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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014647

Secondary Accession Numbers

HMDB14647

Metabolite Identification

Common Name

Levallorphan

Description

Levallorphan, also known as lorfan or naloxiphan, 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. Levallorphan is a drug which is used for the complete or partial reversal of narcotic depression, including respiratory depression, induced by opioids. In humans, levallorphan is involved in the levallorphan action pathway. Levallorphan is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Levallorphan.

Structure

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

HMDB0014647
     RDKit          3D
Levallorphan
 46 49  0  0  0  0  0  0  0  0999 V2000
    4.7676    0.5417    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585   -0.4929    0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.6790    1.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -0.7472    1.2157 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6777   -1.1339    2.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740   -0.5693    1.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -0.5183    0.3850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3053   -1.3305    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544   -2.5910   -0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3734   -2.1749   -2.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -1.0517   -1.8916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0361   -1.0658   -0.4561 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3205   -0.3587   -0.0990 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2179    1.1168   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1573    1.6433   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332    2.9661   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832    3.5692   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    2.7833   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423    3.3377   -0.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5475    1.4559   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    0.9112   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7950    1.3315    1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4327    0.5827   -0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9488   -1.2902   -0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677   -1.5200    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383    0.2439    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -0.7233    3.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -2.2473    2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6461    0.4940    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.0587    2.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8547   -1.5697    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -0.7788   -0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -3.0537   -0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -3.3301   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -3.0445   -2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218   -1.8229   -2.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7882   -0.1384   -2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511   -1.3735   -2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2204   -2.1497   -0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0852   -0.7045   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7705    1.5085   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146    1.6388    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5118    3.5994   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6773    4.6063   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715    4.2747   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426    0.9133    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  6  1  1
  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  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13  4  1  0
 21 15  1  0
 12  7  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  1
 13 40  1  6
 14 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
M  END

 
  Mrv0541 02231214432D          
 
 22 25  0  0  1  0            999 V2000
   14.4191  -12.1888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1319  -12.6085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4191  -11.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1319  -11.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7065  -12.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8447  -12.1961    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1680  -13.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1392  -10.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7028  -10.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5684  -11.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7425  -13.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5611  -12.6122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8484  -11.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4517  -13.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1392  -10.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7028  -10.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4801  -12.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4191   -9.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9864   -9.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1494  -12.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8152  -12.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9279  -13.1440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  1  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 15  1  0  0  0  0
  9 16  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
  8 13  1  0  0  0  0
 10 12  1  0  0  0  0
 11 14  1  0  0  0  0
 16 18  1  0  0  0  0
  2 22  1  1  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  2  0  0  0  0
  3  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014647

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1

> <INCHI_KEY>
OZYUPQUCAUTOBP-QXAKKESOSA-N

> <FORMULA>
C19H25NO

> <MOLECULAR_WEIGHT>
283.4079

> <EXACT_MASS>
283.193614427

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.67748687345353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
3.755367301791382

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.362761115328947

> <JCHEM_PKA_STRONGEST_BASIC>
9.40708250750897

> <JCHEM_POLAR_SURFACE_AREA>
23.47

> <JCHEM_REFRACTIVITY>
87.2436

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
levallorphan

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014647
     RDKit          3D
Levallorphan
 46 49  0  0  0  0  0  0  0  0999 V2000
    4.7676    0.5417    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585   -0.4929    0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.6790    1.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -0.7472    1.2157 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6777   -1.1339    2.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740   -0.5693    1.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -0.5183    0.3850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3053   -1.3305    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544   -2.5910   -0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3734   -2.1749   -2.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -1.0517   -1.8916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0361   -1.0658   -0.4561 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3205   -0.3587   -0.0990 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2179    1.1168   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1573    1.6433   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332    2.9661   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832    3.5692   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    2.7833   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423    3.3377   -0.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5475    1.4559   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    0.9112   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7950    1.3315    1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4327    0.5827   -0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9488   -1.2902   -0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677   -1.5200    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383    0.2439    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -0.7233    3.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -2.2473    2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6461    0.4940    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.0587    2.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8547   -1.5697    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -0.7788   -0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -3.0537   -0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -3.3301   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -3.0445   -2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218   -1.8229   -2.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7882   -0.1384   -2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511   -1.3735   -2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2204   -2.1497   -0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0852   -0.7045   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7705    1.5085   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146    1.6388    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5118    3.5994   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6773    4.6063   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715    4.2747   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426    0.9133    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  6  1  1
  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  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13  4  1  0
 21 15  1  0
 12  7  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  1
 13 40  1  6
 14 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      26.916 -22.752   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.246 -23.536   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.916 -21.219   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.246 -21.800   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.585 -23.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.577 -22.766   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.314 -25.075   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.260 -20.449   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.579 -20.449   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.928 -21.800   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.653 -25.056   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      30.914 -23.543   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      29.584 -21.226   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.977 -25.825   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.260 -18.909   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.579 -18.909   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      32.630 -22.658   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.916 -18.133   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      24.241 -18.133   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      33.879 -23.435   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.122 -22.739   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      29.732 -24.535   0.000  0.00  0.00           H+0
CONECT    1    2    3    4    5                                             
CONECT    2   22    1    6    7                                             
CONECT    3    1    8    9                                                  
CONECT    4   10    1                                                       
CONECT    5   11    1                                                       
CONECT    6   12   13    2                                                  
CONECT    7   14    2                                                       
CONECT    8   15   13    3                                                  
CONECT    9   16    3                                                       
CONECT   10    4   12                                                       
CONECT   11    5   14                                                       
CONECT   12    6   17   10                                                  
CONECT   13    6    8                                                       
CONECT   14    7   11                                                       
CONECT   15    8   18                                                       
CONECT   16    9   19   18                                                  
CONECT   17   12   20                                                       
CONECT   18   15   16                                                       
CONECT   19   16                                                            
CONECT   20   17   21                                                       
CONECT   21   20                                                            
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0014647
HETATM    1  C1  UNL     1       4.768   0.542   0.350  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.958  -0.493   0.477  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.018  -0.679   1.618  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.669  -0.747   1.216  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.678  -1.134   2.120  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.674  -0.569   1.823  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.079  -0.518   0.385  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.305  -1.331   0.046  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.954  -2.591  -0.753  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.373  -2.175  -2.077  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.337  -1.052  -1.892  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.036  -1.066  -0.456  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.321  -0.359  -0.099  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.218   1.117  -0.230  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.157   1.643  -0.291  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.333   2.966  -0.636  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.583   3.569  -0.706  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.684   2.783  -0.412  1.00  0.00           C  
HETATM   19  O1  UNL     1      -3.942   3.338  -0.463  1.00  0.00           O  
HETATM   20  C18 UNL     1      -2.547   1.456  -0.065  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.297   0.911  -0.010  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.795   1.332   1.082  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.433   0.583  -0.527  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.949  -1.290  -0.294  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.368  -1.520   2.279  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.138   0.244   2.263  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.966  -0.723   3.141  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.631  -2.247   2.304  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.646   0.494   2.217  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.442  -1.059   2.467  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.855  -1.570   0.967  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.998  -0.779  -0.641  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.963  -3.054  -0.986  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.398  -3.330  -0.196  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.928  -3.044  -2.599  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.222  -1.823  -2.719  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.788  -0.138  -2.277  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.551  -1.374  -2.503  1.00  0.00           H  
HETATM   39  H18 UNL     1       0.220  -2.150  -0.177  1.00  0.00           H  
HETATM   40  H19 UNL     1       2.085  -0.705  -0.857  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.771   1.509  -1.134  1.00  0.00           H  
HETATM   42  H21 UNL     1       1.715   1.639   0.632  1.00  0.00           H  
HETATM   43  H22 UNL     1       0.512   3.599  -0.864  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.677   4.606  -0.979  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.171   4.275  -0.694  1.00  0.00           H  
HETATM   46  H25 UNL     1      -3.443   0.913   0.152  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3   24
CONECT    3    4   25   26
CONECT    4    5   13
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   12   21
CONECT    8    9   31   32
CONECT    9   10   33   34
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   39
CONECT   13   14   40
CONECT   14   15   41   42
CONECT   15   16   16   21
CONECT   16   17   43
CONECT   17   18   18   44
CONECT   18   19   20
CONECT   19   45
CONECT   20   21   21   46
END

HMDB0014647
     RDKit          3D
Levallorphan
 46 49  0  0  0  0  0  0  0  0999 V2000
    4.7676    0.5417    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9585   -0.4929    0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0181   -0.6790    1.6185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6692   -0.7472    1.2157 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6777   -1.1339    2.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740   -0.5693    1.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -0.5183    0.3850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3053   -1.3305    0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544   -2.5910   -0.7531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3734   -2.1749   -2.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374   -1.0517   -1.8916 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0361   -1.0658   -0.4561 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3205   -0.3587   -0.0990 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2179    1.1168   -0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1573    1.6433   -0.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3332    2.9661   -0.6359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832    3.5692   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6840    2.7833   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9423    3.3377   -0.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5475    1.4559   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    0.9112   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7950    1.3315    1.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4327    0.5827   -0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9488   -1.2902   -0.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3677   -1.5200    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383    0.2439    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9662   -0.7233    3.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6312   -2.2473    2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6461    0.4940    2.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.0587    2.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8547   -1.5697    0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9980   -0.7788   -0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9627   -3.0537   -0.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -3.3301   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -3.0445   -2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218   -1.8229   -2.7186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7882   -0.1384   -2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511   -1.3735   -2.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2204   -2.1497   -0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0852   -0.7045   -0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7705    1.5085   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7146    1.6388    0.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5118    3.5994   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6773    4.6063   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1715    4.2747   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426    0.9133    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  6  1  1
  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  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13  4  1  0
 21 15  1  0
 12  7  1  0
 21  7  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  1
 13 40  1  6
 14 41  1  0
 14 42  1  0
 16 43  1  0
 17 44  1  0
 19 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lorfan	HMDB
Naloxiphan	HMDB

Chemical Formula

C₁₉H₂₅NO

Average Molecular Weight

283.4079

Monoisotopic Molecular Weight

283.193614427

IUPAC Name

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

Traditional Name

levallorphan

CAS Registry Number

152-02-3

SMILES

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

InChI Identifier

InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1

InChI Key

OZYUPQUCAUTOBP-QXAKKESOSA-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:6431 )

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: HMDB0014647)

Source

Exogenous

Exogenous (HMDB: HMDB0014647)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Levallorphan Action Pathway (PathBank: SMP0000683)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	181 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.025 g/L	Not Available
LogP	3.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.025 g/L	ALOGPS
logP	3.91	ALOGPS
logP	3.76	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	10.36	ChemAxon
pKa (Strongest Basic)	9.41	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	2	ChemAxon
Refractivity	87.24 m³·mol⁻¹	ChemAxon
Polarizability	32.68 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]+	165.859	31661259
DarkChem	[M-H]-	162.686	31661259
DeepCCS	[M-2H]-	204.565	30932474
DeepCCS	[M+Na]+	179.871	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	175.9	32859911
AllCCS	[M+Na-2H]-	175.8	32859911
AllCCS	[M+HCOO]-	175.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levallorphan	[H][C@@]12CCCC[C@@]11CCN(CC=C)[C@@H]2CC2=C1C=C(O)C=C2	3642.8	Standard polar	33892256
Levallorphan	[H][C@@]12CCCC[C@@]11CCN(CC=C)[C@@H]2CC2=C1C=C(O)C=C2	2401.4	Standard non polar	33892256
Levallorphan	[H][C@@]12CCCC[C@@]11CCN(CC=C)[C@@H]2CC2=C1C=C(O)C=C2	2385.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Levallorphan,1TMS,isomer #1	C=CCN1CC[C@]23CCCC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C)C=C13	2318.4	Semi standard non polar	33892256
Levallorphan,1TBDMS,isomer #1	C=CCN1CC[C@]23CCCC[C@H]2[C@H]1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13	2592.9	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 - Levallorphan GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-2090000000-e1bfcb97bfa878802044	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levallorphan GC-MS (1 TMS) - 70eV, Positive	splash10-01tc-3049000000-4352cd28b7455258b001	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levallorphan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 10V, Positive-QTOF	splash10-001i-0090000000-c886e11a52629d3b6ace	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 20V, Positive-QTOF	splash10-000x-5090000000-a50bd8ddd987c3505bed	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 40V, Positive-QTOF	splash10-0006-9020000000-78f892a0fe089e1dc675	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 10V, Negative-QTOF	splash10-001i-0090000000-d24e2a1bbf1c331446e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 20V, Negative-QTOF	splash10-001l-0090000000-f90e6f45cb42029ac3f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 40V, Negative-QTOF	splash10-0006-1290000000-a9303de3f0f8a329e2f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 10V, Negative-QTOF	splash10-001i-0090000000-de4c3229168dbf071089	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 20V, Negative-QTOF	splash10-001l-0090000000-6bded21078e814eff199	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 40V, Negative-QTOF	splash10-001i-0290000000-d27c8821f73ae54df17f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 10V, Positive-QTOF	splash10-001i-0090000000-3c4b9ea0fce2ba47ecaf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 20V, Positive-QTOF	splash10-001i-0090000000-5b62cdc6cd2bda1045b6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levallorphan 40V, Positive-QTOF	splash10-01ow-1960000000-890603e347ff7eb26f47	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Levallorphan 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 DB00504	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00504	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00504

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10481920

KEGG Compound ID

C07069

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levallorphan

METLIN ID

Not Available

PubChem Compound

5359371

PDB ID

Not Available

ChEBI ID

804148

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. 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

Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41. [PubMed:8968334 ]
Traynor JR, Nahorski SR: Modulation by mu-opioid agonists of guanosine-5'-O-(3-[35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells. Mol Pharmacol. 1995 Apr;47(4):848-54. [PubMed:7723747 ]
Selley DE, Sim LJ, Xiao R, Liu Q, Childers SR: mu-Opioid receptor-stimulated guanosine-5'-O-(gamma-thio)-triphosphate binding in rat thalamus and cultured cell lines: signal transduction mechanisms underlying agonist efficacy. Mol Pharmacol. 1997 Jan;51(1):87-96. [PubMed:9016350 ]
Emmerson PJ, Clark MJ, Mansour A, Akil H, Woods JH, Medzihradsky F: Characterization of opioid agonist efficacy in a C6 glioma cell line expressing the mu opioid receptor. J Pharmacol Exp Ther. 1996 Sep;278(3):1121-7. [PubMed:8819494 ]
Morgan D, Picker MJ: The mu opioid irreversible antagonist beta-funaltrexamine differentiates the discriminative stimulus effects of opioids with high and low efficacy at the mu opioid receptor. Psychopharmacology (Berl). 1998 Nov;140(1):20-8. [PubMed:9862398 ]

Showing metabocard for Levallorphan (HMDB0014647)

MOL for HMDB0014647 (Levallorphan)

3D MOL for HMDB0014647 (Levallorphan)

3D SDF for HMDB0014647 (Levallorphan)

3D-SDF for HMDB0014647 (Levallorphan)

PDB for HMDB0014647 (Levallorphan)

3D PDB for HMDB0014647 (Levallorphan)

SMILES for HMDB0014647 (Levallorphan)

INCHI for HMDB0014647 (Levallorphan)

Structure for HMDB0014647 (Levallorphan)

3D Structure for HMDB0014647 (Levallorphan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References