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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:56 UTC

Update Date

2021-09-14 15:47:58 UTC

HMDB ID

HMDB0014045

Secondary Accession Numbers

HMDB14045

Metabolite Identification

Common Name

3-Methoxymorphinan

Description

3-Methoxymorphinan is only found in individuals that have used or taken Dextromethorphan. 3-Methoxymorphinan is a metabolite of Dextromethorphan. 3-methoxymorphinan belongs to the family of Morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Structure

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

HMDB0014045
     RDKit          3D
3-Methoxymorphinan
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.0543    1.9217    1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512    0.7102    0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230    0.0877    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0243   -1.1127   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9284   -1.7721   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -1.2157   -0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269   -0.0096   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6539    0.6108    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403    0.5452   -0.1648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9928    1.5756    0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    1.0872    2.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816   -0.2767    2.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1519   -1.2486    1.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7369   -0.6478    0.1793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8125   -1.5424   -1.0030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4909   -1.9695   -1.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785   -0.7925   -2.0041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308    0.3366   -2.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2088    1.1936   -1.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1567    1.9691    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1133    2.8128    0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9771    1.9232    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915   -1.5782   -0.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -2.7257   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5206    1.5396    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0186    2.0251    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943    2.4044    0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282    1.0942    2.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776    1.7926    2.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -0.6495    3.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.1946    2.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501   -1.3455    1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -2.2110    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7567   -0.2725    0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -2.4347   -0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3140   -3.0405   -1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4665   -1.8850   -2.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -1.3941   -2.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1077   -0.0157   -3.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669    0.9683   -3.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2491    1.6017   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8085    2.1349   -1.2816 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  8  3  1  0
 14  9  1  0
 16  6  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  1
 15 35  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
M  END

 
  Mrv0541 02271201042D          
 
 19 22  0  0  1  0            999 V2000
   20.5481  -11.8974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5516  -11.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2641  -12.3113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.1382  -11.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8323  -12.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2714  -10.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8466  -10.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9800  -11.9046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.2641  -13.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6816  -11.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8323  -13.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9836  -11.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2786   -9.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8539   -9.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6924  -12.3220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5481  -13.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5698   -9.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1414   -9.4114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4219   -9.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  1  5  1  0  0  0  0
  2  6  2  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  2  0  0  0  0
  8 15  1  6  0  0  0
  9 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014045

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C[C@@H]3NCC[C@]22CCCC[C@H]32)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H23NO/c1-19-13-6-5-12-10-16-14-4-2-3-7-17(14,8-9-18-16)15(12)11-13/h5-6,11,14,16,18H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1

> <INCHI_KEY>
ILNSWVUXAPSPEH-PVAVHDDUSA-N

> <FORMULA>
C17H23NO

> <MOLECULAR_WEIGHT>
257.3706

> <EXACT_MASS>
257.177964363

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.606283549365315

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S,10S)-4-methoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
3.110726413333334

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.21950278594474

> <JCHEM_POLAR_SURFACE_AREA>
21.259999999999998

> <JCHEM_REFRACTIVITY>
77.26850000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S,10S)-4-methoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014045
     RDKit          3D
3-Methoxymorphinan
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.0543    1.9217    1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512    0.7102    0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230    0.0877    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0243   -1.1127   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9284   -1.7721   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -1.2157   -0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269   -0.0096   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6539    0.6108    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403    0.5452   -0.1648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9928    1.5756    0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    1.0872    2.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816   -0.2767    2.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1519   -1.2486    1.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7369   -0.6478    0.1793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8125   -1.5424   -1.0030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4909   -1.9695   -1.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785   -0.7925   -2.0041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308    0.3366   -2.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2088    1.1936   -1.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1567    1.9691    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1133    2.8128    0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9771    1.9232    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915   -1.5782   -0.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -2.7257   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5206    1.5396    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0186    2.0251    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943    2.4044    0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282    1.0942    2.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776    1.7926    2.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -0.6495    3.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.1946    2.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501   -1.3455    1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -2.2110    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7567   -0.2725    0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -2.4347   -0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3140   -3.0405   -1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4665   -1.8850   -2.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -1.3941   -2.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1077   -0.0157   -3.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669    0.9683   -3.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2491    1.6017   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8085    2.1349   -1.2816 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  8  3  1  0
 14  9  1  0
 16  6  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  1
 15 35  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      38.356 -22.208   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      38.363 -20.671   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      39.693 -22.981   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      39.458 -21.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      37.020 -22.974   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      39.707 -19.905   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.047 -19.892   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.029 -22.222   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.693 -24.519   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      42.339 -21.107   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      37.020 -24.519   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      41.036 -20.684   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.720 -18.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.061 -18.354   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      42.359 -23.001   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      38.356 -25.298   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.397 -17.595   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      35.731 -17.568   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      34.388 -18.327   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8    9                                                  
CONECT    4    1   10                                                       
CONECT    5    1   11                                                       
CONECT    6    2   12   13                                                  
CONECT    7    2   14                                                       
CONECT    8    3   15   12                                                  
CONECT    9    3   16                                                       
CONECT   10    4   15                                                       
CONECT   11    5   16                                                       
CONECT   12    6    8                                                       
CONECT   13    6   17                                                       
CONECT   14    7   18   17                                                  
CONECT   15    8   10                                                       
CONECT   16    9   11                                                       
CONECT   17   13   14                                                       
CONECT   18   14   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0014045
HETATM    1  C1  UNL     1       4.054   1.922   1.239  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.051   0.710   0.550  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.923   0.088   0.054  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.024  -1.113  -0.615  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.928  -1.772  -1.128  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.651  -1.216  -0.974  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.527  -0.010  -0.305  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.654   0.611   0.190  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.840   0.545  -0.165  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.993   1.576   0.911  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.902   1.087   2.300  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.482  -0.277   2.544  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.152  -1.249   1.423  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.737  -0.648   0.179  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.813  -1.542  -1.003  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.491  -1.970  -1.543  1.00  0.00           C  
HETATM   17  N1  UNL     1      -2.578  -0.793  -2.004  1.00  0.00           N  
HETATM   18  C16 UNL     1      -1.831   0.337  -2.494  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.209   1.194  -1.467  1.00  0.00           C  
HETATM   20  H1  UNL     1       3.157   1.969   1.901  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.113   2.813   0.588  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.977   1.923   1.889  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.991  -1.578  -0.757  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.027  -2.726  -1.657  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.521   1.540   0.702  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.019   2.025   0.751  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.294   2.404   0.709  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.128   1.094   2.720  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.478   1.793   2.970  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.147  -0.650   3.529  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.588  -0.195   2.580  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.050  -1.346   1.364  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.625  -2.211   1.704  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.757  -0.272   0.399  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.419  -2.435  -0.768  1.00  0.00           H  
HETATM   36  H17 UNL     1      -0.314  -3.040  -1.312  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.466  -1.885  -2.647  1.00  0.00           H  
HETATM   38  H19 UNL     1      -2.812  -1.394  -2.822  1.00  0.00           H  
HETATM   39  H20 UNL     1      -1.108  -0.016  -3.278  1.00  0.00           H  
HETATM   40  H21 UNL     1      -2.567   0.968  -3.072  1.00  0.00           H  
HETATM   41  H22 UNL     1      -0.249   1.602  -1.907  1.00  0.00           H  
HETATM   42  H23 UNL     1      -1.809   2.135  -1.282  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   16
CONECT    7    8    8    9
CONECT    8   25
CONECT    9   10   14   19
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   32   33
CONECT   14   15   34
CONECT   15   16   17   35
CONECT   16   36   37
CONECT   17   18   38
CONECT   18   19   39   40
CONECT   19   41   42
END

HMDB0014045
     RDKit          3D
3-Methoxymorphinan
 42 45  0  0  0  0  0  0  0  0999 V2000
    4.0543    1.9217    1.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0512    0.7102    0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230    0.0877    0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0243   -1.1127   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9284   -1.7721   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -1.2157   -0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269   -0.0096   -0.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6539    0.6108    0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8403    0.5452   -0.1648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9928    1.5756    0.9114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    1.0872    2.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4816   -0.2767    2.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1519   -1.2486    1.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7369   -0.6478    0.1793 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8125   -1.5424   -1.0030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4909   -1.9695   -1.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5785   -0.7925   -2.0041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308    0.3366   -2.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2088    1.1936   -1.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1567    1.9691    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1133    2.8128    0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9771    1.9232    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9915   -1.5782   -0.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -2.7257   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5206    1.5396    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0186    2.0251    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943    2.4044    0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1282    1.0942    2.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776    1.7926    2.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1468   -0.6495    3.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -0.1946    2.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0501   -1.3455    1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -2.2110    1.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7567   -0.2725    0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -2.4347   -0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3140   -3.0405   -1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4665   -1.8850   -2.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -1.3941   -2.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1077   -0.0157   -3.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669    0.9683   -3.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2491    1.6017   -1.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8085    2.1349   -1.2816 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  8  3  1  0
 14  9  1  0
 16  6  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  1
 15 35  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methoxymorphinan hydrochloride	HMDB
3-Methoxymorphinan hydrochloride, (14alpha)-(+-)-isomer	HMDB
3-Methoxymorphinan, (+-)-isomer	HMDB
3-Methoxymorphinan, (14alpha)-(+-)-isomer	HMDB
3-Methoxymorphinan, (14alpha)-isomer	HMDB
LK-3 Compound	HMDB
3-Methoxymorphinan hydrobromide, (9alpha,13alpha,14alpha)-isomer	HMDB
3-Methoxymorphinan hydrochloride, (14alpha)-isomer	HMDB
3-Methoxymorphinan, (9alpha,13alpha,14alpha)-isomer	HMDB
3-Methoxymorphinan	MeSH

Chemical Formula

C₁₇H₂₃NO

Average Molecular Weight

257.3706

Monoisotopic Molecular Weight

257.177964363

IUPAC Name

(1S,9S,10S)-4-methoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene

Traditional Name

(1S,9S,10S)-4-methoxy-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene

CAS Registry Number

1531-25-5

SMILES

COC1=CC2=C(C[C@@H]3NCC[C@]22CCCC[C@H]32)C=C1

InChI Identifier

InChI=1S/C17H23NO/c1-19-13-6-5-12-10-16-14-4-2-3-7-17(14,8-9-18-16)15(12)11-13/h5-6,11,14,16,18H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1

InChI Key

ILNSWVUXAPSPEH-PVAVHDDUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
Phenanthrene
Benzazocine
Tetralin
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Secondary aliphatic amine
Ether
Azacycle
Secondary amine
Organoheterocyclic compound
Organonitrogen compound
Organopnictogen compound
Amine
Organooxygen compound
Hydrocarbon derivative
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: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Organ

Liver (HMDB: HMDB0014045)
Kidney (HMDB: HMDB0014045)

Cellular substructure

Extracellular (HMDB: HMDB0014045)

Source

Endogenous

Endogenous (HMDB: HMDB0014045)

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
Water Solubility	0.0027 g/L	ALOGPS
logP	3.8	ALOGPS
logP	3.11	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	10.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	21.26 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.27 m³·mol⁻¹	ChemAxon
Polarizability	29.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.965	31661259
DarkChem	[M-H]-	160.988	31661259
DeepCCS	[M-2H]-	203.593	30932474
DeepCCS	[M+Na]+	178.82	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	160.0	32859911
AllCCS	[M+NH4]+	166.9	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	170.0	32859911
AllCCS	[M+Na-2H]-	169.8	32859911
AllCCS	[M+HCOO]-	169.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxymorphinan	COC1=CC2=C(C[C@@H]3NCC[C@]22CCCC[C@H]32)C=C1	3225.0	Standard polar	33892256
3-Methoxymorphinan	COC1=CC2=C(C[C@@H]3NCC[C@]22CCCC[C@H]32)C=C1	2152.5	Standard non polar	33892256
3-Methoxymorphinan	COC1=CC2=C(C[C@@H]3NCC[C@]22CCCC[C@H]32)C=C1	2212.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methoxymorphinan,1TMS,isomer #1	COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C)C2=C1	2257.2	Semi standard non polar	33892256
3-Methoxymorphinan,1TMS,isomer #1	COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C)C2=C1	2345.5	Standard non polar	33892256
3-Methoxymorphinan,1TMS,isomer #1	COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C)C2=C1	2744.8	Standard polar	33892256
3-Methoxymorphinan,1TBDMS,isomer #1	COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C(C)(C)C)C2=C1	2477.0	Semi standard non polar	33892256
3-Methoxymorphinan,1TBDMS,isomer #1	COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C(C)(C)C)C2=C1	2599.2	Standard non polar	33892256
3-Methoxymorphinan,1TBDMS,isomer #1	COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3[Si](C)(C)C(C)(C)C)C2=C1	2921.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxymorphinan GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ou-0090000000-02c7b32ac3081ebf5923	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methoxymorphinan 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 - 3-Methoxymorphinan 10V, Positive-QTOF	splash10-0a4i-0090000000-f0acbe633f1ef78e7216	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 20V, Positive-QTOF	splash10-0a4i-0090000000-54662e3182c939714161	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 40V, Positive-QTOF	splash10-000f-5970000000-35b194f29f27675f40cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 10V, Negative-QTOF	splash10-0a4i-0090000000-089e7bdb4af372e7486c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 20V, Negative-QTOF	splash10-0a4i-0090000000-905d2c5b908a1ef3c9c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 40V, Negative-QTOF	splash10-0006-0290000000-d37c96e4f09b8d560625	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 10V, Positive-QTOF	splash10-0a4i-0090000000-07569ae87a2b34cbffc0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 20V, Positive-QTOF	splash10-0a4i-0190000000-1cb112d5f9e3bc10fa01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 40V, Positive-QTOF	splash10-07er-0890000000-5131521492963ed9e005	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 10V, Negative-QTOF	splash10-0a4i-0090000000-4d2203d29a4418e5d773	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 20V, Negative-QTOF	splash10-0a4i-0090000000-2c191d5d743de9bed35d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methoxymorphinan 40V, Negative-QTOF	splash10-0udi-0090000000-e25cdc87cd670c87eff3	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

24693630

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3-Methoxymorphinan

METLIN ID

Not Available

PubChem Compound

6603912

PDB ID

Not Available

ChEBI ID

580449

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

Not Available

Showing metabocard for 3-Methoxymorphinan (HMDB0014045)

MOL for HMDB0014045 (3-Methoxymorphinan)

3D MOL for HMDB0014045 (3-Methoxymorphinan)

3D SDF for HMDB0014045 (3-Methoxymorphinan)

3D-SDF for HMDB0014045 (3-Methoxymorphinan)

PDB for HMDB0014045 (3-Methoxymorphinan)

3D PDB for HMDB0014045 (3-Methoxymorphinan)

SMILES for HMDB0014045 (3-Methoxymorphinan)

INCHI for HMDB0014045 (3-Methoxymorphinan)

Structure for HMDB0014045 (3-Methoxymorphinan)

3D Structure for HMDB0014045 (3-Methoxymorphinan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra