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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015554

Secondary Accession Numbers

HMDB15554

Metabolite Identification

Common Name

Alverine

Description

Alverine is a smooth muscle relaxant. Smooth muscle is a type of muscle that is not under voluntary control; it is the muscle present in places such as the gut and uterus. Alverine acts directly on the muscle in the gut, causing it to relax. This prevents the muscle spasms which occur in the gut in conditions such as irritable bowel syndrome and diverticular disease. It is used to relieve cramps or spasms of the stomach and intestines. It is also useful in treating irritable bowel syndrome (IBS) and similar conditions. It can also be used to help relieve period pain. Alverine is formulated as the citrate salt (5982-87-6).

Structure

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

HMDB0015554
     RDKit          3D
Alverine
 48 49  0  0  0  0  0  0  0  0999 V2000
   -0.0860   -3.0706   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3282   -1.7848    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -0.7557   -0.5887 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7014   -1.0061   -1.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0758    0.1620   -2.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3411    1.3526   -1.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4636    0.9885   -0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726    1.1847   -0.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8464    0.8696    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6448    0.3511    1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3350    0.1674    1.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478    0.4709    0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278   -0.4495   -1.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8080    0.2265   -0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5708   -0.4347    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144    0.3712    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8279    1.3493    1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9785    2.0786    1.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1423    1.8297    1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    0.8471    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9810    0.1168   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1446   -3.0697   -0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -3.8967    0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -3.3727   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486   -1.4977    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -2.0034    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367   -1.9263   -1.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -1.2682   -0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0552   -0.0655   -2.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774    0.4728   -2.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6148    2.1949   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177    1.5550   -0.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9290    1.5940   -1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8778    1.0223   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4725    0.0981    1.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1861   -0.2401    2.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337    0.3197    1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897    0.0777   -2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088   -1.4442   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5560    0.2963   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    1.3205   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365   -1.4610    0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -0.3014    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9071    1.5485    2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9583    2.8407    2.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0515    2.3815    1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0119    0.6078   -0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9707   -0.6476   -0.8343 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12  7  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
M  END

1616
  Mrv0541 02231215362D          

 21 22  0  0  0  0            999 V2000
    3.7935    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  6  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 10 12  2  0  0  0  0
 10 14  1  0  0  0  0
 11 13  2  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 20  2  0  0  0  0
 17 21  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015554

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H27N/c1-2-21(17-9-15-19-11-5-3-6-12-19)18-10-16-20-13-7-4-8-14-20/h3-8,11-14H,2,9-10,15-18H2,1H3

> <INCHI_KEY>
ZPFXAOWNKLFJDN-UHFFFAOYSA-N

> <FORMULA>
C20H27N

> <MOLECULAR_WEIGHT>
281.4351

> <EXACT_MASS>
281.214349869

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
35.41602767875713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethylbis(3-phenylpropyl)amine

> <ALOGPS_LOGP>
5.73

> <JCHEM_LOGP>
5.462383394999999

> <ALOGPS_LOGS>
-5.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.441444870189164

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
92.67390000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.60e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alverine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015554
     RDKit          3D
Alverine
 48 49  0  0  0  0  0  0  0  0999 V2000
   -0.0860   -3.0706   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3282   -1.7848    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -0.7557   -0.5887 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7014   -1.0061   -1.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0758    0.1620   -2.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3411    1.3526   -1.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4636    0.9885   -0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726    1.1847   -0.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8464    0.8696    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6448    0.3511    1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3350    0.1674    1.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478    0.4709    0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278   -0.4495   -1.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8080    0.2265   -0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5708   -0.4347    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144    0.3712    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8279    1.3493    1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9785    2.0786    1.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1423    1.8297    1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    0.8471    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9810    0.1168   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1446   -3.0697   -0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -3.8967    0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -3.3727   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486   -1.4977    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -2.0034    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367   -1.9263   -1.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -1.2682   -0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0552   -0.0655   -2.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774    0.4728   -2.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6148    2.1949   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177    1.5550   -0.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9290    1.5940   -1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8778    1.0223   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4725    0.0981    1.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1861   -0.2401    2.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337    0.3197    1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897    0.0777   -2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088   -1.4442   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5560    0.2963   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    1.3205   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365   -1.4610    0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -0.3014    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9071    1.5485    2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9583    2.8407    2.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0515    2.3815    1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0119    0.6078   -0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9707   -0.6476   -0.8343 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12  7  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1616                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       7.081   0.385   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.748  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   5.005   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -4.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748   6.545   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -5.005   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082   4.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -5.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   7.315   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -6.545   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.416   5.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -6.545   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.416   6.545   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414  -7.315   0.000  0.00  0.00           C+0
CONECT    1    2    3    6                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    1    9                                                       
CONECT    7    4   10                                                       
CONECT    8    5   11                                                       
CONECT    9    6                                                            
CONECT   10    7   12   14                                                  
CONECT   11    8   13   15                                                  
CONECT   12   10   16                                                       
CONECT   13   11   17                                                       
CONECT   14   10   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   20                                                       
CONECT   17   13   21                                                       
CONECT   18   14   20                                                       
CONECT   19   15   21                                                       
CONECT   20   16   18                                                       
CONECT   21   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0015554
HETATM    1  C1  UNL     1      -0.086  -3.071  -0.248  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.328  -1.785   0.402  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.512  -0.756  -0.589  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.701  -1.006  -1.369  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.076   0.162  -2.210  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.341   1.353  -1.283  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.464   0.989  -0.357  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.773   1.185  -0.779  1.00  0.00           C  
HETATM    9  C8  UNL     1       5.846   0.870   0.037  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.645   0.351   1.297  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.335   0.167   1.690  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.248   0.471   0.901  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.628  -0.449  -1.355  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.808   0.227  -0.831  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.571  -0.435   0.272  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.814   0.371   0.602  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.828   1.349   1.555  1.00  0.00           C  
HETATM   18  C17 UNL     1      -4.979   2.079   1.835  1.00  0.00           C  
HETATM   19  C18 UNL     1      -6.142   1.830   1.151  1.00  0.00           C  
HETATM   20  C19 UNL     1      -6.140   0.847   0.190  1.00  0.00           C  
HETATM   21  C20 UNL     1      -4.981   0.117  -0.087  1.00  0.00           C  
HETATM   22  H1  UNL     1      -1.145  -3.070  -0.590  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.064  -3.897   0.535  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.647  -3.373  -1.003  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.149  -1.498   1.307  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.420  -2.003   0.739  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.537  -1.926  -1.999  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.497  -1.268  -0.675  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.055  -0.065  -2.750  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.377   0.473  -2.980  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.615   2.195  -1.919  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.418   1.555  -0.710  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.929   1.594  -1.775  1.00  0.00           H  
HETATM   34  H13 UNL     1       6.878   1.022  -0.292  1.00  0.00           H  
HETATM   35  H14 UNL     1       6.472   0.098   1.955  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.186  -0.240   2.679  1.00  0.00           H  
HETATM   37  H16 UNL     1       2.234   0.320   1.240  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.290   0.078  -2.299  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.009  -1.444  -1.806  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.556   0.296  -1.694  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.640   1.320  -0.605  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.837  -1.461   0.046  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.970  -0.301   1.219  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.907   1.549   2.100  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.958   2.841   2.592  1.00  0.00           H  
HETATM   46  H25 UNL     1      -7.051   2.382   1.352  1.00  0.00           H  
HETATM   47  H26 UNL     1      -7.012   0.608  -0.372  1.00  0.00           H  
HETATM   48  H27 UNL     1      -4.971  -0.648  -0.834  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   13
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8    8   12
CONECT    8    9   33
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   12   36
CONECT   12   37
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17   17   21
CONECT   17   18   44
CONECT   18   19   19   45
CONECT   19   20   46
CONECT   20   21   21   47
CONECT   21   48
END

HMDB0015554
     RDKit          3D
Alverine
 48 49  0  0  0  0  0  0  0  0999 V2000
   -0.0860   -3.0706   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3282   -1.7848    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5124   -0.7557   -0.5887 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7014   -1.0061   -1.3694 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0758    0.1620   -2.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3411    1.3526   -1.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4636    0.9885   -0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7726    1.1847   -0.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8464    0.8696    0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6448    0.3511    1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3350    0.1674    1.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478    0.4709    0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278   -0.4495   -1.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8080    0.2265   -0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5708   -0.4347    0.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8144    0.3712    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8279    1.3493    1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9785    2.0786    1.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1423    1.8297    1.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1402    0.8471    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9810    0.1168   -0.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1446   -3.0697   -0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0643   -3.8967    0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -3.3727   -1.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1486   -1.4977    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -2.0034    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367   -1.9263   -1.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -1.2682   -0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0552   -0.0655   -2.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3774    0.4728   -2.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6148    2.1949   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177    1.5550   -0.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9290    1.5940   -1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8778    1.0223   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4725    0.0981    1.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1861   -0.2401    2.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337    0.3197    1.2404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2897    0.0777   -2.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088   -1.4442   -1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5560    0.2963   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    1.3205   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8365   -1.4610    0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696   -0.3014    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9071    1.5485    2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9583    2.8407    2.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0515    2.3815    1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0119    0.6078   -0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9707   -0.6476   -0.8343 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12  7  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Alverina	ChEBI
Alverinum	ChEBI
Bis(gamma-phenylpropyl)ethylamine	ChEBI
Di(phenylpropyl)ethylamine	ChEBI
N,N-Bis(3-phenylpropyl)ethylamine	ChEBI
N-Ethyl-3,3'-diphenyldipropylamine	ChEBI
N-Ethyl-3-phenyl-N-(3-phenylpropyl)-1-propanamine	ChEBI
N-Ethyl-N-(3-phenylpropyl)benzenepropanamine	ChEBI
Phenopropamine	ChEBI
Phenpropamine	ChEBI
Bis(g-phenylpropyl)ethylamine	Generator
Bis(γ-phenylpropyl)ethylamine	Generator
N-Ethyl-bis(3-phenylpropyl)amin	HMDB
Spasmonal	HMDB
Alverine citrate	HMDB
Spasmaverine	HMDB
United drug brand OF alverine citrate	HMDB
Alverine hydrochloride	HMDB
Norgine brand OF alverine citrate	HMDB

Chemical Formula

C₂₀H₂₇N

Average Molecular Weight

281.4351

Monoisotopic Molecular Weight

281.214349869

IUPAC Name

ethylbis(3-phenylpropyl)amine

Traditional Name

alverine

CAS Registry Number

150-59-4

SMILES

CCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C20H27N/c1-2-21(17-9-15-19-11-5-3-6-12-19)18-10-16-20-13-7-4-8-14-20/h3-8,11-14H,2,9-10,15-18H2,1H3

InChI Key

ZPFXAOWNKLFJDN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropylamines. Phenylpropylamines are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropylamines

Direct Parent

Phenylpropylamines

Alternative Parents

Substituents

Phenylpropylamine
Aralkylamine
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amine (CHEBI:518413 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015554)

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	0.00096 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	168.392	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000739

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00096 g/L	ALOGPS
logP	5.73	ALOGPS
logP	5.46	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	10.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	92.67 m³·mol⁻¹	ChemAxon
Polarizability	35.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.415	31661259
DarkChem	[M-H]-	170.089	31661259
DeepCCS	[M+H]+	169.512	30932474
DeepCCS	[M-H]-	167.154	30932474
DeepCCS	[M-2H]-	200.04	30932474
DeepCCS	[M+Na]+	175.605	30932474
AllCCS	[M+H]+	171.8	32859911
AllCCS	[M+H-H2O]+	168.3	32859911
AllCCS	[M+NH4]+	175.0	32859911
AllCCS	[M+Na]+	175.9	32859911
AllCCS	[M-H]-	177.1	32859911
AllCCS	[M+Na-2H]-	177.3	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alverine	CCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1	2802.3	Standard polar	33892256
Alverine	CCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1	2162.6	Standard non polar	33892256
Alverine	CCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1	2199.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alverine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ox-7920000000-c8c9f49008d42192bf43	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alverine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alverine 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 - Alverine 10V, Positive-QTOF	splash10-001i-0190000000-fa5d943a706cbacc2966	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 20V, Positive-QTOF	splash10-001i-2590000000-5670c74b8576969d473e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 40V, Positive-QTOF	splash10-00kf-9700000000-0ca8414132b5d9b38dc0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 10V, Negative-QTOF	splash10-001i-0090000000-3436180aa1a55dae3c0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 20V, Negative-QTOF	splash10-001i-0190000000-4f76075ca6910a6f99f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 40V, Negative-QTOF	splash10-0hgo-4920000000-8a9772388b6011f2db4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 10V, Positive-QTOF	splash10-001i-0090000000-6c46192dea07b9977057	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 20V, Positive-QTOF	splash10-001i-0190000000-116fee06af3fb48655ac	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 40V, Positive-QTOF	splash10-0006-9710000000-88ece644f51433dcc79c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 10V, Negative-QTOF	splash10-001i-0090000000-78e4f4cb0fda655af884	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 20V, Negative-QTOF	splash10-001i-0290000000-8bc76e555b532b4d0ea2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alverine 40V, Negative-QTOF	splash10-0006-9740000000-30aa7cd1d162b50b60bc	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 DB01616	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01616	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01616

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3550

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alverine

METLIN ID

Not Available

PubChem Compound

3678

PDB ID

Not Available

ChEBI ID

518413

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

Hayase M, Hashitani H, Suzuki H, Kohri K, Brading AF: Evolving mechanisms of action of alverine citrate on phasic smooth muscles. Br J Pharmacol. 2007 Dec;152(8):1228-38. Epub 2007 Oct 15. [PubMed:17934514 ]
Ju D, Wang X, Xie Y: Dyclonine and alverine citrate enhance the cytotoxic effects of proteasome inhibitor MG132 on breast cancer cells. Int J Mol Med. 2009 Feb;23(2):205-9. [PubMed:19148544 ]
Wittmann T, Paradowski L, Ducrotte P, Bueno L, Andro Delestrain MC: Clinical trial: the efficacy of alverine citrate/simeticone combination on abdominal pain/discomfort in irritable bowel syndrome--a randomized, double-blind, placebo-controlled study. Aliment Pharmacol Ther. 2010 Mar;31(6):615-24. doi: 10.1111/j.1365-2036.2009.04216.x. Epub 2009 Dec 10. [PubMed:20003095 ]
Spasmonal Package Insert [Link]

Enzymes

Enzyme Details

1. 5-hydroxytryptamine receptor 1A

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

References

Coelho AM, Jacob L, Fioramonti J, Bueno L: Rectal antinociceptive properties of alverine citrate are linked to antagonism at the 5-HT1A receptor subtype. J Pharm Pharmacol. 2001 Oct;53(10):1419-26. [PubMed:11697552 ]

Showing metabocard for Alverine (HMDB0015554)

MOL for HMDB0015554 (Alverine)

3D MOL for HMDB0015554 (Alverine)

3D SDF for HMDB0015554 (Alverine)

3D-SDF for HMDB0015554 (Alverine)

PDB for HMDB0015554 (Alverine)

3D PDB for HMDB0015554 (Alverine)

SMILES for HMDB0015554 (Alverine)

INCHI for HMDB0015554 (Alverine)

Structure for HMDB0015554 (Alverine)

3D Structure for HMDB0015554 (Alverine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References