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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 17:47:51 UTC

Update Date

2021-09-14 15:19:07 UTC

HMDB ID

HMDB0060657

Secondary Accession Numbers

HMDB60657

Metabolite Identification

Common Name

Norcodeine

Description

Norcodeine, also known as N-demethylcodeine, 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. Norcodeine is a very strong basic compound (based on its pKa). Norcodeine has relatively little opioid activity in its own right, but is formed as a metabolite of codeine following ingestion. norcodeine and formaldehyde can be biosynthesized from codeine; which is catalyzed by the enzyme cytochrome P450 3A4. In humans, norcodeine is involved in codeine metabolism pathway. Norcodeine is a metabolite of codeine. Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine.

Structure

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

HMDB0060657
     RDKit          3D
Norcodeine
 40 44  0  0  0  0  0  0  0  0999 V2000
    5.0132   -0.0909   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326    0.3581    0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -0.2274   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882   -1.2842   -1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2432   -1.8365   -1.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -1.3496   -0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2948   -0.3197    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723    0.2821    0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2018    1.2803    1.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    1.6214    1.1955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4191    2.7176    0.2170 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7633    3.4341   -0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0447    2.3563   -1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7749    1.2714   -1.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.3772   -0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3367   -1.0343   -0.4438 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2529   -1.8676   -1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -1.6731    0.7131 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -1.0722    1.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1231   -0.5649    1.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7829    0.3237    0.8287 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8810    0.3874   -0.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0321    0.1800   -1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781   -1.1957   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -1.6560   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -2.6567   -2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4905    1.8839    2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    3.4786    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    2.9731   -0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    3.0434   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2156    1.0547   -2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267    0.7660    0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1276   -0.9391   -1.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -2.8835   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -2.0657   -2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.5986    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258   -0.2678    2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6069   -1.8736    2.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.3938    2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    0.0619    2.9143 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  1  1
  8  3  1  0
 21 10  1  0
 17  6  1  0
 21  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  1
 11 28  1  1
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  6
 17 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
M  END

 
  Mrv0541 06181310422D          
 
 22 26  0  0  1  0            999 V2000
   16.0011  -12.7252    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9828  -11.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6921  -13.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.2665  -13.1309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.6921  -12.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2665  -11.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6956  -11.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4084  -12.7323    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.6885  -13.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4478  -12.2559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2629  -13.9532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1470  -12.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2665  -10.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4119  -11.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6956  -10.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1249  -13.1487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9722  -14.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5431  -14.3660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9864  -10.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5502  -10.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8339  -10.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4791  -13.7098    0.0000 H   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  0  0  0  0
  1  5  1  1  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  0  0  0  0
  4 10  1  6  0  0  0
  4 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  2  0  0  0  0
  8 16  1  1  0  0  0
  9 17  2  0  0  0  0
 11 18  1  6  0  0  0
 13 19  2  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
  6 10  1  0  0  0  0
  8 14  1  0  0  0  0
 11 17  1  0  0  0  0
 12 16  1  0  0  0  0
 15 19  1  0  0  0  0
  3 22  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0060657

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1NCC[C@@]235)=CC=C4OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/c1-20-13-5-2-9-8-11-10-3-4-12(19)16-17(10,6-7-18-11)14(9)15(13)21-16/h2-5,10-12,16,18-19H,6-8H2,1H3/t10-,11+,12-,16-,17-/m0/s1

> <INCHI_KEY>
HKOIXWVRNLGFOR-KOFBORESSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.3377

> <EXACT_MASS>
285.136493479

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.758613461360177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,13R,14S,17R)-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-14-ol

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
0.9599033456666661

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.782815528826653

> <JCHEM_PKA_STRONGEST_BASIC>
10.067862464745385

> <JCHEM_POLAR_SURFACE_AREA>
50.72

> <JCHEM_REFRACTIVITY>
79.31

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-norcodeine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060657
     RDKit          3D
Norcodeine
 40 44  0  0  0  0  0  0  0  0999 V2000
    5.0132   -0.0909   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326    0.3581    0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -0.2274   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882   -1.2842   -1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2432   -1.8365   -1.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -1.3496   -0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2948   -0.3197    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723    0.2821    0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2018    1.2803    1.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    1.6214    1.1955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4191    2.7176    0.2170 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7633    3.4341   -0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0447    2.3563   -1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7749    1.2714   -1.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.3772   -0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3367   -1.0343   -0.4438 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2529   -1.8676   -1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -1.6731    0.7131 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -1.0722    1.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1231   -0.5649    1.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7829    0.3237    0.8287 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8810    0.3874   -0.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0321    0.1800   -1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781   -1.1957   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -1.6560   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -2.6567   -2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4905    1.8839    2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    3.4786    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    2.9731   -0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    3.0434   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2156    1.0547   -2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267    0.7660    0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1276   -0.9391   -1.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -2.8835   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -2.0657   -2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.5986    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258   -0.2678    2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6069   -1.8736    2.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.3938    2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    0.0619    2.9143 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  1  1
  8  3  1  0
 21 10  1  0
 17  6  1  0
 21  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  1
 11 28  1  1
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  6
 17 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 18-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-13         0                                  
HETATM    1  C   UNK     0      29.869 -23.754   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.835 -22.219   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.159 -24.531   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.498 -24.511   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.159 -22.970   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.498 -21.455   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.165 -21.455   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.496 -23.767   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.152 -26.066   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      26.969 -22.878   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      28.491 -26.046   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.874 -23.024   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.498 -19.907   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.502 -22.225   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.165 -19.907   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      33.833 -24.544   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      29.815 -26.823   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      27.147 -26.817   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      29.841 -19.136   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      27.160 -19.136   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      25.823 -19.907   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      32.628 -25.592   0.000  0.00  0.00           H+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8    9   22                                             
CONECT    4    1   10   11                                                  
CONECT    5    1   12                                                       
CONECT    6    2   13   10                                                  
CONECT    7    2   14   15                                                  
CONECT    8    3   16   14                                                  
CONECT    9    3   17                                                       
CONECT   10    4    6                                                       
CONECT   11    4   18   17                                                  
CONECT   12    5   16                                                       
CONECT   13    6   19   20                                                  
CONECT   14    7    8                                                       
CONECT   15    7   19                                                       
CONECT   16    8   12                                                       
CONECT   17    9   11                                                       
CONECT   18   11                                                            
CONECT   19   13   15                                                       
CONECT   20   13   21                                                       
CONECT   21   20                                                            
CONECT   22    3                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0060657
HETATM    1  C1  UNL     1       5.013  -0.091  -0.601  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.833   0.358   0.004  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.607  -0.227  -0.280  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.488  -1.284  -1.175  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.243  -1.836  -1.427  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.103  -1.350  -0.796  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.295  -0.320   0.063  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.472   0.282   0.369  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.202   1.280   1.282  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.195   1.621   1.195  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.419   2.718   0.217  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.763   3.434  -0.061  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.045   2.356  -1.047  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.775   1.271  -1.192  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.984   0.377  -0.064  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.337  -1.034  -0.444  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.253  -1.868  -1.005  1.00  0.00           C  
HETATM   18  N1  UNL     1      -2.909  -1.673   0.713  1.00  0.00           N  
HETATM   19  C15 UNL     1      -2.520  -1.072   1.958  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.123  -0.565   1.996  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.783   0.324   0.829  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.881   0.387  -0.076  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.032   0.180  -1.687  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.078  -1.196  -0.486  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.379  -1.656  -1.660  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.140  -2.657  -2.120  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.490   1.884   2.245  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.078   3.479   0.730  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.281   2.973  -0.764  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.882   3.043  -1.901  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.216   1.055  -2.158  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.827   0.766   0.550  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.128  -0.939  -1.248  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.292  -2.883  -0.546  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.372  -2.066  -2.111  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.950  -1.599   0.646  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.226  -0.268   2.289  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.607  -1.874   2.744  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.388  -1.394   2.105  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.014   0.062   2.914  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   17
CONECT    7    8    8   21
CONECT    8    9
CONECT    9   10
CONECT   10   11   21   27
CONECT   11   12   13   28
CONECT   12   29
CONECT   13   14   14   30
CONECT   14   15   31
CONECT   15   16   21   32
CONECT   16   17   18   33
CONECT   17   34   35
CONECT   18   19   36
CONECT   19   20   37   38
CONECT   20   21   39   40
END

HMDB0060657
     RDKit          3D
Norcodeine
 40 44  0  0  0  0  0  0  0  0999 V2000
    5.0132   -0.0909   -0.6012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326    0.3581    0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6072   -0.2274   -0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882   -1.2842   -1.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2432   -1.8365   -1.4267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -1.3496   -0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2948   -0.3197    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723    0.2821    0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2018    1.2803    1.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    1.6214    1.1955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4191    2.7176    0.2170 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7633    3.4341   -0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0447    2.3563   -1.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7749    1.2714   -1.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9842    0.3772   -0.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3367   -1.0343   -0.4438 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2529   -1.8676   -1.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -1.6731    0.7131 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -1.0722    1.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1231   -0.5649    1.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7829    0.3237    0.8287 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8810    0.3874   -0.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0321    0.1800   -1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781   -1.1957   -0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -1.6560   -1.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -2.6567   -2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4905    1.8839    2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    3.4786    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814    2.9731   -0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8816    3.0434   -1.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2156    1.0547   -2.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267    0.7660    0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1276   -0.9391   -1.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2918   -2.8835   -0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3717   -2.0657   -2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.5986    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2258   -0.2678    2.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6069   -1.8736    2.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -1.3938    2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    0.0619    2.9143 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 21 20  1  1
  8  3  1  0
 21 10  1  0
 17  6  1  0
 21  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 10 27  1  1
 11 28  1  1
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  6
 17 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-N-Norcodeine	ChEBI
N-Demethylcodeine	ChEBI
N-Desmethylcodeine	ChEBI
Norcodeina	ChEBI
Norcodeinum	ChEBI
Norcodeine hydrochloride	HMDB

Chemical Formula

C₁₇H₁₉NO₃

Average Molecular Weight

285.3377

Monoisotopic Molecular Weight

285.136493479

IUPAC Name

(1S,5R,13R,14S,17R)-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-14-ol

Traditional Name

N-norcodeine

CAS Registry Number

Not Available

SMILES

[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1NCC[C@@]235)=CC=C4OC

InChI Identifier

InChI=1S/C17H19NO3/c1-20-13-5-2-9-8-11-10-3-4-12(19)16-17(10,6-7-18-11)14(9)15(13)21-16/h2-5,10-12,16,18-19H,6-8H2,1H3/t10-,11+,12-,16-,17-/m0/s1

InChI Key

HKOIXWVRNLGFOR-KOFBORESSA-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
Tetralin
Coumaran
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Secondary alcohol
Secondary aliphatic amine
Ether
Oxacycle
Azacycle
Secondary amine
Organoheterocyclic compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:80579 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060657)

Organ

Liver (HMDB: HMDB0060657)
Kidney (HMDB: HMDB0060657)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060657)

Cellular substructure

Cytoplasm (HMDB: HMDB0060657)

Source

Endogenous

Endogenous (HMDB: HMDB0060657)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Codeine Action Pathway (PathBank: SMP0000405)

Metabolic pathway

Codeine Metabolism Pathway (PathBank: SMP0000621)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	166.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	0.99	ALOGPS
logP	0.96	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	10.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.72 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.31 m³·mol⁻¹	ChemAxon
Polarizability	29.76 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]+	167.883	31661259
DarkChem	[M-H]-	165.926	31661259
DeepCCS	[M-2H]-	207.472	30932474
DeepCCS	[M+Na]+	182.363	30932474
AllCCS	[M+H]+	169.0	32859911
AllCCS	[M+H-H2O]+	165.5	32859911
AllCCS	[M+NH4]+	172.2	32859911
AllCCS	[M+Na]+	173.1	32859911
AllCCS	[M-H]-	173.6	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	172.4	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.	2.35 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9133 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1230.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	213.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	127.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	271.7 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	293.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	507.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	756.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	305.8 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	867.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	217.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	460.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	376.8 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	65.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norcodeine	[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1NCC[C@@]235)=CC=C4OC	3852.8	Standard polar	33892256
Norcodeine	[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1NCC[C@@]235)=CC=C4OC	2329.3	Standard non polar	33892256
Norcodeine	[H][C@]12C=C[C@H](O)[C@@H]3OC4=C5C(C[C@H]1NCC[C@@]235)=CC=C4OC	2511.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norcodeine,1TMS,isomer #1	COC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C)C=C[C@@H]35	2458.7	Semi standard non polar	33892256
Norcodeine,1TMS,isomer #2	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C	2485.8	Semi standard non polar	33892256
Norcodeine,2TMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C	2494.6	Semi standard non polar	33892256
Norcodeine,2TMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C	2565.0	Standard non polar	33892256
Norcodeine,2TMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C	3033.2	Standard polar	33892256
Norcodeine,1TBDMS,isomer #1	COC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C=C[C@@H]35	2727.3	Semi standard non polar	33892256
Norcodeine,1TBDMS,isomer #2	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	2707.3	Semi standard non polar	33892256
Norcodeine,2TBDMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	2956.5	Semi standard non polar	33892256
Norcodeine,2TBDMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	3039.7	Standard non polar	33892256
Norcodeine,2TBDMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C	3281.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norcodeine GC-MS (Non-derivatized) - 70eV, Positive	splash10-06fu-3090000000-def0952ab891094dac50	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norcodeine GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9024000000-4a5042616f41430320ca	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norcodeine 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 - Norcodeine 10V, Positive-QTOF	splash10-000i-0090000000-2b2a065b9ef804290085	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 20V, Positive-QTOF	splash10-000i-0090000000-c4a4c893f35ec4ef5e42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 40V, Positive-QTOF	splash10-0pds-2290000000-77037cb876f15ead4614	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 10V, Negative-QTOF	splash10-001i-0090000000-ef3058bd2e10c146303a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 20V, Negative-QTOF	splash10-001i-0090000000-43f5eb0c5e5b500e3376	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 40V, Negative-QTOF	splash10-02dj-0290000000-035b6759d7af2f780ae5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 10V, Positive-QTOF	splash10-000i-0090000000-12d6d7cf9e71a6a9ec09	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 20V, Positive-QTOF	splash10-000i-0090000000-541a4195765a2fac68a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 40V, Positive-QTOF	splash10-00m0-0090000000-ffff010c1fecc953cf8f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 10V, Negative-QTOF	splash10-001i-0090000000-793f02ff50658d83401d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 20V, Negative-QTOF	splash10-001i-0090000000-793f02ff50658d83401d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norcodeine 40V, Negative-QTOF	splash10-001i-0090000000-b7393b65969f408660ab	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Codeine Action Pathway		Not Available
Codeine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

C16576

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norcodeine

METLIN ID

Not Available

PubChem Compound

9925873

PDB ID

Not Available

ChEBI ID

80579

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 Norcodeine (HMDB0060657)

MOL for HMDB0060657 (Norcodeine)

3D MOL for HMDB0060657 (Norcodeine)

3D SDF for HMDB0060657 (Norcodeine)

3D-SDF for HMDB0060657 (Norcodeine)

PDB for HMDB0060657 (Norcodeine)

3D PDB for HMDB0060657 (Norcodeine)

SMILES for HMDB0060657 (Norcodeine)

INCHI for HMDB0060657 (Norcodeine)

Structure for HMDB0060657 (Norcodeine)

3D Structure for HMDB0060657 (Norcodeine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra