Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:43:19 UTC

Update Date

2022-03-07 02:53:55 UTC

HMDB ID

HMDB0033948

Secondary Accession Numbers

HMDB33948

Metabolite Identification

Common Name

Codeine N-oxide

Description

Codeine N-oxide, also known as genocodein or codeigene, 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. Codeine N-oxide is a moderately basic compound (based on its pKa). Outside of the human body, codeine N-oxide has been detected, but not quantified in, opium poppies. This could make codeine N-oxide a potential biomarker for the consumption of these foods.

Structure

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

HMDB0033948
     RDKit          3D
Codeine N-oxide
 44 48  0  0  0  0  0  0  0  0999 V2000
    5.6614    0.2521   -0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4268   -0.3586   -0.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2106    0.2471   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660    1.5442    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    2.1709    0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7742    1.5076    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    0.2535   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334   -0.4237   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7131   -1.6859   -1.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3064   -1.8983   -0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0170   -2.7488    0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -4.0367    0.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4774   -2.7172    0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0276   -1.4897    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223   -0.3667    0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6495    1.0134    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    2.0708    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897    1.2624   -0.4352 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.9372    1.1712    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496    2.4818   -1.0016 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.4753    0.2996   -1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -0.0887   -1.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2934   -0.5446   -0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8056    1.0297   -1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6460    0.7882    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4874   -0.4817   -0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877    2.0811    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488    3.1782    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619   -2.4144   -1.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -2.2935    1.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2133   -4.4660   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816   -3.6122    0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1104   -1.4641    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -0.4322    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    1.1765    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916    2.8487   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460    2.6000    1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    0.7838    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772    0.5027   -0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3779    2.1871    0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1221   -0.6090   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    0.7695   -2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0997   -0.8807   -2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5858    0.7926   -2.3226 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
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 10  1  0
 17  6  1  0
 23  7  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  CHG  2  18   1  20  -1
M  END


  Mrv0541 02241218242D          

 23 27  0  0  0  0            999 V2000
    1.9972   -0.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972   -1.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3025   -1.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3025   -2.3444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404   -2.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379    1.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077    0.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1735   -0.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6944   -0.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -1.3891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5642   -1.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5642   -0.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2589    0.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1287    0.9553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3472    1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3472    0.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3025    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7799    0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4759   -0.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0404   -1.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1738    2.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    1.9537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 11  2  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
  6 22  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 19  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033948

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2OC3C(O)C=CC4C5CC(C=C1)=C2C34CCN5(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3

> <INCHI_KEY>
BDLSDHWCOJPHIE-UHFFFAOYSA-N

> <FORMULA>
C18H21NO4

> <MOLECULAR_WEIGHT>
315.3636

> <EXACT_MASS>
315.147058165

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.146969202584486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-10-methoxy-4-methyl-12-oxa-4λ⁵-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-4-one

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
0.2185760996666672

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.78246759479445

> <JCHEM_PKA_STRONGEST_BASIC>
2.749304125830027

> <JCHEM_POLAR_SURFACE_AREA>
65.57

> <JCHEM_REFRACTIVITY>
86.6496

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-10-methoxy-4-methyl-12-oxa-4λ⁵-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033948
     RDKit          3D
Codeine N-oxide
 44 48  0  0  0  0  0  0  0  0999 V2000
    5.6614    0.2521   -0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4268   -0.3586   -0.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2106    0.2471   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660    1.5442    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    2.1709    0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7742    1.5076    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    0.2535   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334   -0.4237   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7131   -1.6859   -1.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3064   -1.8983   -0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0170   -2.7488    0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -4.0367    0.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4774   -2.7172    0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0276   -1.4897    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223   -0.3667    0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6495    1.0134    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    2.0708    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897    1.2624   -0.4352 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.9372    1.1712    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496    2.4818   -1.0016 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.4753    0.2996   -1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -0.0887   -1.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2934   -0.5446   -0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8056    1.0297   -1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6460    0.7882    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4874   -0.4817   -0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877    2.0811    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488    3.1782    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619   -2.4144   -1.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -2.2935    1.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2133   -4.4660   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816   -3.6122    0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1104   -1.4641    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -0.4322    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    1.1765    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916    2.8487   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460    2.6000    1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    0.7838    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772    0.5027   -0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3779    2.1871    0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1221   -0.6090   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    0.7695   -2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0997   -0.8807   -2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5858    0.7926   -2.3226 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
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 10  1  0
 17  6  1  0
 23  7  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  CHG  2  18   1  20  -1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.728  -0.486   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.728  -2.026   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.431  -2.836   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.431  -4.376   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.809  -5.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.377   2.837   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.134   1.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.324  -0.081   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.296  -1.296   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.405  -2.593   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.053  -2.107   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.053  -0.567   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.350   0.243   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.107   1.783   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.648   2.269   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.648   1.377   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.431   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.322   0.324   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.755  -1.134   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.809  -2.269   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.324   5.106   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       0.001   3.647   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       1.540   3.647   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    7   22                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12   16                                             
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11    3   10   12                                                  
CONECT   12    8   11   13                                                  
CONECT   13    1   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16    8   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19    9   18   20                                                  
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22    6   15   21   23                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0033948
HETATM    1  C1  UNL     1       5.661   0.252  -0.290  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.427  -0.359  -0.532  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.211   0.247  -0.282  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.166   1.544   0.243  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.936   2.171   0.503  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.774   1.508   0.239  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.896   0.254  -0.272  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.033  -0.424  -0.548  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.713  -1.686  -1.046  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.306  -1.898  -0.792  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.017  -2.749   0.400  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.483  -4.037   0.295  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.477  -2.717   0.612  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.028  -1.490   0.744  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.122  -0.367   0.667  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.650   1.013   0.634  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.573   2.071   0.548  1.00  0.00           C  
HETATM   18  N1  UNL     1      -2.590   1.262  -0.435  1.00  0.00           N1+
HETATM   19  C15 UNL     1      -3.937   1.171   0.083  1.00  0.00           C  
HETATM   20  O4  UNL     1      -2.450   2.482  -1.002  1.00  0.00           O1-
HETATM   21  C16 UNL     1      -2.475   0.300  -1.511  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.054  -0.089  -1.806  1.00  0.00           C  
HETATM   23  C18 UNL     1      -0.293  -0.545  -0.618  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.806   1.030  -1.072  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.646   0.788   0.698  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.487  -0.482  -0.301  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.088   2.081   0.456  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.949   3.178   0.912  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.062  -2.414  -1.708  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.496  -2.294   1.307  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.213  -4.466  -0.557  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.082  -3.612   0.656  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.110  -1.464   0.899  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.421  -0.432   1.538  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.178   1.176   1.622  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.792   2.849  -0.202  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.446   2.600   1.532  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.891   0.784   1.139  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.577   0.503  -0.540  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.378   2.187   0.115  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.122  -0.609  -1.336  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.915   0.770  -2.416  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.100  -0.881  -2.593  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.586   0.793  -2.323  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   17
CONECT    7    8    8   23
CONECT    8    9
CONECT    9   10
CONECT   10   11   23   29
CONECT   11   12   13   30
CONECT   12   31
CONECT   13   14   14   32
CONECT   14   15   33
CONECT   15   16   23   34
CONECT   16   17   18   35
CONECT   17   36   37
CONECT   18   19   20   21
CONECT   19   38   39   40
CONECT   21   22   41   42
CONECT   22   23   43   44
END

HMDB0033948
     RDKit          3D
Codeine N-oxide
 44 48  0  0  0  0  0  0  0  0999 V2000
    5.6614    0.2521   -0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4268   -0.3586   -0.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2106    0.2471   -0.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660    1.5442    0.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    2.1709    0.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7742    1.5076    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8957    0.2535   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0334   -0.4237   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7131   -1.6859   -1.0465 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3064   -1.8983   -0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0170   -2.7488    0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834   -4.0367    0.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4774   -2.7172    0.6115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0276   -1.4897    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223   -0.3667    0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6495    1.0134    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    2.0708    0.5476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5897    1.2624   -0.4352 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.9372    1.1712    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496    2.4818   -1.0016 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.4753    0.2996   -1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -0.0887   -1.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2934   -0.5446   -0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8056    1.0297   -1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6460    0.7882    0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4874   -0.4817   -0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0877    2.0811    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9488    3.1782    0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0619   -2.4144   -1.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -2.2935    1.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2133   -4.4660   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0816   -3.6122    0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1104   -1.4641    0.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4215   -0.4322    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1785    1.1765    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7916    2.8487   -0.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460    2.6000    1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    0.7838    1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5772    0.5027   -0.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3779    2.1871    0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1221   -0.6090   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    0.7695   -2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0997   -0.8807   -2.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5858    0.7926   -2.3226 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
 18 20  1  0
 18 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 10  1  0
 17  6  1  0
 23  7  1  0
 23 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  CHG  2  18   1  20  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Codeigene	HMDB
Codeine aminoxyde	HMDB
Codeine-N-oxide	HMDB
Genocodein	HMDB
Genocodeine	HMDB

Chemical Formula

C₁₈H₂₁NO₄

Average Molecular Weight

315.3636

Monoisotopic Molecular Weight

315.147058165

IUPAC Name

14-hydroxy-10-methoxy-4-methyl-12-oxa-4λ⁵-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-4-one

Traditional Name

14-hydroxy-10-methoxy-4-methyl-12-oxa-4λ⁵-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-4-one

CAS Registry Number

3688-65-1

SMILES

COC1=C2OC3C(O)C=CC4C5CC(C=C1)=C2C34CCN5(C)=O

InChI Identifier

InChI=1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3

InChI Key

BDLSDHWCOJPHIE-UHFFFAOYSA-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
Piperidine
Benzenoid
Trialkyl amine oxide
Secondary alcohol
N-oxide
Ether
Oxacycle
Azacycle
Trisubstituted n-oxide
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic zwitterion
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033948)
Cytoplasm (HMDB: HMDB0033948)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033948)

Source

Endogenous

Endogenous (HMDB: HMDB0033948)

Plant

Plant (HMDB: HMDB0033948)

Exogenous

Food

Food (HMDB: HMDB0033948)

Herb and spice

Spice

Opium poppy (FooDB: FOOD00438)

Process

Not Available

Role

Industrial application

Drug (HMDB: HMDB0033948)

Biological role

Nutrient

Nutrient (HMDB: HMDB0033948)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	231 - 232 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	0.22	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	2.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	65.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.65 m³·mol⁻¹	ChemAxon
Polarizability	33.15 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]+	171.931	31661259
DarkChem	[M-H]-	170.207	31661259
DeepCCS	[M-2H]-	209.727	30932474
DeepCCS	[M+Na]+	184.955	30932474
AllCCS	[M+H]+	175.6	32859911
AllCCS	[M+H-H2O]+	172.4	32859911
AllCCS	[M+NH4]+	178.5	32859911
AllCCS	[M+Na]+	179.3	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	179.8	32859911
AllCCS	[M+HCOO]-	179.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Codeine N-oxide	COC1=C2OC3C(O)C=CC4C5CC(C=C1)=C2C34CCN5(C)=O	3770.5	Standard polar	33892256
Codeine N-oxide	COC1=C2OC3C(O)C=CC4C5CC(C=C1)=C2C34CCN5(C)=O	2332.8	Standard non polar	33892256
Codeine N-oxide	COC1=C2OC3C(O)C=CC4C5CC(C=C1)=C2C34CCN5(C)=O	2584.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Codeine N-oxide,1TMS,isomer #1	COC1=CC=C2CC3C4C=CC(O[Si](C)(C)C)C5OC1=C2C45CC[N+]3(C)[O-]	2591.1	Semi standard non polar	33892256
Codeine N-oxide,1TBDMS,isomer #1	COC1=CC=C2CC3C4C=CC(O[Si](C)(C)C(C)(C)C)C5OC1=C2C45CC[N+]3(C)[O-]	2836.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k95-2091000000-f2b624aa7b40f7e8d4c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine N-oxide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7029000000-b51b315ac721d6bb56ff	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine N-oxide 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 - Codeine N-oxide 10V, Positive-QTOF	splash10-014i-0029000000-3f592f0b3f690a122d6f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 20V, Positive-QTOF	splash10-014i-0094000000-c9d9692f4b694aeb690b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 40V, Positive-QTOF	splash10-0aor-1090000000-bf263d1ef668bb5c7a2f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 10V, Negative-QTOF	splash10-03di-0029000000-b5c958bfe36fb99d2586	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 20V, Negative-QTOF	splash10-03di-0019000000-012613d35b990195d94c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 40V, Negative-QTOF	splash10-052g-2090000000-c5bbe6ee6976c9cd1a67	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 10V, Negative-QTOF	splash10-03di-0009000000-a9f6ec6e6fe2a282293c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 20V, Negative-QTOF	splash10-03di-0009000000-a9f6ec6e6fe2a282293c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 40V, Negative-QTOF	splash10-03di-0039000000-203d518fe0ac3bc02090	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 10V, Positive-QTOF	splash10-014i-0009000000-135924c69299cfc5fa80	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 20V, Positive-QTOF	splash10-014j-0098000000-50c20f9220bd84f13446	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine N-oxide 40V, Positive-QTOF	splash10-03xr-0094000000-631ad7f02a74441a9c3e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB012159

KNApSAcK ID

C00034467

Chemspider ID

10700944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19073920

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Codeine N-oxide (HMDB0033948)

MOL for HMDB0033948 (Codeine N-oxide)

3D MOL for HMDB0033948 (Codeine N-oxide)

3D SDF for HMDB0033948 (Codeine N-oxide)

3D-SDF for HMDB0033948 (Codeine N-oxide)

PDB for HMDB0033948 (Codeine N-oxide)

3D PDB for HMDB0033948 (Codeine N-oxide)

SMILES for HMDB0033948 (Codeine N-oxide)

INCHI for HMDB0033948 (Codeine N-oxide)

Structure for HMDB0033948 (Codeine N-oxide)

3D Structure for HMDB0033948 (Codeine N-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra