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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 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 02:52:03 UTC

HMDB ID

HMDB0015623

Secondary Accession Numbers

HMDB15623

Metabolite Identification

Common Name

Rimonabant

Description

Rimonabant is an anorectic anti-obesity drug produced and marketed by Sanofi-Aventis. It is an inverse agonist for the cannabinoid receptor CB1. Its main avenue of effect is reduction in appetite. Rimonabant is the first selective CB1 receptor blocker to be approved for use anywhere in the world. Rimonabant is approved in 38 countries including the E.U., Mexico, and Brazil. It was rejected for approval for use in the United States. This decision was made after a U.S. advisory panel recommended the medicine not be approved because it may increase suicidal thinking and depression.

Structure

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


  Mrv0541 02231218142D          

 30 33  0  0  0  0            999 V2000
    3.7293   -1.1447    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.9643   -0.8545    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.1583   -3.6198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5965    2.3710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    2.1986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4404    1.5312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583   -0.3197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4909    0.1653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    3.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    3.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350    2.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    2.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2609    1.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458    0.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5709    0.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8258    0.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105   -0.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0558    1.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583   -1.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2235    0.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7820   -0.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4439   -1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728   -1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0082    0.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5666   -1.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4439   -2.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728   -2.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1797   -0.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583   -2.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 29  1  0  0  0  0
  3 30  1  0  0  0  0
  4 14  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 17  1  0  0  0  0
  7 20  1  0  0  0  0
  8 15  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  2  0  0  0  0
 18 22  1  0  0  0  0
 20 23  2  0  0  0  0
 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 28  2  0  0  0  0
 25 29  2  0  0  0  0
 26 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 30  1  0  0  0  0
M  END

HMDB0015623
     RDKit          3D
Rimonabant
 51 54  0  0  0  0  0  0  0  0999 V2000
   -0.3259   -2.7060   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -1.2503   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -0.2319   -0.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7816   -0.4284   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585   -1.5585   -0.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6097    0.7147   -0.2819 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    0.6899   -0.2660 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6086    1.0800    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8425    0.2205    1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7339    0.2383   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9957   -0.1844   -1.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5254   -0.4792   -0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317    0.9236   -0.2645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559    0.6917   -0.2386 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096    1.7451   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889    1.9948    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2075    3.0197    0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786    3.8158   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6640    5.1261   -0.0502 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7832    3.5409   -1.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8668    2.5296   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9863    2.1906   -2.8432 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8595   -0.6238   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407   -1.2948   -0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2586   -2.5429    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861   -3.2171    0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6405   -2.6739    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1867   -3.5140    0.2908 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415   -1.4401   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3139   -0.7663   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916   -2.8597   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1102   -3.1638    0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943   -3.2944   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    1.6838   -0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    0.9723    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9884    2.1375    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5526   -0.7925    1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4016    0.7375    2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563    1.2593   -0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6181   -0.4269    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9437    0.6488   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3952   -1.1211   -1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5134   -1.3744   -0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0163   -0.7429   -1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1066    1.3824    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344    3.1985    1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9740    4.1564   -2.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4008   -3.0257    1.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5358   -4.1887    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4283   -0.9742   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2860    0.1780   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  3 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 14 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 23  2  2  0
 30 24  1  0
 12  7  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 16 45  1  0
 17 46  1  0
 20 47  1  0
 25 48  1  0
 26 49  1  0
 29 50  1  0
 30 51  1  0
M  END


  Mrv0541 02231218142D          

 30 33  0  0  0  0            999 V2000
    3.7293   -1.1447    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.9643   -0.8545    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.1583   -3.6198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5965    2.3710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555    2.1986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4404    1.5312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583   -0.3197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4909    0.1653    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856    3.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.7798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061    3.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350    2.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    2.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2609    1.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458    0.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5709    0.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8258    0.1653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105   -0.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0558    1.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583   -1.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2235    0.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7820   -0.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4439   -1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728   -1.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0082    0.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5666   -1.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4439   -2.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728   -2.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1797   -0.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583   -2.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 29  1  0  0  0  0
  3 30  1  0  0  0  0
  4 14  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 17  1  0  0  0  0
  7 20  1  0  0  0  0
  8 15  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 21  2  0  0  0  0
 18 22  1  0  0  0  0
 20 23  2  0  0  0  0
 20 24  1  0  0  0  0
 21 25  1  0  0  0  0
 22 26  2  0  0  0  0
 23 27  1  0  0  0  0
 24 28  2  0  0  0  0
 25 29  2  0  0  0  0
 26 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015623

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)

> <INCHI_KEY>
JZCPYUJPEARBJL-UHFFFAOYSA-N

> <FORMULA>
C22H21Cl3N4O

> <MOLECULAR_WEIGHT>
463.787

> <EXACT_MASS>
462.078094435

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
47.96057719350162

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
5.907997435000002

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.421861716989987

> <JCHEM_PKA_STRONGEST_BASIC>
1.6813636475741176

> <JCHEM_POLAR_SURFACE_AREA>
50.160000000000004

> <JCHEM_REFRACTIVITY>
122.83080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rimonabant

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015623
     RDKit          3D
Rimonabant
 51 54  0  0  0  0  0  0  0  0999 V2000
   -0.3259   -2.7060   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161   -1.2503   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -0.2319   -0.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7816   -0.4284   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585   -1.5585   -0.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6097    0.7147   -0.2819 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    0.6899   -0.2660 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6086    1.0800    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8425    0.2205    1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7339    0.2383   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9957   -0.1844   -1.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5254   -0.4792   -0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317    0.9236   -0.2645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559    0.6917   -0.2386 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096    1.7451   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889    1.9948    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2075    3.0197    0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786    3.8158   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6640    5.1261   -0.0502 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7832    3.5409   -1.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8668    2.5296   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9863    2.1906   -2.8432 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8595   -0.6238   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407   -1.2948   -0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2586   -2.5429    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861   -3.2171    0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6405   -2.6739    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1867   -3.5140    0.2908 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415   -1.4401   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3139   -0.7663   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916   -2.8597   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1102   -3.1638    0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943   -3.2944   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    1.6838   -0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    0.9723    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9884    2.1375    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5526   -0.7925    1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4016    0.7375    2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563    1.2593   -0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6181   -0.4269    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9437    0.6488   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3952   -1.1211   -1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5134   -1.3744   -0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0163   -0.7429   -1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1066    1.3824    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344    3.1985    1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9740    4.1564   -2.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4008   -3.0257    1.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5358   -4.1887    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4283   -0.9742   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2860    0.1780   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  3 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 14 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 23  2  2  0
 30 24  1  0
 12  7  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 16 45  1  0
 17 46  1  0
 20 47  1  0
 25 48  1  0
 26 49  1  0
 29 50  1  0
 30 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       6.961  -2.137   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0      16.733  -1.595   0.000  0.00  0.00          Cl+0
HETATM    3 Cl   UNK     0       9.629  -6.757   0.000  0.00  0.00          Cl+0
HETATM    4  O   UNK     0       8.580   4.426   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.517   4.104   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.422   2.858   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.629  -0.597   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       8.383   0.309   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.706   6.596   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080   5.189   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.238   6.757   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.985   3.943   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.143   5.511   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.954   3.019   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.859   1.773   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.399   1.773   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.875   0.309   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.340  -0.167   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.304   3.019   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.629  -2.137   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.484   0.863   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.660  -1.674   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.295  -2.907   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.963  -2.907   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.949   0.387   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.124  -2.150   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.295  -4.447   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.963  -4.447   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.269  -1.119   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.629  -5.217   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   29                                                            
CONECT    3   30                                                            
CONECT    4   14                                                            
CONECT    5    6   12   13                                                  
CONECT    6    5   14                                                       
CONECT    7    8   17   20                                                  
CONECT    8    7   15                                                       
CONECT    9   10   11                                                       
CONECT   10    9   12                                                       
CONECT   11    9   13                                                       
CONECT   12    5   10                                                       
CONECT   13    5   11                                                       
CONECT   14    4    6   15                                                  
CONECT   15    8   14   16                                                  
CONECT   16   15   17   19                                                  
CONECT   17    7   16   18                                                  
CONECT   18   17   21   22                                                  
CONECT   19   16                                                            
CONECT   20    7   23   24                                                  
CONECT   21   18   25                                                       
CONECT   22   18   26                                                       
CONECT   23    1   20   27                                                  
CONECT   24   20   28                                                       
CONECT   25   21   29                                                       
CONECT   26   22   29                                                       
CONECT   27   23   30                                                       
CONECT   28   24   30                                                       
CONECT   29    2   25   26                                                  
CONECT   30    3   27   28                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0015623
HETATM    1  C1  UNL     1      -0.326  -2.706  -0.171  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.616  -1.250  -0.161  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.341  -0.232  -0.217  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.782  -0.428  -0.194  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.258  -1.559  -0.098  1.00  0.00           O  
HETATM    6  N1  UNL     1       2.610   0.715  -0.282  1.00  0.00           N  
HETATM    7  N2  UNL     1       3.980   0.690  -0.266  1.00  0.00           N  
HETATM    8  C5  UNL     1       4.609   1.080   0.946  1.00  0.00           C  
HETATM    9  C6  UNL     1       5.842   0.221   1.198  1.00  0.00           C  
HETATM   10  C7  UNL     1       6.734   0.238  -0.004  1.00  0.00           C  
HETATM   11  C8  UNL     1       5.996  -0.184  -1.242  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.525  -0.479  -0.871  1.00  0.00           C  
HETATM   13  N3  UNL     1      -0.332   0.924  -0.264  1.00  0.00           N  
HETATM   14  N4  UNL     1      -1.656   0.692  -0.239  1.00  0.00           N  
HETATM   15  C10 UNL     1      -2.610   1.745  -0.255  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.289   1.995   0.916  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.208   3.020   0.961  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.479   3.816  -0.127  1.00  0.00           C  
HETATM   19 CL1  UNL     1      -5.664   5.126  -0.050  1.00  0.00          CL  
HETATM   20  C14 UNL     1      -3.783   3.541  -1.282  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.867   2.530  -1.352  1.00  0.00           C  
HETATM   22 CL2  UNL     1      -1.986   2.191  -2.843  1.00  0.00          CL  
HETATM   23  C16 UNL     1      -1.860  -0.624  -0.174  1.00  0.00           C  
HETATM   24  C17 UNL     1      -3.141  -1.295  -0.006  1.00  0.00           C  
HETATM   25  C18 UNL     1      -3.259  -2.543   0.584  1.00  0.00           C  
HETATM   26  C19 UNL     1      -4.486  -3.217   0.672  1.00  0.00           C  
HETATM   27  C20 UNL     1      -5.641  -2.674   0.179  1.00  0.00           C  
HETATM   28 CL3  UNL     1      -7.187  -3.514   0.291  1.00  0.00          CL  
HETATM   29  C21 UNL     1      -5.542  -1.440  -0.407  1.00  0.00           C  
HETATM   30  C22 UNL     1      -4.314  -0.766  -0.497  1.00  0.00           C  
HETATM   31  H1  UNL     1       0.592  -2.860  -0.842  1.00  0.00           H  
HETATM   32  H2  UNL     1      -0.110  -3.164   0.779  1.00  0.00           H  
HETATM   33  H3  UNL     1      -1.094  -3.294  -0.758  1.00  0.00           H  
HETATM   34  H4  UNL     1       2.154   1.684  -0.367  1.00  0.00           H  
HETATM   35  H5  UNL     1       3.904   0.972   1.779  1.00  0.00           H  
HETATM   36  H6  UNL     1       4.988   2.138   0.927  1.00  0.00           H  
HETATM   37  H7  UNL     1       5.553  -0.792   1.530  1.00  0.00           H  
HETATM   38  H8  UNL     1       6.402   0.737   2.021  1.00  0.00           H  
HETATM   39  H9  UNL     1       7.156   1.259  -0.107  1.00  0.00           H  
HETATM   40  H10 UNL     1       7.618  -0.427   0.172  1.00  0.00           H  
HETATM   41  H11 UNL     1       5.944   0.649  -1.985  1.00  0.00           H  
HETATM   42  H12 UNL     1       6.395  -1.121  -1.669  1.00  0.00           H  
HETATM   43  H13 UNL     1       4.513  -1.374  -0.193  1.00  0.00           H  
HETATM   44  H14 UNL     1       4.016  -0.743  -1.800  1.00  0.00           H  
HETATM   45  H15 UNL     1      -3.107   1.382   1.821  1.00  0.00           H  
HETATM   46  H16 UNL     1      -4.734   3.199   1.893  1.00  0.00           H  
HETATM   47  H17 UNL     1      -3.974   4.156  -2.176  1.00  0.00           H  
HETATM   48  H18 UNL     1      -2.401  -3.026   1.036  1.00  0.00           H  
HETATM   49  H19 UNL     1      -4.536  -4.189   1.138  1.00  0.00           H  
HETATM   50  H20 UNL     1      -6.428  -0.974  -0.810  1.00  0.00           H  
HETATM   51  H21 UNL     1      -4.286   0.178  -0.981  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   23   23
CONECT    3    4   13   13
CONECT    4    5    5    6
CONECT    6    7   34
CONECT    7    8   12
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11   39   40
CONECT   11   12   41   42
CONECT   12   43   44
CONECT   13   14
CONECT   14   15   23
CONECT   15   16   16   21
CONECT   16   17   45
CONECT   17   18   18   46
CONECT   18   19   20
CONECT   20   21   21   47
CONECT   21   22
CONECT   23   24
CONECT   24   25   25   30
CONECT   25   26   48
CONECT   26   27   27   49
CONECT   27   28   29
CONECT   29   30   30   50
CONECT   30   51
END

HMDB0015623
     RDKit          3D
Rimonabant
 51 54  0  0  0  0  0  0  0  0999 V2000
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   -0.6161   -1.2503   -0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -0.2319   -0.2165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7816   -0.4284   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585   -1.5585   -0.0977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6097    0.7147   -0.2819 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    0.6899   -0.2660 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6086    1.0800    0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8425    0.2205    1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7339    0.2383   -0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9957   -0.1844   -1.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5254   -0.4792   -0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3317    0.9236   -0.2645 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6559    0.6917   -0.2386 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096    1.7451   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889    1.9948    0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2075    3.0197    0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786    3.8158   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6640    5.1261   -0.0502 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7832    3.5409   -1.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8668    2.5296   -1.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9863    2.1906   -2.8432 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8595   -0.6238   -0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1407   -1.2948   -0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2586   -2.5429    0.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861   -3.2171    0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6405   -2.6739    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1867   -3.5140    0.2908 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415   -1.4401   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3139   -0.7663   -0.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916   -2.8597   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1102   -3.1638    0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0943   -3.2944   -0.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540    1.6838   -0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    0.9723    1.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9884    2.1375    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5526   -0.7925    1.5296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4016    0.7375    2.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563    1.2593   -0.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6181   -0.4269    0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9437    0.6488   -1.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3952   -1.1211   -1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5134   -1.3744   -0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0163   -0.7429   -1.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1066    1.3824    1.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7344    3.1985    1.8934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9740    4.1564   -2.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4008   -3.0257    1.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5358   -4.1887    1.1376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4283   -0.9742   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2860    0.1780   -0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  3 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 14 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 23  2  2  0
 30 24  1  0
 12  7  1  0
 21 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 16 45  1  0
 17 46  1  0
 20 47  1  0
 25 48  1  0
 26 49  1  0
 29 50  1  0
 30 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide	ChEBI
a 281	ChEBI
Acomplia	ChEBI
N-(1-Piperidinyl)-1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxamide	ChEBI
Rimonabantum	ChEBI
SR 141716	ChEBI
SR141716	ChEBI
Zimulti	ChEBI
SR 141716a	HMDB
SR141716a	HMDB
N-(Piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochloride	HMDB
Rimonabant hydrochloride	HMDB
Rimonabant	KEGG

Chemical Formula

C₂₂H₂₁Cl₃N₄O

Average Molecular Weight

463.787

Monoisotopic Molecular Weight

462.078094435

IUPAC Name

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide

Traditional Name

rimonabant

CAS Registry Number

158681-13-1

SMILES

CC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)

InChI Key

JZCPYUJPEARBJL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Phenylpyrazoles

Alternative Parents

Substituents

Phenylpyrazole
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Piperidine
Heteroaromatic compound
Azacycle
Hydrazone
Organohalogen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazoles (CHEBI:34967 )
ring assembly (CHEBI:34967 )

Ontology

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	0.002 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5.47	ALOGPS
logP	5.91	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	12.42	ChemAxon
pKa (Strongest Basic)	1.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.83 m³·mol⁻¹	ChemAxon
Polarizability	47.96 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	202.556	30932474
DeepCCS	[M-H]-	200.198	30932474
DeepCCS	[M-2H]-	234.151	30932474
DeepCCS	[M+Na]+	209.235	30932474
AllCCS	[M+H]+	202.8	32859911
AllCCS	[M+H-H2O]+	200.6	32859911
AllCCS	[M+NH4]+	204.9	32859911
AllCCS	[M+Na]+	205.5	32859911
AllCCS	[M-H]-	196.3	32859911
AllCCS	[M+Na-2H]-	196.1	32859911
AllCCS	[M+HCOO]-	196.0	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.	7.34 minutes	32390414
Predicted by Siyang on May 30, 2022	23.461 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2983.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	719.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	295.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	412.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	558.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	977.4 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	998.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2155.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	814.9 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	2121.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	724.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	516.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	322.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	440.0 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	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rimonabant	CC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C1	4570.3	Standard polar	33892256
Rimonabant	CC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C1	3505.1	Standard non polar	33892256
Rimonabant	CC1=C(N(N=C1C(=O)NN1CCCCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(Cl)C=C1	3605.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rimonabant,1TMS,isomer #1	CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C	3519.2	Semi standard non polar	33892256
Rimonabant,1TMS,isomer #1	CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C	3097.6	Standard non polar	33892256
Rimonabant,1TMS,isomer #1	CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C	4812.9	Standard polar	33892256
Rimonabant,1TBDMS,isomer #1	CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C(C)(C)C	3674.3	Semi standard non polar	33892256
Rimonabant,1TBDMS,isomer #1	CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C(C)(C)C	3266.6	Standard non polar	33892256
Rimonabant,1TBDMS,isomer #1	CC1=C(C2=CC=C(Cl)C=C2)N(C2=CC=C(Cl)C=C2Cl)N=C1C(=O)N(N1CCCCC1)[Si](C)(C)C(C)(C)C	4765.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rimonabant GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9404100000-b4e952d6cb28f37a5bcf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rimonabant GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rimonabant 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 - Rimonabant , positive-QTOF	splash10-03xr-0007900000-a3e664246f26a3081b28	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 10V, Positive-QTOF	splash10-03dj-6000900000-c7a63eca60b5ae34236e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 20V, Positive-QTOF	splash10-01qa-9001500000-6c82c44c31b95dd57e6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 40V, Positive-QTOF	splash10-0002-9000000000-c4706c1b75e67ecce758	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 10V, Negative-QTOF	splash10-03di-0003900000-bd4dcdb5302a69cef5c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 20V, Negative-QTOF	splash10-03di-4109700000-88f8f41955e94367f7ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 40V, Negative-QTOF	splash10-0a4i-1129000000-96c60b95d7ed3d764d64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 10V, Positive-QTOF	splash10-03di-0000900000-b3e191c61bc8a15ef9d5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 20V, Positive-QTOF	splash10-03di-0009800000-e0b76fde9003187eb29a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 40V, Positive-QTOF	splash10-03di-1019200000-431bb0dcf166a142d11e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 10V, Negative-QTOF	splash10-03di-0003900000-89545a97026620833ccc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 20V, Negative-QTOF	splash10-03e9-1009800000-7405fd5c69583a970fc0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rimonabant 40V, Negative-QTOF	splash10-001i-8029100000-d24cda966a3633c58081	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 DB06155	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06155	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06155

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00053749

Chemspider ID

94641

KEGG Compound ID

C14319

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rimonabant

METLIN ID

Not Available

PubChem Compound

104850

PDB ID

Not Available

ChEBI ID

34967

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

Huestis MA, Gorelick DA, Heishman SJ, Preston KL, Nelson RA, Moolchan ET, Frank RA: Blockade of effects of smoked marijuana by the CB1-selective cannabinoid receptor antagonist SR141716. Arch Gen Psychiatry. 2001 Apr;58(4):322-8. [PubMed:11296091 ]
Maldonado R, Valverde O, Berrendero F: Involvement of the endocannabinoid system in drug addiction. Trends Neurosci. 2006 Apr;29(4):225-32. Epub 2006 Feb 17. [PubMed:16483675 ]
Gelfand EV, Cannon CP: Rimonabant: a selective blocker of the cannabinoid CB1 receptors for the management of obesity, smoking cessation and cardiometabolic risk factors. Expert Opin Investig Drugs. 2006 Mar;15(3):307-15. [PubMed:16503766 ]
Xie S, Furjanic MA, Ferrara JJ, McAndrew NR, Ardino EL, Ngondara A, Bernstein Y, Thomas KJ, Kim E, Walker JM, Nagar S, Ward SJ, Raffa RB: The endocannabinoid system and rimonabant: a new drug with a novel mechanism of action involving cannabinoid CB1 receptor antagonism--or inverse agonism--as potential obesity treatment and other therapeutic use. J Clin Pharm Ther. 2007 Jun;32(3):209-31. [PubMed:17489873 ]
Deadwyler SA, Goonawardena AV, Hampson RE: Short-term memory is modulated by the spontaneous release of endocannabinoids: evidence from hippocampal population codes. Behav Pharmacol. 2007 Sep;18(5-6):571-80. [PubMed:17762525 ]
Cahill K, Ussher M: Cannabinoid type 1 receptor antagonists (rimonabant) for smoking cessation. Cochrane Database Syst Rev. 2007 Oct 17;(4):CD005353. [PubMed:17943852 ]

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

Leite CE, Mocelin CA, Petersen GO, Leal MB, Thiesen FV: Rimonabant: an antagonist drug of the endocannabinoid system for the treatment of obesity. Pharmacol Rep. 2009 Mar-Apr;61(2):217-24. [PubMed:19443932 ]
Lazary J, Juhasz G, Hunyady L, Bagdy G: Personalized medicine can pave the way for the safe use of CB(1) receptor antagonists. Trends Pharmacol Sci. 2011 May;32(5):270-80. doi: 10.1016/j.tips.2011.02.013. Epub 2011 Apr 16. [PubMed:21497918 ]

Enzyme Details

2. Cannabinoid receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding
Gene Name:: CNR1
Uniprot ID:: P21554
Molecular weight:: 52857.4

References

Shire D, Calandra B, Delpech M, Dumont X, Kaghad M, Le Fur G, Caput D, Ferrara P: Structural features of the central cannabinoid CB1 receptor involved in the binding of the specific CB1 antagonist SR 141716A. J Biol Chem. 1996 Mar 22;271(12):6941-6. [PubMed:8636122 ]
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 Rimonabant (HMDB0015623)

MOL for HMDB0015623 (Rimonabant)

3D MOL for HMDB0015623 (Rimonabant)

3D SDF for HMDB0015623 (Rimonabant)

3D-SDF for HMDB0015623 (Rimonabant)

PDB for HMDB0015623 (Rimonabant)

3D PDB for HMDB0015623 (Rimonabant)

SMILES for HMDB0015623 (Rimonabant)

INCHI for HMDB0015623 (Rimonabant)

Structure for HMDB0015623 (Rimonabant)

3D Structure for HMDB0015623 (Rimonabant)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References