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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-01 23:14:56 UTC

Update Date

2021-09-26 22:50:10 UTC

HMDB ID

HMDB0242610

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Racemethorphan

Description

CHEMBL22207, also known as levomethorphan or delsym, 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. CHEMBL22207 is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Racemethorphan is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Racemethorphan is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0242610
     RDKit          3D
Racemethorphan
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.5532   -0.8444    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3783   -0.0999    0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1385   -0.4560   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0486   -1.5850   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7949   -1.9044   -1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -1.1377   -1.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8077   -0.0262   -0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0495    0.3310    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    0.8646    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1362    2.2818    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    3.2081   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322    2.9053   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6319    1.4893   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173    0.7083   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694   -0.7633   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -1.5469   -1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2380   -1.1998    0.2283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9023   -2.4586    0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230   -1.0421    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    0.3727    1.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580   -0.5902    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9321   -0.6573   -0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3129   -1.9182    0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9135   -2.2062   -1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263   -2.7904   -1.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    1.2220    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    2.6782    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095    2.3690   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943    3.1328   -1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6090    4.2602   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3085    3.0660    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9364    3.6330   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1971    1.0402    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112    1.5460   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0927    1.0643   -1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6119   -0.8317   -1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -1.3984   -2.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -2.6258   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -2.3118   -0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422   -2.8169    1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3571   -3.2558   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478   -1.3027    2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -1.7527    1.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0249    0.3703    2.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279    0.9794    1.8755 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 14  9  1  0
 16  6  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
M  END


  Mrv1533004241521092D          

 20 23  0  0  0  0            999 V2000
    1.1093    1.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6425    0.9592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    0.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5168   -0.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -1.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8402   -1.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7068   -0.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3452    0.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1169   -0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282    1.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1618    0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4135    0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0360   -0.6858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4825   -1.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3065   -1.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840   -0.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375    0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7530   -2.0334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5771   -1.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242610

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(CC3C4CCCCC24CCN3C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3

> <INCHI_KEY>
MKXZASYAUGDDCJ-UHFFFAOYSA-N

> <FORMULA>
C18H25NO

> <MOLECULAR_WEIGHT>
271.404

> <EXACT_MASS>
271.193614429

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.925676142917197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.493774350666667

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.846303987808813

> <JCHEM_POLAR_SURFACE_AREA>
12.47

> <JCHEM_REFRACTIVITY>
82.5632

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0242610
     RDKit          3D
Racemethorphan
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.5532   -0.8444    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3783   -0.0999    0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1385   -0.4560   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0486   -1.5850   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7949   -1.9044   -1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -1.1377   -1.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8077   -0.0262   -0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0495    0.3310    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    0.8646    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1362    2.2818    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    3.2081   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322    2.9053   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6319    1.4893   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173    0.7083   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694   -0.7633   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -1.5469   -1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2380   -1.1998    0.2283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9023   -2.4586    0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230   -1.0421    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    0.3727    1.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580   -0.5902    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9321   -0.6573   -0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3129   -1.9182    0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9135   -2.2062   -1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263   -2.7904   -1.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    1.2220    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    2.6782    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095    2.3690   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943    3.1328   -1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6090    4.2602   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3085    3.0660    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9364    3.6330   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1971    1.0402    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112    1.5460   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0927    1.0643   -1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6119   -0.8317   -1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -1.3984   -2.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -2.6258   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -2.3118   -0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422   -2.8169    1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3571   -3.2558   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478   -1.3027    2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -1.7527    1.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0249    0.3703    2.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279    0.9794    1.8755 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 14  9  1  0
 16  6  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.071   2.966   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.066   1.790   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.974   0.621   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.831  -1.045   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.201  -1.750   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.009  -2.726   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.568  -2.181   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.319  -0.662   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.511   0.314   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.952  -0.230   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.533   2.260   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.902   1.556   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.372   0.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.667  -1.280   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.501  -2.575   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.039  -2.501   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.744  -1.131   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.910   0.163   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.872  -3.796   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.411  -3.721   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10   14                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0242610
HETATM    1  C1  UNL     1       5.553  -0.844   0.155  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.378  -0.100   0.421  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.138  -0.456  -0.079  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.049  -1.585  -0.870  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.795  -1.904  -1.348  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.683  -1.138  -1.054  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.808  -0.026  -0.268  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.050   0.331   0.234  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.330   0.865   0.107  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.136   2.282   0.136  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.817   3.208  -0.615  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.232   2.905  -0.191  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.632   1.489  -0.520  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.417   0.708  -0.928  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.769  -0.763  -1.043  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.629  -1.547  -1.604  1.00  0.00           C  
HETATM   17  N1  UNL     1      -2.238  -1.200   0.228  1.00  0.00           N  
HETATM   18  C16 UNL     1      -2.902  -2.459   0.234  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.323  -1.042   1.312  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.831   0.373   1.447  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.358  -0.590   0.869  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.932  -0.657  -0.860  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.313  -1.918   0.338  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.913  -2.206  -1.116  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.726  -2.790  -1.968  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.175   1.222   0.870  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.346   2.678   1.141  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.109   2.369  -0.432  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.694   3.133  -1.708  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.609   4.260  -0.299  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.308   3.066   0.909  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.936   3.633  -0.646  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.197   1.040   0.301  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.311   1.546  -1.414  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.093   1.064  -1.910  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.612  -0.832  -1.762  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.596  -1.398  -2.716  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.749  -2.626  -1.435  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.911  -2.312  -0.233  1.00  0.00           H  
HETATM   40  H20 UNL     1      -3.042  -2.817   1.255  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.357  -3.256  -0.327  1.00  0.00           H  
HETATM   42  H22 UNL     1      -1.848  -1.303   2.249  1.00  0.00           H  
HETATM   43  H23 UNL     1      -0.474  -1.753   1.217  1.00  0.00           H  
HETATM   44  H24 UNL     1       0.025   0.370   2.157  1.00  0.00           H  
HETATM   45  H25 UNL     1      -1.628   0.979   1.875  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   16
CONECT    7    8    8    9
CONECT    8   26
CONECT    9   10   14   20
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   33   34
CONECT   14   15   35
CONECT   15   16   17   36
CONECT   16   37   38
CONECT   17   18   19
CONECT   18   39   40   41
CONECT   19   20   42   43
CONECT   20   44   45
END

HMDB0242610
     RDKit          3D
Racemethorphan
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.5532   -0.8444    0.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3783   -0.0999    0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1385   -0.4560   -0.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0486   -1.5850   -0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7949   -1.9044   -1.3481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -1.1377   -1.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8077   -0.0262   -0.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0495    0.3310    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    0.8646    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1362    2.2818    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    3.2081   -0.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322    2.9053   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6319    1.4893   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4173    0.7083   -0.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694   -0.7633   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -1.5469   -1.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2380   -1.1998    0.2283 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9023   -2.4586    0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3230   -1.0421    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8314    0.3727    1.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580   -0.5902    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9321   -0.6573   -0.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3129   -1.9182    0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9135   -2.2062   -1.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7263   -2.7904   -1.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1749    1.2220    0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460    2.6782    1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095    2.3690   -0.4325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943    3.1328   -1.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6090    4.2602   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3085    3.0660    0.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9364    3.6330   -0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1971    1.0402    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3112    1.5460   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0927    1.0643   -1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6119   -0.8317   -1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958   -1.3984   -2.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -2.6258   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9106   -2.3118   -0.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0422   -2.8169    1.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3571   -3.2558   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8478   -1.3027    2.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -1.7527    1.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0249    0.3703    2.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279    0.9794    1.8755 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
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
  8  3  1  0
 14  9  1  0
 16  6  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Levomethorphan	MeSH
Dextromethorphan	MeSH
Dextromethorphan hydrobromide	MeSH
Dextromethorphan hydrobromide, monohydrate	MeSH
L-Methorphan	MeSH
Hydrobromide, dextromethorphan	MeSH
Dextromethorphan, (+-)-isomer	MeSH
Dextromethorphan hydrochloride	MeSH
Dextromethorphan hydrobromide, (+-)-isomer	MeSH
D-Methorphan	MeSH
Delsym	MeSH
Hydrochloride, dextromethorphan	MeSH
Racemethorphan	MeSH

Chemical Formula

C₁₈H₂₅NO

Average Molecular Weight

271.404

Monoisotopic Molecular Weight

271.193614429

IUPAC Name

4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene

Traditional Name

4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-triene

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(CC3C4CCCCC24CCN3C)C=C1

InChI Identifier

InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3

InChI Key

MKXZASYAUGDDCJ-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
Benzazocine
Tetralin
Anisole
Alkyl aryl ether
Aralkylamine
Piperidine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Ether
Organoheterocyclic compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.75	ALOGPS
logP	3.49	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	9.85	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.56 m³·mol⁻¹	ChemAxon
Polarizability	31.93 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M-2H]-	202.337	30932474
DeepCCS	[M+Na]+	177.902	30932474
AllCCS	[M+H]+	168.4	32859911
AllCCS	[M+H-H2O]+	165.1	32859911
AllCCS	[M+NH4]+	171.6	32859911
AllCCS	[M+Na]+	172.5	32859911
AllCCS	[M-H]-	172.4	32859911
AllCCS	[M+Na-2H]-	172.3	32859911
AllCCS	[M+HCOO]-	172.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Racemethorphan	COC1=CC2=C(CC3C4CCCCC24CCN3C)C=C1	3277.3	Standard polar	33892256
Racemethorphan	COC1=CC2=C(CC3C4CCCCC24CCN3C)C=C1	2160.8	Standard non polar	33892256
Racemethorphan	COC1=CC2=C(CC3C4CCCCC24CCN3C)C=C1	2182.2	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 - Racemethorphan GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-0090000000-7d8219beca9ea999c49c	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Racemethorphan 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Racemethorphan 10V, Positive-QTOF	splash10-00di-0090000000-97b78b7ee9ffa5104c51	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Racemethorphan 40V, Positive-QTOF	splash10-00di-0900000000-7e8f0927b5537de7f3aa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Racemethorphan 20V, Positive-QTOF	splash10-00di-0090000000-7e67942b65678f597fb4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Racemethorphan 50V, Positive-QTOF	splash10-00fr-0900000000-da5ea2c66ccccb0dae4e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Racemethorphan 30V, Positive-QTOF	splash10-02mj-0890000000-391eb8d24dce2a22a1fd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Racemethorphan 50V, Positive-QTOF	splash10-00fr-0900000000-1f5525a7ae87ae78cd31	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Racemethorphan 50V, Positive-QTOF	splash10-00fr-0900000000-9b6268ed09eeea7a0fe9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Racemethorphan 30V, Positive-QTOF	splash10-02mj-0890000000-b13030a0828d8bcc5b20	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Racemethorphan 10V, Positive-QTOF	splash10-00di-0090000000-01488ff14969daea9a7c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Racemethorphan 20V, Positive-QTOF	splash10-00di-0190000000-fc2df4dddabae2157e91	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Racemethorphan 40V, Positive-QTOF	splash10-0006-3590000000-c1f9dda873aa91b3eaa2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Racemethorphan 10V, Negative-QTOF	splash10-00di-0090000000-429ffca83bb47ee26787	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Racemethorphan 20V, Negative-QTOF	splash10-00di-0090000000-ea5226a510381ff28221	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Racemethorphan 40V, Negative-QTOF	splash10-0v4i-0190000000-a8421af8f9594c3bc931	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3008

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Racemethorphan (HMDB0242610)

MOL for HMDB0242610 (Racemethorphan)

3D MOL for HMDB0242610 (Racemethorphan)

3D SDF for HMDB0242610 (Racemethorphan)

3D-SDF for HMDB0242610 (Racemethorphan)

PDB for HMDB0242610 (Racemethorphan)

3D PDB for HMDB0242610 (Racemethorphan)

SMILES for HMDB0242610 (Racemethorphan)

INCHI for HMDB0242610 (Racemethorphan)

Structure for HMDB0242610 (Racemethorphan)

3D Structure for HMDB0242610 (Racemethorphan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra