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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:05 UTC

Update Date

2022-03-07 02:52:08 UTC

HMDB ID

HMDB0029381

Secondary Accession Numbers

HMDB29381

Metabolite Identification

Common Name

6-O-Methylcodeine

Description

6-O-Methylcodeine, also known as codeine methyl ether or OCME, 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. Based on a literature review very few articles have been published on 6-O-Methylcodeine.

Structure

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

HMDB0029381
     RDKit          3D
6-O-Methylcodeine
 46 50  0  0  0  0  0  0  0  0999 V2000
    4.8563   -2.3449    0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -1.4593   -0.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -1.5284    0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -2.4845    0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -2.5154    1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1072   -1.6273    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870   -0.7389   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518   -0.6271   -0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    0.4592   -1.3787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5325    1.2194   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5843    2.4451   -0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1555    2.3238    0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1971    3.2345    0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    2.9664   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7684    2.0958    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    0.7550    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418   -0.3059    0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248   -1.5786    1.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1198   -0.7113   -0.1979 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0639    0.2681   -0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393   -1.2786   -1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -0.3929   -1.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5069    0.2559   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5120   -3.3927    0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1568   -1.9985    1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7519   -2.3569   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671   -3.1977    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953   -3.2677    2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892    1.4837   -2.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152    3.2467   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571    4.2932    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875    3.0899    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    3.1803    1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    3.9882   -0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7573    2.4971    0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410    0.8356    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8979    0.0309    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858   -2.4902    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856   -1.5659    2.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4923    0.8646    0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647    0.9684   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9560   -0.1908   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0648   -1.4568   -2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9219   -2.2572   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -1.0557   -2.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6265    0.3211   -2.5613 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
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 10  1  0
 18  6  1  0
 23  7  1  0
 23 16  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
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
M  END

  Mrv0541 02241214562D          

 23 27  0  0  0  0            999 V2000
   -1.5219   -0.0001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9445   -0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9445   -1.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563   -1.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3539   -1.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9406   -0.8235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5398   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563   -0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992   -0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1992    0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039    2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9445    1.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9445    0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    0.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563    1.6484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3397   -1.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3539    1.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  3 21  1  0  0  0  0
  4  5  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 23  1  0  0  0  0
 15 16  2  0  0  0  0
 15 20  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  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029381

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1C=CC2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,12-13,15,18H,8-10H2,1-3H3

> <INCHI_KEY>
HGPQAWTZLJXCTC-UHFFFAOYSA-N

> <FORMULA>
C19H23NO3

> <MOLECULAR_WEIGHT>
313.3908

> <EXACT_MASS>
313.167793607

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
34.31413812291376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.986077786666666

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.192785336544262

> <JCHEM_POLAR_SURFACE_AREA>
30.930000000000003

> <JCHEM_REFRACTIVITY>
89.35590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0029381
     RDKit          3D
6-O-Methylcodeine
 46 50  0  0  0  0  0  0  0  0999 V2000
    4.8563   -2.3449    0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -1.4593   -0.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -1.5284    0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -2.4845    0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -2.5154    1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1072   -1.6273    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870   -0.7389   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518   -0.6271   -0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    0.4592   -1.3787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5325    1.2194   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5843    2.4451   -0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1555    2.3238    0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1971    3.2345    0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    2.9664   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7684    2.0958    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    0.7550    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418   -0.3059    0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248   -1.5786    1.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1198   -0.7113   -0.1979 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0639    0.2681   -0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393   -1.2786   -1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -0.3929   -1.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5069    0.2559   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5120   -3.3927    0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1568   -1.9985    1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7519   -2.3569   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671   -3.1977    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953   -3.2677    2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892    1.4837   -2.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152    3.2467   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571    4.2932    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875    3.0899    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    3.1803    1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    3.9882   -0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7573    2.4971    0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410    0.8356    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8979    0.0309    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858   -2.4902    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856   -1.5659    2.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4923    0.8646    0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647    0.9684   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9560   -0.1908   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0648   -1.4568   -2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9219   -2.2572   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -1.0557   -2.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6265    0.3211   -2.5613 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
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 10  1  0
 18  6  1  0
 23  7  1  0
 23 16  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
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
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  O   UNK     0      -2.841  -0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.763  -1.537   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.763  -3.077   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.377  -3.849   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.852  -3.077   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.394  -2.924   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.622  -1.537   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.087  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.008  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.377  -0.769   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.852  -1.537   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.239  -0.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.239   0.769   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.994   3.849   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.763   3.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.763   1.537   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.377   0.769   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.852   1.537   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.852   3.077   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.377   3.849   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.994  -3.849   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.367  -3.056   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.394   3.106   0.000  0.00  0.00           C+0
CONECT    1    2   16                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4   11                                                       
CONECT    6    7                                                            
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    2    9   11   17                                             
CONECT   11    5   10   12                                                  
CONECT   12    7   11   13                                                  
CONECT   13   12   18                                                       
CONECT   14   15   23                                                       
CONECT   15   14   16   20                                                  
CONECT   16    1   15   17                                                  
CONECT   17   10   16   18                                                  
CONECT   18   13   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   15   19                                                       
CONECT   21    3   22                                                       
CONECT   22   21                                                            
CONECT   23   14                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0029381
HETATM    1  C1  UNL     1       4.856  -2.345   0.147  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.885  -1.459  -0.347  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.561  -1.528   0.068  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.148  -2.484   0.995  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.816  -2.515   1.382  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.107  -1.627   0.872  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.387  -0.739  -0.024  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.652  -0.627  -0.455  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.714   0.459  -1.379  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.533   1.219  -1.236  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.584   2.445  -0.410  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.156   2.324   0.825  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.197   3.234   0.961  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.836   2.966  -0.226  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.768   2.096   0.231  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.291   0.755   0.494  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.242  -0.306   0.893  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.525  -1.579   1.326  1.00  0.00           C  
HETATM   19  N1  UNL     1      -3.120  -0.711  -0.198  1.00  0.00           N  
HETATM   20  C16 UNL     1      -4.064   0.268  -0.602  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.339  -1.279  -1.275  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.269  -0.393  -1.774  1.00  0.00           C  
HETATM   23  C19 UNL     1      -0.507   0.256  -0.691  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.512  -3.393   0.217  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.157  -1.998   1.162  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.752  -2.357  -0.511  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.867  -3.198   1.408  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.495  -3.268   2.111  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.189   1.484  -2.265  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.115   3.247  -0.972  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.857   4.293   0.848  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.987   3.090   0.199  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.676   3.180   1.958  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.097   3.988  -0.448  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.757   2.497   0.349  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.541   0.836   1.363  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.898   0.031   1.722  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.086  -2.490   1.045  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.486  -1.566   2.455  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.492   0.865   0.205  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.565   0.968  -1.313  1.00  0.00           H  
HETATM   42  H19 UNL     1      -4.956  -0.191  -1.122  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.065  -1.457  -2.118  1.00  0.00           H  
HETATM   44  H21 UNL     1      -1.922  -2.257  -0.974  1.00  0.00           H  
HETATM   45  H22 UNL     1      -0.536  -1.056  -2.334  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.626   0.321  -2.561  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   18
CONECT    7    8    8   23
CONECT    8    9
CONECT    9   10
CONECT   10   11   23   29
CONECT   11   12   14   30
CONECT   12   13
CONECT   13   31   32   33
CONECT   14   15   15   34
CONECT   15   16   35
CONECT   16   17   23   36
CONECT   17   18   19   37
CONECT   18   38   39
CONECT   19   20   21
CONECT   20   40   41   42
CONECT   21   22   43   44
CONECT   22   23   45   46
END

HMDB0029381
     RDKit          3D
6-O-Methylcodeine
 46 50  0  0  0  0  0  0  0  0999 V2000
    4.8563   -2.3449    0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847   -1.4593   -0.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -1.5284    0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -2.4845    0.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159   -2.5154    1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1072   -1.6273    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870   -0.7389   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518   -0.6271   -0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7136    0.4592   -1.3787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5325    1.2194   -1.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5843    2.4451   -0.4104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1555    2.3238    0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1971    3.2345    0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    2.9664   -0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7684    2.0958    0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914    0.7550    0.4943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418   -0.3059    0.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5248   -1.5786    1.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1198   -0.7113   -0.1979 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0639    0.2681   -0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393   -1.2786   -1.2747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -0.3929   -1.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5069    0.2559   -0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5120   -3.3927    0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1568   -1.9985    1.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7519   -2.3569   -0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671   -3.1977    1.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4953   -3.2677    2.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1892    1.4837   -2.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152    3.2467   -0.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571    4.2932    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875    3.0899    0.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    3.1803    1.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    3.9882   -0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7573    2.4971    0.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5410    0.8356    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8979    0.0309    1.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858   -2.4902    1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4856   -1.5659    2.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4923    0.8646    0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647    0.9684   -1.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9560   -0.1908   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0648   -1.4568   -2.1176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9219   -2.2572   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -1.0557   -2.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6265    0.3211   -2.5613 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
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 23 10  1  0
 18  6  1  0
 23  7  1  0
 23 16  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
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Codeine methyl ether	HMDB
O(6)-Codeine methyl ether	HMDB
O(6)-Codeine methyl ether sulfate	MeSH
O(6)-Codeine methyl ether, (5alpha,6beta)-isomer	MeSH
OCME	MeSH

Chemical Formula

C₁₉H₂₃NO₃

Average Molecular Weight

313.3908

Monoisotopic Molecular Weight

313.167793607

IUPAC Name

10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene

Traditional Name

10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraene

CAS Registry Number

2859-16-7

SMILES

COC1C=CC2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4

InChI Identifier

InChI=1S/C19H23NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,12-13,15,18H,8-10H2,1-3H3

InChI Key

HGPQAWTZLJXCTC-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
Aralkylamine
Alkyl aryl ether
Piperidine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen 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: HMDB0029381)
Cytoplasm (HMDB: HMDB0029381)

Source

Endogenous

Endogenous (HMDB: HMDB0029381)

Exogenous

Food

Food (HMDB: HMDB0029381)

Exogenous (HMDB: HMDB0029381)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 - 141 °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	0.17 g/L	ALOGPS
logP	1.89	ALOGPS
logP	1.99	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	9.19	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.93 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.36 m³·mol⁻¹	ChemAxon
Polarizability	34.31 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	173.005	31661259
DarkChem	[M-H]-	170.496	31661259
DeepCCS	[M-2H]-	207.553	30932474
DeepCCS	[M+Na]+	183.015	30932474
AllCCS	[M+H]+	177.0	32859911
AllCCS	[M+H-H2O]+	173.8	32859911
AllCCS	[M+NH4]+	179.9	32859911
AllCCS	[M+Na]+	180.8	32859911
AllCCS	[M-H]-	182.9	32859911
AllCCS	[M+Na-2H]-	182.5	32859911
AllCCS	[M+HCOO]-	182.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-O-Methylcodeine	COC1C=CC2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4	3669.7	Standard polar	33892256
6-O-Methylcodeine	COC1C=CC2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4	2417.7	Standard non polar	33892256
6-O-Methylcodeine	COC1C=CC2C3CC4=C5C(OC1C25CCN3C)=C(OC)C=C4	2403.6	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 - 6-O-Methylcodeine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00l2-4090000000-ebe294350fd7ef8320cb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-O-Methylcodeine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-O-Methylcodeine 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 - 6-O-Methylcodeine 10V, Positive-QTOF	splash10-03di-0029000000-b5955286a95c62fae48c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 20V, Positive-QTOF	splash10-03di-1079000000-399a8ffe64cba70ec3a9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 40V, Positive-QTOF	splash10-08fu-2090000000-8e18948533bf24351ca5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 10V, Negative-QTOF	splash10-03di-0009000000-c0e61fdd071ff2e44be8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 20V, Negative-QTOF	splash10-03di-0098000000-42fecf1fdec5877538ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 40V, Negative-QTOF	splash10-00r7-0090000000-43cd457be57793dfc35a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 10V, Negative-QTOF	splash10-03di-0009000000-19200665d806a98057c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 20V, Negative-QTOF	splash10-03di-0019000000-32485e8c827091ca88c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 40V, Negative-QTOF	splash10-0296-0091000000-1a54014c213ba5ce97bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 10V, Positive-QTOF	splash10-03di-0009000000-879645690cd5fc806db2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 20V, Positive-QTOF	splash10-03di-0009000000-879645690cd5fc806db2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-O-Methylcodeine 40V, Positive-QTOF	splash10-03di-1095000000-99fb1adacf8d4e3ef199	2021-09-22	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

FDB000458

KNApSAcK ID

Not Available

Chemspider ID

545921

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

628577

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 6-O-Methylcodeine (HMDB0029381)

MOL for HMDB0029381 (6-O-Methylcodeine)

3D MOL for HMDB0029381 (6-O-Methylcodeine)

3D SDF for HMDB0029381 (6-O-Methylcodeine)

3D-SDF for HMDB0029381 (6-O-Methylcodeine)

PDB for HMDB0029381 (6-O-Methylcodeine)

3D PDB for HMDB0029381 (6-O-Methylcodeine)

SMILES for HMDB0029381 (6-O-Methylcodeine)

INCHI for HMDB0029381 (6-O-Methylcodeine)

Structure for HMDB0029381 (6-O-Methylcodeine)

3D Structure for HMDB0029381 (6-O-Methylcodeine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra