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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2019-10-11 16:13:15 UTC

Update Date

2022-03-07 03:18:18 UTC

HMDB ID

HMDB0240546

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Naringenin 5-sulfate

Description

Naringenin 5-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 5-sulfate.

Structure

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

HMDB0240546
     RDKit          3D
Naringenin 5-sulfate
 37 39  0  0  0  0  0  0  0  0999 V2000
    1.9470    2.1188    0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3283    1.0870    0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    1.1964   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    0.0952    0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883    0.2301    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303   -0.1076   -1.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717    0.0417   -1.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554    0.5305   -0.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3994    0.6671   -0.6009 O   0  0  0  0  0  3  0  0  0  0  0  0
   -4.5054    0.8679    0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441    0.7165    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163   -1.1378    0.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0435   -1.3363    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5979   -2.5893    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9457   -2.7903    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -4.0701    0.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -1.6831    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574   -0.3994    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678    0.7267    0.7397 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7850    1.3912   -0.6692 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.8155    0.3801   -1.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904    1.5253   -1.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4660    2.8713   -0.3333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -0.2449    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1071    0.9676   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4950    2.1972   -0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    0.2054    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1471   -0.4896   -1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6114   -0.2193   -2.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7665    1.5207   -0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0187   -0.0906   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1782    1.2513    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.9877    2.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9222   -3.4354    0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -4.5077    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394   -1.8032    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488    3.3289    0.3810 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
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  2  0
 20 23  1  0
 18 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  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 23 37  1  0
M  CHG  1   9   1
M  END


  Mrv1652310111918132D          

 24 26  0  0  0  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
    2.1434   -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
    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
    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
    2.1434    1.2375    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  3  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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    1.7605    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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 S   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  7  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  2  0  0  0  0
 15 11  1  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 22 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 14  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
M  CHG  1  16   1
M  END
> <DATABASE_ID>
HMDB0240546

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C(=O)CC(O2)C2=CC=C([OH2+])C=C2)C(OS(O)(=O)=O)=C1

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

> <INCHI_KEY>
TUKMNFQGFNNJQM-UHFFFAOYSA-O

> <FORMULA>
C15H13O8S

> <MOLECULAR_WEIGHT>
353.32

> <EXACT_MASS>
353.032564973

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
32.951196141511716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{4-[7-hydroxy-4-oxo-5-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}oxidanium

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
1.7097947039999997

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.40602953832143

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.412391595631447

> <JCHEM_PKA_STRONGEST_BASIC>
-4.954980589808111

> <JCHEM_POLAR_SURFACE_AREA>
123.72

> <JCHEM_REFRACTIVITY>
93.4319

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4-[7-hydroxy-4-oxo-5-(sulfooxy)-2,3-dihydro-1-benzopyran-2-yl]phenyl}oxidanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240546
     RDKit          3D
Naringenin 5-sulfate
 37 39  0  0  0  0  0  0  0  0999 V2000
    1.9470    2.1188    0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3283    1.0870    0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    1.1964   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    0.0952    0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883    0.2301    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303   -0.1076   -1.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717    0.0417   -1.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554    0.5305   -0.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3994    0.6671   -0.6009 O   0  0  0  0  0  3  0  0  0  0  0  0
   -4.5054    0.8679    0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441    0.7165    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163   -1.1378    0.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0435   -1.3363    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5979   -2.5893    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9457   -2.7903    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -4.0701    0.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -1.6831    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574   -0.3994    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678    0.7267    0.7397 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7850    1.3912   -0.6692 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.8155    0.3801   -1.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904    1.5253   -1.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4660    2.8713   -0.3333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -0.2449    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1071    0.9676   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4950    2.1972   -0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    0.2054    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1471   -0.4896   -1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6114   -0.2193   -2.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7665    1.5207   -0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0187   -0.0906   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1782    1.2513    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.9877    2.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9222   -3.4354    0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -4.5077    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394   -1.8032    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488    3.3289    0.3810 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
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  2  0
 20 23  1  0
 18 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  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 23 37  1  0
M  CHG  1   9   1
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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   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+1
HETATM   17  O   UNK     0       1.334  -0.770   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   5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.437   5.954   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.897   3.286   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       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       2.667   4.620   0.000  0.00  0.00           S+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   13                                                       
CONECT    6   10   14                                                       
CONECT    7   11   12                                                       
CONECT    8    1    2   12                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   17                                                  
CONECT   11    7   15   18                                                  
CONECT   12    7    8   22                                                  
CONECT   13    5   15   22                                                  
CONECT   14    6   15   23                                                  
CONECT   15   11   13   14                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   24                                                            
CONECT   20   24                                                            
CONECT   21   24                                                            
CONECT   22   12   13                                                       
CONECT   23   14   24                                                       
CONECT   24   19   20   21   23                                             
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0240546
HETATM    1  O1  UNL     1       1.947   2.119   0.640  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.328   1.087   0.301  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.052   1.196  -0.224  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.854   0.095   0.470  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.288   0.230   0.156  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.830  -0.108  -1.066  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.172   0.042  -1.294  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.055   0.531  -0.336  1.00  0.00           C  
HETATM    9  O2  UNL     1      -6.399   0.667  -0.601  1.00  0.00           O1+
HETATM   10  C8  UNL     1      -4.505   0.868   0.890  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.144   0.716   1.122  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.316  -1.138   0.040  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.044  -1.336   0.258  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.598  -2.589   0.348  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.946  -2.790   0.564  1.00  0.00           C  
HETATM   16  O4  UNL     1       3.456  -4.070   0.648  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.759  -1.683   0.693  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.257  -0.399   0.611  1.00  0.00           C  
HETATM   19  O5  UNL     1       4.068   0.727   0.740  1.00  0.00           O  
HETATM   20  S1  UNL     1       4.785   1.391  -0.669  1.00  0.00           S  
HETATM   21  O6  UNL     1       5.815   0.380  -1.133  1.00  0.00           O  
HETATM   22  O7  UNL     1       3.790   1.525  -1.780  1.00  0.00           O  
HETATM   23  O8  UNL     1       5.466   2.871  -0.333  1.00  0.00           O  
HETATM   24  C15 UNL     1       1.899  -0.245   0.394  1.00  0.00           C  
HETATM   25  H1  UNL     1      -0.107   0.968  -1.307  1.00  0.00           H  
HETATM   26  H2  UNL     1      -0.495   2.197  -0.042  1.00  0.00           H  
HETATM   27  H3  UNL     1      -0.681   0.205   1.539  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.147  -0.490  -1.819  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.611  -0.219  -2.249  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.766   1.521  -0.983  1.00  0.00           H  
HETATM   31  H7  UNL     1      -7.019  -0.091  -0.412  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.178   1.251   1.652  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.737   0.988   2.090  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.922  -3.435   0.241  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.490  -4.508   1.555  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.839  -1.803   0.866  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.949   3.329   0.381  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   31
CONECT   10   11   11   32
CONECT   11   33
CONECT   12   13
CONECT   13   14   14   24
CONECT   14   15   34
CONECT   15   16   17   17
CONECT   16   35
CONECT   17   18   36
CONECT   18   19   24   24
CONECT   19   20
CONECT   20   21   21   22   22
CONECT   20   23
CONECT   23   37
END

HMDB0240546
     RDKit          3D
Naringenin 5-sulfate
 37 39  0  0  0  0  0  0  0  0999 V2000
    1.9470    2.1188    0.6403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3283    1.0870    0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    1.1964   -0.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    0.0952    0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2883    0.2301    0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8303   -0.1076   -1.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1717    0.0417   -1.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0554    0.5305   -0.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3994    0.6671   -0.6009 O   0  0  0  0  0  3  0  0  0  0  0  0
   -4.5054    0.8679    0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1441    0.7165    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3163   -1.1378    0.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0435   -1.3363    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5979   -2.5893    0.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9457   -2.7903    0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -4.0701    0.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -1.6831    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2574   -0.3994    0.6114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678    0.7267    0.7397 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7850    1.3912   -0.6692 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.8155    0.3801   -1.1326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7904    1.5253   -1.7803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4660    2.8713   -0.3333 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -0.2449    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1071    0.9676   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4950    2.1972   -0.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    0.2054    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1471   -0.4896   -1.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6114   -0.2193   -2.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7665    1.5207   -0.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0187   -0.0906   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1782    1.2513    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7365    0.9877    2.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9222   -3.4354    0.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -4.5077    1.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8394   -1.8032    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9488    3.3289    0.3810 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
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  2  0
 20 23  1  0
 18 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  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 23 37  1  0
M  CHG  1   9   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Naringenin 5-sulfuric acid	Generator
Naringenin 5-sulphate	Generator
Naringenin 5-sulphuric acid	Generator
{4-[7-hydroxy-4-oxo-5-(sulphooxy)-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}oxidanium	HMDB

Chemical Formula

C₁₅H₁₃O₈S

Average Molecular Weight

353.32

Monoisotopic Molecular Weight

353.032564973

IUPAC Name

{4-[7-hydroxy-4-oxo-5-(sulfooxy)-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}oxidanium

Traditional Name

{4-[7-hydroxy-4-oxo-5-(sulfooxy)-2,3-dihydro-1-benzopyran-2-yl]phenyl}oxidanium

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C(=O)CC(O2)C2=CC=C([OH2+])C=C2)C(OS(O)(=O)=O)=C1

InChI Identifier

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

InChI Key

TUKMNFQGFNNJQM-UHFFFAOYSA-O

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Citrus (HMDB: HMDB0240546)

Vegetable

Tomato (HMDB: HMDB0240546)

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	0.48	ALOGPS
logP	1.71	ChemAxon
logS	-3.4	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	123.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.43 m³·mol⁻¹	ChemAxon
Polarizability	32.95 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]+	185.835	30932474
DeepCCS	[M-H]-	183.477	30932474
DeepCCS	[M-2H]-	216.361	30932474
DeepCCS	[M+Na]+	191.928	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naringenin 5-sulfate	OC1=CC2=C(C(=O)CC(O2)C2=CC=C([OH2+])C=C2)C(OS(O)(=O)=O)=C1	4813.6	Standard polar	33892256
Naringenin 5-sulfate	OC1=CC2=C(C(=O)CC(O2)C2=CC=C([OH2+])C=C2)C(OS(O)(=O)=O)=C1	2905.5	Standard non polar	33892256
Naringenin 5-sulfate	OC1=CC2=C(C(=O)CC(O2)C2=CC=C([OH2+])C=C2)C(OS(O)(=O)=O)=C1	3217.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Naringenin 5-sulfate,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C([OH2+])C=C3)O2)C(OS(=O)(=O)O)=C1	3167.7	Semi standard non polar	33892256
Naringenin 5-sulfate,1TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC(O)=CC2=C1C(=O)CC(C1=CC=C([OH2+])C=C1)O2	3159.9	Semi standard non polar	33892256
Naringenin 5-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C([OH2+])C=C3)O2)C(OS(=O)(=O)O[Si](C)(C)C)=C1	3149.3	Semi standard non polar	33892256
Naringenin 5-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C([OH2+])C=C3)O2)C(OS(=O)(=O)O[Si](C)(C)C)=C1	3230.8	Standard non polar	33892256
Naringenin 5-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C([OH2+])C=C3)O2)C(OS(=O)(=O)O[Si](C)(C)C)=C1	3904.8	Standard polar	33892256
Naringenin 5-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C([OH2+])C=C3)O2)C(OS(=O)(=O)O)=C1	3444.5	Semi standard non polar	33892256
Naringenin 5-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(O)=CC2=C1C(=O)CC(C1=CC=C([OH2+])C=C1)O2	3424.7	Semi standard non polar	33892256
Naringenin 5-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C([OH2+])C=C3)O2)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1	3639.3	Semi standard non polar	33892256
Naringenin 5-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C([OH2+])C=C3)O2)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1	3762.3	Standard non polar	33892256
Naringenin 5-sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)CC(C3=CC=C([OH2+])C=C3)O2)C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=C1	3970.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Naringenin 5-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 5-sulfate 10V, Positive-QTOF	splash10-004i-0900000000-d7ab7e389b965eeae26b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 5-sulfate 20V, Positive-QTOF	splash10-003s-0970000000-010ed37020f564ed177f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 5-sulfate 40V, Positive-QTOF	splash10-001i-0390000000-7c365d19a6517c18501c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 5-sulfate 10V, Negative-QTOF	splash10-0udi-0009000000-3e2dc10b974595b0b2ba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 5-sulfate 20V, Negative-QTOF	splash10-0ue9-0179000000-8c498827ab77b3e8e667	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naringenin 5-sulfate 40V, Negative-QTOF	splash10-00di-0900000000-335a2a705fa32f848031	2021-09-24	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

FDB093741

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

Not Available

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 5-sulfate (HMDB0240546)

MOL for HMDB0240546 (Naringenin 5-sulfate)

3D MOL for HMDB0240546 (Naringenin 5-sulfate)

3D SDF for HMDB0240546 (Naringenin 5-sulfate)

3D-SDF for HMDB0240546 (Naringenin 5-sulfate)

PDB for HMDB0240546 (Naringenin 5-sulfate)

3D PDB for HMDB0240546 (Naringenin 5-sulfate)

SMILES for HMDB0240546 (Naringenin 5-sulfate)

INCHI for HMDB0240546 (Naringenin 5-sulfate)

Structure for HMDB0240546 (Naringenin 5-sulfate)

3D Structure for HMDB0240546 (Naringenin 5-sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra