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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:16:13 UTC

Update Date

2022-03-07 02:55:09 UTC

HMDB ID

HMDB0037028

Secondary Accession Numbers

HMDB37028

Metabolite Identification

Common Name

Deoxyloganic acid

Description

Deoxyloganic acid, also known as deoxyloganate, belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Based on a literature review a significant number of articles have been published on Deoxyloganic acid.

Structure

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

HMDB0037028
     RDKit          3D
Deoxyloganic acid
 49 51  0  0  0  0  0  0  0  0999 V2000
    2.3965   -1.1154    2.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    0.0271    1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    1.0697    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956    1.1854   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492    0.0694   -0.9905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344    0.6073   -2.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260    1.0949   -3.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1614    1.0247   -2.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242    1.6255   -4.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442    0.6779   -2.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5666    0.2344   -2.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474   -0.1649   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1554    0.7054   -0.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4160    0.2841    0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196    1.0645   -0.2065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5930    0.3332   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345   -0.3607   -1.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8340   -1.2633   -1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7010   -0.6688    0.8610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0464   -0.8793    1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278    0.0347    2.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -0.7079    3.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318    0.1456    1.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005   -1.0640    2.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8767   -0.4384   -0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -2.0219    1.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -1.2309    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0799   -0.8204    3.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612    0.5209    1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368    0.7325    1.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042    2.0506    1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848    1.1419   -0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215    2.1905   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631   -0.7124   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2584    2.4016   -4.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5897    1.1053   -3.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0946   -1.1038   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354   -0.7370   -0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4712    1.0330   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0375    0.3461   -2.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7809   -0.9487   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9960   -2.1097   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -1.6257    0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4587   -1.4983    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5569    1.0663    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -1.3101    3.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725    0.9796    2.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083   -1.4019    2.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057   -1.5685   -0.1943 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  2  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 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 25  1  0
 25  2  1  0
 25  5  1  0
 23 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
M  END

  Mrv0541 05061309312D          

 25 27  0  0  0  0            999 V2000
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17  4  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23  5  1  0  0  0  0
 23 15  1  0  0  0  0
 24  9  1  0  0  0  0
 24 16  1  0  0  0  0
 25 15  1  0  0  0  0
 25 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037028

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C1C(OC1OC(CO)C(O)C(O)C1O)OC=C2C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O9/c1-6-2-3-7-8(14(21)22)5-23-15(10(6)7)25-16-13(20)12(19)11(18)9(4-17)24-16/h5-7,9-13,15-20H,2-4H2,1H3,(H,21,22)

> <INCHI_KEY>
DSXFHNSGLYXPNG-UHFFFAOYSA-N

> <FORMULA>
C16H24O9

> <MOLECULAR_WEIGHT>
360.3564

> <EXACT_MASS>
360.142032366

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
35.59972753542546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <ALOGPS_LOGP>
-1.09

> <JCHEM_LOGP>
-0.9076080566666671

> <ALOGPS_LOGS>
-1.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.207031738473338

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.334425979290826

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601512

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
81.11280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037028
     RDKit          3D
Deoxyloganic acid
 49 51  0  0  0  0  0  0  0  0999 V2000
    2.3965   -1.1154    2.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    0.0271    1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    1.0697    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956    1.1854   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492    0.0694   -0.9905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344    0.6073   -2.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260    1.0949   -3.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1614    1.0247   -2.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242    1.6255   -4.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442    0.6779   -2.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5666    0.2344   -2.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474   -0.1649   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1554    0.7054   -0.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4160    0.2841    0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196    1.0645   -0.2065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5930    0.3332   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345   -0.3607   -1.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8340   -1.2633   -1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7010   -0.6688    0.8610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0464   -0.8793    1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278    0.0347    2.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -0.7079    3.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318    0.1456    1.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005   -1.0640    2.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8767   -0.4384   -0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -2.0219    1.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -1.2309    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0799   -0.8204    3.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612    0.5209    1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368    0.7325    1.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042    2.0506    1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848    1.1419   -0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215    2.1905   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631   -0.7124   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2584    2.4016   -4.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5897    1.1053   -3.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0946   -1.1038   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354   -0.7370   -0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4712    1.0330   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0375    0.3461   -2.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7809   -0.9487   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9960   -2.1097   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -1.6257    0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4587   -1.4983    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5569    1.0663    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -1.3101    3.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725    0.9796    2.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083   -1.4019    2.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057   -1.5685   -0.1943 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  2  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 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 25  1  0
 25  2  1  0
 25  5  1  0
 23 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.788  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.122  -7.700   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      11.455  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      11.455  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.787   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.454   4.620   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.454  -4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    9   17                                                       
CONECT    5    8   23                                                       
CONECT    6    1    2   10                                                  
CONECT    7    3    8   10                                                  
CONECT    8    5    7   14                                                  
CONECT    9    4   11   24                                                  
CONECT   10    6    7   15                                                  
CONECT   11    9   12   18                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   16   20                                                  
CONECT   14    8   21   22                                                  
CONECT   15   10   23   25                                                  
CONECT   16   13   24   25                                                  
CONECT   17    4                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23    5   15                                                       
CONECT   24    9   16                                                       
CONECT   25   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0037028
HETATM    1  C1  UNL     1       2.397  -1.115   2.116  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.049   0.027   1.182  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.144   1.070   1.203  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.696   1.185  -0.173  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.049   0.069  -0.990  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.834   0.607  -2.319  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.026   1.095  -3.059  1.00  0.00           C  
HETATM    8  O1  UNL     1       5.161   1.025  -2.526  1.00  0.00           O  
HETATM    9  O2  UNL     1       3.924   1.626  -4.320  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.644   0.678  -2.873  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.567   0.234  -2.183  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.547  -0.165  -0.817  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.155   0.705  -0.032  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.416   0.284   0.363  1.00  0.00           C  
HETATM   15  O5  UNL     1      -2.420   1.064  -0.206  1.00  0.00           O  
HETATM   16  C11 UNL     1      -3.593   0.333  -0.263  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.834  -0.361  -1.568  1.00  0.00           C  
HETATM   18  O6  UNL     1      -2.834  -1.263  -1.897  1.00  0.00           O  
HETATM   19  C13 UNL     1      -3.701  -0.669   0.861  1.00  0.00           C  
HETATM   20  O7  UNL     1      -5.046  -0.879   1.112  1.00  0.00           O  
HETATM   21  C14 UNL     1      -3.128   0.035   2.094  1.00  0.00           C  
HETATM   22  O8  UNL     1      -3.364  -0.708   3.230  1.00  0.00           O  
HETATM   23  C15 UNL     1      -1.632   0.146   1.829  1.00  0.00           C  
HETATM   24  O9  UNL     1      -1.000  -1.064   2.204  1.00  0.00           O  
HETATM   25  C16 UNL     1       1.877  -0.438  -0.240  1.00  0.00           C  
HETATM   26  H1  UNL     1       1.851  -2.022   1.788  1.00  0.00           H  
HETATM   27  H2  UNL     1       3.500  -1.231   2.106  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.080  -0.820   3.130  1.00  0.00           H  
HETATM   29  H4  UNL     1       1.161   0.521   1.609  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.937   0.732   1.919  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.804   2.051   1.596  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.785   1.142  -0.174  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.421   2.191  -0.598  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.863  -0.712  -1.066  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.258   2.402  -4.441  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.590   1.105  -3.890  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.095  -1.104  -0.866  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.535  -0.737  -0.082  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.471   1.033  -0.124  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.037   0.346  -2.403  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.781  -0.949  -1.447  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.996  -2.110  -1.397  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.216  -1.626   0.674  1.00  0.00           H  
HETATM   44  H19 UNL     1      -5.459  -1.498   0.445  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.557   1.066   2.140  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.119  -1.310   3.117  1.00  0.00           H  
HETATM   47  H22 UNL     1      -1.273   0.980   2.450  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.508  -1.402   2.984  1.00  0.00           H  
HETATM   49  H24 UNL     1       2.006  -1.568  -0.194  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   25   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   25   34
CONECT    6    7   10   10
CONECT    7    8    8    9
CONECT    9   35
CONECT   10   11   36
CONECT   11   12
CONECT   12   13   25   37
CONECT   13   14
CONECT   14   15   23   38
CONECT   15   16
CONECT   16   17   19   39
CONECT   17   18   40   41
CONECT   18   42
CONECT   19   20   21   43
CONECT   20   44
CONECT   21   22   23   45
CONECT   22   46
CONECT   23   24   47
CONECT   24   48
CONECT   25   49
END

HMDB0037028
     RDKit          3D
Deoxyloganic acid
 49 51  0  0  0  0  0  0  0  0999 V2000
    2.3965   -1.1154    2.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0491    0.0271    1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1441    1.0697    1.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956    1.1854   -0.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492    0.0694   -0.9905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8344    0.6073   -2.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260    1.0949   -3.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1614    1.0247   -2.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9242    1.6255   -4.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6442    0.6779   -2.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5666    0.2344   -2.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5474   -0.1649   -0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1554    0.7054   -0.0317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4160    0.2841    0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4196    1.0645   -0.2065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5930    0.3332   -0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8345   -0.3607   -1.5683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8340   -1.2633   -1.8966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7010   -0.6688    0.8610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0464   -0.8793    1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278    0.0347    2.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639   -0.7079    3.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318    0.1456    1.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0005   -1.0640    2.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8767   -0.4384   -0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8506   -2.0219    1.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -1.2309    2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0799   -0.8204    3.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1612    0.5209    1.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368    0.7325    1.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042    2.0506    1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848    1.1419   -0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4215    2.1905   -0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631   -0.7124   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2584    2.4016   -4.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5897    1.1053   -3.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0946   -1.1038   -0.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354   -0.7370   -0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4712    1.0330   -0.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0375    0.3461   -2.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7809   -0.9487   -1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9960   -2.1097   -1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -1.6257    0.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4587   -1.4983    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5569    1.0663    2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -1.3101    3.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2725    0.9796    2.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083   -1.4019    2.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0057   -1.5685   -0.1943 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  2  0
  7  9  1  0
  6 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 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 25  1  0
 25  2  1  0
 25  5  1  0
 23 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Deoxyloganate	Generator
1,5,9-Epideoxyloganic acid	HMDB
5-Epideoxyloganic acid	HMDB
8-Epideoxyloganic acid	HMDB
Deoxyloganic acid tetraacetate	HMDB
7-Methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylate	Generator
7-Deoxyloganic acid	MeSH
Deoxyloganic acid	MeSH

Chemical Formula

C₁₆H₂₄O₉

Average Molecular Weight

360.3564

Monoisotopic Molecular Weight

360.142032366

IUPAC Name

7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

Traditional Name

7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylic acid

CAS Registry Number

92842-56-3

SMILES

CC1CCC2C1C(OC1OC(CO)C(O)C(O)C1O)OC=C2C(O)=O

InChI Identifier

InChI=1S/C16H24O9/c1-6-2-3-7-8(14(21)22)5-23-15(10(6)7)25-16-13(20)12(19)11(18)9(4-17)24-16/h5-7,9-13,15-20H,2-4H2,1H3,(H,21,22)

InChI Key

DSXFHNSGLYXPNG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Vinylogous ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037028)

Source

Endogenous

Endogenous (HMDB: HMDB0037028)

Plant

Plant (HMDB: HMDB0037028)

Animal

Animal (HMDB: HMDB0037028)

Exogenous

Food

Food (HMDB: HMDB0037028)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0037028)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037028)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037028)

Lipid metabolism pathway (HMDB: HMDB0037028)

Cellular process

Cell signaling (HMDB: HMDB0037028)

Biochemical process

Lipid transport (HMDB: HMDB0037028)

Role

Biological role

Energy source (HMDB: HMDB0037028)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037028)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	106 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	114300 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	20.3 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.91	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.11 m³·mol⁻¹	ChemAxon
Polarizability	35.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	182.535	31661259
DarkChem	[M-H]-	176.637	31661259
DeepCCS	[M+H]+	182.014	30932474
DeepCCS	[M-H]-	179.656	30932474
DeepCCS	[M-2H]-	212.543	30932474
DeepCCS	[M+Na]+	188.107	30932474
AllCCS	[M+H]+	183.8	32859911
AllCCS	[M+H-H2O]+	181.0	32859911
AllCCS	[M+NH4]+	186.3	32859911
AllCCS	[M+Na]+	187.0	32859911
AllCCS	[M-H]-	181.8	32859911
AllCCS	[M+Na-2H]-	181.7	32859911
AllCCS	[M+HCOO]-	181.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deoxyloganic acid	CC1CCC2C1C(OC1OC(CO)C(O)C(O)C1O)OC=C2C(O)=O	4137.8	Standard polar	33892256
Deoxyloganic acid	CC1CCC2C1C(OC1OC(CO)C(O)C(O)C1O)OC=C2C(O)=O	2915.8	Standard non polar	33892256
Deoxyloganic acid	CC1CCC2C1C(OC1OC(CO)C(O)C(O)C1O)OC=C2C(O)=O	3058.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Deoxyloganic acid,1TMS,isomer #1	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O)C12	3035.4	Semi standard non polar	33892256
Deoxyloganic acid,1TMS,isomer #2	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O)C12	2996.3	Semi standard non polar	33892256
Deoxyloganic acid,1TMS,isomer #3	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O)C12	3006.9	Semi standard non polar	33892256
Deoxyloganic acid,1TMS,isomer #4	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C)C12	3007.7	Semi standard non polar	33892256
Deoxyloganic acid,1TMS,isomer #5	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO)C(O)C(O)C3O)C12	2964.0	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #1	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O)C12	2935.3	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #10	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C)C12	2948.3	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #2	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O)C12	2999.0	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #3	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O)C12	3000.6	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #4	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O[Si](C)(C)C)C12	3008.2	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #5	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O)C12	2942.2	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #6	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)C12	2993.6	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #7	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)C12	2982.1	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #8	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O)C12	2937.9	Semi standard non polar	33892256
Deoxyloganic acid,2TMS,isomer #9	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	3005.1	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #1	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O)C12	2897.1	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #10	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2887.6	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #2	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O)C12	2891.3	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #3	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O[Si](C)(C)C)C12	2888.8	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #4	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)C12	2977.2	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #5	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)C12	2964.4	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #6	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2960.7	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #7	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)C12	2900.7	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #8	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)C12	2897.0	Semi standard non polar	33892256
Deoxyloganic acid,3TMS,isomer #9	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2995.9	Semi standard non polar	33892256
Deoxyloganic acid,4TMS,isomer #1	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)C12	2822.7	Semi standard non polar	33892256
Deoxyloganic acid,4TMS,isomer #2	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)C12	2817.8	Semi standard non polar	33892256
Deoxyloganic acid,4TMS,isomer #3	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2794.0	Semi standard non polar	33892256
Deoxyloganic acid,4TMS,isomer #4	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2930.2	Semi standard non polar	33892256
Deoxyloganic acid,4TMS,isomer #5	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2814.6	Semi standard non polar	33892256
Deoxyloganic acid,5TMS,isomer #1	CC1CCC2C(C(=O)O[Si](C)(C)C)=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2742.4	Semi standard non polar	33892256
Deoxyloganic acid,1TBDMS,isomer #1	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O)C12	3278.5	Semi standard non polar	33892256
Deoxyloganic acid,1TBDMS,isomer #2	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)C12	3279.7	Semi standard non polar	33892256
Deoxyloganic acid,1TBDMS,isomer #3	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3280.9	Semi standard non polar	33892256
Deoxyloganic acid,1TBDMS,isomer #4	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3281.7	Semi standard non polar	33892256
Deoxyloganic acid,1TBDMS,isomer #5	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO)C(O)C(O)C3O)C12	3226.6	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #1	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O)C12	3386.3	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #10	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3414.0	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #2	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)C12	3456.0	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #3	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3473.8	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #4	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3458.8	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #5	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)C12	3411.2	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #6	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3475.2	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #7	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3469.4	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #8	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3394.8	Semi standard non polar	33892256
Deoxyloganic acid,2TBDMS,isomer #9	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3475.9	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #1	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)C12	3573.3	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #10	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3582.8	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #2	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3569.0	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #3	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3571.6	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #4	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[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)C3O)C12	3662.3	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #5	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3653.6	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #6	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3653.1	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #7	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3582.2	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #8	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3582.5	Semi standard non polar	33892256
Deoxyloganic acid,3TBDMS,isomer #9	CC1CCC2C(C(=O)O)=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3661.9	Semi standard non polar	33892256
Deoxyloganic acid,4TBDMS,isomer #1	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO[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)C3O)C12	3737.7	Semi standard non polar	33892256
Deoxyloganic acid,4TBDMS,isomer #2	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3733.5	Semi standard non polar	33892256
Deoxyloganic acid,4TBDMS,isomer #3	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3726.5	Semi standard non polar	33892256
Deoxyloganic acid,4TBDMS,isomer #4	CC1CCC2C(C(=O)O)=COC(OC3OC(CO[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)C3O[Si](C)(C)C(C)(C)C)C12	3826.5	Semi standard non polar	33892256
Deoxyloganic acid,4TBDMS,isomer #5	CC1CCC2C(C(=O)O[Si](C)(C)C(C)(C)C)=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3714.2	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 - Deoxyloganic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9243000000-43372982d3a9b122d7ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyloganic acid GC-MS (4 TMS) - 70eV, Positive	splash10-001i-4262149000-7f06b76b28466a7a47ed	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyloganic acid 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 - Deoxyloganic acid 6V, Negative-QTOF	splash10-052b-0902000000-11d93cbeb8af54b8be2a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 10V, Positive-QTOF	splash10-03ea-0903000000-903f3233a9d004c8a670	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 20V, Positive-QTOF	splash10-0gwb-0900000000-16a2a61f6e5048510028	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 40V, Positive-QTOF	splash10-0f89-8900000000-d5581b1774594a18f3ac	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 10V, Negative-QTOF	splash10-0k92-1916000000-085a5cc78cd6cef3002f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 20V, Negative-QTOF	splash10-0gvk-2901000000-1d6ff12cb7f9a07d4ede	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 40V, Negative-QTOF	splash10-02pm-5900000000-eacdc982c84260461c14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 10V, Positive-QTOF	splash10-03e9-0905000000-bb25e21a7bce7031ca95	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 20V, Positive-QTOF	splash10-01q9-1901000000-ade8544912ace44459cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 40V, Positive-QTOF	splash10-000t-9600000000-bde85ac4775cebdf5d57	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 10V, Negative-QTOF	splash10-0a4i-0109000000-daebe79714eeb047d4f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 20V, Negative-QTOF	splash10-0pb9-3916000000-30a970c565499ecb61bb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyloganic acid 40V, Negative-QTOF	splash10-0a6u-6910000000-812f9f177e9f0c38daa8	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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

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

4490284

PDB ID

Not Available

ChEBI ID

167915

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1858781

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Deoxyloganic acid (HMDB0037028)

MOL for HMDB0037028 (Deoxyloganic acid)

3D MOL for HMDB0037028 (Deoxyloganic acid)

3D SDF for HMDB0037028 (Deoxyloganic acid)

3D-SDF for HMDB0037028 (Deoxyloganic acid)

PDB for HMDB0037028 (Deoxyloganic acid)

3D PDB for HMDB0037028 (Deoxyloganic acid)

SMILES for HMDB0037028 (Deoxyloganic acid)

INCHI for HMDB0037028 (Deoxyloganic acid)

Structure for HMDB0037028 (Deoxyloganic acid)

3D Structure for HMDB0037028 (Deoxyloganic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra