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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 18:41:54 UTC

Update Date

2021-09-26 23:14:10 UTC

HMDB ID

HMDB0257666

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

Description

3-hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review very few articles have been published on 3-hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (1r,2r,3s,5s)-3-hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid 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

HMDB0257666
     RDKit          3D
(1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octa...
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.3185    0.9745   -2.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225    0.7654   -0.7379 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8180   -0.1147   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839   -1.4395   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036   -1.4165   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6656    0.0587   -0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217    0.1872    0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644    1.0469    0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181    2.1051    1.6188 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168    0.7580    0.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891    1.6367    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702    1.3383   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7861    0.1789   -1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0072   -0.0719   -1.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072   -0.6712   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907   -0.3991   -0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007    0.6849    1.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    2.0467    1.5234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.0032    1.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -1.2270    2.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5282   -1.2465    3.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093   -2.4089    2.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446    0.3284   -2.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778    2.0417   -2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4432    0.9322   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9485   -1.4197   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952   -2.3148   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4258   -2.0559   -0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -1.6621   -1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912    0.4251   -1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1906   -0.8055    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    2.5433    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3972    2.0546   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7397   -0.5730   -1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491   -1.5835   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -1.1511   -0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    0.4785    2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0329    2.3595    0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2871    0.7443    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338   -3.2739    2.0278 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
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  8 10  1  0
 10 11  2  0
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 13 14  1  0
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  7 17  1  0
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  6  2  1  0
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 19  3  1  0
  1 23  1  0
  1 24  1  0
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  3 26  1  0
  4 27  1  0
  4 28  1  0
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 14 35  1  0
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 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 22 41  1  0
M  END


  Mrv1652309112120422D          

 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
    2.4811    1.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2969    1.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    2.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3639    2.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    3.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5769    3.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3927    3.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6941    2.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2755    4.4601    0.0000 O   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
    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
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  8 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>
HMDB0257666

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2CCC1C(C(O)C2C(O)=O)C(=O)C1=CC=C(O)C=C1

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

> <INCHI_KEY>
PGTXQDJJERPUPG-UHFFFAOYSA-N

> <FORMULA>
C16H19NO5

> <MOLECULAR_WEIGHT>
305.33

> <EXACT_MASS>
305.126322716

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.92576752484772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
-2.0331907988217295

> <ALOGPS_LOGS>
-0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.665524673670059

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.942070897223237

> <JCHEM_PKA_STRONGEST_BASIC>
8.578214066364284

> <JCHEM_POLAR_SURFACE_AREA>
98.07000000000001

> <JCHEM_REFRACTIVITY>
78.3428

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257666
     RDKit          3D
(1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octa...
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.3185    0.9745   -2.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225    0.7654   -0.7379 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8180   -0.1147   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839   -1.4395   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036   -1.4165   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6656    0.0587   -0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217    0.1872    0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644    1.0469    0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181    2.1051    1.6188 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168    0.7580    0.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891    1.6367    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702    1.3383   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7861    0.1789   -1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0072   -0.0719   -1.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072   -0.6712   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907   -0.3991   -0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007    0.6849    1.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    2.0467    1.5234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.0032    1.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -1.2270    2.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5282   -1.2465    3.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093   -2.4089    2.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446    0.3284   -2.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778    2.0417   -2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4432    0.9322   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494    0.1486   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -1.4197   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952   -2.3148   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4258   -2.0559   -0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -1.6621   -1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912    0.4251   -1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1906   -0.8055    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    2.5433    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3972    2.0546   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7397   -0.5730   -1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491   -1.5835   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -1.1511   -0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    0.4785    2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0329    2.3595    0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2871    0.7443    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338   -3.2739    2.0278 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
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  7 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  6  2  1  0
 16 10  1  0
 19  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
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 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  C   UNK     0       4.631   2.591   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.154   2.362   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.069   4.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.546   4.254   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.983   5.688   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.944   6.892   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.466   6.662   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.029   5.229   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.381   8.326   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.879  -0.000   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   19                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19    8                                                            
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    HMDB0257666
HETATM    1  C1  UNL     1      -2.318   0.975  -2.094  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.922   0.765  -0.738  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.818  -0.115  -0.008  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.484  -1.440  -0.629  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.004  -1.416  -0.844  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.666   0.059  -0.603  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.122   0.187   0.778  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.064   1.047   0.904  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.018   2.105   1.619  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.317   0.758   0.245  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.389   1.637   0.335  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.570   1.338  -0.281  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.786   0.179  -1.016  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.007  -0.072  -1.620  1.00  0.00           O  
HETATM   15  C12 UNL     1       3.707  -0.671  -1.087  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.491  -0.399  -0.473  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.201   0.685   1.732  1.00  0.00           C  
HETATM   18  O3  UNL     1      -1.361   2.047   1.523  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.509  -0.003   1.437  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.697  -1.227   2.222  1.00  0.00           C  
HETATM   21  O4  UNL     1      -3.528  -1.246   3.163  1.00  0.00           O  
HETATM   22  O5  UNL     1      -2.009  -2.409   2.006  1.00  0.00           O  
HETATM   23  H1  UNL     1      -1.845   0.328  -2.830  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.078   2.042  -2.356  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.443   0.932  -2.125  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.849   0.149  -0.287  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.949  -1.420  -1.660  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.895  -2.315  -0.141  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.426  -2.056  -0.180  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.719  -1.662  -1.895  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.091   0.425  -1.325  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.191  -0.806   1.207  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.228   2.543   0.907  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.397   2.055  -0.190  1.00  0.00           H  
HETATM   35  H13 UNL     1       6.740  -0.573  -1.126  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.849  -1.583  -1.655  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.738  -1.151  -0.599  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.887   0.478   2.788  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.033   2.359   0.661  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.287   0.744   1.825  1.00  0.00           H  
HETATM   41  H19 UNL     1      -2.534  -3.274   2.028  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    6
CONECT    3    4   19   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31
CONECT    7    8   17   32
CONECT    8    9    9   10
CONECT   10   11   11   16
CONECT   11   12   33
CONECT   12   13   13   34
CONECT   13   14   15
CONECT   14   35
CONECT   15   16   16   36
CONECT   16   37
CONECT   17   18   19   38
CONECT   18   39
CONECT   19   20   40
CONECT   20   21   21   22
CONECT   22   41
END

HMDB0257666
     RDKit          3D
(1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octa...
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.3185    0.9745   -2.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225    0.7654   -0.7379 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8180   -0.1147   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4839   -1.4395   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0036   -1.4165   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6656    0.0587   -0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217    0.1872    0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644    1.0469    0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181    2.1051    1.6188 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3168    0.7580    0.2452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891    1.6367    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5702    1.3383   -0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7861    0.1789   -1.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0072   -0.0719   -1.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7072   -0.6712   -1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4907   -0.3991   -0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007    0.6849    1.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614    2.0467    1.5234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.0032    1.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -1.2270    2.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5282   -1.2465    3.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093   -2.4089    2.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8446    0.3284   -2.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0778    2.0417   -2.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4432    0.9322   -2.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494    0.1486   -0.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -1.4197   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952   -2.3148   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4258   -2.0559   -0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -1.6621   -1.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912    0.4251   -1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1906   -0.8055    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2282    2.5433    0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3972    2.0546   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7397   -0.5730   -1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491   -1.5835   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378   -1.1511   -0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8875    0.4785    2.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0329    2.3595    0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2871    0.7443    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5338   -3.2739    2.0278 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
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  7 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
  6  2  1  0
 16 10  1  0
 19  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
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate	Generator
(1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate	Generator

Chemical Formula

C₁₆H₁₉NO₅

Average Molecular Weight

305.33

Monoisotopic Molecular Weight

305.126322716

IUPAC Name

3-hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

Traditional Name

3-hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CN1C2CCC1C(C(O)C2C(O)=O)C(=O)C1=CC=C(O)C=C1

InChI Identifier

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

InChI Key

PGTXQDJJERPUPG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Tropane alkaloid
Piperidinecarboxylic acid
Aryl alkyl ketone
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
Benzenoid
N-alkylpyrrolidine
Piperidine
Hydroxy acid
Beta-aminoketone
Monocyclic benzene moiety
Pyrrolidine
Cyclic alcohol
Amino acid
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Amine
Alcohol
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)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.73	ALOGPS
logP	-2	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	2.94	ChemAxon
pKa (Strongest Basic)	8.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	98.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.34 m³·mol⁻¹	ChemAxon
Polarizability	30.93 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]+	170.689	30932474
DeepCCS	[M-H]-	168.331	30932474
DeepCCS	[M-2H]-	201.217	30932474
DeepCCS	[M+Na]+	176.782	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	CN1C2CCC1C(C(O)C2C(O)=O)C(=O)C1=CC=C(O)C=C1	3916.0	Standard polar	33892256
(1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	CN1C2CCC1C(C(O)C2C(O)=O)C(=O)C1=CC=C(O)C=C1	2646.0	Standard non polar	33892256
(1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	CN1C2CCC1C(C(O)C2C(O)=O)C(=O)C1=CC=C(O)C=C1	2917.2	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 - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4940000000-b4071bd699469fbe2ef8	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13304234

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 (1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid (HMDB0257666)

MOL for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

3D MOL for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

3D SDF for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

3D-SDF for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

PDB for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

3D PDB for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

SMILES for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

INCHI for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

Structure for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

3D Structure for HMDB0257666 ((1R,2R,3S,5S)-3-Hydroxy-4-(4-hydroxybenzoyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra