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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-12 23:47:18 UTC

Update Date

2021-09-14 15:15:54 UTC

HMDB ID

HMDB0003563

Secondary Accession Numbers

HMDB03563

Metabolite Identification

Common Name

Morphinone

Description

Morphinone 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. Morphinone has been detected, but not quantified in, several different foods, such as blackcurrants (Ribes nigrum), coconuts (Cocos nucifera), nectarines (Prunus persica var. nucipersica), summer savories (Satureja hortensis), and savoy cabbages (Brassica oleracea var. sabauda). This could make morphinone a potential biomarker for the consumption of these foods. Morphinone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Morphinone.

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>
HMDB0003563

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₁₇H₁₇NO₃

Average Molecular Weight

283.3218

Monoisotopic Molecular Weight

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

467-02-7

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 )

Ontology

Not Available

Physical Properties

State

Solid

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	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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.282	31661259
DarkChem	[M-H]-	159.765	31661259
DeepCCS	[M-2H]-	205.892	30932474
DeepCCS	[M+Na]+	181.424	30932474
AllCCS	[M+H]+	167.2	32859911
AllCCS	[M+H-H2O]+	163.7	32859911
AllCCS	[M+NH4]+	170.4	32859911
AllCCS	[M+Na]+	171.3	32859911
AllCCS	[M-H]-	172.9	32859911
AllCCS	[M+Na-2H]-	172.1	32859911
AllCCS	[M+HCOO]-	171.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.29 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0126 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	94.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1043.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	222.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	128.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	287.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	304.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	535.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	741.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	230.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	960.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	239.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	464.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	441.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	85.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Morphinone	[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@H](C4)[C@]1([H])C=CC2=O	4043.0	Standard polar	33892256
Morphinone	[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@H](C4)[C@]1([H])C=CC2=O	2412.8	Standard non polar	33892256
Morphinone	[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@H](C4)[C@]1([H])C=CC2=O	2541.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Morphinone,1TMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2C(=O)C=C[C@H]3[C@H]1C5	2634.4	Semi standard non polar	33892256
Morphinone,1TMS,isomer #2	CN1CC[C@]23C4=C(O[Si](C)(C)C)C=C[C@H]2[C@H]1CC1=CC=C(O)C(=C13)O4	2607.8	Semi standard non polar	33892256
Morphinone,2TMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C)C=C[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O4	2608.7	Semi standard non polar	33892256
Morphinone,2TMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C)C=C[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O4	2489.0	Standard non polar	33892256
Morphinone,2TMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C)C=C[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C)C(=C13)O4	3013.2	Standard polar	33892256
Morphinone,1TBDMS,isomer #1	CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2C(=O)C=C[C@H]3[C@H]1C5	2890.1	Semi standard non polar	33892256
Morphinone,1TBDMS,isomer #2	CN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)C=C[C@H]2[C@H]1CC1=CC=C(O)C(=C13)O4	2864.9	Semi standard non polar	33892256
Morphinone,2TBDMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)C=C[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O4	3087.7	Semi standard non polar	33892256
Morphinone,2TBDMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)C=C[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O4	2971.1	Standard non polar	33892256
Morphinone,2TBDMS,isomer #1	CN1CC[C@]23C4=C(O[Si](C)(C)C(C)(C)C)C=C[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(=C13)O4	3261.8	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Rapoport, Henry; Baker, Don R.; Reist, Helen N. Morphinone. Journal of Organic Chemistry (1957), 22 1489-92.

Material Safety Data Sheet (MSDS)

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. [PubMed:15997113 ]

Showing metabocard for Morphinone (HMDB0003563)

MOL for HMDB0003563 (Morphinone)

3D MOL for HMDB0003563 (Morphinone)

3D SDF for HMDB0003563 (Morphinone)

3D-SDF for HMDB0003563 (Morphinone)

PDB for HMDB0003563 (Morphinone)

3D PDB for HMDB0003563 (Morphinone)

SMILES for HMDB0003563 (Morphinone)

INCHI for HMDB0003563 (Morphinone)

Structure for HMDB0003563 (Morphinone)

3D Structure for HMDB0003563 (Morphinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized