MiMeDB: Showing metabocard for cis-beta-D-Glucosyl-2-hydroxycinnamate (MMDBc0049627)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:38:26 UTC

Update Date

2024-04-30 20:38:26 UTC

Metabolite ID

MMDBc0049627

Metabolite Identification

Common Name

cis-beta-D-Glucosyl-2-hydroxycinnamate

Description

cis-Melilotoside, also known as cis-beta-D-glucosyl-2-hydroxycinnamate or cis-coumarinic acid-beta-D-glucoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans and flavonoids. cis-Melilotoside is an extremely weak basic (essentially neutral) compound (based on its pKa) and is a beta-D-glucoside consisting of cis-2-coumaric acid having a beta-D-glucosyl residue attached to the phenolic hydroxy group. cis-Melilotoside has been detected, but not quantified in, several different foods, such as globe artichokes, mentha (mint), Malabar spinach, plains prickly pears, and winter savouries. This could make cis-melilotoside a potential biomarker for the consumption of these foods.

Structure

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

HMDB0060077
     RDKit          3D
cis-Melilotoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3135   -0.2438    0.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1082    0.6908    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1855    1.6223    0.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9933    0.9719   -0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9026    0.3065   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695   -0.9583   -0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960   -1.9265   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1059   -3.0783    0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8295   -3.2831    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9179   -2.2772    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374   -1.1430    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -0.1679   -0.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9981   -0.0438    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8236    0.0292   -0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539    0.0687   -0.5595 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0233   -0.1272   -1.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7687   -1.3473   -2.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5075    1.4012    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1311    1.2735    1.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118    2.1545    0.2818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7561    2.6771   -0.9034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    1.2270    0.9531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7856    0.8386    2.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873    2.5622    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0697    1.9495   -1.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629    0.7621   -1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5259   -1.9094   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520   -3.8472    0.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245   -4.1713    1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030   -2.4591    1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378   -0.9423    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -0.7162    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1091   -0.0720   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721    0.6875   -2.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4552   -1.9708   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1291    2.0239   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570    0.3538    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3974    2.9969    0.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730    2.7584   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    1.7740    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6842    1.5549    2.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  6  1  0
 22 13  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  1
 15 32  1  1
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  1
 21 39  1  0
 22 40  1  1
 23 41  1  0
M  END


  Mrv1652309042000402D          

 23 24  0  0  0  0            999 V2000
10000.0216 9999.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5923 9998.9786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4492 9998.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.592310002.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1610 9999.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1631 9998.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.877710002.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.161010001.4539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.592310001.4538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.877810001.0413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.877810000.2162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5923 9999.8038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.306810000.2162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.306810001.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.449910001.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.735510001.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.735510000.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4499 9999.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.164410000.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.164410001.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8778 9998.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8784 9999.8022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5920 9998.5642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
  1 17  1  0  0  0  0
 18  3  1  0  0  0  0
 13  1  1  1  0  0  0
 12  2  1  6  0  0  0
  9  4  1  1  0  0  0
 11  5  1  1  0  0  0
 10  8  1  6  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0049627

> <DATABASE_NAME>
MIME

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(\C=C/C(O)=O)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5-/t10-,12-,13+,14-,15-/m1/s1

> <INCHI_KEY>
GVRIYIMNJGULCZ-QLFWQTQQSA-N

> <FORMULA>
C15H18O8

> <MOLECULAR_WEIGHT>
326.2986

> <EXACT_MASS>
326.100167552

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.48046575536168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-3-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-0.43554715499999985

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.200113282770712

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.202715684013416

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923461838152

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
77.18520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-melilotoside

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060077
     RDKit          3D
cis-Melilotoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3135   -0.2438    0.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1082    0.6908    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1855    1.6223    0.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9933    0.9719   -0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9026    0.3065   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695   -0.9583   -0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960   -1.9265   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1059   -3.0783    0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8295   -3.2831    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9179   -2.2772    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374   -1.1430    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -0.1679   -0.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9981   -0.0438    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8236    0.0292   -0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539    0.0687   -0.5595 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0233   -0.1272   -1.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7687   -1.3473   -2.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5075    1.4012    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1311    1.2735    1.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118    2.1545    0.2818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7561    2.6771   -0.9034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    1.2270    0.9531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7856    0.8386    2.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873    2.5622    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0697    1.9495   -1.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629    0.7621   -1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5259   -1.9094   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520   -3.8472    0.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245   -4.1713    1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030   -2.4591    1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378   -0.9423    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -0.7162    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1091   -0.0720   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721    0.6875   -2.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4552   -1.9708   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1291    2.0239   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570    0.3538    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3974    2.9969    0.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730    2.7584   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    1.7740    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6842    1.5549    2.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  6  1  0
 22 13  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  1
 15 32  1  1
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  1
 21 39  1  0
 22 40  1  1
 23 41  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.7078666.301   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8664.0398664.760   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8669.3728664.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.0398670.921   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8661.3678666.301   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8670.7048663.988   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8662.7058671.691   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8661.3678669.381   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8664.0398669.380   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.7058668.610   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.7058667.070   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0398666.300   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3738667.070   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8665.3738668.610   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8669.3738669.380   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.0408668.610   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8668.0408667.070   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.3738666.300   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.7078667.070   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.7078668.610   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.0398664.757   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8672.0408666.297   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8673.3728663.987   0.000  0.00  0.00           O+0
CONECT    1   17   13                                                       
CONECT    2   12                                                            
CONECT    3    6   18                                                       
CONECT    4    7    9                                                       
CONECT    5   11                                                            
CONECT    6    3   21                                                       
CONECT    7    4                                                            
CONECT    8   10                                                            
CONECT    9   10   14    4                                                  
CONECT   10    9   11    8                                                  
CONECT   11   10   12    5                                                  
CONECT   12   11   13    2                                                  
CONECT   13   12   14    1                                                  
CONECT   14    9   13                                                       
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18    1                                                  
CONECT   18   17   19    3                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    6   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0060077
HETATM    1  O1  UNL     1       5.314  -0.244   0.884  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.108   0.691   0.087  1.00  0.00           C  
HETATM    3  O2  UNL     1       6.186   1.622   0.019  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.993   0.972  -0.751  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.903   0.307  -0.957  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.569  -0.958  -0.356  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.496  -1.926  -0.122  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.106  -3.078   0.573  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.830  -3.283   1.028  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.918  -2.277   0.766  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.237  -1.143   0.102  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.341  -0.168  -0.149  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.998  -0.044   0.154  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.824   0.029  -0.972  1.00  0.00           O  
HETATM   15  C11 UNL     1      -3.154   0.069  -0.560  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.023  -0.127  -1.784  1.00  0.00           C  
HETATM   17  O5  UNL     1      -3.769  -1.347  -2.401  1.00  0.00           O  
HETATM   18  C13 UNL     1      -3.507   1.401   0.064  1.00  0.00           C  
HETATM   19  O6  UNL     1      -4.131   1.273   1.290  1.00  0.00           O  
HETATM   20  C14 UNL     1      -2.212   2.155   0.282  1.00  0.00           C  
HETATM   21  O7  UNL     1      -1.756   2.677  -0.903  1.00  0.00           O  
HETATM   22  C15 UNL     1      -1.250   1.227   0.953  1.00  0.00           C  
HETATM   23  O8  UNL     1      -1.786   0.839   2.179  1.00  0.00           O  
HETATM   24  H1  UNL     1       5.987   2.562   0.395  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.070   1.950  -1.342  1.00  0.00           H  
HETATM   26  H3  UNL     1       2.163   0.762  -1.663  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.526  -1.909  -0.509  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.852  -3.847   0.760  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.525  -4.171   1.565  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.103  -2.459   1.137  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.338  -0.942   0.704  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.377  -0.716   0.165  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.109  -0.072  -1.511  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.872   0.687  -2.528  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.455  -1.971  -1.688  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.129   2.024  -0.616  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.157   0.354   1.641  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.397   2.997   0.976  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.773   2.758  -0.957  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.318   1.774   1.170  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.684   1.555   2.876  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   24
CONECT    4    5    5   25
CONECT    5    6   26
CONECT    6    7    7   11
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12
CONECT   12   13
CONECT   13   14   22   31
CONECT   14   15
CONECT   15   16   18   32
CONECT   16   17   33   34
CONECT   17   35
CONECT   18   19   20   36
CONECT   19   37
CONECT   20   21   22   38
CONECT   21   39
CONECT   22   23   40
CONECT   23   41
END

HMDB0060077
     RDKit          3D
cis-Melilotoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3135   -0.2438    0.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1082    0.6908    0.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1855    1.6223    0.0189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9933    0.9719   -0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9026    0.3065   -0.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695   -0.9583   -0.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960   -1.9265   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1059   -3.0783    0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8295   -3.2831    1.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9179   -2.2772    0.7659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374   -1.1430    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -0.1679   -0.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9981   -0.0438    0.1539 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8236    0.0292   -0.9719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1539    0.0687   -0.5595 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0233   -0.1272   -1.7839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7687   -1.3473   -2.4008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5075    1.4012    0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1311    1.2735    1.2898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118    2.1545    0.2818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7561    2.6771   -0.9034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504    1.2270    0.9531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7856    0.8386    2.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873    2.5622    0.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0697    1.9495   -1.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629    0.7621   -1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5259   -1.9094   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520   -3.8472    0.7598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245   -4.1713    1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1030   -2.4591    1.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378   -0.9423    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -0.7162    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1091   -0.0720   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721    0.6875   -2.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4552   -1.9708   -1.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1291    2.0239   -0.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570    0.3538    1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3974    2.9969    0.9763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730    2.7584   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182    1.7740    1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6842    1.5549    2.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  6  1  0
 22 13  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  1
 15 32  1  1
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  1
 21 39  1  0
 22 40  1  1
 23 41  1  0
M  END

Synonyms

Value	Source
(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylic acid	ChEBI
beta-D-Glucosyl-2-coumarinate	ChEBI
beta-D-Glucosyl-2-coumarinic acid	ChEBI
cis-beta-D-Glucosyl-2-hydroxycinnamic acid	ChEBI
cis-Coumarinic acid-beta-D-glucoside	ChEBI
cis-Melilotoside	ChEBI
(2Z)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2Z)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylic acid	Generator
(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]acrylic acid	Generator
cis-Coumarinate-β-D-glucoside	Generator
b-D-Glucosyl-2-coumarinate	Generator
b-D-Glucosyl-2-coumarinic acid	Generator
β-D-Glucosyl-2-coumarinate	Generator
β-D-Glucosyl-2-coumarinic acid	Generator
cis-b-D-Glucosyl-2-hydroxycinnamate	Generator
cis-b-D-Glucosyl-2-hydroxycinnamic acid	Generator
cis-beta-D-Glucosyl-2-hydroxycinnamate	Generator
cis-β-D-Glucosyl-2-hydroxycinnamate	Generator
cis-β-D-Glucosyl-2-hydroxycinnamic acid	Generator
cis-Coumarinate-b-D-glucoside	Generator
cis-Coumarinate-beta-D-glucoside	Generator
cis-Coumarinic acid-b-D-glucoside	Generator
cis-Coumarinic acid-β-D-glucoside	Generator
(2Z)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
(2Z)-3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
2'-(beta-D-Glucopyranosyloxy)cinnamic acid	HMDB
2'-(β-D-Glucopyranosyloxy)cinnamic acid	HMDB
2’-(β-D-Glucopyranosyloxy)cinnamic acid	HMDB
3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
3-[2-(β-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
Coumarin glucoside	HMDB
Coumarinate glucoside	HMDB
Coumarinic acid glucoside	HMDB
beta-D-Glucosyl-2-coumarate	HMDB
beta-D-Glucosyl-2-coumaric acid	HMDB
cis-o-Hydroxycinnamic acid glucoside	HMDB
o-(Glucosyloxy)cinnamic acid	HMDB
o-Coumaroyl beta-D-glucopyranoside	HMDB
o-Coumaroyl β-D-glucopyranoside	HMDB
β-D-Glucosyl-2-coumarate	HMDB
β-D-Glucosyl-2-coumaric acid	HMDB

Molecular Formula

C₁₅H₁₈O₈

Average Mass

326.2986

Monoisotopic Mass

326.100167552

IUPAC Name

(2Z)-3-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid

Traditional Name

cis-melilotoside

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C(\C=C/C(O)=O)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5-/t10-,12-,13+,14-,15-/m1/s1

InChI Key

GVRIYIMNJGULCZ-QLFWQTQQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Cinnamic acid
Cinnamic acid or derivatives
Coumaric acid
Coumaric acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Styrene
Phenol ether
Phenoxy compound
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Secondary alcohol
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:62251 )
Monolignols (C05839 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	6.6 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	-0.44	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.19 m³·mol⁻¹	ChemAxon
Polarizability	31.48 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-5943000000-c492ad4cea7748c10d1d	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-00di-1020229000-cd5e122c29a7c414bbb3	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aos-0937000000-443e87b5dc30d11c2254	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0900000000-efd45bdfdb0cc42c2cb9	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-2900000000-be6e64ff24e527eb6506	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01t9-0829000000-6df80077de9156a07096	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-1911000000-4ab9ec4cd0e2b2cb4feb	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0295-2900000000-78489653a0fdafbd5401	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00mk-0904000000-3dd34e382ba43fc1764f	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0arr-0596000000-829180a1d0df8715f61c	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-2900000000-e9a87fed398fa7e220c1	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-07f0-0598000000-7c06dab5e1ee09a3e269	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0j4i-1931000000-be23d1fceb38e06a6c84	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3900000000-c4aef0c58740bba64b21	2021-10-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193791	Cytosolic beta-glucosidase	Unknown	Q9H227	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000378	cis-beta-D-Glucosyl-2-hydroxycinnamate	Coumaric acid	glucosidase, beta, acid 3 (gene/pseudogene)		VMH	6796580

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0060077

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030731

KNApSAcK ID

Not Available

Chemspider ID

22912899

KEGG Compound ID

C05839

BioCyc ID

CPD-7417

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316113

PDB ID

Not Available

ChEBI ID

62251

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]

Showing metabocard for cis-beta-D-Glucosyl-2-hydroxycinnamate (MMDBc0049627)

MOL for #<Metabolite:0x00007fdafe72f6b0>

3D MOL for #<Metabolite:0x00007fdafe72f6b0>

3D SDF for #<Metabolite:0x00007fdafe72f6b0>

3D-SDF for #<Metabolite:0x00007fdafe72f6b0>

PDB for #<Metabolite:0x00007fdafe72f6b0>

3D PDB for #<Metabolite:0x00007fdafe72f6b0>

SMILES for #<Metabolite:0x00007fdafe72f6b0>

INCHI for #<Metabolite:0x00007fdafe72f6b0>

Structure for #<Metabolite:0x00007fdafe72f6b0>

3D Structure for #<Metabolite:0x00007fdafe72f6b0>