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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:05:29 UTC

Update Date

2022-03-07 02:53:41 UTC

HMDB ID

HMDB0033375

Secondary Accession Numbers

HMDB33375

Metabolite Identification

Common Name

Octyl gallate

Description

Octyl gallate, also known as octyl gallic acid, belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. Octyl gallate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Octyl gallate.

Structure

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

HMDB0033375
     RDKit          3D
Octyl gallate
 42 42  0  0  0  0  0  0  0  0999 V2000
   -6.9455   -0.0921    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1246    0.9079   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6625    0.8247   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0665   -0.5177   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5780   -0.4270   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8789   -1.7209   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337   -1.5864    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040   -0.4887   -0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5811   -0.4184   -0.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4628    0.4924   -0.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0743    1.2777   -1.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8555    0.5384   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2950   -0.3256    0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6145   -0.3298    1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9648   -1.2444    2.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4894    0.5758    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8036    0.6071    0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0391    1.4502   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9503    2.3673   -1.0391 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    1.4360   -0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0153    0.2004    0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8814   -1.0976   -0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6504   -0.1131    1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3446    0.8197   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4740    1.9166   -0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5427    1.0101    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1409    1.5748   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637   -0.7474   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5515   -1.3522    0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807    0.3550   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5399   -0.1679    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8976   -1.9776   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3594   -2.5699    0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276   -2.5325    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4288   -1.2267    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.6077   -1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006    0.5116   -0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267   -1.0510    1.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8578   -1.3535    2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1244   -0.0229    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6615    3.0048   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3823    2.1004   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 13 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
M  END


  Mrv1652305271900242D          

 20 20  0  0  0  0            999 V2000
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  2  0  0  0  0
 20  8  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033375

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-2-3-4-5-6-7-8-20-15(19)11-9-12(16)14(18)13(17)10-11/h9-10,16-18H,2-8H2,1H3

> <INCHI_KEY>
NRPKURNSADTHLJ-UHFFFAOYSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.3322

> <EXACT_MASS>
282.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.800227098701434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
octyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
4.168200489666666

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.285154439669183

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.109859002482771

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548890486979826

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
76.3036

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
octyl gallate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033375
     RDKit          3D
Octyl gallate
 42 42  0  0  0  0  0  0  0  0999 V2000
   -6.9455   -0.0921    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1246    0.9079   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6625    0.8247   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0665   -0.5177   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5780   -0.4270   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8789   -1.7209   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337   -1.5864    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040   -0.4887   -0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5811   -0.4184   -0.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4628    0.4924   -0.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0743    1.2777   -1.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8555    0.5384   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2950   -0.3256    0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6145   -0.3298    1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9648   -1.2444    2.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4894    0.5758    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8036    0.6071    0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0391    1.4502   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9503    2.3673   -1.0391 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    1.4360   -0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0153    0.2004    0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8814   -1.0976   -0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6504   -0.1131    1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3446    0.8197   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4740    1.9166   -0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5427    1.0101    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1409    1.5748   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637   -0.7474   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5515   -1.3522    0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807    0.3550   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5399   -0.1679    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8976   -1.9776   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3594   -2.5699    0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276   -2.5325    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4288   -1.2267    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.6077   -1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006    0.5116   -0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267   -1.0510    1.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8578   -1.3535    2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1244   -0.0229    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6615    3.0048   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3823    2.1004   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 13 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.671 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.005 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.672 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.339 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      22.673 -11.550   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      20.005 -16.170   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      22.673 -14.630   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      17.338 -10.010   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   20                                                       
CONECT    9   11   12                                                       
CONECT   10   11   13                                                       
CONECT   11    9   10   15                                                  
CONECT   12    9   14   16                                                  
CONECT   13   10   14   17                                                  
CONECT   14   12   13   18                                                  
CONECT   15   11   19   20                                                  
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0033375
HETATM    1  C1  UNL     1      -6.946  -0.092   0.370  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.125   0.908  -0.412  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.663   0.825  -0.095  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.067  -0.518  -0.396  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.578  -0.427  -0.016  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.879  -1.721  -0.277  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.434  -1.586   0.119  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.204  -0.489  -0.698  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.581  -0.418  -0.282  1.00  0.00           O  
HETATM   10  C9  UNL     1       2.463   0.492  -0.836  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.074   1.278  -1.717  1.00  0.00           O  
HETATM   12  C10 UNL     1       3.856   0.538  -0.391  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.295  -0.326   0.583  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.614  -0.330   1.050  1.00  0.00           C  
HETATM   15  O3  UNL     1       5.965  -1.244   2.040  1.00  0.00           O  
HETATM   16  C13 UNL     1       6.489   0.576   0.498  1.00  0.00           C  
HETATM   17  O4  UNL     1       7.804   0.607   0.930  1.00  0.00           O  
HETATM   18  C14 UNL     1       6.039   1.450  -0.489  1.00  0.00           C  
HETATM   19  O5  UNL     1       6.950   2.367  -1.039  1.00  0.00           O  
HETATM   20  C15 UNL     1       4.746   1.436  -0.930  1.00  0.00           C  
HETATM   21  H1  UNL     1      -8.015   0.200   0.347  1.00  0.00           H  
HETATM   22  H2  UNL     1      -6.881  -1.098  -0.119  1.00  0.00           H  
HETATM   23  H3  UNL     1      -6.650  -0.113   1.432  1.00  0.00           H  
HETATM   24  H4  UNL     1      -6.345   0.820  -1.482  1.00  0.00           H  
HETATM   25  H5  UNL     1      -6.474   1.917  -0.095  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.543   1.010   0.989  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.141   1.575  -0.717  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.064  -0.747  -1.488  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.552  -1.352   0.110  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.181   0.355  -0.697  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.540  -0.168   1.043  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.898  -1.978  -1.356  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.359  -2.570   0.251  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.128  -2.533   0.003  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.429  -1.227   1.177  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.100  -0.608  -1.775  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.201   0.512  -0.408  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.627  -1.051   1.036  1.00  0.00           H  
HETATM   39  H19 UNL     1       6.858  -1.353   2.457  1.00  0.00           H  
HETATM   40  H20 UNL     1       8.124  -0.023   1.640  1.00  0.00           H  
HETATM   41  H21 UNL     1       6.661   3.005  -1.745  1.00  0.00           H  
HETATM   42  H22 UNL     1       4.382   2.100  -1.687  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   13   20
CONECT   13   14   38
CONECT   14   15   16   16
CONECT   15   39
CONECT   16   17   18
CONECT   17   40
CONECT   18   19   20   20
CONECT   19   41
CONECT   20   42
END

HMDB0033375
     RDKit          3D
Octyl gallate
 42 42  0  0  0  0  0  0  0  0999 V2000
   -6.9455   -0.0921    0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1246    0.9079   -0.4117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6625    0.8247   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0665   -0.5177   -0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5780   -0.4270   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8789   -1.7209   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337   -1.5864    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2040   -0.4887   -0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5811   -0.4184   -0.2818 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4628    0.4924   -0.8361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0743    1.2777   -1.7173 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8555    0.5384   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2950   -0.3256    0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6145   -0.3298    1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9648   -1.2444    2.0401 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4894    0.5758    0.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8036    0.6071    0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0391    1.4502   -0.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9503    2.3673   -1.0391 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7462    1.4360   -0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0153    0.2004    0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8814   -1.0976   -0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6504   -0.1131    1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3446    0.8197   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4740    1.9166   -0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5427    1.0101    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1409    1.5748   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637   -0.7474   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5515   -1.3522    0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807    0.3550   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5399   -0.1679    1.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8976   -1.9776   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3594   -2.5699    0.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1276   -2.5325    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4288   -1.2267    1.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001   -0.6077   -1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006    0.5116   -0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267   -1.0510    1.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8578   -1.3535    2.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1244   -0.0229    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6615    3.0048   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3823    2.1004   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 13 38  1  0
 15 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Gallic acid octyl ester	ChEBI
N-Octyl gallate	ChEBI
Gallate octyl ester	Generator
N-Octyl gallic acid	Generator
Octyl gallic acid	Generator
3,4,5-Trihydroxybenzoic acid octyl ester	MeSH
Octyl gallate dihydrate	MeSH
Benzoic acid, 3,4,5-trihydroxy-, octyl ester	HMDB
e311	HMDB
GA 8	HMDB
Gallic acid, octyl ester	HMDB
N-Octyl ester OF 3,4,5-trihydroxybenzoic acid	HMDB
N-Octylgallate	HMDB
Octyl 3,4,5-trihydroxybenzoate	HMDB
Octylgallate	HMDB
Oktylester kyseliny gallove	HMDB
Progallin O	HMDB
Stabilizer ga 8	HMDB

Chemical Formula

C₁₅H₂₂O₅

Average Molecular Weight

282.3322

Monoisotopic Molecular Weight

282.146723814

IUPAC Name

octyl 3,4,5-trihydroxybenzoate

Traditional Name

octyl gallate

CAS Registry Number

1034-01-1

SMILES

CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H22O5/c1-2-3-4-5-6-7-8-20-15(19)11-9-12(16)14(18)13(17)10-11/h9-10,16-18H,2-8H2,1H3

InChI Key

NRPKURNSADTHLJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

gallate ester (CHEBI:83631 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033375)

Cellular substructure

Membrane (HMDB: HMDB0033375)

Source

Exogenous

Food

Food (HMDB: HMDB0033375)

Not Available

Nutrient (HMDB: HMDB0033375)

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antiviral

Antiviral (HMDB: HMDB0033375)

Food and nutrition

Food and nutrition (HMDB: HMDB0033375)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	94 - 95 °C	Not Available
Boiling Point	482.86 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.036 mg/mL at 20 °C	Not Available
LogP	3.66	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	4.1	ALOGPS
logP	4.17	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	76.3 m³·mol⁻¹	ChemAxon
Polarizability	31.8 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	170.43	31661259
DarkChem	[M-H]-	168.005	31661259
DeepCCS	[M+H]+	177.852	30932474
DeepCCS	[M-H]-	175.494	30932474
DeepCCS	[M-2H]-	208.381	30932474
DeepCCS	[M+Na]+	183.945	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.8	32859911
AllCCS	[M+NH4]+	169.9	32859911
AllCCS	[M+Na]+	170.8	32859911
AllCCS	[M-H]-	169.3	32859911
AllCCS	[M+Na-2H]-	169.9	32859911
AllCCS	[M+HCOO]-	170.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Octyl gallate	CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1	3628.9	Standard polar	33892256
Octyl gallate	CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1	2492.3	Standard non polar	33892256
Octyl gallate	CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1	2426.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Octyl gallate,1TMS,isomer #1	CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C)=C1	2445.5	Semi standard non polar	33892256
Octyl gallate,1TMS,isomer #2	CCCCCCCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O)=C1	2425.2	Semi standard non polar	33892256
Octyl gallate,2TMS,isomer #1	CCCCCCCCOC(=O)C1=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C1	2455.7	Semi standard non polar	33892256
Octyl gallate,2TMS,isomer #2	CCCCCCCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2422.9	Semi standard non polar	33892256
Octyl gallate,3TMS,isomer #1	CCCCCCCCOC(=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2468.2	Semi standard non polar	33892256
Octyl gallate,1TBDMS,isomer #1	CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2698.7	Semi standard non polar	33892256
Octyl gallate,1TBDMS,isomer #2	CCCCCCCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2683.5	Semi standard non polar	33892256
Octyl gallate,2TBDMS,isomer #1	CCCCCCCCOC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2942.0	Semi standard non polar	33892256
Octyl gallate,2TBDMS,isomer #2	CCCCCCCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2916.5	Semi standard non polar	33892256
Octyl gallate,3TBDMS,isomer #1	CCCCCCCCOC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3164.8	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 - Octyl gallate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4900000000-878a0a7a4a67ed06c0ff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Octyl gallate GC-MS (3 TMS) - 70eV, Positive	splash10-01c0-5209400000-3d5229f775270bdd8868	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Octyl gallate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Octyl gallate 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 45V, Positive-QTOF	splash10-019r-0920000000-dd0646e49d169d2d39a4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 90V, Negative-QTOF	splash10-020c-2900000000-2dfd6a3290e77879474e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 45V, Negative-QTOF	splash10-017i-0920000000-b750c5426d2367f6bfda	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 30V, Negative-QTOF	splash10-001i-0190000000-eb4afbede645135b7663	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 60V, Negative-QTOF	splash10-004i-1900000000-34fdedc0e3ae08ef6c4c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 75V, Negative-QTOF	splash10-004u-1900000000-41eaaa406b8a3f84606b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 15V, Negative-QTOF	splash10-001i-0090000000-6eb2ef731eb900efa48a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 40V, Positive-QTOF	splash10-0a59-9500000000-25e3c2fbd78d072d820b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 10V, Positive-QTOF	splash10-00di-1900000000-f97f06cdbe5ca99b4bae	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Octyl gallate 20V, Positive-QTOF	splash10-0pdi-3900000000-169a117fdd40fbb3f66b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 10V, Positive-QTOF	splash10-001i-0790000000-1a568cbe925ce46780bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 20V, Positive-QTOF	splash10-0ik9-2910000000-32a6f3e83cb258626b0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 40V, Positive-QTOF	splash10-0kbf-9600000000-c74166cded4e492c3e24	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 10V, Negative-QTOF	splash10-001i-0590000000-150fabd6eb0d5e81d0b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 20V, Negative-QTOF	splash10-016r-0910000000-652ef7ed882c584e3879	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 40V, Negative-QTOF	splash10-0fvi-1900000000-0a04645a38fadbbab692	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 10V, Negative-QTOF	splash10-001i-0290000000-c333499f784512ab5549	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 20V, Negative-QTOF	splash10-0fw9-0930000000-d3463202c650e369f74d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 40V, Negative-QTOF	splash10-00vi-5900000000-e9a5b02eb650d4f7a67c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 10V, Positive-QTOF	splash10-001i-0590000000-18e43656b88b6abb544e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 20V, Positive-QTOF	splash10-0f89-3950000000-cb1f00495f16a31abcb0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Octyl gallate 40V, Positive-QTOF	splash10-0udi-8900000000-38f3d1a994ec952bab6a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Membrane

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

FDB011405

KNApSAcK ID

Not Available

Chemspider ID

55194

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Octyl_gallate

METLIN ID

Not Available

PubChem Compound

61253

PDB ID

Not Available

ChEBI ID

83631

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1270671

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yamasaki H, Uozaki M, Katsuyama Y, Utsunomiya H, Arakawa T, Higuchi M, Higuti T, Koyama AH: Antiviral effect of octyl gallate against influenza and other RNA viruses. Int J Mol Med. 2007 Apr;19(4):685-8. [PubMed:17334645 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Octyl gallate (HMDB0033375)

MOL for HMDB0033375 (Octyl gallate)

3D MOL for HMDB0033375 (Octyl gallate)

3D SDF for HMDB0033375 (Octyl gallate)

3D-SDF for HMDB0033375 (Octyl gallate)

PDB for HMDB0033375 (Octyl gallate)

3D PDB for HMDB0033375 (Octyl gallate)

SMILES for HMDB0033375 (Octyl gallate)

INCHI for HMDB0033375 (Octyl gallate)

Structure for HMDB0033375 (Octyl gallate)

3D Structure for HMDB0033375 (Octyl gallate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra