Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:19:35 UTC

Update Date

2022-03-07 02:53:46 UTC

HMDB ID

HMDB0033581

Secondary Accession Numbers

HMDB33581

Metabolite Identification

Common Name

Melilotoside

Description

Melilotoside, also known as trans-beta-D-glucosyl-2-hydroxycinnamic acid or beta-D-glucosyl-2-coumarate, 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. Melilotoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Melilotoside is found in herbs and spices. Melilotoside has been isolated from Melilotus alba (white melilot), Melilotus altissimus (tall yellow sweet clover), and other plants.

Structure

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

HMDB0033581
     RDKit          3D
Melilotoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3547    1.4928    3.2811 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    1.1600    2.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2022    0.7715    3.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1700    1.1945    1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347    0.8459    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270    0.8442   -0.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829    1.2015   -1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    1.1866   -2.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223    0.8037   -3.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    0.4316   -2.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5642    0.4496   -1.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239    0.0967   -0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896   -0.3288   -0.4476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5088    0.6342    0.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8149    0.2111    0.0634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8215    1.3117    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0902    0.7384    0.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -0.8800    1.0803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3072   -1.1925    1.3300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -2.0703    0.5444 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1998   -3.1074    1.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170   -1.6789    0.2036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2979   -2.6251   -0.6813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2263   -0.1052    4.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223    1.5040    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    0.5477    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7788    1.5147   -1.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3314    1.4785   -3.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0934    0.7767   -4.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478    0.1280   -2.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446   -0.3636   -1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -0.2491   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7105    1.9680   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6887    1.9213    1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8065    1.3351    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663   -0.5637    2.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6803   -0.5614    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7476   -2.4221   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0700   -3.5736    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -1.7440    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0452   -3.0822   -1.1403 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  6
 15 32  1  6
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  1
 19 37  1  0
 20 38  1  6
 21 39  1  0
 22 40  1  1
 23 41  1  0
M  END

  Mrv1652303272016282D          

 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
10002.1631 9997.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8789 9997.3282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.4492 9997.3282    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
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  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
 12 17  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
  1 20  1  0  0  0  0
 21  3  1  0  0  0  0
 16  1  1  1  0  0  0
 15  2  1  6  0  0  0
 12  4  1  1  0  0  0
 14  5  1  1  0  0  0
 13  8  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0033581

> <DATABASE_NAME>
hmdb

> <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-ZMKUSUEASA-N

> <FORMULA>
C15H18O8

> <MOLECULAR_WEIGHT>
326.301

> <EXACT_MASS>
326.10016754

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.424053962801366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-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>
12.20011328362007

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7027156712501847

> <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>
β-D-glucosyl-2-coumarate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033581
     RDKit          3D
Melilotoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3547    1.4928    3.2811 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    1.1600    2.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2022    0.7715    3.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1700    1.1945    1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347    0.8459    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270    0.8442   -0.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829    1.2015   -1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    1.1866   -2.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223    0.8037   -3.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    0.4316   -2.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5642    0.4496   -1.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239    0.0967   -0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896   -0.3288   -0.4476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5088    0.6342    0.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8149    0.2111    0.0634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8215    1.3117    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0902    0.7384    0.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -0.8800    1.0803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3072   -1.1925    1.3300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -2.0703    0.5444 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1998   -3.1074    1.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170   -1.6789    0.2036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2979   -2.6251   -0.6813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2263   -0.1052    4.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223    1.5040    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    0.5477    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7788    1.5147   -1.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3314    1.4785   -3.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0934    0.7767   -4.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478    0.1280   -2.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446   -0.3636   -1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -0.2491   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7105    1.9680   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6887    1.9213    1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8065    1.3351    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663   -0.5637    2.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6803   -0.5614    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7476   -2.4221   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0700   -3.5736    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -1.7440    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0452   -3.0822   -1.1403 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  6
 15 32  1  6
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  1
 19 37  1  0
 20 38  1  6
 21 39  1  0
 22 40  1  1
 23 41  1  0
M  END

HEADER    PROTEIN                                 27-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAR-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    8670.7048662.448   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8672.0418661.679   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8669.3728661.679   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8664.0398669.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.7058668.610   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.7058667.070   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.0398666.300   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.3738667.070   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8665.3738668.610   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8669.3738669.380   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.0408668.610   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.0408667.070   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3738666.300   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.7078667.070   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.7078668.610   0.000  0.00  0.00           C+0
CONECT    1   20   16                                                       
CONECT    2   15                                                            
CONECT    3    6   21                                                       
CONECT    4    7   12                                                       
CONECT    5   14                                                            
CONECT    6    3    9                                                       
CONECT    7    4                                                            
CONECT    8   13                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12   13   17    4                                                  
CONECT   13   12   14    8                                                  
CONECT   14   13   15    5                                                  
CONECT   15   14   16    2                                                  
CONECT   16   15   17    1                                                  
CONECT   17   12   16                                                       
CONECT   18   19   23                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21    1                                                  
CONECT   21   20   22    3                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0033581
HETATM    1  O1  UNL     1       5.355   1.493   3.281  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.270   1.160   2.742  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.202   0.772   3.516  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.170   1.194   1.289  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.035   0.846   0.725  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.827   0.844  -0.712  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.783   1.201  -1.612  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.546   1.187  -2.975  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.322   0.804  -3.427  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.321   0.432  -2.527  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.564   0.450  -1.189  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.624   0.097  -0.274  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.690  -0.329  -0.448  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.509   0.634   0.139  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.815   0.211   0.063  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.822   1.312   0.190  1.00  0.00           C  
HETATM   17  O5  UNL     1      -5.090   0.738   0.095  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.992  -0.880   1.080  1.00  0.00           C  
HETATM   19  O6  UNL     1      -4.307  -1.193   1.330  1.00  0.00           O  
HETATM   20  C14 UNL     1      -2.208  -2.070   0.544  1.00  0.00           C  
HETATM   21  O7  UNL     1      -2.200  -3.107   1.478  1.00  0.00           O  
HETATM   22  C15 UNL     1      -0.817  -1.679   0.204  1.00  0.00           C  
HETATM   23  O8  UNL     1      -0.298  -2.625  -0.681  1.00  0.00           O  
HETATM   24  H1  UNL     1       3.226  -0.105   4.041  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.022   1.504   0.680  1.00  0.00           H  
HETATM   26  H3  UNL     1       2.226   0.548   1.402  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.779   1.515  -1.276  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.331   1.479  -3.678  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.093   0.777  -4.471  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.348   0.128  -2.911  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.945  -0.364  -1.514  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.954  -0.249  -0.954  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.711   1.968  -0.702  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.689   1.921   1.086  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.807   1.335   0.431  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.466  -0.564   2.009  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.680  -0.561   2.009  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.748  -2.422  -0.359  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.070  -3.574   1.387  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.184  -1.744   1.127  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.045  -3.082  -1.140  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

HMDB0033581
     RDKit          3D
Melilotoside
 41 42  0  0  0  0  0  0  0  0999 V2000
    5.3547    1.4928    3.2811 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    1.1600    2.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2022    0.7715    3.5162 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1700    1.1945    1.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347    0.8459    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270    0.8442   -0.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829    1.2015   -1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    1.1866   -2.9752 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223    0.8037   -3.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    0.4316   -2.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5642    0.4496   -1.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239    0.0967   -0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896   -0.3288   -0.4476 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5088    0.6342    0.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8149    0.2111    0.0634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8215    1.3117    0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0902    0.7384    0.0953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -0.8800    1.0803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3072   -1.1925    1.3300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -2.0703    0.5444 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1998   -3.1074    1.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8170   -1.6789    0.2036 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2979   -2.6251   -0.6813 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2263   -0.1052    4.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223    1.5040    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    0.5477    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7788    1.5147   -1.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3314    1.4785   -3.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0934    0.7767   -4.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478    0.1280   -2.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446   -0.3636   -1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -0.2491   -0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7105    1.9680   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6887    1.9213    1.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8065    1.3351    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663   -0.5637    2.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6803   -0.5614    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7476   -2.4221   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0700   -3.5736    1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -1.7440    1.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0452   -3.0822   -1.1403 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  6
 15 32  1  6
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  1
 19 37  1  0
 20 38  1  6
 21 39  1  0
 22 40  1  1
 23 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2E)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylic acid	ChEBI
beta-D-Glucosyl-2-coumarate	ChEBI
trans-beta-D-Glucosyl-2-hydroxycinnamate	ChEBI
(2E)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2E)-3-[2-(b-D-Glucopyranosyloxy)phenyl]acrylic acid	Generator
(2E)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]acrylate	Generator
(2E)-3-[2-(Β-D-glucopyranosyloxy)phenyl]acrylate	Generator
(2E)-3-[2-(Β-D-glucopyranosyloxy)phenyl]acrylic acid	Generator
b-D-Glucosyl-2-coumarate	Generator
b-D-Glucosyl-2-coumaric acid	Generator
beta-D-Glucosyl-2-coumaric acid	Generator
Β-D-glucosyl-2-coumarate	Generator
Β-D-glucosyl-2-coumaric acid	Generator
trans-b-D-Glucosyl-2-hydroxycinnamate	Generator
trans-b-D-Glucosyl-2-hydroxycinnamic acid	Generator
trans-beta-D-Glucosyl-2-hydroxycinnamic acid	Generator
trans-Β-D-glucosyl-2-hydroxycinnamate	Generator
trans-Β-D-glucosyl-2-hydroxycinnamic acid	Generator
(2E)-3-[2-(beta-D-Glucopyranosyloxy)phenyl]-2-propenoic acid	HMDB
(2E)-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
O-(Glucosyloxy)cinnamic acid	HMDB
O-Coumaroyl beta-D-glucopyranoside	HMDB
O-Coumaroyl β-D-glucopyranoside	HMDB
trans-Melilotoside	HMDB
trans-O-Coumarate 2-glucoside	HMDB
trans-O-Coumaric acid 2-glucoside	HMDB
trans-O-Hydroxycinnamic acid glucoside	HMDB
Coumarinate glucoside	HMDB
Coumarinic acid glucoside	HMDB
trans-Coumarinic acid-beta-D-glucoside	HMDB
trans-Coumarinic acid-β-D-glucoside	HMDB
Melilotoside	HMDB

Chemical Formula

C₁₅H₁₈O₈

Average Molecular Weight

326.301

Monoisotopic Molecular Weight

326.10016754

IUPAC Name

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

Traditional Name

β-D-glucosyl-2-coumarate

CAS Registry Number

618-67-7

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-ZMKUSUEASA-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

glucosyl hydroxycinnamic acid (CHEBI:17531 )
Monolignols (C05158 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033581)
Cytoplasm (HMDB: HMDB0033581)

Source

Exogenous

Exogenous (HMDB: HMDB0033581)

Food

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

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
Water Solubility	6.6 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	-0.44	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.7	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	31.42 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
DeepCCS	[M+H]+	169.046	30932474
DeepCCS	[M-H]-	166.651	30932474
DeepCCS	[M-2H]-	200.402	30932474
DeepCCS	[M+Na]+	175.331	30932474
AllCCS	[M+H]+	175.7	32859911
AllCCS	[M+H-H2O]+	172.6	32859911
AllCCS	[M+NH4]+	178.6	32859911
AllCCS	[M+Na]+	179.4	32859911
AllCCS	[M-H]-	172.3	32859911
AllCCS	[M+Na-2H]-	172.3	32859911
AllCCS	[M+HCOO]-	172.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Melilotoside	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	4771.8	Standard polar	33892256
Melilotoside	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	3017.0	Standard non polar	33892256
Melilotoside	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	2921.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Melilotoside,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@@H](O)[C@@H]1O	2891.0	Semi standard non polar	33892256
Melilotoside,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	2908.5	Semi standard non polar	33892256
Melilotoside,1TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@H](CO)[C@@H](O)[C@@H]1O	2878.9	Semi standard non polar	33892256
Melilotoside,1TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@H](CO)[C@H]1O	2875.2	Semi standard non polar	33892256
Melilotoside,1TMS,isomer #5	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@H]1O	2882.5	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H]1O	2842.2	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #10	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@H]1O[Si](C)(C)C	2834.1	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	2828.6	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	2839.9	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	2843.6	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #5	C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2855.0	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #6	C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2852.3	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #7	C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2864.4	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #8	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@@H]1CO	2847.0	Semi standard non polar	33892256
Melilotoside,2TMS,isomer #9	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@H](CO)[C@H]1O	2834.9	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	2804.0	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #10	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@H](CO)[C@H]1O[Si](C)(C)C	2830.3	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	2814.4	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	2809.1	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2823.5	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #5	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2848.5	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #6	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2830.7	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #7	C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2810.8	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #8	C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2825.2	Semi standard non polar	33892256
Melilotoside,3TMS,isomer #9	C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2810.6	Semi standard non polar	33892256
Melilotoside,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	2804.7	Semi standard non polar	33892256
Melilotoside,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	2836.8	Semi standard non polar	33892256
Melilotoside,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2819.1	Semi standard non polar	33892256
Melilotoside,4TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2867.3	Semi standard non polar	33892256
Melilotoside,4TMS,isomer #5	C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2809.5	Semi standard non polar	33892256
Melilotoside,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2838.6	Semi standard non polar	33892256
Melilotoside,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@@H](O)[C@@H]1O	3143.8	Semi standard non polar	33892256
Melilotoside,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	3158.1	Semi standard non polar	33892256
Melilotoside,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@H](CO)[C@@H](O)[C@@H]1O	3144.0	Semi standard non polar	33892256
Melilotoside,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@H](CO)[C@H]1O	3144.4	Semi standard non polar	33892256
Melilotoside,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@H]1O	3147.3	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H]1O	3351.3	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3324.6	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3316.7	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3330.1	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3325.0	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3362.5	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3369.7	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3377.8	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@@H]1CO	3332.1	Semi standard non polar	33892256
Melilotoside,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@H](CO)[C@H]1O	3325.0	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3550.6	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC2=CC=CC=C2/C=C/C(=O)O)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C	3485.8	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3539.4	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3540.5	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3480.2	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3526.1	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3489.2	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3528.2	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3551.5	Semi standard non polar	33892256
Melilotoside,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3535.0	Semi standard non polar	33892256
Melilotoside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3682.1	Semi standard non polar	33892256
Melilotoside,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3716.3	Semi standard non polar	33892256
Melilotoside,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3685.2	Semi standard non polar	33892256
Melilotoside,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3702.4	Semi standard non polar	33892256
Melilotoside,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3665.5	Semi standard non polar	33892256
Melilotoside,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](OC2=CC=CC=C2/C=C/C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3878.3	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 - Melilotoside 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 - Melilotoside 10V, Positive-QTOF	splash10-00mk-0904000000-3dd34e382ba43fc1764f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotoside 20V, Positive-QTOF	splash10-0arr-0596000000-829180a1d0df8715f61c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotoside 40V, Positive-QTOF	splash10-014i-2900000000-e9a87fed398fa7e220c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotoside 10V, Negative-QTOF	splash10-07f0-0598000000-7c06dab5e1ee09a3e269	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotoside 20V, Negative-QTOF	splash10-0j4i-1931000000-be23d1fceb38e06a6c84	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Melilotoside 40V, Negative-QTOF	splash10-014i-3900000000-c4aef0c58740bba64b21	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB011656

KNApSAcK ID

Not Available

Chemspider ID

4444329

KEGG Compound ID

C05158

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280759

PDB ID

Not Available

ChEBI ID

17531

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Melilotoside (HMDB0033581)

MOL for HMDB0033581 (Melilotoside)

3D MOL for HMDB0033581 (Melilotoside)

3D SDF for HMDB0033581 (Melilotoside)

3D-SDF for HMDB0033581 (Melilotoside)

PDB for HMDB0033581 (Melilotoside)

3D PDB for HMDB0033581 (Melilotoside)

SMILES for HMDB0033581 (Melilotoside)

INCHI for HMDB0033581 (Melilotoside)

Structure for HMDB0033581 (Melilotoside)

3D Structure for HMDB0033581 (Melilotoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra