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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0014992

Secondary Accession Numbers

HMDB14992

Metabolite Identification

Common Name

Levorphanol

Description

Levorphanol, also known as levo dromoran or dea no. 9220, 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. It is the "left-handed" (levorotatory) stereoisomer of racemorphan, that is the racemic mixture of the two stereoisomers with differing pharmacology. Levorphanol is a drug which is used for the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate. Levorphanol shows a high rate of psychotomimetic side effects such as hallucinations and delirium, which have been attributed to its binding to and activation of the KOR. Levorphanol is the INN, BAN, and DCF. Levorphanol is a very strong basic compound (based on its pKa). In humans, levorphanol is involved in levorphanol action pathway. The duration of action is generally long compared to other comparable analgesics and varies from 4 hours to as much as 15 hours. Levorphanol is listed under the Single Convention On Narcotic Drugs 1961 and is regulated like morphine in most countries. The drug has been in medical use in the United States since 1953. Levorphanol is a potentially toxic compound.

Structure

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

HMDB0014992
     RDKit          3D
Levorphanol
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.8952   -2.5493    0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -1.7005    0.8527 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -1.0085    2.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1722   -0.3613    2.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0782    0.4698    0.8744 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3661    1.8878    1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    2.8317    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    2.7981   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0179    1.3865   -1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2028    0.4887    0.0579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5675   -0.9235   -0.3254 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5205   -1.5664   -1.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397   -1.0515   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8682   -1.5744   -1.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1810   -1.1941   -1.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4672   -0.2480   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7856    0.1523   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612    0.2934    0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.1100    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -2.3694    0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674   -2.5102    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297   -3.6052    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191   -0.2888    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246   -1.7758    2.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    0.2520    3.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -1.1260    2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2164    1.9630    1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351    2.2143    1.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566    3.8446    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235    2.5268   -0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474    3.5641   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6605    2.9113    0.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0424    1.1667   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8368    1.2896   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    0.9011    0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -0.8463   -0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788   -1.4825   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960   -2.6678   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6624   -2.3287   -2.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -1.6114   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.9261   -0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7008    1.0316    0.9451 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

854
  Mrv0541 02231215032D          

 20 23  0  0  1  0            999 V2000
    2.0103   -0.3755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9304    0.6944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8064   -0.3564    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4924    0.0397    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4924    0.8317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6456   -0.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7937   -1.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2132   -0.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8064    1.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    0.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5050   -1.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2195   -1.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204    0.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124   -0.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930    1.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124    1.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6947    0.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6947    0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2069    0.4522    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  5  2  1  1  0  0  0
  2 11  1  0  0  0  0
  2 16  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
  4 20  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0014992

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(O)C=C2

> <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+/m0/s1

> <INCHI_KEY>
JAQUASYNZVUNQP-USXIJHARSA-N

> <FORMULA>
C17H23NO

> <MOLECULAR_WEIGHT>
257.3706

> <EXACT_MASS>
257.177964363

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.835843009547546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,10R)-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>
levorphanol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014992
     RDKit          3D
Levorphanol
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.8952   -2.5493    0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -1.7005    0.8527 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -1.0085    2.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1722   -0.3613    2.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0782    0.4698    0.8744 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3661    1.8878    1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    2.8317    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    2.7981   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0179    1.3865   -1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2028    0.4887    0.0579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5675   -0.9235   -0.3254 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5205   -1.5664   -1.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397   -1.0515   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8682   -1.5744   -1.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1810   -1.1941   -1.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4672   -0.2480   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7856    0.1523   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612    0.2934    0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.1100    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -2.3694    0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674   -2.5102    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297   -3.6052    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191   -0.2888    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246   -1.7758    2.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    0.2520    3.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -1.1260    2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2164    1.9630    1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351    2.2143    1.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566    3.8446    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235    2.5268   -0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474    3.5641   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6605    2.9113    0.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0424    1.1667   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8368    1.2896   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    0.9011    0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -0.8463   -0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788   -1.4825   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960   -2.6678   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6624   -2.3287   -2.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -1.6114   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.9261   -0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7008    1.0316    0.9451 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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 854                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.753  -0.701   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       9.203   1.296   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       8.972  -0.665   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.252   0.074   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.252   1.553   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.672  -0.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.948  -2.205   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.598  -0.675   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.691   0.074   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.972   2.292   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.548   0.724   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.276  -2.985   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.610  -2.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.691   1.553   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.370  -0.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.387   2.135   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.370   2.343   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.030   0.043   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.030   1.583   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      11.586   0.844   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2    5   11   16                                                  
CONECT    3    4    6    7    9                                             
CONECT    4    3    5    8   20                                             
CONECT    5    2    4   10                                                  
CONECT    6    3   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   13                                                       
CONECT    9    3   14   15                                                  
CONECT   10    5   14                                                       
CONECT   11    2    6                                                       
CONECT   12    7   13                                                       
CONECT   13    8   12                                                       
CONECT   14    9   10   17                                                  
CONECT   15    9   18                                                       
CONECT   16    2                                                            
CONECT   17   14   19                                                       
CONECT   18    1   15   19                                                  
CONECT   19   17   18                                                       
CONECT   20    4                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0014992
HETATM    1  C1  UNL     1      -2.895  -2.549   0.853  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.740  -1.701   0.853  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.524  -1.008   2.082  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.172  -0.361   2.095  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.078   0.470   0.874  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.366   1.888   1.310  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.466   2.832   0.142  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.876   2.798  -0.597  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.018   1.387  -1.135  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.203   0.489   0.058  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.568  -0.924  -0.325  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.521  -1.566  -1.192  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.840  -1.051  -0.915  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.868  -1.574  -1.686  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.181  -1.194  -1.544  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.467  -0.248  -0.586  1.00  0.00           C  
HETATM   17  O1  UNL     1       4.786   0.152  -0.423  1.00  0.00           O  
HETATM   18  C16 UNL     1       2.461   0.293   0.201  1.00  0.00           C  
HETATM   19  C17 UNL     1       1.135  -0.110   0.037  1.00  0.00           C  
HETATM   20  H1  UNL     1      -3.587  -2.369   0.012  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.467  -2.510   1.802  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.530  -3.605   0.747  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.319  -0.289   2.353  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.525  -1.776   2.901  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.113   0.252   3.041  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.631  -1.126   2.210  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.216   1.963   1.989  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.535   2.214   1.899  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.657   3.845   0.556  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.224   2.527  -0.599  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.947   3.564  -1.366  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.661   2.911   0.202  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.042   1.167  -1.660  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.837   1.290  -1.859  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.999   0.901   0.677  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.505  -0.846  -0.943  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.779  -1.482  -2.285  1.00  0.00           H  
HETATM   38  H19 UNL     1      -0.496  -2.668  -0.989  1.00  0.00           H  
HETATM   39  H20 UNL     1       1.662  -2.329  -2.455  1.00  0.00           H  
HETATM   40  H21 UNL     1       3.982  -1.611  -2.155  1.00  0.00           H  
HETATM   41  H22 UNL     1       5.137   0.926  -0.952  1.00  0.00           H  
HETATM   42  H23 UNL     1       2.701   1.032   0.945  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

HMDB0014992
     RDKit          3D
Levorphanol
 42 45  0  0  0  0  0  0  0  0999 V2000
   -2.8952   -2.5493    0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398   -1.7005    0.8527 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236   -1.0085    2.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1722   -0.3613    2.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0782    0.4698    0.8744 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3661    1.8878    1.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665    2.8317    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    2.7981   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0179    1.3865   -1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2028    0.4887    0.0579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5675   -0.9235   -0.3254 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5205   -1.5664   -1.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8397   -1.0515   -0.9150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8682   -1.5744   -1.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1810   -1.1941   -1.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4672   -0.2480   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7856    0.1523   -0.4235 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612    0.2934    0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.1100    0.0367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5873   -2.3694    0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4674   -2.5102    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5297   -3.6052    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191   -0.2888    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5246   -1.7758    2.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    0.2520    3.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -1.1260    2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2164    1.9630    1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351    2.2143    1.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6566    3.8446    0.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2235    2.5268   -0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9474    3.5641   -1.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6605    2.9113    0.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0424    1.1667   -1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8368    1.2896   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9990    0.9011    0.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5053   -0.8463   -0.9433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788   -1.4825   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960   -2.6678   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6624   -2.3287   -2.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9817   -1.6114   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1375    0.9261   -0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7008    1.0316    0.9451 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
Dea no. 9220	HMDB
Dea no. 9733	HMDB
Levorfanolo	HMDB
Levorphan	HMDB
Levorphanal	HMDB
Levorphanol DL-form	HMDB
Methorphinan	HMDB
Racemethorphanum	HMDB
3 Hydroxy N methylmorphinan	HMDB
L Dromoran	HMDB
Levo dromoran	HMDB
Tartrate, levorphanol	HMDB
3-Hydroxy-N-methylmorphinan	HMDB
ICN brand OF levorphanol tartrate	HMDB
L-Dromoran	HMDB
Levorphanol tartrate	HMDB
Levo-dromoran	HMDB
LevoDromoran	HMDB

Chemical Formula

C₁₇H₂₃NO

Average Molecular Weight

257.3706

Monoisotopic Molecular Weight

257.177964363

IUPAC Name

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

Traditional Name

levorphanol

CAS Registry Number

77-07-6

SMILES

[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(O)C=C2

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+/m0/s1

InChI Key

JAQUASYNZVUNQP-USXIJHARSA-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:6444 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014992)

Source

Exogenous

Exogenous (HMDB: HMDB0014992)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Levorphanol Action Pathway (PathBank: SMP0000673)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	198 - 199 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.17 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	161.7	30932474

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	29.84 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]+	159.032	31661259
DarkChem	[M-H]-	158.34	31661259
DeepCCS	[M-2H]-	196.973	30932474
DeepCCS	[M+Na]+	172.2	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]-	170.0	32859911
AllCCS	[M+Na-2H]-	169.8	32859911
AllCCS	[M+HCOO]-	169.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levorphanol	[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(O)C=C2	3377.3	Standard polar	33892256
Levorphanol	[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(O)C=C2	2303.5	Standard non polar	33892256
Levorphanol	[H][C@@]12CCCC[C@@]11CCN(C)[C@@H]2CC2=C1C=C(O)C=C2	2223.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Levorphanol,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
Levorphanol,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 - Levorphanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ou-0190000000-14189f3c821f5d9240bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levorphanol GC-MS (1 TMS) - 70eV, Positive	splash10-0hbi-2096000000-da9354b628843987f142	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levorphanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levorphanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-5930000000-4593c62f1e2a0579a248	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 10V, Positive-QTOF	splash10-0a4i-0090000000-6ba0fc98a8d249fe2da0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 20V, Positive-QTOF	splash10-0a4i-0090000000-d3e64fd4fd1d790a54bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 40V, Positive-QTOF	splash10-0596-6790000000-7a77fc910d8d984d1012	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 10V, Negative-QTOF	splash10-0a4i-0090000000-503f808754310f636373	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 20V, Negative-QTOF	splash10-0a4i-0090000000-bce69f729c40b2f3bed9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 40V, Negative-QTOF	splash10-002g-1290000000-97ee80b268d9fa4de679	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 10V, Positive-QTOF	splash10-0a4i-0090000000-07569ae87a2b34cbffc0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 20V, Positive-QTOF	splash10-0a4i-0090000000-02552f8621a9e610534e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 40V, Positive-QTOF	splash10-03di-2960000000-72882cb61c3a77dadafb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 10V, Negative-QTOF	splash10-0a4i-0090000000-4d2203d29a4418e5d773	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 20V, Negative-QTOF	splash10-0a4i-0090000000-4d2203d29a4418e5d773	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levorphanol 40V, Negative-QTOF	splash10-0f6t-0490000000-d5048ebe52cdbfced464	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Levorphanol Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00854	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00854	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00854

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16736212

KEGG Compound ID

C08014

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levorphanol

METLIN ID

Not Available

PubChem Compound

5359272

PDB ID

Not Available

ChEBI ID

119572

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

Enzymes

Enzyme Details

1. Delta-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
Gene Name:: OPRD1
Uniprot ID:: P41143
Molecular weight:: 40412.3

References

Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. [PubMed:17039381 ]

Enzyme Details

2. Mu-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:: OPRM1
Uniprot ID:: P35372
Molecular weight:: 44778.9

References

Allen RM, Granger AL, Dykstra LA: The competitive N-methyl-D-aspartate receptor antagonist (-)-6-phosphonomethyl-deca-hydroisoquinoline-3-carboxylic acid (LY235959) potentiates the antinociceptive effects of opioids that vary in efficacy at the mu-opioid receptor. J Pharmacol Exp Ther. 2003 Nov;307(2):785-92. Epub 2003 Sep 15. [PubMed:12975489 ]
Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. [PubMed:17039381 ]

Enzyme Details

3. Kappa-type opioid receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:: OPRK1
Uniprot ID:: P41145
Molecular weight:: 42644.7

References

Prommer E: Levorphanol: the forgotten opioid. Support Care Cancer. 2007 Mar;15(3):259-64. Epub 2006 Oct 13. [PubMed:17039381 ]

Showing metabocard for Levorphanol (HMDB0014992)

MOL for HMDB0014992 (Levorphanol)

3D MOL for HMDB0014992 (Levorphanol)

3D SDF for HMDB0014992 (Levorphanol)

3D-SDF for HMDB0014992 (Levorphanol)

PDB for HMDB0014992 (Levorphanol)

3D PDB for HMDB0014992 (Levorphanol)

SMILES for HMDB0014992 (Levorphanol)

INCHI for HMDB0014992 (Levorphanol)

Structure for HMDB0014992 (Levorphanol)

3D Structure for HMDB0014992 (Levorphanol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References