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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:29:02 UTC

Update Date

2022-09-22 17:44:24 UTC

HMDB ID

HMDB0254275

Secondary Accession Numbers

None

Metabolite Identification

Common Name

m-Hydroxybenzoylecgonine

Description

m-Hydroxybenzoylecgonine belongs to the class of organic compounds known as m-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is meta-substituted with a hydroxy group. Based on a literature review a significant number of articles have been published on m-Hydroxybenzoylecgonine. This compound has been identified in human blood as reported by (PMID: 31557052 ). M-hydroxybenzoylecgonine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically m-Hydroxybenzoylecgonine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254275
     RDKit          3D
m-Hydroxybenzoylecgonine
 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.1374    0.9014    1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8520    0.5391    0.9999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6852   -0.9152    1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087   -1.4664   -0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8100   -0.2204   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7405    0.7632   -0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153    0.2617   -0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450    1.1993   -1.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4389    0.9065   -3.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4448    2.4676   -1.3907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5256   -0.0437    0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -0.4135   -0.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    0.3270    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6869    1.3124    1.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868   -0.0549   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4110   -1.1314   -0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836   -1.4889   -1.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7621   -0.7548   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5596    0.3169   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6888    1.0232    0.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2995    0.6628    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2004   -1.1779    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7752    0.0071    1.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6559    1.6718    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772    1.3600    2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1017   -1.3425    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3416   -1.9780    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -2.1442   -0.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6718   -0.3534   -2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8166    0.1313   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641    1.7933   -0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020   -0.7134   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194    2.7890   -1.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5210    0.8407    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5588   -1.7045   -1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378   -2.3484   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7651   -1.0566   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5444    1.8148    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1764    1.5099    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464   -2.1623    0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -1.1287    2.0651 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  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 11 22  1  0
  6  2  1  0
 21 15  1  0
 22  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END


  Mrv1652309112115292D          

 22 24  0  0  0  0            999 V2000
    2.1787    0.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3941   -0.0001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624    0.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174   -0.4126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1624   -0.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -0.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1497   -0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5622    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1497    1.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3872    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997    1.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6247    1.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0372    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6247   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0372    2.1433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811   -1.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2969   -1.2655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797   -2.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254275

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2CCC1C(C(C2)OC(=O)C1=CC(O)=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO5/c1-17-10-5-6-12(17)14(15(19)20)13(8-10)22-16(21)9-3-2-4-11(18)7-9/h2-4,7,10,12-14,18H,5-6,8H2,1H3,(H,19,20)

> <INCHI_KEY>
XCJJCRPRQYXLRE-UHFFFAOYSA-N

> <FORMULA>
C16H19NO5

> <MOLECULAR_WEIGHT>
305.33

> <EXACT_MASS>
305.126322716

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.892470527790255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(3-hydroxybenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
-0.8987067913365266

> <ALOGPS_LOGS>
-1.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.975895002794063

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9218811825434012

> <JCHEM_PKA_STRONGEST_BASIC>
9.693859824566236

> <JCHEM_POLAR_SURFACE_AREA>
87.07000000000001

> <JCHEM_REFRACTIVITY>
78.37219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3-hydroxybenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254275
     RDKit          3D
m-Hydroxybenzoylecgonine
 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.1374    0.9014    1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8520    0.5391    0.9999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6852   -0.9152    1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087   -1.4664   -0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8100   -0.2204   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7405    0.7632   -0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153    0.2617   -0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450    1.1993   -1.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4389    0.9065   -3.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4448    2.4676   -1.3907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5256   -0.0437    0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -0.4135   -0.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    0.3270    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6869    1.3124    1.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868   -0.0549   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4110   -1.1314   -0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836   -1.4889   -1.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7621   -0.7548   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5596    0.3169   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6888    1.0232    0.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2995    0.6628    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2004   -1.1779    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7752    0.0071    1.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6559    1.6718    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772    1.3600    2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1017   -1.3425    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3416   -1.9780    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -2.1442   -0.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6718   -0.3534   -2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8166    0.1313   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641    1.7933   -0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020   -0.7134   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194    2.7890   -1.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5210    0.8407    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5588   -1.7045   -1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378   -2.3484   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7651   -1.0566   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5444    1.8148    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1764    1.5099    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464   -2.1623    0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -1.1287    2.0651 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  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 11 22  1  0
  6  2  1  0
 21 15  1  0
 22  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       4.067   0.476   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.602  -0.000   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.170   1.730   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.966   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.966  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170  -1.730   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.671  -1.388   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.339  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.671   1.387   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.879  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.649   1.333   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.879   2.667   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.189   1.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.959   2.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.499   2.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.269   1.333   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.499  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.959  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.269   4.001   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.631  -2.592   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.154  -2.362   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.069  -4.025   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   15                                                            
CONECT   20    7   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0254275
HETATM    1  C1  UNL     1      -4.137   0.901   1.505  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.852   0.539   1.000  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.685  -0.915   1.049  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.409  -1.466  -0.144  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.810  -0.220  -0.943  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.741   0.763  -0.447  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.415   0.262  -0.935  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.745   1.199  -1.864  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.439   0.906  -3.043  1.00  0.00           O  
HETATM   10  O2  UNL     1      -0.445   2.468  -1.391  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.526  -0.044   0.273  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.773  -0.413  -0.133  1.00  0.00           O  
HETATM   13  C9  UNL     1       1.853   0.327   0.318  1.00  0.00           C  
HETATM   14  O4  UNL     1       1.687   1.312   1.077  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.187  -0.055  -0.101  1.00  0.00           C  
HETATM   16  C11 UNL     1       3.411  -1.131  -0.933  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.684  -1.489  -1.328  1.00  0.00           C  
HETATM   18  C13 UNL     1       5.762  -0.755  -0.881  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.560   0.317  -0.054  1.00  0.00           C  
HETATM   20  O5  UNL     1       6.689   1.023   0.367  1.00  0.00           O  
HETATM   21  C15 UNL     1       4.299   0.663   0.330  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.200  -1.178   1.017  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.775   0.007   1.687  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.656   1.672   0.902  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.977   1.360   2.522  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.102  -1.343   1.966  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.342  -1.978   0.154  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.788  -2.144  -0.754  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.672  -0.353  -2.017  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.817   0.131  -0.655  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.964   1.793  -0.725  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.502  -0.713  -1.479  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.519   2.789  -1.571  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.521   0.841   0.938  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.559  -1.704  -1.281  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.838  -2.348  -1.990  1.00  0.00           H  
HETATM   37  H15 UNL     1       6.765  -1.057  -1.207  1.00  0.00           H  
HETATM   38  H16 UNL     1       6.544   1.815   0.977  1.00  0.00           H  
HETATM   39  H17 UNL     1       4.176   1.510   0.980  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.946  -2.162   0.629  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.840  -1.129   2.065  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    6
CONECT    3    4   22   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31
CONECT    7    8   11   32
CONECT    8    9    9   10
CONECT   10   33
CONECT   11   12   22   34
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   16   21
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   37
CONECT   19   20   21   21
CONECT   20   38
CONECT   21   39
CONECT   22   40   41
END

HMDB0254275
     RDKit          3D
m-Hydroxybenzoylecgonine
 41 43  0  0  0  0  0  0  0  0999 V2000
   -4.1374    0.9014    1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8520    0.5391    0.9999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6852   -0.9152    1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4087   -1.4664   -0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8100   -0.2204   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7405    0.7632   -0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4153    0.2617   -0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7450    1.1993   -1.8636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4389    0.9065   -3.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4448    2.4676   -1.3907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5256   -0.0437    0.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -0.4135   -0.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527    0.3270    0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6869    1.3124    1.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868   -0.0549   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4110   -1.1314   -0.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6836   -1.4889   -1.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7621   -0.7548   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5596    0.3169   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6888    1.0232    0.3667 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2995    0.6628    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2004   -1.1779    1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7752    0.0071    1.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6559    1.6718    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9772    1.3600    2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1017   -1.3425    1.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3416   -1.9780    0.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -2.1442   -0.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6718   -0.3534   -2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8166    0.1313   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641    1.7933   -0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020   -0.7134   -1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5194    2.7890   -1.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5210    0.8407    0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5588   -1.7045   -1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378   -2.3484   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7651   -1.0566   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5444    1.8148    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1764    1.5099    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9464   -2.1623    0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -1.1287    2.0651 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  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 11 22  1  0
  6  2  1  0
 21 15  1  0
 22  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Hydroxybenzoylecgonine	HMDB
p-Hydroxybenzoylecgonine	HMDB

Chemical Formula

C₁₆H₁₉NO₅

Average Molecular Weight

305.33

Monoisotopic Molecular Weight

305.126322716

IUPAC Name

3-(3-hydroxybenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

Traditional Name

3-(3-hydroxybenzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CN1C2CCC1C(C(C2)OC(=O)C1=CC(O)=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C16H19NO5/c1-17-10-5-6-12(17)14(15(19)20)13(8-10)22-16(21)9-3-2-4-11(18)7-9/h2-4,7,10,12-14,18H,5-6,8H2,1H3,(H,19,20)

InChI Key

XCJJCRPRQYXLRE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is meta-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

m-Hydroxybenzoic acid esters

Alternative Parents

Substituents

M-hydroxybenzoic acid ester
Piperidinecarboxylic acid
Tropane alkaloid
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Dicarboxylic acid or derivatives
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Amino acid
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.32	ALOGPS
logP	-0.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.92	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.37 m³·mol⁻¹	ChemAxon
Polarizability	30.89 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
DeepCCS	[M+H]+	169.742	30932474
DeepCCS	[M-H]-	167.384	30932474
DeepCCS	[M-2H]-	200.27	30932474
DeepCCS	[M+Na]+	175.835	30932474
AllCCS	[M+H]+	172.2	32859911
AllCCS	[M+H-H2O]+	169.1	32859911
AllCCS	[M+NH4]+	175.1	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	171.3	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	171.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.0078 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.8 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1036.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	209.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	115.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	291.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	327.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	772.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	674.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	223.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	977.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	250.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	537.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	405.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	251.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
m-Hydroxybenzoylecgonine	CN1C2CCC1C(C(C2)OC(=O)C1=CC(O)=CC=C1)C(O)=O	3743.7	Standard polar	33892256
m-Hydroxybenzoylecgonine	CN1C2CCC1C(C(C2)OC(=O)C1=CC(O)=CC=C1)C(O)=O	2713.0	Standard non polar	33892256
m-Hydroxybenzoylecgonine	CN1C2CCC1C(C(C2)OC(=O)C1=CC(O)=CC=C1)C(O)=O	2702.4	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 - m-Hydroxybenzoylecgonine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9300000000-3fad7b919adc2acb02e1	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxybenzoylecgonine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxybenzoylecgonine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxybenzoylecgonine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxybenzoylecgonine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxybenzoylecgonine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxybenzoylecgonine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - m-Hydroxybenzoylecgonine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	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 - m-Hydroxybenzoylecgonine 10V, Positive-QTOF	splash10-0a4r-0937000000-6fab0c8fbfbd9cce1c3b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxybenzoylecgonine 20V, Positive-QTOF	splash10-06y9-2971000000-b4f8699e0d17e74def02	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxybenzoylecgonine 40V, Positive-QTOF	splash10-00di-3910000000-0eecf1ba181c59c4b7de	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxybenzoylecgonine 10V, Negative-QTOF	splash10-03dr-0491000000-07e1cf01571a55ae4ce2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxybenzoylecgonine 20V, Negative-QTOF	splash10-0006-9300000000-2ba3f52fd264d81cf0c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - m-Hydroxybenzoylecgonine 40V, Negative-QTOF	splash10-0006-9000000000-46a081b6ea429651c476	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

15607453

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56677797

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for m-Hydroxybenzoylecgonine (HMDB0254275)

MOL for HMDB0254275 (m-Hydroxybenzoylecgonine)

3D MOL for HMDB0254275 (m-Hydroxybenzoylecgonine)

3D SDF for HMDB0254275 (m-Hydroxybenzoylecgonine)

3D-SDF for HMDB0254275 (m-Hydroxybenzoylecgonine)

PDB for HMDB0254275 (m-Hydroxybenzoylecgonine)

3D PDB for HMDB0254275 (m-Hydroxybenzoylecgonine)

SMILES for HMDB0254275 (m-Hydroxybenzoylecgonine)

INCHI for HMDB0254275 (m-Hydroxybenzoylecgonine)

Structure for HMDB0254275 (m-Hydroxybenzoylecgonine)

3D Structure for HMDB0254275 (m-Hydroxybenzoylecgonine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra