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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-08 14:59:50 UTC

Update Date

2021-09-14 15:16:44 UTC

HMDB ID

HMDB0029209

Secondary Accession Numbers

HMDB29209

Metabolite Identification

Common Name

naringenin-7-O-glucuronide

Description

naringenin-7-O-glucuronide belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. naringenin-7-O-glucuronide has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make naringenin-7-O-glucuronide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on naringenin-7-O-glucuronide.

Structure

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

  Mrv1652303102016542D          

 32 35  0  0  0  0            999 V2000
   -1.8562   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0534    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0534    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4823    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4823    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -2.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562   -2.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2852   -0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9997   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5830    0.1119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7965   -0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2975   -0.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0944   -0.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5110   -0.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132   -1.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3079   -0.8839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9194   -0.0870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7100    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2975    1.1284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4245    0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 10 13  1  0  0  0  0
 16 17  1  0  0  0  0
  8 18  2  0  0  0  0
  4 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 23  1  0  0  0  0
 23 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END

HMDB0029209
     RDKit          3D
naringenin-7-O-glucuronide
 52 55  0  0  0  0  0  0  0  0999 V2000
    3.3212   -1.9735   -2.2639 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1178   -1.9673   -1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147   -2.4442   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -1.3487    0.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9649   -0.1634    0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9483    0.9867    1.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167    2.1280    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966    2.0739   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9858    3.2029   -0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3278    0.9448   -1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6459   -0.2054   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678   -1.0323    1.5220 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859   -0.9974    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163   -0.5129    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757   -0.4779    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197    0.0167    1.2140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9934    0.1380    0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230    1.4591    0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5786    1.6159   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9338    3.0315   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1968    3.9586    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0626    3.4240   -1.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7483    0.8551    0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8219    0.7988   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3954   -0.5412    0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6710   -1.4454   -0.2126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0178   -0.7284    1.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6976   -2.0807    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006   -0.9491   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6855   -1.4455   -1.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -1.9007   -2.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8364   -1.4680   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0618   -2.7606   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514   -3.3167    0.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8423   -1.7711    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3987    1.0154    2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228    3.0418    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5689    3.9146   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8814    0.9367   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7093   -1.0463   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887   -0.1513    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9815   -0.2323   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4024    1.1585   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9672    3.3233   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0945    1.4354    1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2622   -0.1058   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1108   -0.8469    1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0392   -1.3180   -0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9755   -0.4581    2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -2.5420    0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963   -0.9495   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543   -2.2794   -3.0939 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  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 15 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 11  5  1  0
 32 13  1  0
 27 17  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
  7 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 14 41  1  0
 17 42  1  0
 19 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
 27 49  1  0
 28 50  1  0
 29 51  1  0
 31 52  1  0
M  END

  Mrv1652303102016542D          

 32 35  0  0  0  0            999 V2000
   -1.8562   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1418   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -1.7089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0534    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0534    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4823    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4823    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -2.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562   -2.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2852   -0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9997   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5830    0.1119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7965   -0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2975   -0.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0944   -0.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5110   -0.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132   -1.2683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3079   -0.8839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9194   -0.0870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7100    0.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2975    1.1284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4245    0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 10 13  1  0  0  0  0
 16 17  1  0  0  0  0
  8 18  2  0  0  0  0
  4 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 23  1  0  0  0  0
 23 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029209

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C(O)C(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)OC(C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-6,13,16-19,21-23,25-27H,7H2,(H,28,29)

> <INCHI_KEY>
BDCRTIDKZGEVEN-UHFFFAOYSA-N

> <FORMULA>
C21H20O11

> <MOLECULAR_WEIGHT>
448.3769

> <EXACT_MASS>
448.100561482

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.89437828858187

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.65

> <JCHEM_LOGP>
0.8873144950000008

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.579410954579604

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.731714373899361

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686826778063371

> <JCHEM_POLAR_SURFACE_AREA>
183.21

> <JCHEM_REFRACTIVITY>
103.30159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029209
     RDKit          3D
naringenin-7-O-glucuronide
 52 55  0  0  0  0  0  0  0  0999 V2000
    3.3212   -1.9735   -2.2639 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1178   -1.9673   -1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147   -2.4442   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -1.3487    0.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9649   -0.1634    0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9483    0.9867    1.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167    2.1280    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966    2.0739   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9858    3.2029   -0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3278    0.9448   -1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6459   -0.2054   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678   -1.0323    1.5220 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859   -0.9974    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163   -0.5129    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757   -0.4779    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197    0.0167    1.2140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9934    0.1380    0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230    1.4591    0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5786    1.6159   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9338    3.0315   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1968    3.9586    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0626    3.4240   -1.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7483    0.8551    0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8219    0.7988   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3954   -0.5412    0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6710   -1.4454   -0.2126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0178   -0.7284    1.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6976   -2.0807    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006   -0.9491   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6855   -1.4455   -1.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -1.9007   -2.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8364   -1.4680   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0618   -2.7606   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514   -3.3167    0.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8423   -1.7711    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3987    1.0154    2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228    3.0418    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5689    3.9146   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8814    0.9367   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7093   -1.0463   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887   -0.1513    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9815   -0.2323   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4024    1.1585   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9672    3.3233   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0945    1.4354    1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2622   -0.1058   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1108   -0.8469    1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0392   -1.3180   -0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9755   -0.4581    2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -2.5420    0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963   -0.9495   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543   -2.2794   -3.0939 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  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 15 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 11  5  1  0
 32 13  1  0
 27 17  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
  7 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 14 41  1  0
 17 42  1  0
 19 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
 27 49  1  0
 28 50  1  0
 29 51  1  0
 31 52  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.465  -0.110   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.799  -0.880   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.799  -2.420   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.465  -3.190   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.131  -2.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.131  -0.880   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.798  -0.110   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.798  -3.190   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.536  -2.420   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.536  -0.880   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.300   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.966   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.966   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.300  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.634   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.634   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.967   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.798  -4.730   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.465  -4.730   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -6.132  -0.110   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -7.466  -0.880   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -8.555   0.209   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -8.953  -1.278   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.889  -0.561   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.376  -0.162   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -10.287  -1.251   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.865  -2.367   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0     -11.775  -1.650   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0     -12.916  -0.162   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -10.659   0.773   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -9.889   2.106   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -11.992   1.543   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    7    9   13                                                  
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   10                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   11   15   17                                                  
CONECT   17   16                                                            
CONECT   18    8                                                            
CONECT   19    4                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   24                                                       
CONECT   23   21   26   27                                                  
CONECT   24   22   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   23   28                                                  
CONECT   27   23                                                            
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30   24   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    HMDB0029209
HETATM    1  O1  UNL     1       3.321  -1.974  -2.264  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.118  -1.967  -1.028  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.115  -2.444  -0.026  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.234  -1.349   0.997  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.965  -0.163   0.519  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.948   0.987   1.298  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.617   2.128   0.906  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.297   2.074  -0.285  1.00  0.00           C  
HETATM    9  O2  UNL     1       6.986   3.203  -0.721  1.00  0.00           O  
HETATM   10  C8  UNL     1       6.328   0.945  -1.075  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.646  -0.205  -0.665  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.968  -1.032   1.522  1.00  0.00           O  
HETATM   13  C10 UNL     1       1.786  -0.997   0.795  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.616  -0.513   1.350  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.576  -0.478   0.614  1.00  0.00           C  
HETATM   16  O4  UNL     1      -1.720   0.017   1.214  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.993   0.138   0.665  1.00  0.00           C  
HETATM   18  O5  UNL     1      -3.423   1.459   0.579  1.00  0.00           O  
HETATM   19  C14 UNL     1      -4.579   1.616  -0.137  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.934   3.032  -0.374  1.00  0.00           C  
HETATM   21  O6  UNL     1      -4.197   3.959   0.070  1.00  0.00           O  
HETATM   22  O7  UNL     1      -6.063   3.424  -1.076  1.00  0.00           O  
HETATM   23  C16 UNL     1      -5.748   0.855   0.455  1.00  0.00           C  
HETATM   24  O8  UNL     1      -6.822   0.799  -0.433  1.00  0.00           O  
HETATM   25  C17 UNL     1      -5.395  -0.541   0.837  1.00  0.00           C  
HETATM   26  O9  UNL     1      -5.671  -1.445  -0.213  1.00  0.00           O  
HETATM   27  C18 UNL     1      -4.018  -0.728   1.380  1.00  0.00           C  
HETATM   28  O10 UNL     1      -3.698  -2.081   1.269  1.00  0.00           O  
HETATM   29  C19 UNL     1      -0.501  -0.949  -0.668  1.00  0.00           C  
HETATM   30  C20 UNL     1       0.685  -1.445  -1.244  1.00  0.00           C  
HETATM   31  O11 UNL     1       0.674  -1.901  -2.534  1.00  0.00           O  
HETATM   32  C21 UNL     1       1.836  -1.468  -0.504  1.00  0.00           C  
HETATM   33  H1  UNL     1       5.062  -2.761  -0.453  1.00  0.00           H  
HETATM   34  H2  UNL     1       3.651  -3.317   0.496  1.00  0.00           H  
HETATM   35  H3  UNL     1       4.842  -1.771   1.854  1.00  0.00           H  
HETATM   36  H4  UNL     1       4.399   1.015   2.251  1.00  0.00           H  
HETATM   37  H5  UNL     1       5.623   3.042   1.492  1.00  0.00           H  
HETATM   38  H6  UNL     1       6.569   3.915  -1.299  1.00  0.00           H  
HETATM   39  H7  UNL     1       6.881   0.937  -2.021  1.00  0.00           H  
HETATM   40  H8  UNL     1       5.709  -1.046  -1.317  1.00  0.00           H  
HETATM   41  H9  UNL     1       0.589  -0.151   2.355  1.00  0.00           H  
HETATM   42  H10 UNL     1      -2.982  -0.232  -0.375  1.00  0.00           H  
HETATM   43  H11 UNL     1      -4.402   1.158  -1.152  1.00  0.00           H  
HETATM   44  H12 UNL     1      -6.967   3.323  -0.635  1.00  0.00           H  
HETATM   45  H13 UNL     1      -6.095   1.435   1.354  1.00  0.00           H  
HETATM   46  H14 UNL     1      -7.262  -0.106  -0.420  1.00  0.00           H  
HETATM   47  H15 UNL     1      -6.111  -0.847   1.655  1.00  0.00           H  
HETATM   48  H16 UNL     1      -5.039  -1.318  -0.948  1.00  0.00           H  
HETATM   49  H17 UNL     1      -3.975  -0.458   2.448  1.00  0.00           H  
HETATM   50  H18 UNL     1      -4.254  -2.542   0.585  1.00  0.00           H  
HETATM   51  H19 UNL     1      -1.396  -0.950  -1.296  1.00  0.00           H  
HETATM   52  H20 UNL     1       1.354  -2.279  -3.094  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   32
CONECT    3    4   33   34
CONECT    4    5   12   35
CONECT    5    6    6   11
CONECT    6    7   36
CONECT    7    8    8   37
CONECT    8    9   10
CONECT    9   38
CONECT   10   11   11   39
CONECT   11   40
CONECT   12   13
CONECT   13   14   14   32
CONECT   14   15   41
CONECT   15   16   29   29
CONECT   16   17
CONECT   17   18   27   42
CONECT   18   19
CONECT   19   20   23   43
CONECT   20   21   21   22
CONECT   22   44
CONECT   23   24   25   45
CONECT   24   46
CONECT   25   26   27   47
CONECT   26   48
CONECT   27   28   49
CONECT   28   50
CONECT   29   30   51
CONECT   30   31   32   32
CONECT   31   52
END

HMDB0029209
     RDKit          3D
naringenin-7-O-glucuronide
 52 55  0  0  0  0  0  0  0  0999 V2000
    3.3212   -1.9735   -2.2639 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1178   -1.9673   -1.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147   -2.4442   -0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344   -1.3487    0.9970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9649   -0.1634    0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9483    0.9867    1.2978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167    2.1280    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966    2.0739   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9858    3.2029   -0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3278    0.9448   -1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6459   -0.2054   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678   -1.0323    1.5220 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859   -0.9974    0.7952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6163   -0.5129    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5757   -0.4779    0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197    0.0167    1.2140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9934    0.1380    0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4230    1.4591    0.5792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5786    1.6159   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9338    3.0315   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1968    3.9586    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0626    3.4240   -1.0758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7483    0.8551    0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8219    0.7988   -0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3954   -0.5412    0.8368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6710   -1.4454   -0.2126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0178   -0.7284    1.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6976   -2.0807    1.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006   -0.9491   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6855   -1.4455   -1.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -1.9007   -2.5339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8364   -1.4680   -0.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0618   -2.7606   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6514   -3.3167    0.4956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8423   -1.7711    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3987    1.0154    2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228    3.0418    1.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5689    3.9146   -1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8814    0.9367   -2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7093   -1.0463   -1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5887   -0.1513    2.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9815   -0.2323   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4024    1.1585   -1.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9672    3.3233   -0.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0945    1.4354    1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2622   -0.1058   -0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1108   -0.8469    1.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0392   -1.3180   -0.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9755   -0.4581    2.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2535   -2.5420    0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3963   -0.9495   -1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543   -2.2794   -3.0939 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  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 15 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 11  5  1  0
 32 13  1  0
 27 17  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
  7 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 14 41  1  0
 17 42  1  0
 19 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
 25 47  1  0
 26 48  1  0
 27 49  1  0
 28 50  1  0
 29 51  1  0
 31 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylate	HMDB

Chemical Formula

C₂₁H₂₀O₁₁

Average Molecular Weight

448.3769

Monoisotopic Molecular Weight

448.100561482

IUPAC Name

3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC1C(O)C(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)OC(C1O)C(O)=O

InChI Identifier

InChI=1S/C21H20O11/c22-9-3-1-8(2-4-9)13-7-12(24)15-11(23)5-10(6-14(15)31-13)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-6,13,16-19,21-23,25-27H,7H2,(H,28,29)

InChI Key

BDCRTIDKZGEVEN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Flavanone
Flavan
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Beta-hydroxy acid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Acetal
Ether
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Liver (HMDB: HMDB0029209)
Kidney (HMDB: HMDB0029209)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Endogenous

Endogenous (HMDB: HMDB0029209)

Plant

Plant (HMDB: HMDB0029209)

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Lagomorph

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Poultry

Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)

Equine

Horse (FooDB: FOOD00378)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Process

Not Available

Role

Biological role

Waste product (HMDB: HMDB0029209)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.69 g/L	ALOGPS
logP	0.65	ALOGPS
logP	0.89	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	2.73	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.3 m³·mol⁻¹	ChemAxon
Polarizability	42.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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]+	201.687	31661259
DarkChem	[M-H]-	198.4	31661259
DeepCCS	[M+H]+	199.911	30932474
DeepCCS	[M-H]-	197.515	30932474
DeepCCS	[M-2H]-	230.714	30932474
DeepCCS	[M+Na]+	205.956	30932474
AllCCS	[M+H]+	203.1	32859911
AllCCS	[M+H-H2O]+	200.8	32859911
AllCCS	[M+NH4]+	205.3	32859911
AllCCS	[M+Na]+	205.9	32859911
AllCCS	[M-H]-	199.3	32859911
AllCCS	[M+Na-2H]-	199.7	32859911
AllCCS	[M+HCOO]-	200.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
naringenin-7-O-glucuronide	OC1C(O)C(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)OC(C1O)C(O)=O	5048.7	Standard polar	33892256
naringenin-7-O-glucuronide	OC1C(O)C(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)OC(C1O)C(O)=O	4081.3	Standard non polar	33892256
naringenin-7-O-glucuronide	OC1C(O)C(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)OC(C1O)C(O)=O	4299.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
naringenin-7-O-glucuronide,1TMS,isomer #1	C[Si](C)(C)OC1C(O)C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C1O	4184.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TMS,isomer #2	C[Si](C)(C)OC1C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C(O)C1O	4188.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TMS,isomer #3	C[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O)C(O)C2O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4195.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O)C(O)C4O)C=C3O2)C=C1	4231.9	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TMS,isomer #5	C[Si](C)(C)OC1C(C(=O)O)OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C1O	4166.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TMS,isomer #6	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C(O)C1O	4124.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #1	C[Si](C)(C)OC1C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C(O)C1O[Si](C)(C)C	4087.1	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #10	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O)C(O)C1O	4097.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #11	C[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O)C2O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4105.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #12	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O)C(O)C4O)C=C3O[Si](C)(C)C)O2)C=C1	4163.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #13	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)OC3=C2)C(O)C(O)C1O	4120.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #14	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C)C(O)C4O)C=C3O2)C=C1	4090.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #15	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C(O)C1O[Si](C)(C)C	4056.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #2	C[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C)C2O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4112.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O)C(O[Si](C)(C)C)C4O)C=C3O2)C=C1	4117.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #4	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C(O[Si](C)(C)C)C1O	4067.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #5	C[Si](C)(C)OC1C(C(=O)O)OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C1O[Si](C)(C)C	4077.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #6	C[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O)C(O)C2O[Si](C)(C)C)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4129.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #7	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O)C(O)C4O[Si](C)(C)C)C=C3O2)C=C1	4119.4	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #8	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O[Si](C)(C)C)C(O)C1O	4060.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TMS,isomer #9	C[Si](C)(C)OC1C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C(O[Si](C)(C)C)C1O	4081.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #1	C[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4045.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #10	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	4007.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #11	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C(O)C1O	4034.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #12	C[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4036.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #13	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O)C(O)C4O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	4040.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #14	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)OC3=C2)C(O[Si](C)(C)C)C(O)C1O	4028.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #15	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C)C(O)C4O[Si](C)(C)C)C=C3O2)C=C1	4027.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #16	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	4013.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #17	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O)C(O)C1O	4070.1	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #18	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O)C(O)C1O[Si](C)(C)C	4019.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #19	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C)C(O)C4O)C=C3O[Si](C)(C)C)O2)C=C1	4009.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3O2)C=C1	4045.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #20	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)OC3=C2)C(O)C(O)C1O[Si](C)(C)C	4018.4	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	4016.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #4	C[Si](C)(C)OC1C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	4050.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #5	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O)C(O[Si](C)(C)C)C1O	4015.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #6	C[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4025.4	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #7	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O)C(O[Si](C)(C)C)C4O)C=C3O[Si](C)(C)C)O2)C=C1	4035.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #8	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)OC3=C2)C(O)C(O[Si](C)(C)C)C1O	4037.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O)C=C3O2)C=C1	4025.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	3976.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #10	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)OC3=C2)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3975.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #11	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C(O)C1O	4003.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #12	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	3986.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #13	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C)C(O)C4O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	3987.4	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #14	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)OC3=C2)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	3982.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #15	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O)C(O)C1O[Si](C)(C)C	3995.1	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #2	C[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	3991.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	4001.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #4	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)OC3=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	3983.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3O2)C=C1	3999.9	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #6	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3986.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #7	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O)C(O[Si](C)(C)C)C1O	4002.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #8	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3969.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,4TMS,isomer #9	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O)C=C3O[Si](C)(C)C)O2)C=C1	3986.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	3971.1	Semi standard non polar	33892256
naringenin-7-O-glucuronide,5TMS,isomer #2	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3951.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,5TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C4O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1	3966.1	Semi standard non polar	33892256
naringenin-7-O-glucuronide,5TMS,isomer #4	C[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)OC3=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3952.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,5TMS,isomer #5	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3964.4	Semi standard non polar	33892256
naringenin-7-O-glucuronide,5TMS,isomer #6	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	3985.1	Semi standard non polar	33892256
naringenin-7-O-glucuronide,6TMS,isomer #1	C[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O[Si](C)(C)C)C=C4)O3)C(O[Si](C)(C)C)=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3940.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(O)C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C1O	4485.1	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C(O)C1O	4481.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O)C(O)C2O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4463.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O)C(O)C4O)C=C3O2)C=C1	4501.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1C(C(=O)O)OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C1O	4454.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,1TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C(O)C1O	4413.4	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C(O)C1O[Si](C)(C)C(C)(C)C	4635.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C(C)(C)C)=C2)C(O)C(O)C1O	4605.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4600.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O)C(O)C4O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	4655.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4)OC3=C2)C(O)C(O)C1O	4626.9	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O)C4O)C=C3O2)C=C1	4607.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	4583.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4627.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3O2)C=C1	4654.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	4593.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1C(C(=O)O)OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C1O[Si](C)(C)C(C)(C)C	4622.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4625.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	4638.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	4602.1	Semi standard non polar	33892256
naringenin-7-O-glucuronide,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C1O	4629.1	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4751.4	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	4722.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C(C)(C)C)=C2)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	4734.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4736.0	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	4772.6	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4)OC3=C2)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	4747.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O)C4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	4757.4	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #16	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	4733.2	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #17	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4)O3)C(O[Si](C)(C)C(C)(C)C)=C2)C(O)C(O)C1O	4789.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #18	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C(C)(C)C)=C2)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	4722.9	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O)C4O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	4757.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O)C(O[Si](C)(C)C(C)(C)C)C4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	4782.7	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #20	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4)OC3=C2)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	4737.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	4728.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O)C=C4)OC3=C2)OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	4733.9	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC3=C(C(=O)CC(C4=CC=C(O)C=C4)O3)C(O[Si](C)(C)C(C)(C)C)=C2)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	4727.3	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)=CC2=C1C(=O)CC(C1=CC=C(O)C=C1)O2	4735.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(C=C(OC4OC(C(=O)O)C(O)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1	4796.5	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C1OC(OC2=CC(O)=C3C(=O)CC(C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4)OC3=C2)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	4776.8	Semi standard non polar	33892256
naringenin-7-O-glucuronide,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(C2CC(=O)C3=C(O)C=C(OC4OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C4O)C=C3O2)C=C1	4764.9	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 - naringenin-7-O-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bu0-9115200000-27930d7f2fd2eddf6aac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - naringenin-7-O-glucuronide GC-MS (3 TMS) - 70eV, Positive	splash10-0f6t-5430339000-8a698e9e4ff6a40f95b8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - naringenin-7-O-glucuronide 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-O-glucuronide 10V, Positive-QTOF	splash10-00ea-0291700000-d64b93cbf7380fcecddd	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 20V, Positive-QTOF	splash10-05fr-0490100000-683c27201db7f337e2b8	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 40V, Positive-QTOF	splash10-0pi9-1950000000-1f0e65f8fca829ed6814	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 10V, Negative-QTOF	splash10-0fdk-2251900000-62c0f368cb0dc57c7e85	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 20V, Negative-QTOF	splash10-00di-1291200000-547fccb933ca5a185dc4	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 40V, Negative-QTOF	splash10-00di-4490000000-09c6284c98a6b41b69c8	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 10V, Negative-QTOF	splash10-0002-0030900000-9099ae6cceec31e27e6e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 20V, Negative-QTOF	splash10-00dj-0190700000-32bd1c30a5eaea8d8881	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 40V, Negative-QTOF	splash10-0fk9-0970200000-59bc4407439899017b5f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 10V, Positive-QTOF	splash10-00dj-0090500000-01e33ad94c06b74ac17b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 20V, Positive-QTOF	splash10-00di-0190000000-5be014833fa610089e5b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - naringenin-7-O-glucuronide 40V, Positive-QTOF	splash10-0fk9-0890000000-2b7570a316bc5cbaab9f	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

FDB031401

KNApSAcK ID

Not Available

Chemspider ID

57486817

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71772041

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

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → naringenin-7-O-glucuronide	details
naringenin-7-O-glucuronide → 6-({5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

naringenin-7-O-glucuronide → 3,4,5-trihydroxy-6-({5-hydroxy-4-oxo-2-[4-(sulfooxy)phenyl]-3,4-dihydro-2H-1-benzopyran-7-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for naringenin-7-O-glucuronide (HMDB0029209)

MOL for HMDB0029209 (naringenin-7-O-glucuronide)

3D MOL for HMDB0029209 (naringenin-7-O-glucuronide)

3D SDF for HMDB0029209 (naringenin-7-O-glucuronide)

3D-SDF for HMDB0029209 (naringenin-7-O-glucuronide)

PDB for HMDB0029209 (naringenin-7-O-glucuronide)

3D PDB for HMDB0029209 (naringenin-7-O-glucuronide)

SMILES for HMDB0029209 (naringenin-7-O-glucuronide)

INCHI for HMDB0029209 (naringenin-7-O-glucuronide)

Structure for HMDB0029209 (naringenin-7-O-glucuronide)

3D Structure for HMDB0029209 (naringenin-7-O-glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions