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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:30:29 UTC

Update Date

2022-03-07 02:56:24 UTC

HMDB ID

HMDB0039958

Secondary Accession Numbers

HMDB39958

Metabolite Identification

Common Name

4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde

Description

4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde 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. Based on a literature review very few articles have been published on 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde.

Structure

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

HMDB0039958
     RDKit          3D
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde
 40 41  0  0  0  0  0  0  0  0999 V2000
    5.9556    0.4891   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    0.3576    0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6760    0.3591    1.3062 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    0.2315   -0.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2920    0.1143    0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2846    1.2378   -0.1178 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9196    2.5818   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    1.1655    0.8984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3934   -0.0068    0.8771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1644   -0.1398   -0.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151   -0.2433   -0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105   -0.2289    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -0.3375    0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2840   -0.4656   -0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7305   -0.5805   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4125   -0.5625    0.4368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735   -0.4797   -1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1335   -0.3734   -1.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4916   -1.2386    0.9921 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1699   -1.1714    2.2039 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080   -1.1586   -0.1298 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3041   -2.2743   -0.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3914    1.5006   -0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6609   -0.2605   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8808    0.4000   -1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884    0.1351    1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8106    0.9857   -1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220    2.5617   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705    3.0811   -1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183    3.2414    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879    0.0107    1.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9234   -0.1323    1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2918   -0.3236    1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1763   -0.6792   -1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9804   -0.5815   -2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327   -0.3878   -2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.1151    0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6734   -1.6385    2.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9206   -1.0085   -1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0510   -2.0648   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 14 17  1  0
 17 18  2  0
  9 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21  5  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  1
  6 27  1  6
  7 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  1
 12 32  1  0
 13 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  1
 20 38  1  0
 21 39  1  6
 22 40  1  0
M  END


  Mrv1652309272007372D          

 22 23  0  0  0  0            999 V2000
10013.546210014.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10016.404110016.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.120410013.6888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.690110014.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10012.120410016.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.690110016.1623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.690310015.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.975910016.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.261310015.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.261310014.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.975710014.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.690310014.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.118910016.1631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10011.404410015.7505    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10011.404410014.9256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.118910014.5131    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10012.833410014.9256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10012.833410015.7505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.975410015.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.260310016.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.976010014.9234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10017.118910015.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
  1 10  1  0  0  0  0
  7  2  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
 16 17  1  0  0  0  0
 13 18  1  0  0  0  0
 17 18  1  0  0  0  0
 17  1  1  1  0  0  0
 16  3  1  6  0  0  0
 15  4  1  6  0  0  0
 14  6  1  1  0  0  0
 13  5  1  6  0  0  0
  6 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  2 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039958

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O7/c1-8-14(21-9(2)17)12(18)13(19)15(20-8)22-11-5-3-10(7-16)4-6-11/h3-8,12-15,18-19H,1-2H3/t8-,12-,13+,14-,15-/m0/s1

> <INCHI_KEY>
YHVJUTOZYWQYSQ-QOWRVZOFSA-N

> <FORMULA>
C15H18O7

> <MOLECULAR_WEIGHT>
310.302

> <EXACT_MASS>
310.10525292

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.513342374333106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6S)-6-(4-formylphenoxy)-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
0.6021501226666669

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.87954878683771

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.260449609284034

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6916081753328225

> <JCHEM_POLAR_SURFACE_AREA>
102.28999999999999

> <JCHEM_REFRACTIVITY>
74.37510000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6S)-6-(4-formylphenoxy)-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039958
     RDKit          3D
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde
 40 41  0  0  0  0  0  0  0  0999 V2000
    5.9556    0.4891   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    0.3576    0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6760    0.3591    1.3062 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    0.2315   -0.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2920    0.1143    0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2846    1.2378   -0.1178 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9196    2.5818   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    1.1655    0.8984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3934   -0.0068    0.8771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1644   -0.1398   -0.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151   -0.2433   -0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105   -0.2289    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -0.3375    0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2840   -0.4656   -0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7305   -0.5805   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4125   -0.5625    0.4368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735   -0.4797   -1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1335   -0.3734   -1.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4916   -1.2386    0.9921 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1699   -1.1714    2.2039 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080   -1.1586   -0.1298 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3041   -2.2743   -0.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3914    1.5006   -0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6609   -0.2605   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8808    0.4000   -1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884    0.1351    1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8106    0.9857   -1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220    2.5617   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705    3.0811   -1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183    3.2414    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879    0.0107    1.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9234   -0.1323    1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2918   -0.3236    1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1763   -0.6792   -1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9804   -0.5815   -2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327   -0.3878   -2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.1151    0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6734   -1.6385    2.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9206   -1.0085   -1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0510   -2.0648   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 14 17  1  0
 17 18  2  0
  9 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21  5  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  1
  6 27  1  6
  7 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  1
 12 32  1  0
 13 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  1
 20 38  1  0
 21 39  1  6
 22 40  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8691.9538693.758   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8697.2888696.836   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8689.2918692.219   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8686.6228693.758   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8689.2918698.375   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8686.6228696.836   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8695.9558696.068   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8694.6228696.838   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8693.2888696.067   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8693.2888694.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8694.6218693.758   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8695.9558694.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8689.2898696.838   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8687.9558696.068   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8687.9558694.528   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8689.2898693.758   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8690.6228694.528   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8690.6228696.068   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8685.2878696.064   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8683.9538696.835   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8685.2898694.524   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8698.6228696.065   0.000  0.00  0.00           O+0
CONECT    1   10   17                                                       
CONECT    2    7   22                                                       
CONECT    3   16                                                            
CONECT    4   15                                                            
CONECT    5   13                                                            
CONECT    6   14   19                                                       
CONECT    7    8   12    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    1                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   14   18    5                                                  
CONECT   14   13   15    6                                                  
CONECT   15   14   16    4                                                  
CONECT   16   15   17    3                                                  
CONECT   17   16   18    1                                                  
CONECT   18   13   17                                                       
CONECT   19    6   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0039958
HETATM    1  C1  UNL     1       5.956   0.489  -0.654  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.668   0.358   0.044  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.676   0.359   1.306  1.00  0.00           O  
HETATM    4  O2  UNL     1       3.440   0.231  -0.630  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.292   0.114   0.131  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.285   1.238  -0.118  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.920   2.582  -0.150  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.362   1.166   0.898  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.393  -0.007   0.877  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.164  -0.140  -0.247  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.515  -0.243  -0.280  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.311  -0.229   0.826  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.678  -0.337   0.737  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.284  -0.466  -0.500  1.00  0.00           C  
HETATM   15  C11 UNL     1      -6.730  -0.581  -0.596  1.00  0.00           C  
HETATM   16  O5  UNL     1      -7.413  -0.563   0.437  1.00  0.00           O  
HETATM   17  C12 UNL     1      -4.474  -0.480  -1.619  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.133  -0.373  -1.532  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.492  -1.239   0.992  1.00  0.00           C  
HETATM   20  O6  UNL     1       1.170  -1.171   2.204  1.00  0.00           O  
HETATM   21  C15 UNL     1       1.508  -1.159  -0.130  1.00  0.00           C  
HETATM   22  O7  UNL     1       2.304  -2.274  -0.213  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.391   1.501  -0.410  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.661  -0.261  -0.196  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.881   0.400  -1.740  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.488   0.135   1.229  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.811   0.986  -1.105  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.022   2.562  -0.045  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.671   3.081  -1.121  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.518   3.241   0.638  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.988   0.011   1.804  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.923  -0.132   1.837  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.292  -0.324   1.631  1.00  0.00           H  
HETATM   34  H12 UNL     1      -7.176  -0.679  -1.571  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.980  -0.582  -2.572  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.533  -0.388  -2.420  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.170  -2.115   0.906  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.673  -1.638   2.929  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.921  -1.009  -1.073  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.051  -2.065  -0.828  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   21   26
CONECT    6    7    8   27
CONECT    7   28   29   30
CONECT    8    9
CONECT    9   10   19   31
CONECT   10   11
CONECT   11   12   12   18
CONECT   12   13   32
CONECT   13   14   14   33
CONECT   14   15   17
CONECT   15   16   16   34
CONECT   17   18   18   35
CONECT   18   36
CONECT   19   20   21   37
CONECT   20   38
CONECT   21   22   39
CONECT   22   40
END

HMDB0039958
     RDKit          3D
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde
 40 41  0  0  0  0  0  0  0  0999 V2000
    5.9556    0.4891   -0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    0.3576    0.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6760    0.3591    1.3062 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    0.2315   -0.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2920    0.1143    0.1309 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2846    1.2378   -0.1178 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9196    2.5818   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    1.1655    0.8984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3934   -0.0068    0.8771 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1644   -0.1398   -0.2470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5151   -0.2433   -0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3105   -0.2289    0.8260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6780   -0.3375    0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2840   -0.4656   -0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7305   -0.5805   -0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4125   -0.5625    0.4368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4735   -0.4797   -1.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1335   -0.3734   -1.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4916   -1.2386    0.9921 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1699   -1.1714    2.2039 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080   -1.1586   -0.1298 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3041   -2.2743   -0.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3914    1.5006   -0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6609   -0.2605   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8808    0.4000   -1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4884    0.1351    1.2292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8106    0.9857   -1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220    2.5617   -0.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6705    3.0811   -1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5183    3.2414    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9879    0.0107    1.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9234   -0.1323    1.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2918   -0.3236    1.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1763   -0.6792   -1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9804   -0.5815   -2.5725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5327   -0.3878   -2.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1703   -2.1151    0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6734   -1.6385    2.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9206   -1.0085   -1.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0510   -2.0648   -0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 14 17  1  0
 17 18  2  0
  9 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21  5  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  1
  6 27  1  6
  7 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  1
 12 32  1  0
 13 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  1
 20 38  1  0
 21 39  1  6
 22 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-(4'-O-Acetyl-a-L-rhamnosyloxy)benzaldehyde	Generator
4-(4'-O-Acetyl-α-L-rhamnosyloxy)benzaldehyde	Generator
4-(4’-O-acetyl-α-L-rhamnosyloxy)benzaldehyde	HMDB
4-[(4-O-Acetyl-6-deoxy-alpha-L-mannopyranosyl)oxy]benzaldehyde	HMDB
4-[(4-O-Acetyl-6-deoxy-α-L-mannopyranosyl)oxy]benzaldehyde	HMDB
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde	HMDB

Chemical Formula

C₁₅H₁₈O₇

Average Molecular Weight

310.302

Monoisotopic Molecular Weight

310.10525292

IUPAC Name

(2S,3R,4S,5R,6S)-6-(4-formylphenoxy)-4,5-dihydroxy-2-methyloxan-3-yl acetate

Traditional Name

(2S,3R,4S,5R,6S)-6-(4-formylphenoxy)-4,5-dihydroxy-2-methyloxan-3-yl acetate

CAS Registry Number

159733-92-3

SMILES

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

InChI Identifier

InChI=1S/C15H18O7/c1-8-14(21-9(2)17)12(18)13(19)15(20-8)22-11-5-3-10(7-16)4-6-11/h3-8,12-15,18-19H,1-2H3/t8-,12-,13+,14-,15-/m0/s1

InChI Key

YHVJUTOZYWQYSQ-QOWRVZOFSA-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
Hexose monosaccharide
O-glycosyl compound
Phenoxy compound
Benzaldehyde
Benzoyl
Phenol ether
Aryl-aldehyde
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Carboxylic acid ester
1,2-diol
Secondary alcohol
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Aldehyde
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039958)
Cytoplasm (HMDB: HMDB0039958)

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

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	5.8 g/L	ALOGPS
logP	0.47	ALOGPS
logP	0.6	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	74.38 m³·mol⁻¹	ChemAxon
Polarizability	30.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	172.462	30932474
DeepCCS	[M-H]-	170.067	30932474
DeepCCS	[M-2H]-	204.005	30932474
DeepCCS	[M+Na]+	178.631	30932474
AllCCS	[M+H]+	173.6	32859911
AllCCS	[M+H-H2O]+	170.4	32859911
AllCCS	[M+NH4]+	176.5	32859911
AllCCS	[M+Na]+	177.3	32859911
AllCCS	[M-H]-	172.3	32859911
AllCCS	[M+Na-2H]-	172.3	32859911
AllCCS	[M+HCOO]-	172.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde	C[C@@H]1O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O	3502.8	Standard polar	33892256
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde	C[C@@H]1O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O	2308.0	Standard non polar	33892256
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde	C[C@@H]1O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O	2526.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde,1TMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2366.0	Semi standard non polar	33892256
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde,1TMS,isomer #2	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2383.9	Semi standard non polar	33892256
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde,2TMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2425.9	Semi standard non polar	33892256
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde,1TBDMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2630.3	Semi standard non polar	33892256
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde,1TBDMS,isomer #2	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2638.0	Semi standard non polar	33892256
4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde,2TBDMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(C=O)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2882.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde 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 - 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde 10V, Positive-QTOF	splash10-00dj-3901000000-93f3369af1e595ae28a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde 20V, Positive-QTOF	splash10-00dj-3911000000-d071f3d8190fc59303d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde 40V, Positive-QTOF	splash10-05bb-5900000000-b3557a0ca8b1e04d015a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde 10V, Negative-QTOF	splash10-06di-0963000000-02b3d1184aae03052c95	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde 20V, Negative-QTOF	splash10-00di-3900000000-354e5c2f01e21b4428fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde 40V, Negative-QTOF	splash10-00xu-9700000000-f2b2c673bfdc30a7b9ea	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB019621

KNApSAcK ID

Not Available

Chemspider ID

8193820

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10018247

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde (HMDB0039958)

MOL for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

3D MOL for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

3D SDF for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

3D-SDF for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

PDB for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

3D PDB for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

SMILES for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

INCHI for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

Structure for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

3D Structure for HMDB0039958 (4-(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzaldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra