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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 17:47:41 UTC

Update Date

2021-09-23 17:47:41 UTC

HMDB ID

HMDB0302440

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-O-Caffeoyl-beta-D-glucose

Description

1-o-caffeoyl-beta-d-glucose is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. 1-o-caffeoyl-beta-d-glucose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 1-o-caffeoyl-beta-d-glucose can be found in a number of food items such as wild leek, garden onion, orange bell pepper, and green bell pepper, which makes 1-o-caffeoyl-beta-d-glucose a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302440
     RDKit          3D
1-O-Caffeoyl-beta-D-glucose
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.3603   -2.4456   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -1.3650   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084   -1.2477   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2734   -0.0719   -0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6944    0.0932   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276   -0.9696   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9066   -0.7946   -0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4539    0.4540   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8181    0.6244   -0.9256 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6388    1.5464   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2172    2.8193   -0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2876    1.3593   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -0.2098    0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8357   -0.2206    0.3506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5431    0.4398   -0.6617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8270   -0.0485   -0.6519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6237    0.5306   -1.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0142    0.1814   -3.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5622    0.1619    0.6241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5908   -0.8035    0.6853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7373    0.0196    1.8570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2479    0.9253    2.8104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835    0.3725    1.6567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5810   -0.1182    2.7445 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2801   -2.1334   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757    0.8509   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2068   -1.9936   -0.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5637   -1.6499   -0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4311   -0.1610   -1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050    3.6079   -0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6716    2.2525   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796   -1.2785    0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548   -1.1585   -0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6576    0.1337   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6907    1.6277   -1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949   -0.7059   -2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0932    1.1501    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1231   -1.6842    0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053   -0.9877    2.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0555    1.8511    2.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    1.4945    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3920    0.6598    3.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  1
 16 33  1  6
 17 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  6
 20 38  1  0
 21 39  1  1
 22 40  1  0
 23 41  1  6
 24 42  1  0
M  END

5281761
  Mrv0541 02271201352D          

 24 25  0  0  1  0            999 V2000
    3.5220   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.3967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -3.2217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.3967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.4909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5234    2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.9842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220   -2.3967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8075   -1.1592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2365   -1.9842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2365   -1.1592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0930   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944    2.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8089    2.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 14  1  0  0  0  0
 10  2  1  6  0  0  0
 11  3  1  1  0  0  0
 13  4  1  6  0  0  0
 14  5  1  1  0  0  0
  5 16  1  0  0  0  0
  6 15  1  0  0  0  0
  7 16  2  0  0  0  0
  8 22  1  0  0  0  0
  9 24  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 15  1  1  0  0  0
 13 14  1  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
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302440

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(23-10)24-11(19)4-2-7-1-3-8(17)9(18)5-7/h1-5,10,12-18,20-22H,6H2/b4-2+/t10-,12-,13+,14-,15+/m1/s1

> <INCHI_KEY>
WQSDYZZEIBAPIN-VBQORRLJSA-N

> <FORMULA>
C15H18O9

> <MOLECULAR_WEIGHT>
342.298

> <EXACT_MASS>
342.095082174

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
32.43527321646552

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-0.70

> <JCHEM_LOGP>
-0.5057791433333332

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.05524966156676

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207991379995423

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938220288765

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
79.4529

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.98e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-caffeoyl-β-D-glucose

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302440
     RDKit          3D
1-O-Caffeoyl-beta-D-glucose
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.3603   -2.4456   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -1.3650   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084   -1.2477   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2734   -0.0719   -0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6944    0.0932   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276   -0.9696   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9066   -0.7946   -0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4539    0.4540   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8181    0.6244   -0.9256 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6388    1.5464   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2172    2.8193   -0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2876    1.3593   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -0.2098    0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8357   -0.2206    0.3506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5431    0.4398   -0.6617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8270   -0.0485   -0.6519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6237    0.5306   -1.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0142    0.1814   -3.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5622    0.1619    0.6241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5908   -0.8035    0.6853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7373    0.0196    1.8570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2479    0.9253    2.8104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835    0.3725    1.6567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5810   -0.1182    2.7445 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2801   -2.1334   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757    0.8509   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2068   -1.9936   -0.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5637   -1.6499   -0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4311   -0.1610   -1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050    3.6079   -0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6716    2.2525   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796   -1.2785    0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548   -1.1585   -0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6576    0.1337   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6907    1.6277   -1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949   -0.7059   -2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0932    1.1501    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1231   -1.6842    0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053   -0.9877    2.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0555    1.8511    2.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    1.4945    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3920    0.6598    3.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  1
 16 33  1  6
 17 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  6
 20 38  1  0
 21 39  1  1
 22 40  1  0
 23 41  1  6
 24 42  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 5281761                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       6.574  -1.394   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907  -4.474   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.574  -6.014   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.242  -4.474   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.242  -1.394   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.907   0.146   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.908   0.916   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      15.910   2.456   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      15.910   5.536   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.241  -3.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574  -4.474   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.241  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.908  -3.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908  -2.164   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.907  -1.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.242   0.146   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.576   0.916   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.576   2.456   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.909   3.226   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.243   2.456   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.909   4.766   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.577   3.226   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.243   5.536   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.577   4.766   0.000  0.00  0.00           C+0
CONECT    1   12   14                                                       
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   13                                                            
CONECT    5   14   16                                                       
CONECT    6   15                                                            
CONECT    7   16                                                            
CONECT    8   22                                                            
CONECT    9   24                                                            
CONECT   10    2   11   12                                                  
CONECT   11    3   10   13                                                  
CONECT   12    1   10   15                                                  
CONECT   13    4   11   14                                                  
CONECT   14    1    5   13                                                  
CONECT   15    6   12                                                       
CONECT   16    5    7   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19   23                                                       
CONECT   22    8   20   24                                                  
CONECT   23   21   24                                                       
CONECT   24    9   22   23                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0302440
HETATM    1  O1  UNL     1      -0.360  -2.446  -0.008  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.279  -1.365  -0.021  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.708  -1.248  -0.211  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.273  -0.072  -0.207  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.694   0.093  -0.392  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.528  -0.970  -0.582  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.907  -0.795  -0.760  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.454   0.454  -0.749  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.818   0.624  -0.926  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.639   1.546  -0.560  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.217   2.819  -0.552  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.288   1.359  -0.386  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.457  -0.210   0.161  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.836  -0.221   0.351  1.00  0.00           C  
HETATM   15  O5  UNL     1      -2.543   0.440  -0.662  1.00  0.00           O  
HETATM   16  C11 UNL     1      -3.827  -0.048  -0.652  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.624   0.531  -1.808  1.00  0.00           C  
HETATM   18  O6  UNL     1      -4.014   0.181  -3.018  1.00  0.00           O  
HETATM   19  C13 UNL     1      -4.562   0.162   0.624  1.00  0.00           C  
HETATM   20  O7  UNL     1      -5.591  -0.803   0.685  1.00  0.00           O  
HETATM   21  C14 UNL     1      -3.737   0.020   1.857  1.00  0.00           C  
HETATM   22  O8  UNL     1      -4.248   0.925   2.810  1.00  0.00           O  
HETATM   23  C15 UNL     1      -2.283   0.373   1.657  1.00  0.00           C  
HETATM   24  O9  UNL     1      -1.581  -0.118   2.744  1.00  0.00           O  
HETATM   25  H1  UNL     1       2.280  -2.133  -0.351  1.00  0.00           H  
HETATM   26  H2  UNL     1       1.676   0.851  -0.061  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.207  -1.994  -0.608  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.564  -1.650  -0.910  1.00  0.00           H  
HETATM   29  H5  UNL     1       8.431  -0.161  -1.065  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.605   3.608  -0.412  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.672   2.252  -0.239  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.180  -1.279   0.325  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.755  -1.159  -0.829  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.658   0.134  -1.797  1.00  0.00           H  
HETATM   35  H11 UNL     1      -4.691   1.628  -1.735  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.595  -0.706  -2.866  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.093   1.150   0.609  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.123  -1.684   0.706  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.805  -0.988   2.311  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.055   1.851   2.574  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.229   1.494   1.609  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.392   0.660   3.343  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   12
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   10
CONECT    9   29
CONECT   10   11   12   12
CONECT   11   30
CONECT   12   31
CONECT   13   14
CONECT   14   15   23   32
CONECT   15   16
CONECT   16   17   19   33
CONECT   17   18   34   35
CONECT   18   36
CONECT   19   20   21   37
CONECT   20   38
CONECT   21   22   23   39
CONECT   22   40
CONECT   23   24   41
CONECT   24   42
END

HMDB0302440
     RDKit          3D
1-O-Caffeoyl-beta-D-glucose
 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.3603   -2.4456   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -1.3650   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084   -1.2477   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2734   -0.0719   -0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6944    0.0932   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276   -0.9696   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9066   -0.7946   -0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4539    0.4540   -0.7488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8181    0.6244   -0.9256 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6388    1.5464   -0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2172    2.8193   -0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2876    1.3593   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -0.2098    0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8357   -0.2206    0.3506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5431    0.4398   -0.6617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8270   -0.0485   -0.6519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6237    0.5306   -1.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0142    0.1814   -3.0178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5622    0.1619    0.6241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5908   -0.8035    0.6853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7373    0.0196    1.8570 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2479    0.9253    2.8104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835    0.3725    1.6567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5810   -0.1182    2.7445 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2801   -2.1334   -0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757    0.8509   -0.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2068   -1.9936   -0.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5637   -1.6499   -0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4311   -0.1610   -1.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6050    3.6079   -0.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6716    2.2525   -0.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1796   -1.2785    0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548   -1.1585   -0.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6576    0.1337   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6907    1.6277   -1.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5949   -0.7059   -2.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0932    1.1501    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1231   -1.6842    0.7059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8053   -0.9877    2.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0555    1.8511    2.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    1.4945    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3920    0.6598    3.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  1
 16 33  1  6
 17 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  6
 20 38  1  0
 21 39  1  1
 22 40  1  0
 23 41  1  6
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-O-[(e)-Caffeoyl]-beta-D-glucose	ChEBI
1-O-[(e)-Caffeoyl]-b-D-glucose	Generator
1-O-[(e)-Caffeoyl]-β-D-glucose	Generator
1-Caffeoyl-b-D-glucose	Generator
1-Caffeoyl-β-D-glucose	Generator
1-O-(trans-Caffeoyl)-beta-D-glucose	ChEBI
1-O-(trans-Caffeoyl)-b-D-glucose	Generator
1-O-(trans-Caffeoyl)-β-D-glucose	Generator
1-O-Caffeoyl-b-D-glucose	Generator
1-O-Caffeoyl-β-D-glucose	Generator

Chemical Formula

C₁₅H₁₈O₉

Average Molecular Weight

342.298

Monoisotopic Molecular Weight

342.095082174

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

1-caffeoyl-β-D-glucose

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(23-10)24-11(19)4-2-7-1-3-8(17)9(18)5-7/h1-5,10,12-18,20-22H,6H2/b4-2+/t10-,12-,13+,14-,15+/m1/s1

InChI Key

WQSDYZZEIBAPIN-VBQORRLJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Triterpenoid
Stigmastane-skeleton
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302440)

Food

Vegetable

Fruit vegetable

Onion-family vegetable

Wild leek (FooDB: FOOD00396)
Garden onion (FooDB: FOOD00006)

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	-0.7	ALOGPS
logP	-0.51	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.45 m³·mol⁻¹	ChemAxon
Polarizability	32.44 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	179.576	32859911
AllCCS	[M+H-H2O]+	176.527	32859911
AllCCS	[M+Na]+	183.204	32859911
AllCCS	[M+NH4]+	182.396	32859911
AllCCS	[M-H]-	175.267	32859911
AllCCS	[M+Na-2H]-	175.286	32859911
AllCCS	[M+HCOO]-	175.44	32859911
DeepCCS	[M+H]+	175.02	30932474
DeepCCS	[M-H]-	172.624	30932474
DeepCCS	[M-2H]-	206.374	30932474
DeepCCS	[M+Na]+	181.041	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 - 1-O-Caffeoyl-beta-D-glucose 10V, Positive-QTOF	splash10-03e9-0902000000-060c62eea5ffd46733c3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 20V, Positive-QTOF	splash10-03di-0900000000-4095e641c6e59bd1ad5d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 40V, Positive-QTOF	splash10-03ki-3900000000-2d97576ff9016d49d724	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 10V, Negative-QTOF	splash10-03di-0902000000-392d992c921bed6395a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 20V, Negative-QTOF	splash10-03fr-1900000000-b7971434f49fada40a9a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 40V, Negative-QTOF	splash10-03fu-7900000000-1ffc1c6b603f8d09f1d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 10V, Positive-QTOF	splash10-0006-0509000000-9b898e4eff8d99f014e2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 20V, Positive-QTOF	splash10-03l1-1930000000-11d59e94207bd0cf4bbe	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 40V, Positive-QTOF	splash10-08g0-6900000000-5bf886774fb798c507c8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 10V, Negative-QTOF	splash10-004l-0905000000-a6a2ed371eeb9966c66c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 20V, Negative-QTOF	splash10-000l-3955000000-d99303d226dec38278ed	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-O-Caffeoyl-beta-D-glucose 40V, Negative-QTOF	splash10-0019-1900000000-a534c1d60cc6c2e796c6	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281761

PDB ID

Not Available

ChEBI ID

614

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1858251

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 1-O-Caffeoyl-beta-D-glucose (HMDB0302440)

MOL for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

3D MOL for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

3D SDF for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

3D-SDF for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

PDB for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

3D PDB for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

SMILES for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

INCHI for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

Structure for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

3D Structure for HMDB0302440 (1-O-Caffeoyl-beta-D-glucose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra