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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015115

Secondary Accession Numbers

HMDB15115

Metabolite Identification

Common Name

Ramelteon

Description

Ramelteon, also known as rozerem or TAK-375, belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. Ramelteon is a drug which is used for the treatment of insomnia characterized by difficulty with sleep onset. Ramelteon is a melatonin receptor agonist with both high affinity for melatonin MT1 and MT2 receptors and selectivity over the MT3 receptor. Ramelteon is an extremely weak basic (essentially neutral) compound (based on its pKa). The most frequent adverse events leading to discontinuation were somnolence, dizziness, nausea, fatigue, headache, and insomnia. It is approved by the U.S. Food and Drug Administration (FDA) for long-term use. Ramelteon and fluvoxamine should not be coadministered. Ramelteon can be used for insomnia, particularly delayed sleep onset.

Structure

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

HMDB0015115
     RDKit          3D
Ramelteon
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.6001   -1.8858    1.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343   -0.8962    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176   -1.1707   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -2.1275   -0.0149 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249   -0.3546   -1.5401 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625   -0.5922   -2.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0453   -0.4681   -1.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2877    0.8570   -0.7462 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7459    1.4141    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5026    0.6321    1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954    0.5141    1.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    0.3033    2.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2784    0.2412    2.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093    0.3892    0.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199    0.5978   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4641    0.6533    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5575    0.7203   -1.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9867    0.8792   -1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9720    0.3667    0.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6498   -2.0905    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -1.5449    1.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9983   -2.8395    0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043    0.1212    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1664   -0.9248   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418    0.4241   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1570   -0.0293   -3.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2979   -1.6715   -2.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961   -1.2211   -0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8066   -0.8802   -1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755    1.6006   -1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818    1.3663   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4431    2.4943    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7574    1.3406    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212   -0.3147    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5462    0.1924    3.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9866    0.0775    2.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041   -0.1403   -2.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2652    1.6476   -2.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6793    0.3689   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2865    1.9502   -0.9123 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 16  8  1  0
 16 11  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

980
  Mrv0541 02231215092D          

 19 21  0  0  1  0            999 V2000
    2.1316    3.1623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0172   -2.0952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9536   -1.1408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7993    0.8714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6267    1.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6149    0.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492    1.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    2.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2482    0.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9121    2.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316    1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9121    2.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412    2.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046   -0.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6267    3.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2099   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6589   -2.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9152   -3.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  1 15  1  0  0  0  0
  2 17  2  0  0  0  0
  3 14  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  1  0  0  0
  5  8  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 16  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015115

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)NCC[C@@H]1CCC2=C1C1=C(OCC1)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO2/c1-2-15(18)17-9-7-12-4-3-11-5-6-14-13(16(11)12)8-10-19-14/h5-6,12H,2-4,7-10H2,1H3,(H,17,18)/t12-/m0/s1

> <INCHI_KEY>
YLXDSYKOBKBWJQ-LBPRGKRZSA-N

> <FORMULA>
C16H21NO2

> <MOLECULAR_WEIGHT>
259.3434

> <EXACT_MASS>
259.157228921

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.990198126417273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{2-[(8S)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-8-yl]ethyl}propanamide

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.5705583956666667

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.822429841668786

> <JCHEM_PKA_STRONGEST_BASIC>
-0.40319387136005036

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
75.5185

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ramelteon

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015115
     RDKit          3D
Ramelteon
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.6001   -1.8858    1.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343   -0.8962    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176   -1.1707   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -2.1275   -0.0149 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249   -0.3546   -1.5401 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625   -0.5922   -2.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0453   -0.4681   -1.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2877    0.8570   -0.7462 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7459    1.4141    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5026    0.6321    1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954    0.5141    1.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    0.3033    2.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2784    0.2412    2.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093    0.3892    0.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199    0.5978   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4641    0.6533    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5575    0.7203   -1.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9867    0.8792   -1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9720    0.3667    0.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6498   -2.0905    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -1.5449    1.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9983   -2.8395    0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043    0.1212    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1664   -0.9248   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418    0.4241   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1570   -0.0293   -3.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2979   -1.6715   -2.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961   -1.2211   -0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8066   -0.8802   -1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755    1.6006   -1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818    1.3663   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4431    2.4943    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7574    1.3406    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212   -0.3147    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5462    0.1924    3.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9866    0.0775    2.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041   -0.1403   -2.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2652    1.6476   -2.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6793    0.3689   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2865    1.9502   -0.9123 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 16  8  1  0
 16 11  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 980                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.979   5.903   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.499  -3.911   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.513  -2.130   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.092   1.627   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.770   3.123   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.615   1.468   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.238   2.866   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.104   3.893   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.063   0.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.436   3.893   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.979   3.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.436   5.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.104   5.433   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.542  -0.983   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   4.663   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.770   6.203   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.992  -3.593   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.963  -4.740   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.442  -6.203   0.000  0.00  0.00           C+0
CONECT    1   12   15                                                       
CONECT    2   17                                                            
CONECT    3   14   17                                                       
CONECT    4    5    6    9                                                  
CONECT    5    4    8   10                                                  
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    5    7   13                                                  
CONECT    9    4   14                                                       
CONECT   10    5   11   12                                                  
CONECT   11   10   15                                                       
CONECT   12    1   10   16                                                  
CONECT   13    8   16                                                       
CONECT   14    3    9                                                       
CONECT   15    1   11                                                       
CONECT   16   12   13                                                       
CONECT   17    2    3   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0015115
HETATM    1  C1  UNL     1       4.600  -1.886   1.265  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.334  -0.896   0.169  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.018  -1.171  -0.454  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.343  -2.127  -0.015  1.00  0.00           O  
HETATM    5  N1  UNL     1       2.525  -0.355  -1.540  1.00  0.00           N  
HETATM    6  C4  UNL     1       1.263  -0.592  -2.153  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.045  -0.468  -1.320  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.288   0.857  -0.746  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.746   1.414   0.171  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.503   0.632   1.472  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.995   0.514   1.435  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.928   0.303   2.452  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.278   0.241   2.160  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.709   0.389   0.848  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.820   0.598  -0.178  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.464   0.653   0.164  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.558   0.720  -1.472  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.987   0.879  -1.002  1.00  0.00           C  
HETATM   19  O2  UNL     1      -4.972   0.367   0.318  1.00  0.00           O  
HETATM   20  H1  UNL     1       3.650  -2.090   1.797  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.358  -1.545   1.985  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.998  -2.840   0.826  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.304   0.121   0.615  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.166  -0.925  -0.573  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.142   0.424  -1.864  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.157  -0.029  -3.125  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.298  -1.671  -2.512  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.096  -1.221  -0.475  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.807  -0.880  -1.945  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.576   1.601  -1.547  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.782   1.366  -0.153  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.443   2.494   0.355  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.757   1.341   2.286  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.021  -0.315   1.503  1.00  0.00           H  
HETATM   35  H16 UNL     1      -1.546   0.192   3.467  1.00  0.00           H  
HETATM   36  H17 UNL     1      -3.987   0.077   2.959  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.404  -0.140  -2.122  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.265   1.648  -2.012  1.00  0.00           H  
HETATM   39  H20 UNL     1      -5.679   0.369  -1.669  1.00  0.00           H  
HETATM   40  H21 UNL     1      -5.287   1.950  -0.912  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4    4    5
CONECT    5    6   25
CONECT    6    7   26   27
CONECT    7    8   28   29
CONECT    8    9   16   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   12   16
CONECT   12   13   35
CONECT   13   14   14   36
CONECT   14   15   19
CONECT   15   16   16   17
CONECT   17   18   37   38
CONECT   18   19   39   40
END

HMDB0015115
     RDKit          3D
Ramelteon
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.6001   -1.8858    1.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343   -0.8962    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0176   -1.1707   -0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -2.1275   -0.0149 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5249   -0.3546   -1.5401 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625   -0.5922   -2.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0453   -0.4681   -1.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2877    0.8570   -0.7462 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7459    1.4141    0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5026    0.6321    1.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954    0.5141    1.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9277    0.3033    2.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2784    0.2412    2.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093    0.3892    0.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8199    0.5978   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4641    0.6533    0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5575    0.7203   -1.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9867    0.8792   -1.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9720    0.3667    0.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6498   -2.0905    1.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -1.5449    1.9848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9983   -2.8395    0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043    0.1212    0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1664   -0.9248   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418    0.4241   -1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1570   -0.0293   -3.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2979   -1.6715   -2.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961   -1.2211   -0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8066   -0.8802   -1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5755    1.6006   -1.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818    1.3663   -0.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4431    2.4943    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7574    1.3406    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0212   -0.3147    1.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5462    0.1924    3.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9866    0.0775    2.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041   -0.1403   -2.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2652    1.6476   -2.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6793    0.3689   -1.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2865    1.9502   -0.9123 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 16  8  1  0
 16 11  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Rozerem	Kegg
TAK-375	HMDB
(S)-N-(2-(1,6,7,8-Tetrahydro-2H-indeno-(5,4)furan-8-yl)ethyl)propionamide	HMDB

Chemical Formula

C₁₆H₂₁NO₂

Average Molecular Weight

259.3434

Monoisotopic Molecular Weight

259.157228921

IUPAC Name

N-{2-[(8S)-1H,2H,6H,7H,8H-indeno[5,4-b]furan-8-yl]ethyl}propanamide

Traditional Name

ramelteon

CAS Registry Number

196597-26-9

SMILES

CCC(=O)NCC[C@@H]1CCC2=C1C1=C(OCC1)C=C2

InChI Identifier

InChI=1S/C16H21NO2/c1-2-15(18)17-9-7-12-4-3-11-5-6-14-13(16(11)12)8-10-19-14/h5-6,12H,2-4,7-10H2,1H3,(H,17,18)/t12-/m0/s1

InChI Key

YLXDSYKOBKBWJQ-LBPRGKRZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Indanes

Sub Class

Not Available

Direct Parent

Indanes

Alternative Parents

Substituents

Indane
Coumaran
Alkyl aryl ether
Carboxamide group
Secondary carboxylic acid amide
Oxacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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: HMDB0015115)

Source

Exogenous

Exogenous (HMDB: HMDB0015115)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.016 g/L	Not Available
LogP	2.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	3.03	ALOGPS
logP	2.57	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.82	ChemAxon
pKa (Strongest Basic)	-0.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.52 m³·mol⁻¹	ChemAxon
Polarizability	29.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.192	31661259
DarkChem	[M-H]-	157.179	31661259
DeepCCS	[M+H]+	162.665	30932474
DeepCCS	[M-H]-	160.307	30932474
DeepCCS	[M-2H]-	193.193	30932474
DeepCCS	[M+Na]+	168.758	30932474
AllCCS	[M+H]+	161.8	32859911
AllCCS	[M+H-H2O]+	158.4	32859911
AllCCS	[M+NH4]+	165.0	32859911
AllCCS	[M+Na]+	165.9	32859911
AllCCS	[M-H]-	167.5	32859911
AllCCS	[M+Na-2H]-	167.5	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.12 minutes	32390414
Predicted by Siyang on May 30, 2022	13.5146 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.8 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1948.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	334.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	170.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	509.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	576.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1134.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	464.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1445.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	360.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	318.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	255.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	13.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ramelteon	CCC(=O)NCC[C@@H]1CCC2=C1C1=C(OCC1)C=C2	3458.8	Standard polar	33892256
Ramelteon	CCC(=O)NCC[C@@H]1CCC2=C1C1=C(OCC1)C=C2	2324.6	Standard non polar	33892256
Ramelteon	CCC(=O)NCC[C@@H]1CCC2=C1C1=C(OCC1)C=C2	2432.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ramelteon,1TMS,isomer #1	CCC(=O)N(CC[C@@H]1CCC2=CC=C3OCCC3=C21)[Si](C)(C)C	2392.5	Semi standard non polar	33892256
Ramelteon,1TMS,isomer #1	CCC(=O)N(CC[C@@H]1CCC2=CC=C3OCCC3=C21)[Si](C)(C)C	2344.6	Standard non polar	33892256
Ramelteon,1TMS,isomer #1	CCC(=O)N(CC[C@@H]1CCC2=CC=C3OCCC3=C21)[Si](C)(C)C	2930.5	Standard polar	33892256
Ramelteon,1TBDMS,isomer #1	CCC(=O)N(CC[C@@H]1CCC2=CC=C3OCCC3=C21)[Si](C)(C)C(C)(C)C	2601.4	Semi standard non polar	33892256
Ramelteon,1TBDMS,isomer #1	CCC(=O)N(CC[C@@H]1CCC2=CC=C3OCCC3=C21)[Si](C)(C)C(C)(C)C	2609.3	Standard non polar	33892256
Ramelteon,1TBDMS,isomer #1	CCC(=O)N(CC[C@@H]1CCC2=CC=C3OCCC3=C21)[Si](C)(C)C(C)(C)C	3060.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ramelteon GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7r-9870000000-1c290026ffceb3eef315	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ramelteon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ramelteon GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ramelteon , positive-QTOF	splash10-0nmi-2980000000-5ee1e7ec83e5c4578dfe	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 10V, Positive-QTOF	splash10-0w29-0190000000-5ab5aa60e4a12e68a700	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 20V, Positive-QTOF	splash10-0uki-2950000000-2f78e21b2259ce9f7f74	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 40V, Positive-QTOF	splash10-0a4i-1900000000-72904ed8a2217e0540cf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 10V, Negative-QTOF	splash10-0a4i-1090000000-86053c1f7ca9207210fd	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 20V, Negative-QTOF	splash10-0ab9-6290000000-07567898b89338a73662	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 40V, Negative-QTOF	splash10-00dl-9200000000-fd494970ea1477bf6bff	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 10V, Positive-QTOF	splash10-03dr-0490000000-7c5eda0bc1fa87f8d3fe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 20V, Positive-QTOF	splash10-0f79-0960000000-bc3bd3e1b1625882b5e5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 40V, Positive-QTOF	splash10-0a4r-1900000000-4d81e2b61e8cc443fe5c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 10V, Negative-QTOF	splash10-0a4i-0090000000-c0454357e4d45524bed6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 20V, Negative-QTOF	splash10-006x-9020000000-247d500a821bd4bc62c3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ramelteon 40V, Negative-QTOF	splash10-006x-3910000000-9a203e7c37bf89bf657d	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 DB00980	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00980	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00980

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

181000

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ramelteon

METLIN ID

Not Available

PubChem Compound

208902

PDB ID

Not Available

ChEBI ID

321962

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

Karim A, Tolbert D, Cao C: Disposition kinetics and tolerance of escalating single doses of ramelteon, a high-affinity MT1 and MT2 melatonin receptor agonist indicated for treatment of insomnia. J Clin Pharmacol. 2006 Feb;46(2):140-8. [PubMed:16432265 ]
Roth T, Stubbs C, Walsh JK: Ramelteon (TAK-375), a selective MT1/MT2-receptor agonist, reduces latency to persistent sleep in a model of transient insomnia related to a novel sleep environment. Sleep. 2005 Mar;28(3):303-7. [PubMed:16173650 ]
Miyamoto M: Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders. CNS Neurosci Ther. 2009 Winter;15(1):32-51. doi: 10.1111/j.1755-5949.2008.00066.x. [PubMed:19228178 ]
Pandi-Perumal SR, Srinivasan V, Spence DW, Moscovitch A, Hardeland R, Brown GM, Cardinali DP: Ramelteon: a review of its therapeutic potential in sleep disorders. Adv Ther. 2009 Jun;26(6):613-26. doi: 10.1007/s12325-009-0041-6. Epub 2009 Jun 30. [PubMed:19568703 ]
Borja NL, Daniel KL: Ramelteon for the treatment of insomnia. Clin Ther. 2006 Oct;28(10):1540-55. [PubMed:17157111 ]
Simpson D, Curran MP: Ramelteon: a review of its use in insomnia. Drugs. 2008;68(13):1901-19. [PubMed:18729542 ]

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

Obach RS, Ryder TF: Metabolism of ramelteon in human liver microsomes and correlation with the effect of fluvoxamine on ramelteon pharmacokinetics. Drug Metab Dispos. 2010 Aug;38(8):1381-91. doi: 10.1124/dmd.110.034009. Epub 2010 May 17. [PubMed:20478852 ]

Enzyme Details

2. 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

Obach RS, Ryder TF: Metabolism of ramelteon in human liver microsomes and correlation with the effect of fluvoxamine on ramelteon pharmacokinetics. Drug Metab Dispos. 2010 Aug;38(8):1381-91. doi: 10.1124/dmd.110.034009. Epub 2010 May 17. [PubMed:20478852 ]

Enzyme Details

3. 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

Obach RS, Ryder TF: Metabolism of ramelteon in human liver microsomes and correlation with the effect of fluvoxamine on ramelteon pharmacokinetics. Drug Metab Dispos. 2010 Aug;38(8):1381-91. doi: 10.1124/dmd.110.034009. Epub 2010 May 17. [PubMed:20478852 ]

Enzyme Details

4. Melatonin receptor type 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: High affinity receptor for melatonin. Likely to mediates the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity
Gene Name:: MTNR1A
Uniprot ID:: P48039
Molecular weight:: 39374.3

References

Kato K, Hirai K, Nishiyama K, Uchikawa O, Fukatsu K, Ohkawa S, Kawamata Y, Hinuma S, Miyamoto M: Neurochemical properties of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist. Neuropharmacology. 2005 Feb;48(2):301-10. [PubMed:15695169 ]
Karim A, Tolbert D, Cao C: Disposition kinetics and tolerance of escalating single doses of ramelteon, a high-affinity MT1 and MT2 melatonin receptor agonist indicated for treatment of insomnia. J Clin Pharmacol. 2006 Feb;46(2):140-8. [PubMed:16432265 ]
Greenblatt DJ, Harmatz JS, Karim A: Age and gender effects on the pharmacokinetics and pharmacodynamics of ramelteon, a hypnotic agent acting via melatonin receptors MT1 and MT2. J Clin Pharmacol. 2007 Apr;47(4):485-96. [PubMed:17389558 ]
Roth T, Stubbs C, Walsh JK: Ramelteon (TAK-375), a selective MT1/MT2-receptor agonist, reduces latency to persistent sleep in a model of transient insomnia related to a novel sleep environment. Sleep. 2005 Mar;28(3):303-7. [PubMed:16173650 ]
Miyamoto M: Effect of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist, on motor performance in mice. Neurosci Lett. 2006 Jul 24;402(3):201-4. Epub 2006 May 24. [PubMed:16730121 ]
Authors unspecified: Ramelteon: TAK 375. Drugs R D. 2005;6(3):186-8. [PubMed:15869323 ]
Miyamoto M: Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders. CNS Neurosci Ther. 2009 Winter;15(1):32-51. doi: 10.1111/j.1755-5949.2008.00066.x. [PubMed:19228178 ]
Miyamoto M: [A novel therapeutic drug: ramelteon]. Nihon Rinsho. 2009 Aug;67(8):1595-600. [PubMed:19768947 ]
Pandi-Perumal SR, Srinivasan V, Spence DW, Moscovitch A, Hardeland R, Brown GM, Cardinali DP: Ramelteon: a review of its therapeutic potential in sleep disorders. Adv Ther. 2009 Jun;26(6):613-26. doi: 10.1007/s12325-009-0041-6. Epub 2009 Jun 30. [PubMed:19568703 ]
Borja NL, Daniel KL: Ramelteon for the treatment of insomnia. Clin Ther. 2006 Oct;28(10):1540-55. [PubMed:17157111 ]
Johnson MW, Suess PE, Griffiths RR: Ramelteon: a novel hypnotic lacking abuse liability and sedative adverse effects. Arch Gen Psychiatry. 2006 Oct;63(10):1149-57. [PubMed:17015817 ]
Zammit G, Erman M, Wang-Weigand S, Sainati S, Zhang J, Roth T: Evaluation of the efficacy and safety of ramelteon in subjects with chronic insomnia. J Clin Sleep Med. 2007 Aug 15;3(5):495-504. [PubMed:17803013 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Melatonin receptor type 1B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: High affinity receptor for melatonin. Likely to mediates the reproductive and circadian actions of melatonin. The activity of this receptor is mediated by pertussis toxin sensitive G proteins that inhibit adenylate cyclase activity
Gene Name:: MTNR1B
Uniprot ID:: P49286
Molecular weight:: 40187.9

References

Kato K, Hirai K, Nishiyama K, Uchikawa O, Fukatsu K, Ohkawa S, Kawamata Y, Hinuma S, Miyamoto M: Neurochemical properties of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist. Neuropharmacology. 2005 Feb;48(2):301-10. [PubMed:15695169 ]
Karim A, Tolbert D, Cao C: Disposition kinetics and tolerance of escalating single doses of ramelteon, a high-affinity MT1 and MT2 melatonin receptor agonist indicated for treatment of insomnia. J Clin Pharmacol. 2006 Feb;46(2):140-8. [PubMed:16432265 ]
Greenblatt DJ, Harmatz JS, Karim A: Age and gender effects on the pharmacokinetics and pharmacodynamics of ramelteon, a hypnotic agent acting via melatonin receptors MT1 and MT2. J Clin Pharmacol. 2007 Apr;47(4):485-96. [PubMed:17389558 ]
Roth T, Stubbs C, Walsh JK: Ramelteon (TAK-375), a selective MT1/MT2-receptor agonist, reduces latency to persistent sleep in a model of transient insomnia related to a novel sleep environment. Sleep. 2005 Mar;28(3):303-7. [PubMed:16173650 ]
Miyamoto M: Effect of ramelteon (TAK-375), a selective MT1/MT2 receptor agonist, on motor performance in mice. Neurosci Lett. 2006 Jul 24;402(3):201-4. Epub 2006 May 24. [PubMed:16730121 ]
Authors unspecified: Ramelteon: TAK 375. Drugs R D. 2005;6(3):186-8. [PubMed:15869323 ]
Miyamoto M: Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders. CNS Neurosci Ther. 2009 Winter;15(1):32-51. doi: 10.1111/j.1755-5949.2008.00066.x. [PubMed:19228178 ]
Miyamoto M: [A novel therapeutic drug: ramelteon]. Nihon Rinsho. 2009 Aug;67(8):1595-600. [PubMed:19768947 ]
Pandi-Perumal SR, Srinivasan V, Spence DW, Moscovitch A, Hardeland R, Brown GM, Cardinali DP: Ramelteon: a review of its therapeutic potential in sleep disorders. Adv Ther. 2009 Jun;26(6):613-26. doi: 10.1007/s12325-009-0041-6. Epub 2009 Jun 30. [PubMed:19568703 ]
Borja NL, Daniel KL: Ramelteon for the treatment of insomnia. Clin Ther. 2006 Oct;28(10):1540-55. [PubMed:17157111 ]
Johnson MW, Suess PE, Griffiths RR: Ramelteon: a novel hypnotic lacking abuse liability and sedative adverse effects. Arch Gen Psychiatry. 2006 Oct;63(10):1149-57. [PubMed:17015817 ]
Zammit G, Erman M, Wang-Weigand S, Sainati S, Zhang J, Roth T: Evaluation of the efficacy and safety of ramelteon in subjects with chronic insomnia. J Clin Sleep Med. 2007 Aug 15;3(5):495-504. [PubMed:17803013 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Ramelteon (HMDB0015115)

MOL for HMDB0015115 (Ramelteon)

3D MOL for HMDB0015115 (Ramelteon)

3D SDF for HMDB0015115 (Ramelteon)

3D-SDF for HMDB0015115 (Ramelteon)

PDB for HMDB0015115 (Ramelteon)

3D PDB for HMDB0015115 (Ramelteon)

SMILES for HMDB0015115 (Ramelteon)

INCHI for HMDB0015115 (Ramelteon)

Structure for HMDB0015115 (Ramelteon)

3D Structure for HMDB0015115 (Ramelteon)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References