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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15)transporters (1) Show 16 proteins XML

enzymes (15)transporters (1) Show 16 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014477

Secondary Accession Numbers

HMDB14477

Metabolite Identification

Common Name

Methadone

Description

A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of morphine. It also has a depressant action on the cough center and may be given to control intractable cough associated with terminal lung cancer. Methadone is also used as part of the treatment of dependence on opioid drugs, although prolonged use of methadone itself may result in dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3)

Structure

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

HMDB0254054
     RDKit          3D
Levomethadone
 50 51  0  0  0  0  0  0  0  0999 V2000
   -0.7397   -4.0389   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6300   -2.7250    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.5957   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -1.8740   -1.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378   -0.1894    0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8572    0.1771    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.0756   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2314   -1.2658   -1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1719    0.4781    0.2490 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0940    1.8527    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527    0.2585   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9946    0.7042   -1.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9464    0.3328   -1.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3777    1.1880   -2.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    2.4453   -3.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973    2.8327   -2.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714    1.9733   -1.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.0800    1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -0.0488    1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6134    0.1998    2.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921    0.5731    3.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479    0.7050    3.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9342    0.4563    2.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -4.4466   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -4.7866    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5671   -3.8581   -1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3075   -2.6297    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5304   -2.6287    1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874   -0.5681    1.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8338    1.1822    0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539    0.8646   -1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3389   -1.4425   -1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8280   -1.2582   -2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171   -2.1309   -0.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    1.9307    1.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378    2.2455    0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139    2.4594   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2055    0.3075   -1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474   -0.6214   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0420    1.1301   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4516   -0.6276   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369    0.8363   -3.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903    3.0982   -3.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945    3.8322   -2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2691    2.4074   -0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2764   -0.3382    0.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6851    0.0975    2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7217    0.7709    4.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084    0.9996    4.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204    0.5798    2.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 12  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
M  END

333
  Mrv0541 02231214362D          

 23 24  0  0  1  0            999 V2000
    5.8950    0.7144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4253   -0.2482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8325    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0572    0.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4825    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9140    1.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8950   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5685   -1.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7200   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6575   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  2  0  0  0  0
  2  5  1  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  9  1  0  0  0  0
  6 11  2  0  0  0  0
  6 13  1  0  0  0  0
  7 12  2  0  0  0  0
  7 14  1  0  0  0  0
  8 10  1  0  0  0  0
 10 17  1  0  0  0  0
 11 18  1  0  0  0  0
 12 19  1  0  0  0  0
 13 20  2  0  0  0  0
 14 21  2  0  0  0  0
 18 22  2  0  0  0  0
 19 23  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014477

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3

> <INCHI_KEY>
USSIQXCVUWKGNF-UHFFFAOYSA-N

> <FORMULA>
C21H27NO

> <MOLECULAR_WEIGHT>
309.4452

> <EXACT_MASS>
309.209264491

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.291649736892055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(dimethylamino)-4,4-diphenylheptan-3-one

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
5.007171635333333

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.780818634444923

> <JCHEM_PKA_STRONGEST_BASIC>
9.117210098088941

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
97.26890000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methadone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254054
     RDKit          3D
Levomethadone
 50 51  0  0  0  0  0  0  0  0999 V2000
   -0.7397   -4.0389   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6300   -2.7250    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.5957   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -1.8740   -1.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378   -0.1894    0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8572    0.1771    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.0756   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2314   -1.2658   -1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1719    0.4781    0.2490 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0940    1.8527    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527    0.2585   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9946    0.7042   -1.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9464    0.3328   -1.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3777    1.1880   -2.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    2.4453   -3.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973    2.8327   -2.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714    1.9733   -1.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.0800    1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -0.0488    1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6134    0.1998    2.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921    0.5731    3.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479    0.7050    3.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9342    0.4563    2.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -4.4466   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -4.7866    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5671   -3.8581   -1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3075   -2.6297    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5304   -2.6287    1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874   -0.5681    1.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8338    1.1822    0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539    0.8646   -1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3389   -1.4425   -1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8280   -1.2582   -2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171   -2.1309   -0.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    1.9307    1.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378    2.2455    0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139    2.4594   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2055    0.3075   -1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474   -0.6214   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0420    1.1301   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4516   -0.6276   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369    0.8363   -3.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903    3.0982   -3.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945    3.8322   -2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2691    2.4074   -0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2764   -0.3382    0.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6851    0.0975    2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7217    0.7709    4.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084    0.9996    4.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204    0.5798    2.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 12  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 333                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.004   1.334   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       4.527  -0.463   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       8.694   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.154   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.707   0.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.694   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.694  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.234   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.439   2.043   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.004  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.360   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.028  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.028   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.360  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   0.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.795  -1.980   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.544  -1.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.360   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.028  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.028   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.360  -3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.694   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.694  -4.620   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    5   15   16                                                  
CONECT    3    4    6    7    8                                             
CONECT    4    3    5                                                       
CONECT    5    2    4    9                                                  
CONECT    6    3   11   13                                                  
CONECT    7    3   12   14                                                  
CONECT    8    1    3   10                                                  
CONECT    9    5                                                            
CONECT   10    8   17                                                       
CONECT   11    6   18                                                       
CONECT   12    7   19                                                       
CONECT   13    6   20                                                       
CONECT   14    7   21                                                       
CONECT   15    2                                                            
CONECT   16    2                                                            
CONECT   17   10                                                            
CONECT   18   11   22                                                       
CONECT   19   12   23                                                       
CONECT   20   13   22                                                       
CONECT   21   14   23                                                       
CONECT   22   18   20                                                       
CONECT   23   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0014477
HETATM    1  C1  UNL     1      -2.438   3.085  -1.211  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.535   1.900  -1.485  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.349   1.113  -0.241  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.893   1.481   0.767  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.506  -0.131  -0.194  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.798   0.073  -0.875  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.711   1.131  -0.361  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.934   1.077  -1.304  1.00  0.00           C  
HETATM    9  N1  UNL     1       2.143   1.005   0.996  1.00  0.00           N  
HETATM   10  C8  UNL     1       3.017   2.140   1.275  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.898  -0.182   1.276  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.450  -0.599   1.195  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.334   0.237   2.282  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.292  -0.257   3.595  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.366  -1.589   3.836  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.481  -2.443   2.782  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.523  -1.948   1.471  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.261  -1.108  -1.033  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.628  -2.170  -1.592  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.302  -3.109  -2.387  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.642  -2.923  -2.589  1.00  0.00           C  
HETATM   22  C20 UNL     1      -3.311  -1.847  -2.029  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.610  -0.942  -1.250  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.392   2.998  -1.763  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.964   4.044  -1.493  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.614   3.163  -0.103  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.006   1.320  -2.308  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.610   2.305  -1.918  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.388  -0.890  -0.958  1.00  0.00           H  
HETATM   30  H7  UNL     1       0.576   0.332  -1.933  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.274   2.121  -0.515  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.406   2.087  -1.374  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.625   0.289  -1.010  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.572   0.848  -2.328  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.210   2.260   2.359  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.961   1.935   0.727  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.596   3.084   0.855  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.850  -0.378   2.368  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.995  -0.051   1.050  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.579  -1.073   0.750  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.261   1.310   2.237  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.200   0.404   4.449  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.332  -1.964   4.858  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.539  -3.503   2.978  1.00  0.00           H  
HETATM   45  H22 UNL     1      -0.617  -2.732   0.733  1.00  0.00           H  
HETATM   46  H23 UNL     1       0.433  -2.415  -1.484  1.00  0.00           H  
HETATM   47  H24 UNL     1      -0.794  -3.949  -2.828  1.00  0.00           H  
HETATM   48  H25 UNL     1      -3.163  -3.657  -3.210  1.00  0.00           H  
HETATM   49  H26 UNL     1      -4.370  -1.765  -2.232  1.00  0.00           H  
HETATM   50  H27 UNL     1      -3.184  -0.118  -0.831  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    4    5
CONECT    5    6   12   18
CONECT    6    7   29   30
CONECT    7    8    9   31
CONECT    8   32   33   34
CONECT    9   10   11
CONECT   10   35   36   37
CONECT   11   38   39   40
CONECT   12   13   13   17
CONECT   13   14   41
CONECT   14   15   15   42
CONECT   15   16   43
CONECT   16   17   17   44
CONECT   17   45
CONECT   18   19   19   23
CONECT   19   20   46
CONECT   20   21   21   47
CONECT   21   22   48
CONECT   22   23   23   49
CONECT   23   50
END

HMDB0254054
     RDKit          3D
Levomethadone
 50 51  0  0  0  0  0  0  0  0999 V2000
   -0.7397   -4.0389   -0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6300   -2.7250    0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -1.5957   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7334   -1.8740   -1.5456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378   -0.1894    0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8572    0.1771    0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.0756   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2314   -1.2658   -1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1719    0.4781    0.2490 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0940    1.8527    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3527    0.2585   -0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9946    0.7042   -1.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9464    0.3328   -1.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3777    1.1880   -2.9853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    2.4453   -3.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973    2.8327   -2.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4714    1.9733   -1.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4418    0.0800    1.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8202   -0.0488    1.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6134    0.1998    2.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921    0.5731    3.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7479    0.7050    3.5646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9342    0.4563    2.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -4.4466   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0110   -4.7866    0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5671   -3.8581   -1.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3075   -2.6297    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5304   -2.6287    1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874   -0.5681    1.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8338    1.1822    0.9269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8539    0.8646   -1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3389   -1.4425   -1.1013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8280   -1.2582   -2.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171   -2.1309   -0.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5624    1.9307    1.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378    2.2455    0.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139    2.4594   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2055    0.3075   -1.6276 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474   -0.6214   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0420    1.1301   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4516   -0.6276   -1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369    0.8363   -3.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1903    3.0982   -3.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945    3.8322   -2.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2691    2.4074   -0.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2764   -0.3382    0.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6851    0.0975    2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7217    0.7709    4.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084    0.9996    4.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204    0.5798    2.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 17 12  1  0
 23 18  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 23 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-(Dimethylamino)-4,4-diphenyl-3-heptanone	ChEBI
(+-)-Methadone	ChEBI
6-dimethylamino-4,4-Diphenyl-3-heptanone	ChEBI
DL-Methadone	ChEBI
Methadonum	ChEBI
(+/-)-methadone	HMDB
(+/-)-methadone hydrochloride	HMDB
DL-Methadone hydrochloride	HMDB
Methadon	HMDB
Methadone HCL	HMDB
Methadone hydrochloride	HMDB
Phenadone hydrochloride	HMDB
Amidone	MeSH, HMDB
Biomet brand OF methadone hydrochloride	MeSH, HMDB
Methadose	MeSH, HMDB
Yamanouchi brand OF methadone hydrochloride	MeSH, HMDB
AddiCare brand OF methadone hydrochloride	MeSH, HMDB
Dolophine	MeSH, HMDB
Generics brand OF methadone hydrochloride	MeSH, HMDB
GlaxoSmithKline brand OF methadone hydrochloride	MeSH, HMDB
Hydrochloride, methadone	MeSH, HMDB
Mallinckrodt brand OF methadone hydrochloride	MeSH, HMDB
Methex	MeSH, HMDB
Pharmascience brand OF methadone hydrochloride	MeSH, HMDB
Phymet	MeSH, HMDB
Physeptone	MeSH, HMDB
Pinadone	MeSH, HMDB
Esteve brand OF methadone hydrochloride	MeSH, HMDB
Metasedin	MeSH, HMDB
Methaddict	MeSH, HMDB
Phenadone	MeSH, HMDB
Rosemont brand OF methadone hydrochloride	MeSH, HMDB
Roxane brand OF methadone hydrochloride	MeSH, HMDB
Symoron	MeSH, HMDB
Biodone	MeSH, HMDB
Martindale brand OF methadone hydrochloride	MeSH, HMDB
Metadol	MeSH, HMDB
Pinewood brand OF methadone hydrochloride	MeSH, HMDB

Chemical Formula

C₂₁H₂₇NO

Average Molecular Weight

309.4452

Monoisotopic Molecular Weight

309.209264491

IUPAC Name

6-(dimethylamino)-4,4-diphenylheptan-3-one

Traditional Name

methadone

CAS Registry Number

76-99-3

SMILES

CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3

InChI Key

USSIQXCVUWKGNF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Aralkylamine
Gamma-aminoketone
Ketone
Tertiary amine
Tertiary aliphatic amine
Carbonyl group
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amine (CHEBI:6807 )
benzenes (CHEBI:6807 )
ketone (CHEBI:6807 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0257401)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235.0 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0059 g/L	Not Available
LogP	3.93	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	177.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0059 g/L	ALOGPS
logP	4.14	ALOGPS
logP	5.01	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	18.78	ChemAxon
pKa (Strongest Basic)	9.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.27 m³·mol⁻¹	ChemAxon
Polarizability	36.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	174.311	31661259
DarkChem	[M-H]-	172.128	31661259
DeepCCS	[M+H]+	177.255	30932474
DeepCCS	[M-H]-	174.897	30932474
DeepCCS	[M-2H]-	208.877	30932474
DeepCCS	[M+Na]+	184.346	30932474
AllCCS	[M+H]+	175.9	32859911
AllCCS	[M+H-H2O]+	172.6	32859911
AllCCS	[M+NH4]+	179.0	32859911
AllCCS	[M+Na]+	179.8	32859911
AllCCS	[M-H]-	184.4	32859911
AllCCS	[M+Na-2H]-	184.5	32859911
AllCCS	[M+HCOO]-	184.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methadone	CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2843.3	Standard polar	33892256
Methadone	CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2199.8	Standard non polar	33892256
Methadone	CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2136.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methadone,1TMS,isomer #1	CC=C(O[Si](C)(C)C)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2267.2	Semi standard non polar	33892256
Methadone,1TMS,isomer #1	CC=C(O[Si](C)(C)C)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2219.8	Standard non polar	33892256
Methadone,1TMS,isomer #1	CC=C(O[Si](C)(C)C)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2698.0	Standard polar	33892256
Methadone,1TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2496.3	Semi standard non polar	33892256
Methadone,1TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2458.3	Standard non polar	33892256
Methadone,1TBDMS,isomer #1	CC=C(O[Si](C)(C)C(C)(C)C)C(CC(C)N(C)C)(C1=CC=CC=C1)C1=CC=CC=C1	2780.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methadone EI-B (Non-derivatized)	splash10-00di-9310000000-d71659ee33e210178a79	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methadone CI-B (Non-derivatized)	splash10-03di-0009000000-c583dd769bf5998ac160	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methadone EI-B (Non-derivatized)	splash10-00di-9310000000-d71659ee33e210178a79	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methadone CI-B (Non-derivatized)	splash10-03di-0009000000-c583dd769bf5998ac160	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methadone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-9080000000-1cd26d01442b30c05512	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methadone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methadone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methadone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methadone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9210000000-7542d8c3f742c7713c13	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-QTOF , positive-QTOF	splash10-03di-0029000000-43d5c8da88c1aa260682	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-QTOF , positive-QTOF	splash10-014i-0090000000-31b8655a24b30962bd8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-QTOF , positive-QTOF	splash10-01b9-0590000000-9894da52e88d32034318	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-QTOF , positive-QTOF	splash10-014i-0940000000-fedb75bd4c80c6c4fea9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-QTOF , positive-QTOF	splash10-0gb9-0940000000-a27b5f75aab7fac8931d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-014i-0090000000-1d4283f6dffa11b765e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-03di-0019000000-416fca50b212d00b968c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-014i-0090000000-ad95925610aed55afe91	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-0aor-1980000000-6d4d0adc4c8db177eaad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-1920000000-0548504791642aa3b2e0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-2920000000-dd2ce03c02a54aa24f83	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-3910000000-1af5f56241eabde05700	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-03di-0019000000-015df6e52b9d5ebe5cb2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-014i-0091000000-b328f3740a7ca4485324	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-0aor-0980000000-24074e0b5c722d7279c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-1920000000-5477eb89abafab290dd1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-2920000000-b4ffdf7888e464422c0c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-0a4i-3910000000-6053da2e4586dbcae300	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methadone LC-ESI-ITFT , positive-QTOF	splash10-014i-0090000000-0863c3130ca5df5f25b6	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methadone 10V, Positive-QTOF	splash10-03di-0069000000-144e893c575a6cb0ceb3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methadone 20V, Positive-QTOF	splash10-0229-8093000000-72ef33a6770239211ec3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methadone 40V, Positive-QTOF	splash10-0aw9-9780000000-930cd0f8dcbecbc72f1b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methadone 10V, Negative-QTOF	splash10-0a4i-0019000000-3418a56694229e2c6595	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methadone 20V, Negative-QTOF	splash10-0a4i-3069000000-10bb89e35854fe0680a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methadone 40V, Negative-QTOF	splash10-00fu-9180000000-abf68f949ff2ecf35fcc	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Methadone Action Pathway		Not Available
Methadone Metabolism 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 DB00333	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00333	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

DB00333

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3953

KEGG Compound ID

C07163

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methadone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

167309

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

Kell MJ: Utilization of plasma and urine methadone concentrations to optimize treatment in maintenance clinics: I. Measurement techniques for a clinical setting. J Addict Dis. 1994;13(1):5-26. [PubMed:8018740 ]
Joseph H, Stancliff S, Langrod J: Methadone maintenance treatment (MMT): a review of historical and clinical issues. Mt Sinai J Med. 2000 Oct-Nov;67(5-6):347-64. [PubMed:11064485 ]
Eap CB, Buclin T, Baumann P: Interindividual variability of the clinical pharmacokinetics of methadone: implications for the treatment of opioid dependence. Clin Pharmacokinet. 2002;41(14):1153-93. [PubMed:12405865 ]
Donny EC, Brasser SM, Bigelow GE, Stitzer ML, Walsh SL: Methadone doses of 100 mg or greater are more effective than lower doses at suppressing heroin self-administration in opioid-dependent volunteers. Addiction. 2005 Oct;100(10):1496-509. [PubMed:16185211 ]
Connock M, Juarez-Garcia A, Jowett S, Frew E, Liu Z, Taylor RJ, Fry-Smith A, Day E, Lintzeris N, Roberts T, Burls A, Taylor RS: Methadone and buprenorphine for the management of opioid dependence: a systematic review and economic evaluation. Health Technol Assess. 2007 Mar;11(9):1-171, iii-iv. [PubMed:17313907 ]
Leander JD, Wood CR: Metkephamid effects on operant behavior. Peptides. 1982 Sep-Oct;3(5):771-3. [PubMed:7177922 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kharasch ED, Hoffer C, Whittington D, Sheffels P: Role of hepatic and intestinal cytochrome P450 3A and 2B6 in the metabolism, disposition, and miotic effects of methadone. Clin Pharmacol Ther. 2004 Sep;76(3):250-69. [PubMed:15371986 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kharasch ED, Hoffer C, Whittington D, Sheffels P: Role of hepatic and intestinal cytochrome P450 3A and 2B6 in the metabolism, disposition, and miotic effects of methadone. Clin Pharmacol Ther. 2004 Sep;76(3):250-69. [PubMed:15371986 ]

Enzyme Details

7. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

8. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

9. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

10. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Stormer E, Perloff MD, von Moltke LL, Greenblatt DJ: Methadone inhibits rhodamine123 transport in Caco-2 cells. Drug Metab Dispos. 2001 Jul;29(7):954-6. [PubMed:11408360 ]
Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [PubMed:19887017 ]

Only showing the first 10 proteins. There are 16 proteins in total.

Show all enzymes and transporters

Showing metabocard for Methadone (HMDB0014477)

MOL for HMDB0014477 (Methadone)

3D MOL for HMDB0014477 (Methadone)

3D SDF for HMDB0014477 (Methadone)

3D-SDF for HMDB0014477 (Methadone)

PDB for HMDB0014477 (Methadone)

3D PDB for HMDB0014477 (Methadone)

SMILES for HMDB0014477 (Methadone)

INCHI for HMDB0014477 (Methadone)

Structure for HMDB0014477 (Methadone)

3D Structure for HMDB0014477 (Methadone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

Transporters

References