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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 01:20:45 UTC

Update Date

2021-09-24 01:20:45 UTC

HMDB ID

HMDB0303364

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Glucosyringic acid

Description

Glucosyringic acid, also known as glucosyringate, is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Glucosyringic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Glucosyringic acid can be found in fennel, which makes glucosyringic acid a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303364
     RDKit          3D
Glucosyringic acid
 45 46  0  0  0  0  0  0  0  0999 V2000
    1.6100    3.6642    1.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1456    2.4829    0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    1.3727    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413    1.3672    0.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0027    0.2340    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3947    0.2352    1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1460   -0.7556    0.9344 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505    1.3423    1.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4370   -0.8640    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1142   -0.8615   -0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5722   -1.9776   -0.9760 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017   -3.1487   -1.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586    0.2773   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    0.3125   -0.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0537   -0.0907    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052   -1.1662   -0.2930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -0.9739   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145   -2.2827   -1.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496   -1.9656   -2.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5043    0.1438   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7987   -0.2686   -1.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3841    0.6722    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6638   -0.2670    1.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9116    1.0980    0.5058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6541    1.6697    1.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4532    4.1098    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0238    3.3338    2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867    4.3589    1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522    2.2560    1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3822    1.8311    2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -1.7154   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315   -3.8082   -1.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3403   -2.9013   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3546   -3.7117   -0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5792   -0.4050    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177   -0.7618   -2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5740   -2.9770   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7449   -2.7205   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0769   -2.5050   -2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2488    0.9995   -1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003    0.1543   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0295    1.5549    0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4793   -0.0968    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.8094   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5522    0.9450    2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 13  3  1  0
 24 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
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 15 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
M  END


  Mrv0541 02241216592D          

 25 26  0  0  0  0            999 V2000
   -0.2587   -3.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -2.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7155   -3.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4308   -0.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1598   -0.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1341   -0.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4051   -0.1459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7155   -0.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7155   -1.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -1.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587   -1.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587   -0.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878    0.6961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822    1.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    0.6515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601    1.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457    0.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341    1.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3034    2.2566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822    1.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    2.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7601    1.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4457    2.1805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0705    3.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 21  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303364

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O10/c1-22-7-3-6(14(20)21)4-8(23-2)13(7)25-15-12(19)11(18)10(17)9(5-16)24-15/h3-4,9-12,15-19H,5H2,1-2H3,(H,20,21)

> <INCHI_KEY>
BLKMDORKRDACEI-UHFFFAOYSA-N

> <FORMULA>
C15H20O10

> <MOLECULAR_WEIGHT>
360.3133

> <EXACT_MASS>
360.10564686

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
33.99617566422313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,5-dimethoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

> <ALOGPS_LOGP>
-0.86

> <JCHEM_LOGP>
-1.2561472223333336

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.199887087122312

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8748979775031454

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092366207709

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
80.36590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dimethoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303364
     RDKit          3D
Glucosyringic acid
 45 46  0  0  0  0  0  0  0  0999 V2000
    1.6100    3.6642    1.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1456    2.4829    0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    1.3727    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413    1.3672    0.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0027    0.2340    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3947    0.2352    1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1460   -0.7556    0.9344 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505    1.3423    1.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4370   -0.8640    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1142   -0.8615   -0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5722   -1.9776   -0.9760 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017   -3.1487   -1.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586    0.2773   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    0.3125   -0.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0537   -0.0907    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052   -1.1662   -0.2930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -0.9739   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145   -2.2827   -1.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496   -1.9656   -2.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5043    0.1438   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7987   -0.2686   -1.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3841    0.6722    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6638   -0.2670    1.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9116    1.0980    0.5058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6541    1.6697    1.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4532    4.1098    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0238    3.3338    2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867    4.3589    1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522    2.2560    1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3822    1.8311    2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -1.7154   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315   -3.8082   -1.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3403   -2.9013   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3546   -3.7117   -0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5792   -0.4050    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177   -0.7618   -2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5740   -2.9770   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7449   -2.7205   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0769   -2.5050   -2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2488    0.9995   -1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003    0.1543   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0295    1.5549    0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4793   -0.0968    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.8094   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5522    0.9450    2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 13  3  1  0
 24 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.483  -5.639   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.844  -4.852   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.202  -5.639   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.804  -0.272   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.165  -1.059   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.850  -1.059   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.490  -0.272   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.202  -0.988   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.202  -2.562   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.844  -3.349   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.483  -2.562   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.483  -0.988   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.844  -0.272   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.844   1.299   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.713   1.929   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.998   1.216   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.286   1.929   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.565   1.216   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.850   1.929   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.566   4.212   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.713   3.352   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.998   4.212   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.286   3.352   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.565   4.070   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.998   5.639   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2                                                            
CONECT    4    5   12                                                       
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    2    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12    4   11   13                                                  
CONECT   13    8   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   15   20   22                                                  
CONECT   22   21   23   25                                                  
CONECT   23   17   22   24                                                  
CONECT   24   23                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0303364
HETATM    1  C1  UNL     1       1.610   3.664   1.325  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.146   2.483   0.703  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.919   1.373   0.491  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.241   1.367   0.898  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.003   0.234   0.674  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.395   0.235   1.105  1.00  0.00           C  
HETATM    7  O2  UNL     1       6.146  -0.756   0.934  1.00  0.00           O  
HETATM    8  O3  UNL     1       5.950   1.342   1.727  1.00  0.00           O  
HETATM    9  C6  UNL     1       3.437  -0.864   0.053  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.114  -0.861  -0.355  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.572  -1.978  -0.976  1.00  0.00           O  
HETATM   12  C8  UNL     1       2.302  -3.149  -1.226  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.359   0.277  -0.127  1.00  0.00           C  
HETATM   14  O5  UNL     1       0.055   0.312  -0.516  1.00  0.00           O  
HETATM   15  C10 UNL     1      -1.054  -0.091   0.294  1.00  0.00           C  
HETATM   16  O6  UNL     1      -1.605  -1.166  -0.293  1.00  0.00           O  
HETATM   17  C11 UNL     1      -2.559  -0.974  -1.255  1.00  0.00           C  
HETATM   18  C12 UNL     1      -3.314  -2.283  -1.548  1.00  0.00           C  
HETATM   19  O7  UNL     1      -4.250  -1.966  -2.532  1.00  0.00           O  
HETATM   20  C13 UNL     1      -3.504   0.144  -1.015  1.00  0.00           C  
HETATM   21  O8  UNL     1      -4.799  -0.269  -1.300  1.00  0.00           O  
HETATM   22  C14 UNL     1      -3.384   0.672   0.406  1.00  0.00           C  
HETATM   23  O9  UNL     1      -3.664  -0.267   1.362  1.00  0.00           O  
HETATM   24  C15 UNL     1      -1.912   1.098   0.506  1.00  0.00           C  
HETATM   25  O10 UNL     1      -1.654   1.670   1.749  1.00  0.00           O  
HETATM   26  H1  UNL     1       2.453   4.110   0.788  1.00  0.00           H  
HETATM   27  H2  UNL     1       2.024   3.334   2.320  1.00  0.00           H  
HETATM   28  H3  UNL     1       0.787   4.359   1.563  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.652   2.256   1.386  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.382   1.831   2.407  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.096  -1.715  -0.088  1.00  0.00           H  
HETATM   32  H7  UNL     1       1.832  -3.808  -1.967  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.340  -2.901  -1.560  1.00  0.00           H  
HETATM   34  H9  UNL     1       2.355  -3.712  -0.265  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.579  -0.405   1.269  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.018  -0.762  -2.202  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.574  -2.977  -1.999  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.745  -2.721  -0.650  1.00  0.00           H  
HETATM   39  H14 UNL     1      -5.077  -2.505  -2.445  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.249   0.999  -1.670  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.400   0.154  -0.656  1.00  0.00           H  
HETATM   42  H17 UNL     1      -4.030   1.555   0.521  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.479  -0.097   1.890  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.767   1.809  -0.331  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.552   0.945   2.395  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   29
CONECT    5    6    9    9
CONECT    6    7    7    8
CONECT    8   30
CONECT    9   10   31
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   32   33   34
CONECT   13   14
CONECT   14   15
CONECT   15   16   24   35
CONECT   16   17
CONECT   17   18   20   36
CONECT   18   19   37   38
CONECT   19   39
CONECT   20   21   22   40
CONECT   21   41
CONECT   22   23   24   42
CONECT   23   43
CONECT   24   25   44
CONECT   25   45
END

HMDB0303364
     RDKit          3D
Glucosyringic acid
 45 46  0  0  0  0  0  0  0  0999 V2000
    1.6100    3.6642    1.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1456    2.4829    0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9185    1.3727    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2413    1.3672    0.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0027    0.2340    0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3947    0.2352    1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1460   -0.7556    0.9344 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505    1.3423    1.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4370   -0.8640    0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1142   -0.8615   -0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5722   -1.9776   -0.9760 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017   -3.1487   -1.2264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586    0.2773   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    0.3125   -0.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0537   -0.0907    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052   -1.1662   -0.2930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5591   -0.9739   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3145   -2.2827   -1.5483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2496   -1.9656   -2.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5043    0.1438   -1.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7987   -0.2686   -1.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3841    0.6722    0.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6638   -0.2670    1.3624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9116    1.0980    0.5058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6541    1.6697    1.7493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4532    4.1098    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0238    3.3338    2.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867    4.3589    1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6522    2.2560    1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3822    1.8311    2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0959   -1.7154   -0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315   -3.8082   -1.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3403   -2.9013   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3546   -3.7117   -0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5792   -0.4050    1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0177   -0.7618   -2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5740   -2.9770   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7449   -2.7205   -0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0769   -2.5050   -2.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2488    0.9995   -1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003    0.1543   -0.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0295    1.5549    0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4793   -0.0968    1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    1.8094   -0.3310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5522    0.9450    2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 13  3  1  0
 24 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Syringate-4-b-D-glucopyranoside	Generator
Syringate-4-beta-D-glucopyranoside	Generator
Syringate-4-β-D-glucopyranoside	Generator
Syringic acid-4-b-D-glucopyranoside	Generator
Syringic acid-4-β-D-glucopyranoside	Generator
Glucosyringate	Generator

Chemical Formula

C₁₅H₂₀O₁₀

Average Molecular Weight

360.3133

Monoisotopic Molecular Weight

360.10564686

IUPAC Name

3,5-dimethoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

Traditional Name

3,5-dimethoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C15H20O10/c1-22-7-3-6(14(20)21)4-8(23-2)13(7)25-15-12(19)11(18)10(17)9(5-16)24-15/h3-4,9-12,15-19H,5H2,1-2H3,(H,20,21)

InChI Key

BLKMDORKRDACEI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Phenolic glycoside
Hexose monosaccharide
Gallic acid or derivatives
M-methoxybenzoic acid or derivatives
O-glycosyl compound
Glycosyl compound
M-dimethoxybenzene
Dimethoxybenzene
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Sugar acid
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Ether
Polyol
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Fennel (FooDB: FOOD00082)

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	-0.86	ALOGPS
logP	-1.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	80.37 m³·mol⁻¹	ChemAxon
Polarizability	34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	182.614	32859911
AllCCS	[M+H-H2O]+	179.757	32859911
AllCCS	[M+Na]+	186.007	32859911
AllCCS	[M+NH4]+	185.251	32859911
AllCCS	[M-H]-	179.472	32859911
AllCCS	[M+Na-2H]-	179.632	32859911
AllCCS	[M+HCOO]-	179.938	32859911
DeepCCS	[M+H]+	182.61	30932474
DeepCCS	[M-H]-	180.252	30932474
DeepCCS	[M-2H]-	213.138	30932474
DeepCCS	[M+Na]+	188.703	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 10V, Positive-QTOF	splash10-01ow-0819000000-475d20183392dbe2ace4	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 20V, Positive-QTOF	splash10-000t-0901000000-eb9db5011e6561aa0d56	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 40V, Positive-QTOF	splash10-001j-1900000000-dbdd8a277b1af149077f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 10V, Negative-QTOF	splash10-0a4j-1619000000-017e226a19fcdd9712b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 20V, Negative-QTOF	splash10-0002-0912000000-350194f74f159801533a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 40V, Negative-QTOF	splash10-001j-2900000000-3601c8a4996d847507bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 10V, Positive-QTOF	splash10-001i-0900000000-8b3684a1f6a94f3a2f91	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 20V, Positive-QTOF	splash10-0f6t-0901000000-1865c7664f6626e810e3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 40V, Positive-QTOF	splash10-0015-7931000000-6605404bf3cef0098b73	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 10V, Negative-QTOF	splash10-0aor-0009000000-2f04ca08d1e8960708aa	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 20V, Negative-QTOF	splash10-052b-2489000000-0b9f2136b8e462a375aa	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glucosyringic acid 40V, Negative-QTOF	splash10-0bu1-3910000000-785afdaefbd4218d0daa	2021-10-21	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

FDB012010

KNApSAcK ID

Not Available

Chemspider ID

57487561

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14132338

PDB ID

Not Available

ChEBI ID

167538

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 Glucosyringic acid (HMDB0303364)

MOL for HMDB0303364 (Glucosyringic acid)

3D MOL for HMDB0303364 (Glucosyringic acid)

3D SDF for HMDB0303364 (Glucosyringic acid)

3D-SDF for HMDB0303364 (Glucosyringic acid)

PDB for HMDB0303364 (Glucosyringic acid)

3D PDB for HMDB0303364 (Glucosyringic acid)

SMILES for HMDB0303364 (Glucosyringic acid)

INCHI for HMDB0303364 (Glucosyringic acid)

Structure for HMDB0303364 (Glucosyringic acid)

3D Structure for HMDB0303364 (Glucosyringic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra