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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:31:18 UTC

Update Date

2021-09-26 22:57:15 UTC

HMDB ID

HMDB0247516

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Didesmethylsibutramine

Description

Didesmethylsibutramine, also known as (R)-DDMS or meridia, belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. Based on a literature review very few articles have been published on Didesmethylsibutramine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Didesmethylsibutramine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Didesmethylsibutramine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247516
     RDKit          3D
Didesmethylsibutramine
 39 40  0  0  0  0  0  0  0  0999 V2000
   -3.6614    1.3151   -1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    0.4744   -0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0167    1.1731    1.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4235    0.3750   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.5122    0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3763   -1.8419    0.4330 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.8133    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7176    0.2300    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    0.7623   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1821    1.7178   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712    2.1323   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0718    3.3046   -0.0256 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3470    1.6096    1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316    0.6756    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7835   -1.8002   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -2.7210   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1929   -1.9920    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    0.6039   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0048    2.0396   -1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    1.7858   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3777   -0.4829   -0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    2.2607    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1214    1.1137    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    0.6229    2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588    1.3951   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844    0.0633   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.0819    1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8077   -2.0028    1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0097   -1.9252   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022    0.4565   -2.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4824    2.1194   -2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360    1.9349    2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    0.3000    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -1.4620   -1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -2.1419   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -3.7837   -0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7263   -2.6398   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681   -1.7295    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669   -2.5352    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17  7  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv1652306031609512D          

 17 18  0  0  0  0            999 V2000
   -2.5908    3.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8092    3.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2976    0.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    2.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2602    3.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892    3.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8292    3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7143    1.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810    1.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534    2.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9845    3.1909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8666    2.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045    3.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7287    2.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2976    1.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    4.6193    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784    3.3202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  9  3  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11 10  1  0  0  0  0
 12  4  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247516

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(N)C1(CCC1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22ClN/c1-11(2)10-14(17)15(8-3-9-15)12-4-6-13(16)7-5-12/h4-7,11,14H,3,8-10,17H2,1-2H3

> <INCHI_KEY>
WQSACWZKKZPCHN-UHFFFAOYSA-N

> <FORMULA>
C15H22ClN

> <MOLECULAR_WEIGHT>
251.8

> <EXACT_MASS>
251.1440774

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.0378292261448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutan-1-amine

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
4.386221752999999

> <ALOGPS_LOGS>
-5.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.740596468425538

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
73.8521

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutan-1-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0247516
     RDKit          3D
Didesmethylsibutramine
 39 40  0  0  0  0  0  0  0  0999 V2000
   -3.6614    1.3151   -1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    0.4744   -0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0167    1.1731    1.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4235    0.3750   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.5122    0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3763   -1.8419    0.4330 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.8133    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7176    0.2300    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    0.7623   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1821    1.7178   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712    2.1323   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0718    3.3046   -0.0256 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3470    1.6096    1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316    0.6756    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7835   -1.8002   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -2.7210   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1929   -1.9920    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    0.6039   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0048    2.0396   -1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    1.7858   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3777   -0.4829   -0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    2.2607    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1214    1.1137    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    0.6229    2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588    1.3951   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844    0.0633   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.0819    1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8077   -2.0028    1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0097   -1.9252   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022    0.4565   -2.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4824    2.1194   -2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360    1.9349    2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    0.3000    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -1.4620   -1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -2.1419   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -3.7837   -0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7263   -2.6398   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681   -1.7295    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669   -2.5352    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17  7  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -4.836   7.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.110   5.916   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.422   1.193   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.078   4.643   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.352   6.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.727   5.956   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.548   7.350   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.333   2.281   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.511   2.281   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.766   4.643   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.571   5.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.618   4.684   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.008   7.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.227   4.684   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.422   3.370   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       0.796   8.623   0.000  0.00  0.00          Cl+0
HETATM   17  N   UNK     0      -2.946   6.198   0.000  0.00  0.00           N+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3    8    9                                                       
CONECT    4    6   12                                                       
CONECT    5    7   12                                                       
CONECT    6    4   13                                                       
CONECT    7    5   13                                                       
CONECT    8    3   15                                                       
CONECT    9    3   15                                                       
CONECT   10   11   14                                                       
CONECT   11    1    2   10                                                  
CONECT   12    4    5   15                                                  
CONECT   13    6    7   16                                                  
CONECT   14   10   15   17                                                  
CONECT   15    8    9   12   14                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0247516
HETATM    1  C1  UNL     1      -3.661   1.315  -1.123  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.863   0.474  -0.114  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.017   1.173   1.236  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.423   0.375  -0.535  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.717  -0.512   0.448  1.00  0.00           C  
HETATM    6  N1  UNL     1      -1.376  -1.842   0.433  1.00  0.00           N  
HETATM    7  C6  UNL     1       0.709  -0.813   0.089  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.718   0.230   0.021  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.157   0.762  -1.146  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.182   1.718  -1.206  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.771   2.132  -0.031  1.00  0.00           C  
HETATM   12 CL1  UNL     1       5.072   3.305  -0.026  1.00  0.00          CL  
HETATM   13  C11 UNL     1       3.347   1.610   1.174  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.332   0.676   1.183  1.00  0.00           C  
HETATM   15  C13 UNL     1       0.783  -1.800  -1.085  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.623  -2.721  -0.275  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.193  -1.992   0.961  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.149   0.604  -1.855  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.005   2.040  -1.647  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.473   1.786  -0.586  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.378  -0.483  -0.016  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.771   2.261   1.169  1.00  0.00           H  
HETATM   23  H6  UNL     1      -4.121   1.114   1.470  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.500   0.623   2.012  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.959   1.395  -0.447  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.284   0.063  -1.568  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.742  -0.082   1.463  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.808  -2.003   1.372  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.010  -1.925  -0.357  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.702   0.457  -2.083  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.482   2.119  -2.179  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.836   1.935   2.092  1.00  0.00           H  
HETATM   33  H16 UNL     1       2.027   0.300   2.139  1.00  0.00           H  
HETATM   34  H17 UNL     1       1.300  -1.462  -1.965  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.256  -2.142  -1.320  1.00  0.00           H  
HETATM   36  H19 UNL     1       1.218  -3.784  -0.378  1.00  0.00           H  
HETATM   37  H20 UNL     1       2.726  -2.640  -0.480  1.00  0.00           H  
HETATM   38  H21 UNL     1       1.968  -1.729   1.687  1.00  0.00           H  
HETATM   39  H22 UNL     1       0.367  -2.535   1.473  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4   21
CONECT    3   22   23   24
CONECT    4    5   25   26
CONECT    5    6    7   27
CONECT    6   28   29
CONECT    7    8   15   17
CONECT    8    9    9   14
CONECT    9   10   30
CONECT   10   11   11   31
CONECT   11   12   13
CONECT   13   14   14   32
CONECT   14   33
CONECT   15   16   34   35
CONECT   16   17   36   37
CONECT   17   38   39
END

HMDB0247516
     RDKit          3D
Didesmethylsibutramine
 39 40  0  0  0  0  0  0  0  0999 V2000
   -3.6614    1.3151   -1.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8634    0.4744   -0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0167    1.1731    1.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4235    0.3750   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170   -0.5122    0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3763   -1.8419    0.4330 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090   -0.8133    0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7176    0.2300    0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    0.7623   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1821    1.7178   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7712    2.1323   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0718    3.3046   -0.0256 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3470    1.6096    1.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3316    0.6756    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7835   -1.8002   -1.0851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6231   -2.7210   -0.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1929   -1.9920    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    0.6039   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0048    2.0396   -1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4728    1.7858   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3777   -0.4829   -0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7711    2.2607    1.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1214    1.1137    1.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    0.6229    2.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588    1.3951   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844    0.0633   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.0819    1.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8077   -2.0028    1.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0097   -1.9252   -0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022    0.4565   -2.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4824    2.1194   -2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8360    1.9349    2.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    0.3000    2.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -1.4620   -1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2559   -2.1419   -1.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -3.7837   -0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7263   -2.6398   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9681   -1.7295    1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3669   -2.5352    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17  7  1  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-DDMS	HMDB
Meridia	HMDB
N-1-(1-(4-Chlorophenyl)cyclobutyl)-3-methylbutyl-N,N-dimethylamine HCL	HMDB
Reductil	HMDB
Di-desmethylsibutramine	HMDB
mono-Desmethylsibutramine	HMDB
Sibutramine	HMDB
Sibutramine hydrochloride	HMDB
Didesmethylsibutramine	MeSH

Chemical Formula

C₁₅H₂₂ClN

Average Molecular Weight

251.8

Monoisotopic Molecular Weight

251.1440774

IUPAC Name

1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutan-1-amine

Traditional Name

1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutan-1-amine

CAS Registry Number

Not Available

SMILES

CC(C)CC(N)C1(CCC1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C15H22ClN/c1-11(2)10-14(17)15(8-3-9-15)12-4-6-13(16)7-5-12/h4-7,11,14H,3,8-10,17H2,1-2H3

InChI Key

WQSACWZKKZPCHN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Aralkylamine
Chlorobenzene
Aryl halide
Aryl chloride
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.84	ALOGPS
logP	4.39	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	9.74	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.85 m³·mol⁻¹	ChemAxon
Polarizability	29.04 Å³	ChemAxon
Number of Rings	2	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
DeepCCS	[M+H]+	169.202	30932474
DeepCCS	[M-H]-	166.844	30932474
DeepCCS	[M-2H]-	199.73	30932474
DeepCCS	[M+Na]+	175.295	30932474
AllCCS	[M+H]+	159.5	32859911
AllCCS	[M+H-H2O]+	155.9	32859911
AllCCS	[M+NH4]+	162.9	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	165.1	32859911
AllCCS	[M+Na-2H]-	165.6	32859911
AllCCS	[M+HCOO]-	166.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Didesmethylsibutramine	CC(C)CC(N)C1(CCC1)C1=CC=C(Cl)C=C1	2423.9	Standard polar	33892256
Didesmethylsibutramine	CC(C)CC(N)C1(CCC1)C1=CC=C(Cl)C=C1	1808.9	Standard non polar	33892256
Didesmethylsibutramine	CC(C)CC(N)C1(CCC1)C1=CC=C(Cl)C=C1	1847.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Didesmethylsibutramine,1TMS,isomer #1	CC(C)CC(N[Si](C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	1901.8	Semi standard non polar	33892256
Didesmethylsibutramine,1TMS,isomer #1	CC(C)CC(N[Si](C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2043.2	Standard non polar	33892256
Didesmethylsibutramine,1TMS,isomer #1	CC(C)CC(N[Si](C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2247.6	Standard polar	33892256
Didesmethylsibutramine,2TMS,isomer #1	CC(C)CC(N([Si](C)(C)C)[Si](C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2072.7	Semi standard non polar	33892256
Didesmethylsibutramine,2TMS,isomer #1	CC(C)CC(N([Si](C)(C)C)[Si](C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2231.6	Standard non polar	33892256
Didesmethylsibutramine,2TMS,isomer #1	CC(C)CC(N([Si](C)(C)C)[Si](C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2260.7	Standard polar	33892256
Didesmethylsibutramine,1TBDMS,isomer #1	CC(C)CC(N[Si](C)(C)C(C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2145.1	Semi standard non polar	33892256
Didesmethylsibutramine,1TBDMS,isomer #1	CC(C)CC(N[Si](C)(C)C(C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2325.1	Standard non polar	33892256
Didesmethylsibutramine,1TBDMS,isomer #1	CC(C)CC(N[Si](C)(C)C(C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2380.2	Standard polar	33892256
Didesmethylsibutramine,2TBDMS,isomer #1	CC(C)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2520.2	Semi standard non polar	33892256
Didesmethylsibutramine,2TBDMS,isomer #1	CC(C)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2722.3	Standard non polar	33892256
Didesmethylsibutramine,2TBDMS,isomer #1	CC(C)CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1(C2=CC=C(Cl)C=C2)CCC1	2449.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Didesmethylsibutramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014u-9630000000-f1d1ff839140afb06648	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Didesmethylsibutramine 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 - Didesmethylsibutramine 10V, Positive-QTOF	splash10-0udr-0090000000-550a84af367501cbcb77	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 20V, Positive-QTOF	splash10-0zic-4790000000-a2bbbbbbe6d43f4df4c0	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 40V, Positive-QTOF	splash10-0a4i-9600000000-f1a8d7b6c63280c49adb	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 10V, Negative-QTOF	splash10-0udi-0090000000-a07891c7c89f85b74c99	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 20V, Negative-QTOF	splash10-0udi-1190000000-909628cb44db2cd642ad	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 40V, Negative-QTOF	splash10-07wc-4920000000-bb3ea361190c0c11c518	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 10V, Positive-QTOF	splash10-0udi-2590000000-597997f1347b1f0e43aa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 20V, Positive-QTOF	splash10-1029-4980000000-95f5b43eefaba6dc2d18	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 40V, Positive-QTOF	splash10-014i-2910000000-81c0857fdaddf22747bd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 10V, Negative-QTOF	splash10-0udi-0190000000-7850ad9d0ed4135d5e2e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 20V, Negative-QTOF	splash10-0udi-0490000000-454e82db2794bd4ffa22	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesmethylsibutramine 40V, Negative-QTOF	splash10-01q9-9700000000-9e258f80c70bb7518767	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

118777

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134772

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Didesmethylsibutramine (HMDB0247516)

MOL for HMDB0247516 (Didesmethylsibutramine)

3D MOL for HMDB0247516 (Didesmethylsibutramine)

3D SDF for HMDB0247516 (Didesmethylsibutramine)

3D-SDF for HMDB0247516 (Didesmethylsibutramine)

PDB for HMDB0247516 (Didesmethylsibutramine)

3D PDB for HMDB0247516 (Didesmethylsibutramine)

SMILES for HMDB0247516 (Didesmethylsibutramine)

INCHI for HMDB0247516 (Didesmethylsibutramine)

Structure for HMDB0247516 (Didesmethylsibutramine)

3D Structure for HMDB0247516 (Didesmethylsibutramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra