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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:33:41 UTC

Update Date

2021-09-14 15:46:18 UTC

HMDB ID

HMDB0060552

Secondary Accession Numbers

HMDB60552

Metabolite Identification

Common Name

Dextrorphan

Description

Dextrorphan is a metabolite of Dextromethorphan. Dextrorphan (DXO) is a psychoactive drug of the morphinan chemical class which acts as an antitussive or cough suppressant and dissociative hallucinogen. It is the dextro-stereoisomer of racemorphan, the levo-half being levorphanol. Dextrorphan is produced by O-demethylation of dextromethorphan by CYP2D6. Dextrorphan is an NMDA antagonist and contributes to the psychoactive effects of dextromethorphan. (Wikipedia )

Structure

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

HMDB0060552
     RDKit          3D
Dextrorphan
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.0147   -1.3452    1.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8632   -0.5694    1.0749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9582   -0.5082    2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248    0.2194    1.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409   -0.0341    0.4314 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2184    0.0396    0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727   -1.3099    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714   -1.9968   -1.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877   -2.0250   -1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -1.3701    0.0863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3191   -1.2016   -0.0894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6501   -0.3393   -1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674    0.9484   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621    2.0539   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462    3.2822   -1.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2683    3.4342   -0.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244    4.6533   -0.7590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325    2.3165   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293    1.0800   -0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3618   -0.8956    2.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8166   -1.3552    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6481   -2.3614    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    0.0675    2.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7668   -1.5107    2.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1288   -0.2566    2.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3074    1.2790    2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867    0.6205   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501    0.6201    1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513   -1.1112   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757   -1.8692    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -1.5015   -2.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7137   -3.0357   -1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4573   -3.0957   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4400   -1.6112   -2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3157   -2.0392    0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7598   -2.2044   -0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -0.8312   -2.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443   -0.1481   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    1.9719   -2.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1986    4.1663   -2.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6608    5.3131   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151    2.4604    0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  2  1  0
 19 13  1  0
 10  5  1  0
 19  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  1
 11 36  1  6
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
M  END

 
  Mrv0541 02271201042D          
 
 19 22  0  0  1  0            999 V2000
   20.5481  -11.8974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5516  -11.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2641  -12.3113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.1382  -11.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8323  -12.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2714  -10.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8466  -10.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9800  -11.9046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.2641  -13.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6816  -11.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8323  -13.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9836  -11.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2786   -9.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8539   -9.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6924  -12.3220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5481  -13.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5698   -9.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1414   -9.4114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5990  -12.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  6  0  0  0
  1  5  1  0  0  0  0
  2  6  2  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  1  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  7 14  2  0  0  0  0
  8 15  1  6  0  0  0
  9 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
  8 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060552

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=C3C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1

> <INCHI_KEY>
JAQUASYNZVUNQP-PVAVHDDUSA-N

> <FORMULA>
C17H23NO

> <MOLECULAR_WEIGHT>
257.3706

> <EXACT_MASS>
257.177964363

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.69516177807219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S,10S)-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-trien-4-ol

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.903043791334286

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.461597359118004

> <JCHEM_PKA_STRONGEST_BASIC>
9.65585507934564

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
78.08090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dextrorphan

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060552
     RDKit          3D
Dextrorphan
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.0147   -1.3452    1.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8632   -0.5694    1.0749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9582   -0.5082    2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248    0.2194    1.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409   -0.0341    0.4314 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2184    0.0396    0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727   -1.3099    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714   -1.9968   -1.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877   -2.0250   -1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -1.3701    0.0863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3191   -1.2016   -0.0894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6501   -0.3393   -1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674    0.9484   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621    2.0539   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462    3.2822   -1.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2683    3.4342   -0.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244    4.6533   -0.7590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325    2.3165   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293    1.0800   -0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3618   -0.8956    2.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8166   -1.3552    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6481   -2.3614    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    0.0675    2.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7668   -1.5107    2.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1288   -0.2566    2.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3074    1.2790    2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867    0.6205   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501    0.6201    1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513   -1.1112   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757   -1.8692    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -1.5015   -2.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7137   -3.0357   -1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4573   -3.0957   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4400   -1.6112   -2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3157   -2.0392    0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7598   -2.2044   -0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -0.8312   -2.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443   -0.1481   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    1.9719   -2.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1986    4.1663   -2.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6608    5.3131   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151    2.4604    0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  2  1  0
 19 13  1  0
 10  5  1  0
 19  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  1
 11 36  1  6
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      38.356 -22.208   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      38.363 -20.671   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      39.693 -22.981   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      39.458 -21.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      37.020 -22.974   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      39.707 -19.905   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.047 -19.892   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.029 -22.222   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      39.693 -24.519   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      42.339 -21.107   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      37.020 -24.519   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      41.036 -20.684   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.720 -18.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.061 -18.354   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      42.359 -23.001   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      38.356 -25.298   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.397 -17.595   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      35.731 -17.568   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      44.051 -22.974   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8    9                                                  
CONECT    4    1   10                                                       
CONECT    5    1   11                                                       
CONECT    6    2   12   13                                                  
CONECT    7    2   14                                                       
CONECT    8    3   15   12                                                  
CONECT    9    3   16                                                       
CONECT   10    4   15                                                       
CONECT   11    5   16                                                       
CONECT   12    6    8                                                       
CONECT   13    6   17                                                       
CONECT   14    7   18   17                                                  
CONECT   15    8   19   10                                                  
CONECT   16    9   11                                                       
CONECT   17   13   14                                                       
CONECT   18   14                                                            
CONECT   19   15                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

COMPND    HMDB0060552
HETATM    1  C1  UNL     1      -3.015  -1.345   1.503  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.863  -0.569   1.075  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.958  -0.508   2.190  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.325   0.219   1.889  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.741  -0.034   0.431  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.218   0.040   0.247  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.873  -1.310   0.099  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.271  -1.997  -1.091  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.788  -2.025  -1.103  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.150  -1.370   0.086  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.319  -1.202  -0.089  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.650  -0.339  -1.295  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.967   0.948  -1.142  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.462   2.054  -1.831  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.846   3.282  -1.712  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.268   3.434  -0.911  1.00  0.00           C  
HETATM   17  O1  UNL     1       0.924   4.653  -0.759  1.00  0.00           O  
HETATM   18  C16 UNL     1       0.733   2.316  -0.242  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.129   1.080  -0.348  1.00  0.00           C  
HETATM   20  H1  UNL     1      -3.362  -0.896   2.466  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.817  -1.355   0.742  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.648  -2.361   1.751  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.472   0.068   2.994  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.767  -1.511   2.605  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.129  -0.257   2.506  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.307   1.279   2.134  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.487   0.621  -0.684  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.650   0.620   1.087  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.951  -1.111  -0.146  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.776  -1.869   1.041  1.00  0.00           H  
HETATM   31  H12 UNL     1       2.695  -1.501  -2.009  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.714  -3.036  -1.117  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.457  -3.096  -1.108  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.440  -1.611  -2.076  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.316  -2.039   0.958  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.760  -2.204  -0.290  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.437  -0.831  -2.250  1.00  0.00           H  
HETATM   38  H19 UNL     1      -2.744  -0.148  -1.268  1.00  0.00           H  
HETATM   39  H20 UNL     1      -2.333   1.972  -2.468  1.00  0.00           H  
HETATM   40  H21 UNL     1      -1.199   4.166  -2.230  1.00  0.00           H  
HETATM   41  H22 UNL     1       0.661   5.313  -0.022  1.00  0.00           H  
HETATM   42  H23 UNL     1       1.615   2.460   0.387  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   11
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6   10   19
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   31   32
CONECT    9   10   33   34
CONECT   10   11   35
CONECT   11   12   36
CONECT   12   13   37   38
CONECT   13   14   14   19
CONECT   14   15   39
CONECT   15   16   16   40
CONECT   16   17   18
CONECT   17   41
CONECT   18   19   19   42
END

HMDB0060552
     RDKit          3D
Dextrorphan
 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.0147   -1.3452    1.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8632   -0.5694    1.0749 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9582   -0.5082    2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248    0.2194    1.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7409   -0.0341    0.4314 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2184    0.0396    0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727   -1.3099    0.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714   -1.9968   -1.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7877   -2.0250   -1.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -1.3701    0.0863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3191   -1.2016   -0.0894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6501   -0.3393   -1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9674    0.9484   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4621    2.0539   -1.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462    3.2822   -1.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2683    3.4342   -0.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9244    4.6533   -0.7590 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7325    2.3165   -0.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293    1.0800   -0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3618   -0.8956    2.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8166   -1.3552    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6481   -2.3614    1.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    0.0675    2.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7668   -1.5107    2.6047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1288   -0.2566    2.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3074    1.2790    2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867    0.6205   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501    0.6201    1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513   -1.1112   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757   -1.8692    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6954   -1.5015   -2.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7137   -3.0357   -1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4573   -3.0957   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4400   -1.6112   -2.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3157   -2.0392    0.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7598   -2.2044   -0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -0.8312   -2.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7443   -0.1481   -1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    1.9719   -2.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1986    4.1663   -2.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6608    5.3131   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151    2.4604    0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  2  1  0
 19 13  1  0
 10  5  1  0
 19  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  1
 11 36  1  6
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-3-Hydroxy-N-methylmorphinan	ChEBI
D-3-Hydroxy-N-methylmorphinan	ChEBI
Dextrorphane	ChEBI
Dextrorphanum	ChEBI
(+-)-17-Methylmorphinan-3-ol	HMDB

Chemical Formula

C₁₇H₂₃NO

Average Molecular Weight

257.3706

Monoisotopic Molecular Weight

257.177964363

IUPAC Name

(1S,9S,10S)-17-methyl-17-azatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),3,5-trien-4-ol

Traditional Name

dextrorphan

CAS Registry Number

Not Available

SMILES

CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=C3C=C(O)C=C1

InChI Identifier

InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1

InChI Key

JAQUASYNZVUNQP-PVAVHDDUSA-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
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:29133 )

Ontology

Not Available

Liver (HMDB: HMDB0060552)
Kidney (HMDB: HMDB0060552)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060552)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060552)

Cellular substructure

Cytoplasm (HMDB: HMDB0060552)
Membrane (HMDB: HMDB0060552)

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
Water Solubility	0.17 g/L	ALOGPS
logP	3.29	ALOGPS
logP	2.9	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.46	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.08 m³·mol⁻¹	ChemAxon
Polarizability	29.7 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
DarkChem	[M+H]+	160.801	31661259
DarkChem	[M-H]-	158.584	31661259
DeepCCS	[M-2H]-	202.709	30932474
DeepCCS	[M+Na]+	177.936	30932474
AllCCS	[M+H]+	163.7	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	167.0	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	170.1	32859911
AllCCS	[M+Na-2H]-	169.9	32859911
AllCCS	[M+HCOO]-	169.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dextrorphan	CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=C3C=C(O)C=C1	3384.8	Standard polar	33892256
Dextrorphan	CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=C3C=C(O)C=C1	2303.8	Standard non polar	33892256
Dextrorphan	CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=C3C=C(O)C=C1	2223.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dextrorphan,1TMS,isomer #1	CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=CC=C(O[Si](C)(C)C)C=C13	2204.7	Semi standard non polar	33892256
Dextrorphan,1TBDMS,isomer #1	CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13	2498.3	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 - Dextrorphan GC-MS (Non-derivatized) - 70eV, Positive	splash10-02bf-0090000000-12982ec002fb66d8d254	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextrorphan GC-MS (1 TMS) - 70eV, Positive	splash10-0hbi-2096000000-da9354b628843987f142	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dextrorphan 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 - Dextrorphan , positive-QTOF	splash10-0a4i-1590000000-b308de853cbd22359927	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dextrorphan 35V, Positive-QTOF	splash10-0a4i-0970000000-1b6c27a0893f6ca3200b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 10V, Positive-QTOF	splash10-0a4i-0090000000-6ba0fc98a8d249fe2da0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 20V, Positive-QTOF	splash10-0a4i-0090000000-d3e64fd4fd1d790a54bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 40V, Positive-QTOF	splash10-0596-6790000000-7a77fc910d8d984d1012	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 10V, Negative-QTOF	splash10-0a4i-0090000000-503f808754310f636373	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 20V, Negative-QTOF	splash10-0a4i-0090000000-bce69f729c40b2f3bed9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 40V, Negative-QTOF	splash10-002g-1290000000-97ee80b268d9fa4de679	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 10V, Positive-QTOF	splash10-0a4i-0090000000-07569ae87a2b34cbffc0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 20V, Positive-QTOF	splash10-0a4i-0090000000-2ae58a148c800ebf61b0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 40V, Positive-QTOF	splash10-03di-1890000000-ba7be4c45f7ec0c83cce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 10V, Negative-QTOF	splash10-0a4i-0090000000-4d2203d29a4418e5d773	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 20V, Negative-QTOF	splash10-0a4i-0090000000-4d2203d29a4418e5d773	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dextrorphan 40V, Negative-QTOF	splash10-0002-0960000000-e8715b9d7acb44e50afb	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dextrorphan

METLIN ID

Not Available

PubChem Compound

5360697

PDB ID

Not Available

ChEBI ID

29133

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Dextrorphan (HMDB0060552)

MOL for HMDB0060552 (Dextrorphan)

3D MOL for HMDB0060552 (Dextrorphan)

3D SDF for HMDB0060552 (Dextrorphan)

3D-SDF for HMDB0060552 (Dextrorphan)

PDB for HMDB0060552 (Dextrorphan)

3D PDB for HMDB0060552 (Dextrorphan)

SMILES for HMDB0060552 (Dextrorphan)

INCHI for HMDB0060552 (Dextrorphan)

Structure for HMDB0060552 (Dextrorphan)

3D Structure for HMDB0060552 (Dextrorphan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra