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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015555

Secondary Accession Numbers

HMDB15555

Metabolite Identification

Common Name

Molindone

Description

An indole derivative effective in schizophrenia and other psychoses and possibly useful in the treatment of the aggressive type of undersocialized conduct disorder. Molindone has much lower affinity for D2 receptors than most antipsychotic agents and has a relatively low affinity for D1 receptors. It has only low to moderate affinity for cholinergic and alpha-adrenergic receptors. Some electrophysiologic data from animals indicate that molindone has certain characteristics that resemble those of clozapine. (From AMA Drug Evaluations Annual, 1994, p283)

Structure

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

HMDB0015555
     RDKit          3D
Molindone
 44 46  0  0  0  0  0  0  0  0999 V2000
    3.9980   -1.5926    1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7258   -1.5626    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1831   -0.2640   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8549    0.9218   -0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3223    1.1728   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9905    1.8560   -0.8662 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7472    1.3282   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542    0.0144   -0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.8252   -0.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672   -2.0737   -0.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332   -0.2480   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770   -0.8328    0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9091   -0.5078    0.5182 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954    0.7206    0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7121    1.0325    0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6172    0.1062    0.6942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2707   -1.1499    0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -1.4146   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6687    1.2418   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388    1.8693   -1.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8948   -2.2200    1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2311   -0.5937    2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1458   -2.0634    2.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -1.7848   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353   -2.4035   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095    0.2294    0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8286    1.4807   -1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5180    1.9478    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737    2.8614   -1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652   -0.4948   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4553   -1.9610    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0563   -0.6026    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7898    1.6082    0.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7561    0.5993    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5338    0.9191   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478    2.0565    0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -1.8457    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9631   -1.4187   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6028   -2.4282    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7815   -1.5394   -1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070    1.6666   -1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4927    1.5781    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    2.9639   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111    1.6520   -2.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
  8  3  1  0
 18 13  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
M  END

1618
  Mrv0541 02231215362D          

 20 22  0  0  1  0            999 V2000
    1.6500   -0.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.4001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176   -0.9139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1991   -0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9739    1.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0241   -0.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7812    1.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  2 11  2  0  0  0  0
  3  7  1  0  0  0  0
  3 13  1  0  0  0  0
  3 14  1  0  0  0  0
  4 10  1  0  0  0  0
  4 15  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 15  2  0  0  0  0
 12 18  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  1  0  0  0  0
 15 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015555

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=C(C)NC2=C1C(=O)C(CN1CCOCC1)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N2O2/c1-3-13-11(2)17-14-5-4-12(16(19)15(13)14)10-18-6-8-20-9-7-18/h12,17H,3-10H2,1-2H3

> <INCHI_KEY>
KLPWJLBORRMFGK-UHFFFAOYSA-N

> <FORMULA>
C16H24N2O2

> <MOLECULAR_WEIGHT>
276.374

> <EXACT_MASS>
276.183778022

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.000152547479566

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.0351150263333335

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.729273140194294

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.337674727361463

> <JCHEM_PKA_STRONGEST_BASIC>
6.650210282855951

> <JCHEM_POLAR_SURFACE_AREA>
45.33

> <JCHEM_REFRACTIVITY>
81.0594

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
molindone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015555
     RDKit          3D
Molindone
 44 46  0  0  0  0  0  0  0  0999 V2000
    3.9980   -1.5926    1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7258   -1.5626    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1831   -0.2640   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8549    0.9218   -0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3223    1.1728   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9905    1.8560   -0.8662 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7472    1.3282   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542    0.0144   -0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.8252   -0.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672   -2.0737   -0.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332   -0.2480   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770   -0.8328    0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9091   -0.5078    0.5182 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954    0.7206    0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7121    1.0325    0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6172    0.1062    0.6942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2707   -1.1499    0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -1.4146   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6687    1.2418   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388    1.8693   -1.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8948   -2.2200    1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2311   -0.5937    2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1458   -2.0634    2.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -1.7848   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353   -2.4035   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095    0.2294    0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8286    1.4807   -1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5180    1.9478    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737    2.8614   -1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652   -0.4948   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4553   -1.9610    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0563   -0.6026    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7898    1.6082    0.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7561    0.5993    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5338    0.9191   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478    2.0565    0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -1.8457    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9631   -1.4187   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6028   -2.4282    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7815   -1.5394   -1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070    1.6666   -1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4927    1.5781    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    2.9639   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111    1.6520   -2.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
  8  3  1  0
 18 13  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1618                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080  -1.237   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.748   2.614   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748   0.303   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      12.540  -1.706   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.415   0.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415  -1.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   1.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748  -2.007   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.082   0.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.082  -1.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748   1.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.540   0.773   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   1.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -1.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.438  -0.467   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   0.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -2.007   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.018   2.237   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.978  -0.467   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.525   2.554   0.000  0.00  0.00           C+0
CONECT    1   16   17                                                       
CONECT    2   11                                                            
CONECT    3    7   13   14                                                  
CONECT    4   10   15                                                       
CONECT    5    6    7   11                                                  
CONECT    6    5    8                                                       
CONECT    7    3    5                                                       
CONECT    8    6   10                                                       
CONECT    9   10   11   12                                                  
CONECT   10    4    8    9                                                  
CONECT   11    2    5    9                                                  
CONECT   12    9   15   18                                                  
CONECT   13    3   16                                                       
CONECT   14    3   17                                                       
CONECT   15    4   12   19                                                  
CONECT   16    1   13                                                       
CONECT   17    1   14                                                       
CONECT   18   12   20                                                       
CONECT   19   15                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0257649
HETATM    1  C1  UNL     1       3.395  -2.571   0.534  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.402  -1.615   1.203  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.502  -0.308   0.478  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.484   0.651   0.605  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.649   0.588   1.523  1.00  0.00           C  
HETATM    6  N1  UNL     1       3.166   1.634  -0.257  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.014   1.323  -0.923  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.581   0.088  -0.461  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.337  -0.472  -1.009  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.264  -1.691  -1.138  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.746   0.490  -1.367  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.664   0.714  -0.184  1.00  0.00           C  
HETATM   13  N2  UNL     1      -2.321  -0.444   0.319  1.00  0.00           N  
HETATM   14  C11 UNL     1      -3.018  -0.176   1.567  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.463   0.149   1.421  1.00  0.00           C  
HETATM   16  O2  UNL     1      -5.118  -0.716   0.539  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.504  -0.772  -0.687  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.081  -1.226  -0.585  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.236   1.832  -1.776  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.219   1.980  -1.978  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.270  -2.385  -0.558  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.421  -2.342   0.821  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.173  -3.632   0.808  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.384  -2.000   1.204  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.797  -1.494   2.254  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.602   0.700   1.008  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.670  -0.343   2.081  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.551   1.400   2.305  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.694   2.519  -0.425  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.314   0.049  -2.189  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.403   1.531  -0.456  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.060   1.178   0.622  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.521   0.738   2.008  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.811  -0.986   2.277  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.942  -0.004   2.419  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.649   1.216   1.155  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.653   0.142  -1.297  1.00  0.00           H  
HETATM   38  H18 UNL     1      -5.047  -1.580  -1.264  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.128  -2.279  -0.190  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.647  -1.222  -1.590  1.00  0.00           H  
HETATM   41  H21 UNL     1      -0.720   2.077  -2.775  1.00  0.00           H  
HETATM   42  H22 UNL     1      -0.542   2.641  -1.036  1.00  0.00           H  
HETATM   43  H23 UNL     1       1.461   3.069  -2.046  1.00  0.00           H  
HETATM   44  H24 UNL     1       1.551   1.548  -2.962  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4    4    8
CONECT    4    5    6
CONECT    5   26   27   28
CONECT    6    7   29
CONECT    7    8    8   20
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   19   30
CONECT   12   13   31   32
CONECT   13   14   18
CONECT   14   15   33   34
CONECT   15   16   35   36
CONECT   16   17
CONECT   17   18   37   38
CONECT   18   39   40
CONECT   19   20   41   42
CONECT   20   43   44
END

HMDB0015555
     RDKit          3D
Molindone
 44 46  0  0  0  0  0  0  0  0999 V2000
    3.9980   -1.5926    1.7018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7258   -1.5626    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1831   -0.2640   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8549    0.9218   -0.4314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3223    1.1728   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9905    1.8560   -0.8662 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7472    1.3282   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542    0.0144   -0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6712   -0.8252   -0.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672   -2.0737   -0.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332   -0.2480   -0.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5770   -0.8328    0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9091   -0.5078    0.5182 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3954    0.7206    0.9356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7121    1.0325    0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6172    0.1062    0.6942 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2707   -1.1499    0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616   -1.4146   -0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6687    1.2418   -0.5760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4388    1.8693   -1.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8948   -2.2200    1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2311   -0.5937    2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1458   -2.0634    2.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6761   -1.7848   -0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0353   -2.4035   -0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8095    0.2294    0.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8286    1.4807   -1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5180    1.9478    0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1737    2.8614   -1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652   -0.4948   -1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4553   -1.9610    0.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0563   -0.6026    1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7898    1.6082    0.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7561    0.5993    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5338    0.9191   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0478    2.0565    0.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -1.8457    1.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9631   -1.4187   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6028   -2.4282    0.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7815   -1.5394   -1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6070    1.6666   -1.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4927    1.5781    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585    2.9639   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111    1.6520   -2.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
  8  3  1  0
 18 13  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Moban	ChEMBL, HMDB
(+-)-Molindone	HMDB
endo Brand OF molindone hydrochloride	MeSH, HMDB
Molindone hydrochloride	MeSH, HMDB
Hydrochloride, molindone	MeSH, HMDB
Molindone monohydrochloride	MeSH, HMDB
Monohydrochloride, molindone	MeSH, HMDB

Chemical Formula

C₁₆H₂₄N₂O₂

Average Molecular Weight

276.374

Monoisotopic Molecular Weight

276.183778022

IUPAC Name

3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one

Traditional Name

molindone

CAS Registry Number

7416-34-4

SMILES

CCC1=C(C)NC2=C1C(=O)C(CN1CCOCC1)CC2

InChI Identifier

InChI=1S/C16H24N2O2/c1-3-13-11(2)17-14-5-4-12(16(19)15(13)14)10-18-6-8-20-9-7-18/h12,17H,3-10H2,1-2H3

InChI Key

KLPWJLBORRMFGK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Aryl ketone
Aryl alkyl ketone
Aralkylamine
Morpholine
Oxazinane
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Vinylogous amide
Ketone
Tertiary amine
Tertiary aliphatic amine
Ether
Dialkyl ether
Oxacycle
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:6965 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015555)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	180.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.47 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	2.09	ALOGPS
logP	2.04	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	15.34	ChemAxon
pKa (Strongest Basic)	6.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	81.06 m³·mol⁻¹	ChemAxon
Polarizability	32 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.037	31661259
DarkChem	[M-H]-	162.911	31661259
DeepCCS	[M+H]+	166.867	30932474
DeepCCS	[M-H]-	164.509	30932474
DeepCCS	[M-2H]-	197.395	30932474
DeepCCS	[M+Na]+	172.96	30932474
AllCCS	[M+H]+	165.7	32859911
AllCCS	[M+H-H2O]+	162.2	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.8	32859911
AllCCS	[M-H]-	172.4	32859911
AllCCS	[M+Na-2H]-	172.5	32859911
AllCCS	[M+HCOO]-	172.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Molindone	CCC1=C(C)NC2=C1C(=O)C(CN1CCOCC1)CC2	2833.3	Standard polar	33892256
Molindone	CCC1=C(C)NC2=C1C(=O)C(CN1CCOCC1)CC2	2473.8	Standard non polar	33892256
Molindone	CCC1=C(C)NC2=C1C(=O)C(CN1CCOCC1)CC2	2503.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Molindone,1TMS,isomer #1	CCC1=C(C)N([Si](C)(C)C)C2=C1C(=O)C(CN1CCOCC1)CC2	2327.9	Semi standard non polar	33892256
Molindone,1TMS,isomer #1	CCC1=C(C)N([Si](C)(C)C)C2=C1C(=O)C(CN1CCOCC1)CC2	2376.9	Standard non polar	33892256
Molindone,1TMS,isomer #1	CCC1=C(C)N([Si](C)(C)C)C2=C1C(=O)C(CN1CCOCC1)CC2	3226.8	Standard polar	33892256
Molindone,1TBDMS,isomer #1	CCC1=C(C)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)C(CN1CCOCC1)CC2	2533.8	Semi standard non polar	33892256
Molindone,1TBDMS,isomer #1	CCC1=C(C)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)C(CN1CCOCC1)CC2	2609.7	Standard non polar	33892256
Molindone,1TBDMS,isomer #1	CCC1=C(C)N([Si](C)(C)C(C)(C)C)C2=C1C(=O)C(CN1CCOCC1)CC2	3245.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Molindone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001j-7690000000-39a1949956d6f8459274	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Molindone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Molindone 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 - Molindone 10V, Positive-QTOF	splash10-004i-0390000000-0fad419a5a8589ce686f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 20V, Positive-QTOF	splash10-0006-0940000000-744eb27b9ac46d4750e8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 40V, Positive-QTOF	splash10-0kml-6900000000-abd5f6ed2234c68e0ad2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 10V, Negative-QTOF	splash10-004i-1090000000-f34c3352e69ca4aeb8c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 20V, Negative-QTOF	splash10-004i-3290000000-8f53dde449874fc02c8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 40V, Negative-QTOF	splash10-052o-9210000000-ae67eeb7ca5afa4f6bcc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 10V, Positive-QTOF	splash10-004i-0090000000-d15f8b1b2509fa118d04	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 20V, Positive-QTOF	splash10-004i-0590000000-6179f9d20bb864ceedb6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 40V, Positive-QTOF	splash10-114i-1930000000-4397387d187aa830ed73	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 10V, Negative-QTOF	splash10-004i-0090000000-a18a8011b0f6da952681	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 20V, Negative-QTOF	splash10-004i-0090000000-fdc24634182dbf5de3fb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Molindone 40V, Negative-QTOF	splash10-0002-1690000000-8acb618be1a6d31626e3	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01618	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01618	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01618

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

22342

KEGG Compound ID

C07230

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Molindone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Seeman P, Tallerico T: Antipsychotic drugs which elicit little or no parkinsonism bind more loosely than dopamine to brain D2 receptors, yet occupy high levels of these receptors. Mol Psychiatry. 1998 Mar;3(2):123-34. [PubMed:9577836 ]
Lidow MS, Goldman-Rakic PS: Differential regulation of D2 and D4 dopamine receptor mRNAs in the primate cerebral cortex vs. neostriatum: effects of chronic treatment with typical and atypical antipsychotic drugs. J Pharmacol Exp Ther. 1997 Nov;283(2):939-46. [PubMed:9353417 ]
Froimowitz M, Cody V: The incorporation of butyrophenones and related compounds into a pharmacophore for dopamine D2 antagonists. Drug Des Discov. 1997 Aug;15(2):63-81. [PubMed:9342550 ]
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Enzyme Details

2. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Nguyen TV, Juorio AV: Down-regulation of tryptamine binding sites following chronic molindone administration. A comparison with responses of dopamine and 5-hydroxytryptamine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1989 Oct;340(4):366-71. [PubMed:2586632 ]

Enzyme Details

3. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Nguyen TV, Juorio AV: Down-regulation of tryptamine binding sites following chronic molindone administration. A comparison with responses of dopamine and 5-hydroxytryptamine receptors. Naunyn Schmiedebergs Arch Pharmacol. 1989 Oct;340(4):366-71. [PubMed:2586632 ]

Enzyme Details

4. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Neeper R, Richelson E, Nelson A: Neuroleptic binding to muscarinic M2 receptors of normal human heart in vitro and comparison with binding to M1 and dopamine D2 receptors of brain. Neuropharmacology. 1991 May;30(5):527-9. [PubMed:1678146 ]

Showing metabocard for Molindone (HMDB0015555)

MOL for HMDB0015555 (Molindone)

3D MOL for HMDB0015555 (Molindone)

3D SDF for HMDB0015555 (Molindone)

3D-SDF for HMDB0015555 (Molindone)

PDB for HMDB0015555 (Molindone)

3D PDB for HMDB0015555 (Molindone)

SMILES for HMDB0015555 (Molindone)

INCHI for HMDB0015555 (Molindone)

Structure for HMDB0015555 (Molindone)

3D Structure for HMDB0015555 (Molindone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References