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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:43:59 UTC

Update Date

2021-09-26 23:09:45 UTC

HMDB ID

HMDB0255157

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Hydroxynorcocaine

Description

N-Hydroxynorcocaine belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Based on a literature review very few articles have been published on N-Hydroxynorcocaine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-hydroxynorcocaine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Hydroxynorcocaine 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

HMDB0255157
     RDKit          3D
N-Hydroxynorcocaine
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.6095    1.9475    3.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3494    1.8416    1.6893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5141    0.8001    1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0383    0.0152    2.1255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    0.6304   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -0.5389   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716   -0.1373   -0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333   -0.5320    0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6841   -1.2806    1.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3799   -0.0322    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266    0.8069   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0130    1.2694   -0.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0243    0.9250   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    0.0850    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922   -0.3787    1.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054   -1.4189   -1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696   -1.4359   -1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8694   -1.7317   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4367   -0.3880   -0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974    0.5583   -0.9140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4395   -0.0643   -2.2078 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865   -0.0407   -2.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989    2.8237    3.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1147    1.0182    3.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6066    1.9529    3.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895    1.5931   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3794   -1.1932    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9131    1.0722   -1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441    1.9172   -1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0439    1.2771   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4827   -0.1983    1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019   -1.0337    2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927   -2.4637   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -1.1139   -2.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3310   -2.1564   -2.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813   -2.2123    0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7211   -2.4113   -0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893   -0.2242    0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4409   -0.2577   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291    1.5512   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8861   -0.8412   -3.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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
 14 15  2  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20  5  1  0
 15 10  1  0
 21 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 22 41  1  0
M  END


  Mrv1652309112116442D          

 22 24  0  0  0  0            999 V2000
    3.1574    2.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6430    2.3449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9444    1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7602    1.4540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300    0.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257    1.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807    0.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -0.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3940    0.1887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5690    0.1887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4300   -0.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880    0.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130    0.1887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -0.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505   -0.5258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130   -1.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0255   -1.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6130   -2.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880   -2.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755   -1.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7880   -1.2403    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  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
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255157

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2O

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

> <INCHI_KEY>
NETRAGHALNKERF-UHFFFAOYSA-N

> <FORMULA>
C16H19NO5

> <MOLECULAR_WEIGHT>
305.33

> <EXACT_MASS>
305.126322716

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.203131708415015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-(benzoyloxy)-8-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.5172123136666662

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.070124832047547

> <JCHEM_PKA_STRONGEST_BASIC>
1.7316825663587199

> <JCHEM_POLAR_SURFACE_AREA>
76.07

> <JCHEM_REFRACTIVITY>
77.63030000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(benzoyloxy)-8-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255157
     RDKit          3D
N-Hydroxynorcocaine
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.6095    1.9475    3.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3494    1.8416    1.6893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5141    0.8001    1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0383    0.0152    2.1255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    0.6304   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -0.5389   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716   -0.1373   -0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333   -0.5320    0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6841   -1.2806    1.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3799   -0.0322    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266    0.8069   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0130    1.2694   -0.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0243    0.9250   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    0.0850    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922   -0.3787    1.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054   -1.4189   -1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696   -1.4359   -1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8694   -1.7317   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4367   -0.3880   -0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974    0.5583   -0.9140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4395   -0.0643   -2.2078 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865   -0.0407   -2.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989    2.8237    3.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1147    1.0182    3.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6066    1.9529    3.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895    1.5931   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3794   -1.1932    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9131    1.0722   -1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441    1.9172   -1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0439    1.2771   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4827   -0.1983    1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019   -1.0337    2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927   -2.4637   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -1.1139   -2.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3310   -2.1564   -2.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813   -2.2123    0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7211   -2.4113   -0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893   -0.2242    0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4409   -0.2577   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291    1.5512   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8861   -0.8412   -3.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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
 14 15  2  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20  5  1  0
 15 10  1  0
 21 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 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       5.894   5.581   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.934   4.377   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.496   2.944   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.019   2.714   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.536   1.740   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.035   2.082   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.831   1.122   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.831  -0.418   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.035  -1.378   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.602   0.352   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       1.062   0.352   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.536  -1.035   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.204   0.352   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.744   0.352   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.514  -0.982   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.054  -0.982   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.744  -2.315   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.514  -3.649   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.744  -4.983   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.204  -4.983   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.434  -3.649   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.204  -2.315   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12    5   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0255157
HETATM    1  C1  UNL     1      -2.609   1.948   3.077  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.349   1.842   1.689  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.514   0.800   1.265  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.038   0.015   2.125  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.197   0.630  -0.194  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.292  -0.539  -0.354  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.072  -0.137  -0.405  1.00  0.00           O  
HETATM    8  C5  UNL     1       2.033  -0.532   0.511  1.00  0.00           C  
HETATM    9  O4  UNL     1       1.684  -1.281   1.431  1.00  0.00           O  
HETATM   10  C6  UNL     1       3.380  -0.032   0.316  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.727   0.807  -0.731  1.00  0.00           C  
HETATM   12  C8  UNL     1       5.013   1.269  -0.897  1.00  0.00           C  
HETATM   13  C9  UNL     1       6.024   0.925  -0.032  1.00  0.00           C  
HETATM   14  C10 UNL     1       5.689   0.085   1.021  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.392  -0.379   1.184  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.605  -1.419  -1.543  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.070  -1.436  -1.833  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.869  -1.732  -0.589  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.437  -0.388  -0.169  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.497   0.558  -0.914  1.00  0.00           C  
HETATM   21  N1  UNL     1      -2.439  -0.064  -2.208  1.00  0.00           N  
HETATM   22  O5  UNL     1      -3.686  -0.041  -2.735  1.00  0.00           O  
HETATM   23  H1  UNL     1      -3.199   2.824   3.338  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.115   1.018   3.460  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.607   1.953   3.596  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.689   1.593  -0.495  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.379  -1.193   0.541  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.913   1.072  -1.410  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.244   1.917  -1.719  1.00  0.00           H  
HETATM   30  H8  UNL     1       7.044   1.277  -0.143  1.00  0.00           H  
HETATM   31  H9  UNL     1       6.483  -0.198   1.718  1.00  0.00           H  
HETATM   32  H10 UNL     1       4.202  -1.034   2.033  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.293  -2.464  -1.319  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.034  -1.114  -2.437  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.331  -2.156  -2.605  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.281  -2.212   0.206  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.721  -2.411  -0.820  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.389  -0.224   0.908  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.441  -0.258  -0.575  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.929   1.551  -1.021  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.886  -0.841  -3.269  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   20   26
CONECT    6    7   16   27
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   11   15
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   32
CONECT   16   17   33   34
CONECT   17   18   21   35
CONECT   18   19   36   37
CONECT   19   20   38   39
CONECT   20   21   40
CONECT   21   22
CONECT   22   41
END

HMDB0255157
     RDKit          3D
N-Hydroxynorcocaine
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.6095    1.9475    3.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3494    1.8416    1.6893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5141    0.8001    1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0383    0.0152    2.1255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1970    0.6304   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -0.5389   -0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0716   -0.1373   -0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333   -0.5320    0.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6841   -1.2806    1.4310 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3799   -0.0322    0.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7266    0.8069   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0130    1.2694   -0.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0243    0.9250   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    0.0850    1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922   -0.3787    1.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054   -1.4189   -1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696   -1.4359   -1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8694   -1.7317   -0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4367   -0.3880   -0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4974    0.5583   -0.9140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4395   -0.0643   -2.2078 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865   -0.0407   -2.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989    2.8237    3.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1147    1.0182    3.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6066    1.9529    3.5958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895    1.5931   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3794   -1.1932    0.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9131    1.0722   -1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441    1.9172   -1.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0439    1.2771   -0.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4827   -0.1983    1.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2019   -1.0337    2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927   -2.4637   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338   -1.1139   -2.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3310   -2.1564   -2.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2813   -2.2123    0.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7211   -2.4113   -0.8203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893   -0.2242    0.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4409   -0.2577   -0.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291    1.5512   -1.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8861   -0.8412   -3.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  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
 14 15  2  0
  6 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20  5  1  0
 15 10  1  0
 21 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 22 41  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
8-Hydroxynorcocaine	MeSH

Chemical Formula

C₁₆H₁₉NO₅

Average Molecular Weight

305.33

Monoisotopic Molecular Weight

305.126322716

IUPAC Name

methyl 3-(benzoyloxy)-8-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

Traditional Name

methyl 3-(benzoyloxy)-8-hydroxy-8-azabicyclo[3.2.1]octane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2O

InChI Identifier

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

InChI Key

NETRAGHALNKERF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Piperidinecarboxylic acid
Tropane alkaloid
Benzoyl
Piperidine
Pyrrolidine
Methyl ester
Carboxylic acid ester
N-organohydroxylamine
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
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	1.45	ALOGPS
logP	1.52	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	15.07	ChemAxon
pKa (Strongest Basic)	1.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.63 m³·mol⁻¹	ChemAxon
Polarizability	31.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	168.975	30932474
DeepCCS	[M-H]-	166.617	30932474
DeepCCS	[M-2H]-	199.611	30932474
DeepCCS	[M+Na]+	175.068	30932474
AllCCS	[M+H]+	172.2	32859911
AllCCS	[M+H-H2O]+	169.1	32859911
AllCCS	[M+NH4]+	175.2	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	171.4	32859911
AllCCS	[M+Na-2H]-	171.2	32859911
AllCCS	[M+HCOO]-	171.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Hydroxynorcocaine	COC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2O	3233.2	Standard polar	33892256
N-Hydroxynorcocaine	COC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2O	2486.4	Standard non polar	33892256
N-Hydroxynorcocaine	COC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2O	2493.1	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 - N-Hydroxynorcocaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-5910000000-553d48763e890855fff2	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Hydroxynorcocaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

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

9897347

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11722631

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 N-Hydroxynorcocaine (HMDB0255157)

MOL for HMDB0255157 (N-Hydroxynorcocaine)

3D MOL for HMDB0255157 (N-Hydroxynorcocaine)

3D SDF for HMDB0255157 (N-Hydroxynorcocaine)

3D-SDF for HMDB0255157 (N-Hydroxynorcocaine)

PDB for HMDB0255157 (N-Hydroxynorcocaine)

3D PDB for HMDB0255157 (N-Hydroxynorcocaine)

SMILES for HMDB0255157 (N-Hydroxynorcocaine)

INCHI for HMDB0255157 (N-Hydroxynorcocaine)

Structure for HMDB0255157 (N-Hydroxynorcocaine)

3D Structure for HMDB0255157 (N-Hydroxynorcocaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

NMR Spectra