MiMeDB: Showing metabocard for morphinone (MMDBc0054567)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:17:59 UTC

Update Date

2024-04-30 20:54:16 UTC

Metabolite ID

MMDBc0054567

Metabolite Identification

Common Name

morphinone

Description

Morphinone is a very strong opioid. It is an intermediary substance in synthesises of semi-synthetic opioids, e.g. Naloxone and Naltrexone and Oxycodone.

Structure

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

HMDB0003563
     RDKit          3D
Morphinone
 38 42  0  0  0  0  0  0  0  0999 V2000
   -3.2845   -1.2955    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5624   -0.0769    0.5667 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754    0.2095    1.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4923    0.0548    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2371    0.7011    0.7421 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9164   -0.3317   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958   -1.1134   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780   -2.0355   -1.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -2.1271   -1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091   -1.2989   -0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580   -1.3755   -0.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208   -0.3671    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    0.5982    1.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640    1.5694    1.1540 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7382    2.4956    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    3.3269    0.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0630    2.4825   -1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250    1.9344   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767    1.3315   -0.1728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7484    0.2358   -0.5747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1409   -0.9394   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7049   -2.1969    0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1996   -1.2373    1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -1.4491   -0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -0.4848    2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    1.2791    2.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246    0.5430    2.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -1.0226    1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -2.6839   -2.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0269   -2.8606   -1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635   -0.7681    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    2.0698    2.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    2.9214   -2.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6095    1.9323   -2.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3672    2.0723    0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    0.7260   -1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -0.9379   -2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -1.8812   -0.8935 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
  5  4  1  1
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 14  5  1  0
 19  5  1  0
 12  6  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 14 32  1  1
 17 33  1  0
 18 34  1  0
 19 35  1  1
 20 36  1  6
 21 37  1  0
 21 38  1  0
M  END


  Mrv0541 02231219452D          

 23 27  0  0  1  0            999 V2000
   12.1861   -8.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740   -8.8955    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0865   -8.1810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4365   -8.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8490   -8.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4365   -9.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6115   -9.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1990   -8.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6115   -8.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1990  -10.3245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3070  -10.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0865   -9.6100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9115   -9.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3240  -10.3245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3240   -8.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9115   -8.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8490   -7.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6740   -7.4666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1464   -6.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8024   -6.7391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4883   -6.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3889   -7.6735    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3193  -10.2181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 12  1  0  0  0  0
  3 16  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17  4  1  0  0  0  0
 18 17  1  0  0  0  0
 18  3  1  0  0  0  0
  2  1  1  1  0  0  0
 19  1  1  0  0  0  0
 20 19  1  0  0  0  0
 18 20  1  1  0  0  0
 21 20  1  0  0  0  0
  3 22  1  1  0  0  0
 12 23  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054567

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@H](C4)[C@]1([H])C=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,16,19H,6-8H2,1H3/t10-,11+,16-,17-/m0/s1

> <INCHI_KEY>
PFBSOANQDDTNGJ-YNHQPCIGSA-N

> <FORMULA>
C17H17NO3

> <MOLECULAR_WEIGHT>
283.3218

> <EXACT_MASS>
283.120843415

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.339159874819494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-one

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
1.6570322429108246

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.758117847148686

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.097181827471367

> <JCHEM_PKA_STRONGEST_BASIC>
8.457881755462797

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
79.35569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
morphinone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003563
     RDKit          3D
Morphinone
 38 42  0  0  0  0  0  0  0  0999 V2000
   -3.2845   -1.2955    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5624   -0.0769    0.5667 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754    0.2095    1.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4923    0.0548    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2371    0.7011    0.7421 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9164   -0.3317   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958   -1.1134   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780   -2.0355   -1.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -2.1271   -1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091   -1.2989   -0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580   -1.3755   -0.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208   -0.3671    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    0.5982    1.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640    1.5694    1.1540 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7382    2.4956    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    3.3269    0.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0630    2.4825   -1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250    1.9344   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767    1.3315   -0.1728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7484    0.2358   -0.5747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1409   -0.9394   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7049   -2.1969    0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1996   -1.2373    1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -1.4491   -0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -0.4848    2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    1.2791    2.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246    0.5430    2.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -1.0226    1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -2.6839   -2.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0269   -2.8606   -1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635   -0.7681    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    2.0698    2.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    2.9214   -2.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6095    1.9323   -2.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3672    2.0723    0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    0.7260   -1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -0.9379   -2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -1.8812   -0.8935 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
  5  4  1  1
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 14  5  1  0
 19  5  1  0
 12  6  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 14 32  1  1
 17 33  1  0
 18 34  1  0
 19 35  1  1
 20 36  1  6
 21 37  1  0
 21 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      22.747 -15.363   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.658 -16.605   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.428 -15.271   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.348 -15.271   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.118 -16.605   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.348 -17.939   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.808 -17.939   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.038 -16.605   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.808 -15.271   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      19.038 -19.272   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      22.973 -18.984   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      24.428 -17.939   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.968 -17.939   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      26.738 -19.272   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      26.738 -16.605   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.968 -15.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.118 -13.938   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.658 -13.938   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.673 -12.580   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      23.898 -12.580   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      25.178 -11.652   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      24.993 -14.324   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      24.863 -19.074   0.000  0.00  0.00           H+0
CONECT    1    2   19                                                       
CONECT    2    3    5   12    1                                             
CONECT    3    2   16   18   22                                             
CONECT    4    5    9   17                                                  
CONECT    5    2    4    6                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    4    8                                                       
CONECT   10    7                                                            
CONECT   11    6   12                                                       
CONECT   12    2   11   13   23                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16    3   15                                                       
CONECT   17    4   18                                                       
CONECT   18   17    3   20                                                  
CONECT   19    1   20                                                       
CONECT   20   19   18   21                                                  
CONECT   21   20                                                            
CONECT   22    3                                                            
CONECT   23   12                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0003563
HETATM    1  C1  UNL     1      -3.285  -1.296   0.476  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.562  -0.077   0.567  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.975   0.209   1.826  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.492   0.055   1.893  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.237   0.701   0.742  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.916  -0.332  -0.065  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.296  -1.113  -0.991  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.078  -2.036  -1.652  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.445  -2.127  -1.350  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.009  -1.299  -0.396  1.00  0.00           C  
HETATM   11  O1  UNL     1       4.358  -1.375  -0.085  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.221  -0.367   0.273  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.427   0.598   1.255  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.364   1.569   1.154  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.738   2.496   0.055  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.666   3.327   0.230  1.00  0.00           O  
HETATM   17  C13 UNL     1       1.063   2.483  -1.244  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.125   1.934  -1.359  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.777   1.331  -0.173  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.748   0.236  -0.575  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.141  -0.939  -1.237  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.705  -2.197   0.821  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.200  -1.237   1.136  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.612  -1.449  -0.564  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.417  -0.485   2.581  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.217   1.279   2.082  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.125   0.543   2.827  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.245  -1.023   1.945  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.636  -2.684  -2.399  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.027  -2.861  -1.887  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.763  -0.768   0.613  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.196   2.070   2.109  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.530   2.921  -2.121  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.609   1.932  -2.320  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.367   2.072   0.403  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.439   0.726  -1.325  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.283  -0.938  -2.350  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.646  -1.881  -0.894  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   14   19
CONECT    6    7    7   12
CONECT    7    8   21
CONECT    8    9    9   29
CONECT    9   10   30
CONECT   10   11   12   12
CONECT   11   31
CONECT   12   13
CONECT   13   14
CONECT   14   15   32
CONECT   15   16   16   17
CONECT   17   18   18   33
CONECT   18   19   34
CONECT   19   20   35
CONECT   20   21   36
CONECT   21   37   38
END

HMDB0003563
     RDKit          3D
Morphinone
 38 42  0  0  0  0  0  0  0  0999 V2000
   -3.2845   -1.2955    0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5624   -0.0769    0.5667 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754    0.2095    1.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4923    0.0548    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2371    0.7011    0.7421 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9164   -0.3317   -0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958   -1.1134   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780   -2.0355   -1.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -2.1271   -1.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091   -1.2989   -0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3580   -1.3755   -0.0850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208   -0.3671    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4274    0.5982    1.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640    1.5694    1.1540 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7382    2.4956    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    3.3269    0.2296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0630    2.4825   -1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250    1.9344   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767    1.3315   -0.1728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7484    0.2358   -0.5747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1409   -0.9394   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7049   -2.1969    0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1996   -1.2373    1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6125   -1.4491   -0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173   -0.4848    2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2166    1.2791    2.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246    0.5430    2.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2452   -1.0226    1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -2.6839   -2.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0269   -2.8606   -1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7635   -0.7681    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959    2.0698    2.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    2.9214   -2.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6095    1.9323   -2.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3672    2.0723    0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    0.7260   -1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -0.9379   -2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6462   -1.8812   -0.8935 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
  5  4  1  1
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 14  5  1  0
 19  5  1  0
 12  6  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 14 32  1  1
 17 33  1  0
 18 34  1  0
 19 35  1  1
 20 36  1  6
 21 37  1  0
 21 38  1  0
M  END

Synonyms

Value	Source
Didehydro-4,5-alpha-epoxy-3-hydroxy-17-methylmorphinan-6-one	ChEBI
Didehydro-4,5-a-epoxy-3-hydroxy-17-methylmorphinan-6-one	Generator
Didehydro-4,5-α-epoxy-3-hydroxy-17-methylmorphinan-6-one	Generator

Molecular Formula

C₁₇H₁₇NO₃

Average Mass

283.3218

Monoisotopic Mass

283.120843415

IUPAC Name

(1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-one

Traditional Name

morphinone

CAS Registry Number

Not Available

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@H](C4)[C@]1([H])C=CC2=O

InChI Identifier

InChI=1S/C17H17NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,16,19H,6-8H2,1H3/t10-,11+,16-,17-/m0/s1

InChI Key

PFBSOANQDDTNGJ-YNHQPCIGSA-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
Isoquinolone
Tetralin
Coumaran
Cyclohexenone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:16315 )
Isoquinoline alkaloids (C01735 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.48 g/L	ALOGPS
logP	1.44	ALOGPS
logP	1.66	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.1	ChemAxon
pKa (Strongest Basic)	8.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.36 m³·mol⁻¹	ChemAxon
Polarizability	29.34 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-067l-1090000000-96ac950a45bc658b6caa	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fnc-7049000000-18819d9ca5c678af23b3	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-3c27f1af346e6c52a551	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-e5cc96a4aaed44ba106e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014m-5390000000-78f5bdb697a9a8997922	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-0966d213bb472b392cdf	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-d1879b97ab02b6e5b29e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0i90-0290000000-4da587484ea3cd5f71b8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-3e8e120b117b579b526d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-3e8e120b117b579b526d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f89-0090000000-40ab6b08cdf9646e4b2f	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-89c9bdd1a019fa2ef1ab	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-88c26e1e8a5751746e18	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001r-0090000000-497925e4360aa12aeb84	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0003563

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Morphinone

METLIN ID

6955

PubChem Compound

5459823

PDB ID

Not Available

ChEBI ID

16315

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Todaka T, Ishida T, Kita H, Narimatsu S, Yamano S: Bioactivation of morphine in human liver: isolation and identification of morphinone, a toxic metabolite. Biol Pharm Bull. 2005 Jul;28(7):1275-80. doi: 10.1248/bpb.28.1275. [PubMed:15997113 ]

Showing metabocard for morphinone (MMDBc0054567)

MOL for #<Metabolite:0x00007fdb71595318>

3D MOL for #<Metabolite:0x00007fdb71595318>

3D SDF for #<Metabolite:0x00007fdb71595318>

3D-SDF for #<Metabolite:0x00007fdb71595318>

PDB for #<Metabolite:0x00007fdb71595318>

3D PDB for #<Metabolite:0x00007fdb71595318>

SMILES for #<Metabolite:0x00007fdb71595318>

INCHI for #<Metabolite:0x00007fdb71595318>

Structure for #<Metabolite:0x00007fdb71595318>

3D Structure for #<Metabolite:0x00007fdb71595318>