  -0.836  1.00  0.00           H  
HETATM   28  H4  UNL     1      -1.966  -0.286  -2.358  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.695   1.522  -2.513  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.210   2.071  -0.846  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.652   0.907   1.561  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.941  -0.875   1.706  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.801   0.074  -2.062  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.124  -1.185  -0.889  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.444   1.624   1.575  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.346   0.931   3.698  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   24
CONECT    3    4   25   26
CONECT    4    5   12   27
CONECT    5    6    6   11
CONECT    6    7   28
CONECT    7    8    8   29
CONECT    8    9   10
CONECT    9   30
CONECT   10   11   11   31
CONECT   11   32
CONECT   12   13
CONECT   13   14   14   24
CONECT   14   15   33
CONECT   15   16   21   21
CONECT   16   17
CONECT   17   18   18   19   19
CONECT   17   20
CONECT   20   34
CONECT   21   22   35
CONECT   22   23   24   24
CONECT   23   36
END

HMDB0240547
     RDKit          3D
Naringenin 7-sulfate
 36 38  0  0  0  0  0  0  0  0999 V2000
   -0.3650   -0.9165    3.0477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1740   -1.1665    1.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9668   -2.2041    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909   -1.7703   -0.2823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3299   -0.7093   -0.3196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -0.0072   -1.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183    0.9847   -1.5896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2848    1.3369   -0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2534    2.3461   -0.5790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0650    0.6580    0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991   -0.3518    0.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0922   -1.3105   -0.9211 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402   -0.5381   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157    0.1680   -0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7605    0.9481   -0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6862    1.6104   -1.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1927    0.9680   -1.5556 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.2217    0.5572   -3.0004 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3055    1.9875   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5971   -0.3687   -0.6309 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7288    1.0268    1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    0.3482    1.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7148    0.3978    3.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8392   -0.4360    1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8452   -2.5522    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2893   -3.1085    1.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5937   -2.6814   -0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9657   -0.2862   -2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6950    1.5218   -2.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2103    2.0715   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6519    0.9074    1.5614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414   -0.8753    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006    0.0741   -2.0618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1240   -1.1853   -0.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.6244    1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462    0.9311    3.6980 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
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24  2  1  0
 11  5  1  0
 24 13  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  6
  6 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 20 34  1  0
 21 35  1  0
 23 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Naringenin 7-sulfuric acid	Generator
Naringenin 7-sulphate	Generator
Naringenin 7-sulphuric acid	Generator

Chemical Formula

C₁₅H₁₂O₈S

Average Molecular Weight

352.31

Monoisotopic Molecular Weight

352.02528852

IUPAC Name

[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxidanesulfonic acid

Traditional Name

[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H12O8S/c16-9-3-1-8(2-4-9)13-7-12(18)15-11(17)5-10(6-14(15)22-13)23-24(19,20)21/h1-6,13,16-17H,7H2,(H,19,20,21)/t13-/m0/s1

InChI Key

LCXKYLMSILXZFG-ZDUSSCGKSA-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
Flavanone
Hydroxyflavonoid
Chromone
Arylsulfate
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Vinylogous acid
Organic sulfuric acid or derivatives
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Citrus (HMDB: HMDB0240547)

Vegetable

Tomato (HMDB: HMDB0240547)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.42	ALOGPS
logP	2.36	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	-2.4	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.28 m³·mol⁻¹	ChemAxon
Polarizability	32.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	179.355	30932474
DeepCCS	[M-H]-	176.997	30932474
DeepCCS	[M-2H]-	211.042	30932474
DeepCCS	[M+Na]+	185.921	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naringenin 7-sulfate	[H][C@]1(CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1)C1=CC=C(O)C=C1	5023.5	Standard polar	33892256
Naringenin 7-sulfate	[H][C@]1(CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1)C1=CC=C(O)C=C1	2896.6	Standard non polar	33892256
Naringenin 7-sulfate	[H][C@]1(CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1)C1=CC=C(O)C=C1	3259.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Naringenin 7-sulfate,1TMS,isomer #1	C[Si](C)(C)OC1=CC(OS(=O)(=O)O)=CC2=C1C(=O)C[C@@H](C1=CC=C(O)C=C1)O2	3197.6	Semi standard non polar	33892256
Naringenin 7-sulfate,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(OS(=O)(=O)O)C=C3O2)C=C1	3251.4	Semi standard non polar	33892256
Naringenin 7-sulfate,1TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)OC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O)C=C3)OC2=C1	3212.6	Semi standard non polar	33892256
Naringenin 7-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(OS(=O)(=O)O)C=C3O[Si](C)(C)C)O2)C=C1	3200.3	Semi standard non polar	33892256
Naringenin 7-sulfate,2TMS,isomer #2	C[Si](C)(C)OC1=CC(OS(=O)(=O)O[Si](C)(C)C)=CC2=C1C(=O)C[C@@H](C1=CC=C(O)C=C1)O2	3135.0	Semi standard non polar	33892256
Naringenin 7-sulfate,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(OS(=O)(=O)O[Si](C)(C)C)C=C3O2)C=C1	3235.9	Semi standard non polar	33892256
Naringenin 7-sulfate,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(OS(=O)(=O)O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	3201.6	Semi standard non polar	33892256
Naringenin 7-sulfate,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(OS(=O)(=O)O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	3226.9	Standard non polar	33892256
Naringenin 7-sulfate,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(OS(=O)(=O)O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	3831.1	Standard polar	33892256
Naringenin 7-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(OS(=O)(=O)O)=CC2=C1C(=O)C[C@@H](C1=CC=C(O)C=C1)O2	3505.9	Semi standard non polar	33892256
Naringenin 7-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(OS(=O)(=O)O)C=C3O2)C=C1	3549.9	Semi standard non polar	33892256
Naringenin 7-sulfate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O)C=C3)OC2=C1	3503.4	Semi standard non polar	33892256
Naringenin 7-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(OS(=O)(=O)O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3776.5	Semi standard non polar	33892256
Naringenin 7-sulfate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C[C@@H](C1=CC=C(O)C=C1)O2	3652.7	Semi standard non polar	33892256
Naringenin 7-sulfate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3762.2	Semi standard non polar	33892256
Naringenin 7-sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3915.3	Semi standard non polar	33892256
Naringenin 7-sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	4009.7	Standard non polar	33892256
Naringenin 7-sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	3956.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Naringenin 7-sulfate 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 - Naringenin 7-sulfate 10V, Positive-QTOF	splash10-0udi-0009000000-2da71d71edbfababfa17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 7-sulfate 20V, Positive-QTOF	splash10-0f8a-0496000000-1fb8c18c45d1d852da7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 7-sulfate 40V, Positive-QTOF	splash10-001i-0390000000-6724e90ef7ba3ff4229c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 7-sulfate 10V, Negative-QTOF	splash10-0udi-0009000000-b53fb8bf65632c2ae731	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 7-sulfate 20V, Negative-QTOF	splash10-0ue9-0179000000-1b80e4c6787be196fe53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 7-sulfate 40V, Negative-QTOF	splash10-014i-0900000000-ad82af81ff6ef45b2415	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB093742

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101019951

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Naringenin 7-sulfate (HMDB0240547)

MOL for HMDB0240547 (Naringenin 7-sulfate)

3D MOL for HMDB0240547 (Naringenin 7-sulfate)

3D SDF for HMDB0240547 (Naringenin 7-sulfate)

3D-SDF for HMDB0240547 (Naringenin 7-sulfate)

PDB for HMDB0240547 (Naringenin 7-sulfate)

3D PDB for HMDB0240547 (Naringenin 7-sulfate)

SMILES for HMDB0240547 (Naringenin 7-sulfate)

INCHI for HMDB0240547 (Naringenin 7-sulfate)

Structure for HMDB0240547 (Naringenin 7-sulfate)

3D Structure for HMDB0240547 (Naringenin 7-sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra