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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-30 02:36:53 UTC

Update Date

2021-09-26 22:48:56 UTC

HMDB ID

HMDB0242351

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one

Description

(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one, also known as ketazocine methanesulfonate or ketocyclazocine, belongs to the class of organic compounds known as 2,6-dimethyl-3-benzazocines. These are aromatic compounds containing a 6,7-benzomorphan skeleton, which is substituted by methyl group at the 2- and 6-positions. Based on a literature review very few articles have been published on (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (1r,9s)-10-(cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one 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

HMDB0242351
     RDKit          3D
(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.0...
 44 47  0  0  0  0  0  0  0  0999 V2000
   -0.5831   -2.0622    1.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243   -0.8625    1.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5638    0.3301    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2727    1.5157    0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513    2.6363    0.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022    1.3798    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5842    2.4564    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284    2.2983    0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4374    1.0582   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117    0.8375   -0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5679   -0.0115   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.1245    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2518   -1.0050    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343   -2.3029    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241   -1.1003   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232   -0.3125   -1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.1053   -0.1163 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633    0.7436   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7111    0.1979   -0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    1.0038   -1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9572   -0.1066   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6881   -2.4751    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1093    3.4200    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6021   -2.4399   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3945   -2.1852   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2345   -0.7050   -2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5712    0.6748   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4205   -0.8653   -2.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2595    1.7132   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957    0.9995    0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5349   -0.5576   -1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6022    0.8775   -1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    2.0562   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5017   -1.0409   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9603    0.2128    0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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M  END

  Mrv1652308302104462D          

 21 24  0  0  0  0            999 V2000
    2.2581    0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717    0.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -0.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6989   -0.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0684   -1.0523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389    0.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    1.1319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    1.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332    1.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931    0.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    0.1662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4853   -0.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5437    0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8628    1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6050    1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9811   -0.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2881    1.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  6 20  1  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242351

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2N(CC3CC3)CCC1(C)C1=C(C=CC(O)=C1)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO2/c1-11-16-17(21)14-6-5-13(20)9-15(14)18(11,2)7-8-19(16)10-12-3-4-12/h5-6,9,11-12,16,20H,3-4,7-8,10H2,1-2H3

> <INCHI_KEY>
HQBZLVPZOGIAIQ-UHFFFAOYSA-N

> <FORMULA>
C18H23NO2

> <MOLECULAR_WEIGHT>
285.387

> <EXACT_MASS>
285.172878985

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.24295403810932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-(cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-8-one

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
2.5174344357122624

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.215570689700595

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.843857630627404

> <JCHEM_PKA_STRONGEST_BASIC>
7.0770099356434795

> <JCHEM_POLAR_SURFACE_AREA>
40.540000000000006

> <JCHEM_REFRACTIVITY>
83.23230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-(cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242351
     RDKit          3D
(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.0...
 44 47  0  0  0  0  0  0  0  0999 V2000
   -0.5831   -2.0622    1.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243   -0.8625    1.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5638    0.3301    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2727    1.5157    0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513    2.6363    0.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022    1.3798    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5842    2.4564    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284    2.2983    0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4374    1.0582   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117    0.8375   -0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5679   -0.0115   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.1245    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2518   -1.0050    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343   -2.3029    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241   -1.1003   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232   -0.3125   -1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.1053   -0.1163 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633    0.7436   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7111    0.1979   -0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    1.0038   -1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9572   -0.1066   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6881   -2.4751    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6032   -1.8030    1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -2.8278    2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9529   -0.7190    2.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1538    0.6095    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1093    3.4200    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5017   -1.0409   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9603    0.2128    0.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
  4  5  2  0
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  9 10  1  0
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 13 14  1  0
 13 15  1  0
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 13  2  1  0
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 17  3  1  0
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 19 40  1  0
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 21 43  1  0
 21 44  1  0
M  END

HEADER    PROTEIN                                 30-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-AUG-21         0                                  
HETATM    1  C   UNK     0       4.215   1.519   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.747   1.053   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.635  -0.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.171  -0.587   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.861  -1.964   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.179   0.577   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.069   2.113   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.905   3.121   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.369   3.011   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.361   1.846   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.471   0.310   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.906  -0.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.192   0.468   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.729   0.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.882   1.845   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.390   4.582   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.344   2.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.729   2.304   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.840   0.768   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.565  -0.096   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.004   3.168   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   20                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    2    9   16                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13                                                       
CONECT   16    8                                                            
CONECT   17    7   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19    6                                                       
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0242523
HETATM    1  C1  UNL     1      -0.747  -2.125   1.124  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.003  -1.385   0.046  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.846  -0.257   0.596  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.008   0.842   1.134  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.490   1.770   1.816  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.457   0.816   0.846  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.330   1.600   1.574  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.687   1.587   1.320  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.218   0.790   0.328  1.00  0.00           C  
HETATM   10  O2  UNL     1      -5.591   0.775   0.068  1.00  0.00           O  
HETATM   11  C9  UNL     1      -3.332   0.013  -0.390  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.965   0.009  -0.153  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.014  -0.813  -0.911  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.658  -1.968  -1.632  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.379   0.074  -1.965  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.647   1.007  -1.362  1.00  0.00           C  
HETATM   17  N1  UNL     1       1.584   0.300  -0.520  1.00  0.00           N  
HETATM   18  C15 UNL     1       2.628   1.217  -0.126  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.653   0.569   0.757  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.420  -0.593   0.243  1.00  0.00           C  
HETATM   21  C18 UNL     1       5.084   0.743   0.330  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.854  -2.121   0.950  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.452  -3.195   1.125  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.599  -1.662   2.114  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.692  -2.076  -0.481  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.520  -0.637   1.403  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.917   2.228   2.355  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.393   2.200   1.885  1.00  0.00           H  
HETATM   29  H8  UNL     1      -6.156   0.086   0.590  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.713  -0.615  -1.165  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.994  -1.612  -2.614  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.446  -2.462  -1.043  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.866  -2.724  -1.817  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.163   0.683  -2.431  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.072  -0.553  -2.742  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.244   1.405  -2.225  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.196   1.889  -0.877  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.232   2.163   0.315  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.129   1.529  -1.065  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.432   0.602   1.858  1.00  0.00           H  
HETATM   41  H20 UNL     1       4.140  -0.931  -0.772  1.00  0.00           H  
HETATM   42  H21 UNL     1       4.784  -1.390   0.927  1.00  0.00           H  
HETATM   43  H22 UNL     1       5.804   0.921   1.170  1.00  0.00           H  
HETATM   44  H23 UNL     1       5.339   1.302  -0.581  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   13   25
CONECT    3    4   17   26
CONECT    4    5    5    6
CONECT    6    7    7   12
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   10   11
CONECT   10   29
CONECT   11   12   12   30
CONECT   12   13
CONECT   13   14   15
CONECT   14   31   32   33
CONECT   15   16   34   35
CONECT   16   17   36   37
CONECT   17   18
CONECT   18   19   38   39
CONECT   19   20   21   40
CONECT   20   21   41   42
CONECT   21   43   44
END

HMDB0242351
     RDKit          3D
(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.0...
 44 47  0  0  0  0  0  0  0  0999 V2000
   -0.5831   -2.0622    1.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243   -0.8625    1.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5638    0.3301    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2727    1.5157    0.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513    2.6363    0.4298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022    1.3798    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5842    2.4564    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284    2.2983    0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4374    1.0582   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8117    0.8375   -0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5679   -0.0115   -0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.1245    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2518   -1.0050    0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0343   -2.3029    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241   -1.1003   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7232   -0.3125   -1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.1053   -0.1163 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633    0.7436   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7111    0.1979   -0.9654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    1.0038   -1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9572   -0.1066   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6881   -2.4751    0.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6032   -1.8030    1.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2082   -2.8278    2.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9529   -0.7190    2.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1538    0.6095    1.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1093    3.4200    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5787    3.1397    0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4665    1.6063   -0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9752   -0.9903   -0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6900   -2.2633    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3217   -3.1500    0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6021   -2.4399   -0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3945   -2.1852   -1.5175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2345   -0.7050   -2.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5712    0.6748   -1.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4205   -0.8653   -2.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2595    1.7132   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957    0.9995    0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5349   -0.5576   -1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6022    0.8775   -1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8612    2.0562   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5017   -1.0409   -0.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9603    0.2128    0.9281 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 13  2  1  0
 21 19  1  0
 17  3  1  0
 12  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-3-(Cyclopropylmethyl)-8-keto-5-(eq)-9-(ax)-dimethyl-6,7-benzomorphan	HMDB
Ketazocine, hydrochloride, (2alpha,6alpha,11S*)-isomer	HMDB
Ketazocine methanesulfonate	HMDB
Ketazocine, (2alpha,6alpha,11S*)-(+-)-isomer	HMDB
Ketazocine, (2alpha,6alpha,11S*)-isomer	HMDB
Ketazocine, mesylate, (2S-(2alpha,6alpha,11S*))-isomer	HMDB
Ketazocine, mesylate, (2alpha,6alpha,11S*)-(+-)-isomer	HMDB
Ketocyclazocine	HMDB

Chemical Formula

C₁₈H₂₃NO₂

Average Molecular Weight

285.387

Monoisotopic Molecular Weight

285.172878985

IUPAC Name

10-(cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-8-one

Traditional Name

10-(cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-8-one

CAS Registry Number

Not Available

SMILES

CC1C2N(CC3CC3)CCC1(C)C1=C(C=CC(O)=C1)C2=O

InChI Identifier

InChI=1S/C18H23NO2/c1-11-16-17(21)14-6-5-13(20)9-15(14)18(11,2)7-8-19(16)10-12-3-4-12/h5-6,9,11-12,16,20H,3-4,7-8,10H2,1-2H3

InChI Key

HQBZLVPZOGIAIQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,6-dimethyl-3-benzazocines. These are aromatic compounds containing a 6,7-benzomorphan skeleton, which is substituted by methyl group at the 2- and 6-positions.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

6,7-benzomorphans

Sub Class

2,6-dimethyl-3-benzazocines

Direct Parent

2,6-dimethyl-3-benzazocines

Alternative Parents

Substituents

2,6-dimethyl-3-benzazocine
4-hydroxy-6,7-benzomorphan
Benzazocine
Tetralin
Aryl ketone
Aryl alkyl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ketone
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen 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)

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	3.41	ALOGPS
logP	2.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.84	ChemAxon
pKa (Strongest Basic)	7.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.23 m³·mol⁻¹	ChemAxon
Polarizability	32.24 Å³	ChemAxon
Number of Rings	4	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]+	172.381	30932474
DeepCCS	[M-H]-	170.023	30932474
DeepCCS	[M-2H]-	202.909	30932474
DeepCCS	[M+Na]+	178.474	30932474
AllCCS	[M+H]+	170.0	32859911
AllCCS	[M+H-H2O]+	166.7	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	175.6	32859911
AllCCS	[M+Na-2H]-	175.3	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one,1TMS,isomer #1	CC1C2C(=O)C3=CC=C(O[Si](C)(C)C)C=C3C1(C)CCN2CC1CC1	2380.1	Semi standard non polar	33892256
(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one,1TMS,isomer #1	CC1C2C(=O)C3=CC=C(O[Si](C)(C)C)C=C3C1(C)CCN2CC1CC1	2658.9	Standard non polar	33892256
(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one,1TMS,isomer #1	CC1C2C(=O)C3=CC=C(O[Si](C)(C)C)C=C3C1(C)CCN2CC1CC1	2726.2	Standard polar	33892256
(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one,1TBDMS,isomer #1	CC1C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C1(C)CCN2CC1CC1	2627.1	Semi standard non polar	33892256
(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one,1TBDMS,isomer #1	CC1C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C1(C)CCN2CC1CC1	2901.6	Standard non polar	33892256
(1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one,1TBDMS,isomer #1	CC1C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3C1(C)CCN2CC1CC1	2863.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-5390000000-f9c0d6cfcef610064e91	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one 10V, Positive-QTOF	splash10-000i-0090000000-1a76e81de47a97ba3149	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one 20V, Positive-QTOF	splash10-000i-0190000000-c8defe1eff72848e7bf5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one 40V, Positive-QTOF	splash10-0a4i-9320000000-bfb64cb32f8d54135fda	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one 10V, Negative-QTOF	splash10-001i-0090000000-47c19a2a8233ff74e1db	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one 20V, Negative-QTOF	splash10-001i-0090000000-9929490e987dc6873a8b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one 40V, Negative-QTOF	splash10-01q9-0290000000-8470fd58b27b7d63cf1d	2021-10-12	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

10764667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12940550

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,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one (HMDB0242351)

MOL for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

3D MOL for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

3D SDF for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

3D-SDF for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

PDB for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

3D PDB for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

SMILES for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

INCHI for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

Structure for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

3D Structure for HMDB0242351 ((1R,9S)-10-(Cyclopropylmethyl)-4-hydroxy-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-8-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra