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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:32:55 UTC

Update Date

2021-09-14 14:59:06 UTC

HMDB ID

HMDB0060540

Secondary Accession Numbers

HMDB60540

Metabolite Identification

Common Name

Norverapamil

Description

Norverapamil is a calcium channel blocker. It is the main active metabolite of verapamil. Verapamil (brand names: Isoptin, Verelan, Verelan PM, Calan, Bosoptin, Covera-HS) is an L-type calcium channel blocker of the phenylalkylamine class. It has been used in the treatment of hypertension, angina pectoris, cardiac arrhythmia, and most recently, cluster headaches. It is also an effective preventive medication for migraine. Verapamil has also been used as a vasodilator during cryopreservation of blood vessels. (Wikipedia )

Structure

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

[NO NAME]
  Mrv0541 04181210192D          
Created with ChemWriter - http://chemwriter.com
 32 33  0  0  0  0            999 V2000
    2.3645   -2.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HMDB0060540
     RDKit          3D
Norverapamil
 68 69  0  0  0  0  0  0  0  0999 V2000
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M  END

[NO NAME]
  Mrv0541 04181210192D          
Created with ChemWriter - http://chemwriter.com
 32 33  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0060540

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C(CCNCCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H36N2O4/c1-19(2)26(18-27,21-9-11-23(30-4)25(17-21)32-6)13-7-14-28-15-12-20-8-10-22(29-3)24(16-20)31-5/h8-11,16-17,19,28H,7,12-15H2,1-6H3

> <INCHI_KEY>
UPKQNCPKPOLASS-UHFFFAOYSA-N

> <FORMULA>
C26H36N2O4

> <MOLECULAR_WEIGHT>
440.575

> <EXACT_MASS>
440.26750765

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
51.47134750390558

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-(propan-2-yl)pentanenitrile

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.660137883666668

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.291138570478047

> <JCHEM_POLAR_SURFACE_AREA>
72.74000000000001

> <JCHEM_REFRACTIVITY>
127.35319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
norverapamil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060540
     RDKit          3D
Norverapamil
 68 69  0  0  0  0  0  0  0  0999 V2000
    8.3702   -0.9934   -3.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1648   -0.6576   -1.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.9433   -1.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769   -1.5801   -1.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820   -1.8687   -1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5953   -1.5217    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3223   -1.8237    0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425   -0.6728    0.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108   -0.8931    1.4212 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1246    0.1852    1.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    0.0964   -0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    1.0379   -0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560    1.4469   -0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0157    2.4733   -1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976    3.2317   -2.3174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7578    0.4695   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5252   -0.7669   -1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952   -1.6617   -1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8789   -1.3371   -0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9755   -2.1958   -0.9830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8059   -3.5086   -1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1151   -0.0909   -0.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4161    0.2601    0.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6427    1.5457    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0421    0.7996   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8047    2.3182    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9449    3.5741    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5529    1.8454    2.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6258   -0.8791    0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8180   -0.5885    0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8684    0.0418    0.8927 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8031    0.4363    2.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2378   -0.3937   -3.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5218   -2.0855   -3.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4808   -0.6413   -3.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0900   -1.8641   -2.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9812   -2.3728   -1.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5339   -1.9004    2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8608   -2.7686    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2080   -0.5145   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8613    0.2480    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6379   -1.7789    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6574   -0.0301    1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    1.1198    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    0.2234   -0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -1.0026   -0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068    2.0457   -0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2969    0.8205   -1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5409   -1.0935   -1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3940   -2.6255   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7114   -4.0754   -1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694   -3.8864   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7827   -3.4954   -2.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9711    1.8142    1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5114    2.3418   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7240    1.6639    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3285    1.7394    0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8565    2.7998    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8914    3.3325    0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0705    3.9578   -0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3047    4.3223    1.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8210    0.7966    2.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2219    2.4408    2.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5308    2.1055    2.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4844   -0.5986    1.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6666    1.1349    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9656   -0.4572    2.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8486    0.8986    2.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  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
 12 13  1  0
 13 14  1  0
 14 15  3  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 13 26  1  0
 26 27  1  0
 26 28  1  0
  6 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 30  3  1  0
 25 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 17 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 29 65  1  0
 32 66  1  0
 32 67  1  0
 32 68  1  0
M  END

HEADER    PROTEIN                                 18-APR-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-12         0                                  
HETATM    1  O   UNK     0       4.414  -3.823   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081  -5.363   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      18.632   2.131   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      20.172   4.799   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.701   3.465   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.001   0.798   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081   0.798   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   2.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.621   0.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.391   2.131   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -0.742   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.931   2.131   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   3.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   3.108   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.541   0.798   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -1.513   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -1.513   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.241   3.465   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748  -3.053   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -3.053   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.011   4.799   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.081  -3.823   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.551   4.799   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.321   3.465   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.321   6.133   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.861   3.465   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080  -3.053   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.861   6.133   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.632   4.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.415  -6.133   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.172   2.131   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.942   6.133   0.000  0.00  0.00           C+0
CONECT    1   19   27                                                       
CONECT    2   22   30                                                       
CONECT    3   26   31                                                       
CONECT    4   29   32                                                       
CONECT    5   12   18                                                       
CONECT    6   15                                                            
CONECT    7    8    9   11   15                                             
CONECT    8    7   13   14                                                  
CONECT    9    7   10                                                       
CONECT   10    9   12                                                       
CONECT   11    7   16   17                                                  
CONECT   12    5   10                                                       
CONECT   13    8                                                            
CONECT   14    8                                                            
CONECT   15    6    7                                                       
CONECT   16   11   19                                                       
CONECT   17   11   20                                                       
CONECT   18    5   21                                                       
CONECT   19    1   16   22                                                  
CONECT   20   17   22                                                       
CONECT   21   18   23                                                       
CONECT   22    2   19   20                                                  
CONECT   23   21   24   25                                                  
CONECT   24   23   26                                                       
CONECT   25   23   28                                                       
CONECT   26    3   24   29                                                  
CONECT   27    1                                                            
CONECT   28   25   29                                                       
CONECT   29    4   26   28                                                  
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0060540
HETATM    1  C1  UNL     1       8.370  -0.993  -3.075  1.00  0.00           C  
HETATM    2  O1  UNL     1       8.165  -0.658  -1.712  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.983  -0.943  -1.058  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.977  -1.580  -1.745  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.782  -1.869  -1.092  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.595  -1.522   0.240  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.322  -1.824   0.972  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.342  -0.673   0.726  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.111  -0.893   1.421  1.00  0.00           N  
HETATM   10  C8  UNL     1       0.125   0.185   1.215  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.391   0.096  -0.169  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.317   1.038  -0.734  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.656   1.447  -0.352  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.016   2.473  -1.464  1.00  0.00           C  
HETATM   15  N2  UNL     1      -3.298   3.232  -2.317  1.00  0.00           N  
HETATM   16  C13 UNL     1      -3.758   0.470  -0.526  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.525  -0.767  -1.053  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.595  -1.662  -1.208  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.879  -1.337  -0.849  1.00  0.00           C  
HETATM   20  O2  UNL     1      -6.975  -2.196  -0.983  1.00  0.00           O  
HETATM   21  C17 UNL     1      -6.806  -3.509  -1.510  1.00  0.00           C  
HETATM   22  C18 UNL     1      -6.115  -0.091  -0.319  1.00  0.00           C  
HETATM   23  O3  UNL     1      -7.416   0.260   0.051  1.00  0.00           O  
HETATM   24  C19 UNL     1      -7.643   1.546   0.589  1.00  0.00           C  
HETATM   25  C20 UNL     1      -5.042   0.800  -0.165  1.00  0.00           C  
HETATM   26  C21 UNL     1      -2.805   2.318   0.848  1.00  0.00           C  
HETATM   27  C22 UNL     1      -1.945   3.574   0.580  1.00  0.00           C  
HETATM   28  C23 UNL     1      -2.553   1.845   2.192  1.00  0.00           C  
HETATM   29  C24 UNL     1       5.626  -0.879   0.914  1.00  0.00           C  
HETATM   30  C25 UNL     1       6.818  -0.589   0.272  1.00  0.00           C  
HETATM   31  O4  UNL     1       7.868   0.042   0.893  1.00  0.00           O  
HETATM   32  C26 UNL     1       7.803   0.436   2.249  1.00  0.00           C  
HETATM   33  H1  UNL     1       9.238  -0.394  -3.435  1.00  0.00           H  
HETATM   34  H2  UNL     1       8.522  -2.085  -3.182  1.00  0.00           H  
HETATM   35  H3  UNL     1       7.481  -0.641  -3.665  1.00  0.00           H  
HETATM   36  H4  UNL     1       6.090  -1.864  -2.778  1.00  0.00           H  
HETATM   37  H5  UNL     1       3.981  -2.373  -1.623  1.00  0.00           H  
HETATM   38  H6  UNL     1       3.534  -1.900   2.049  1.00  0.00           H  
HETATM   39  H7  UNL     1       2.861  -2.769   0.620  1.00  0.00           H  
HETATM   40  H8  UNL     1       2.208  -0.514  -0.345  1.00  0.00           H  
HETATM   41  H9  UNL     1       2.861   0.248   1.125  1.00  0.00           H  
HETATM   42  H10 UNL     1       0.638  -1.779   1.157  1.00  0.00           H  
HETATM   43  H11 UNL     1      -0.657  -0.030   1.993  1.00  0.00           H  
HETATM   44  H12 UNL     1       0.663   1.120   1.378  1.00  0.00           H  
HETATM   45  H13 UNL     1       0.570   0.223  -0.821  1.00  0.00           H  
HETATM   46  H14 UNL     1      -0.574  -1.003  -0.371  1.00  0.00           H  
HETATM   47  H15 UNL     1      -0.707   2.046  -0.807  1.00  0.00           H  
HETATM   48  H16 UNL     1      -1.297   0.820  -1.895  1.00  0.00           H  
HETATM   49  H17 UNL     1      -2.541  -1.094  -1.383  1.00  0.00           H  
HETATM   50  H18 UNL     1      -4.394  -2.626  -1.624  1.00  0.00           H  
HETATM   51  H19 UNL     1      -7.711  -4.075  -1.184  1.00  0.00           H  
HETATM   52  H20 UNL     1      -5.869  -3.886  -1.054  1.00  0.00           H  
HETATM   53  H21 UNL     1      -6.783  -3.495  -2.609  1.00  0.00           H  
HETATM   54  H22 UNL     1      -6.971   1.814   1.421  1.00  0.00           H  
HETATM   55  H23 UNL     1      -7.511   2.342  -0.195  1.00  0.00           H  
HETATM   56  H24 UNL     1      -8.724   1.664   0.893  1.00  0.00           H  
HETATM   57  H25 UNL     1      -5.329   1.739   0.246  1.00  0.00           H  
HETATM   58  H26 UNL     1      -3.857   2.800   0.760  1.00  0.00           H  
HETATM   59  H27 UNL     1      -0.891   3.332   0.860  1.00  0.00           H  
HETATM   60  H28 UNL     1      -2.071   3.958  -0.430  1.00  0.00           H  
HETATM   61  H29 UNL     1      -2.305   4.322   1.342  1.00  0.00           H  
HETATM   62  H30 UNL     1      -2.821   0.797   2.421  1.00  0.00           H  
HETATM   63  H31 UNL     1      -3.222   2.441   2.899  1.00  0.00           H  
HETATM   64  H32 UNL     1      -1.531   2.105   2.593  1.00  0.00           H  
HETATM   65  H33 UNL     1       5.484  -0.599   1.968  1.00  0.00           H  
HETATM   66  H34 UNL     1       8.667   1.135   2.415  1.00  0.00           H  
HETATM   67  H35 UNL     1       7.966  -0.457   2.915  1.00  0.00           H  
HETATM   68  H36 UNL     1       6.849   0.899   2.516  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3
CONECT    3    4    4   30
CONECT    4    5   36
CONECT    5    6    6   37
CONECT    6    7   29
CONECT    7    8   38   39
CONECT    8    9   40   41
CONECT    9   10   42
CONECT   10   11   43   44
CONECT   11   12   45   46
CONECT   12   13   47   48
CONECT   13   14   16   26
CONECT   14   15   15   15
CONECT   16   17   17   25
CONECT   17   18   49
CONECT   18   19   19   50
CONECT   19   20   22
CONECT   20   21
CONECT   21   51   52   53
CONECT   22   23   25   25
CONECT   23   24
CONECT   24   54   55   56
CONECT   25   57
CONECT   26   27   28   58
CONECT   27   59   60   61
CONECT   28   62   63   64
CONECT   29   30   30   65
CONECT   30   31
CONECT   31   32
CONECT   32   66   67   68
END

HMDB0060540
     RDKit          3D
Norverapamil
 68 69  0  0  0  0  0  0  0  0999 V2000
    8.3702   -0.9934   -3.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1648   -0.6576   -1.7116 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.9433   -1.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9769   -1.5801   -1.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7820   -1.8687   -1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5953   -1.5217    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3223   -1.8237    0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3425   -0.6728    0.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1108   -0.8931    1.4212 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1246    0.1852    1.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    0.0964   -0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3166    1.0379   -0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560    1.4469   -0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0157    2.4733   -1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976    3.2317   -2.3174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7578    0.4695   -0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5252   -0.7669   -1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5952   -1.6617   -1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8789   -1.3371   -0.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9755   -2.1958   -0.9830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8059   -3.5086   -1.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1151   -0.0909   -0.3195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4161    0.2601    0.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6427    1.5457    0.5891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0421    0.7996   -0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8047    2.3182    0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9449    3.5741    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5529    1.8454    2.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6258   -0.8791    0.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8180   -0.5885    0.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8684    0.0418    0.8927 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8031    0.4363    2.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2378   -0.3937   -3.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5218   -2.0855   -3.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4808   -0.6413   -3.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0900   -1.8641   -2.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9812   -2.3728   -1.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5339   -1.9004    2.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8608   -2.7686    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2080   -0.5145   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8613    0.2480    1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6379   -1.7789    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6574   -0.0301    1.9928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    1.1198    1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    0.2234   -0.8210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -1.0026   -0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7068    2.0457   -0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2969    0.8205   -1.8955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5409   -1.0935   -1.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3940   -2.6255   -1.6240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7114   -4.0754   -1.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694   -3.8864   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7827   -3.4954   -2.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9711    1.8142    1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5114    2.3418   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7240    1.6639    0.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3285    1.7394    0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8565    2.7998    0.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8914    3.3325    0.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0705    3.9578   -0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3047    4.3223    1.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8210    0.7966    2.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2219    2.4408    2.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5308    2.1055    2.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4844   -0.5986    1.9680 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6666    1.1349    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9656   -0.4572    2.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8486    0.8986    2.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  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
 12 13  1  0
 13 14  1  0
 14 15  3  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
 13 26  1  0
 26 27  1  0
 26 28  1  0
  6 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 30  3  1  0
 25 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  5 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 17 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 21 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 29 65  1  0
 32 66  1  0
 32 67  1  0
 32 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Norverapamil (6%)	HMDB
Norverapamil monohydrochloride	HMDB
Norverapamil, (+-)-isomer	HMDB
N-Demethylverapamil	HMDB

Chemical Formula

C₂₆H₃₆N₂O₄

Average Molecular Weight

440.575

Monoisotopic Molecular Weight

440.26750765

IUPAC Name

2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-2-(propan-2-yl)pentanenitrile

Traditional Name

norverapamil

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C(CCNCCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1

InChI Identifier

InChI=1S/C26H36N2O4/c1-19(2)26(18-27,21-9-11-23(30-4)25(17-21)32-6)13-7-14-28-15-12-20-8-10-22(29-3)24(16-20)31-5/h8-11,16-17,19,28H,7,12-15H2,1-6H3

InChI Key

UPKQNCPKPOLASS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Dimethoxybenzene
O-dimethoxybenzene
Phenethylamine
Phenylpropane
Anisole
Phenol ether
Phenoxy compound
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Secondary amine
Nitrile
Carbonitrile
Ether
Secondary aliphatic amine
Organic oxygen compound
Amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0060540)
Kidney (HMDB: HMDB0060540)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060540)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060540)

Cellular substructure

Cytoplasm (HMDB: HMDB0060540)
Membrane (HMDB: HMDB0060540)

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
Water Solubility	0.0029 g/L	ALOGPS
logP	4.41	ALOGPS
logP	4.66	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.74 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	127.35 m³·mol⁻¹	ChemAxon
Polarizability	51.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	206.112	31661259
DarkChem	[M-H]-	207.338	31661259
DeepCCS	[M+H]+	210.951	30932474
DeepCCS	[M-H]-	208.593	30932474
DeepCCS	[M-2H]-	242.344	30932474
DeepCCS	[M+Na]+	217.753	30932474
AllCCS	[M+H]+	211.0	32859911
AllCCS	[M+H-H2O]+	208.8	32859911
AllCCS	[M+NH4]+	213.0	32859911
AllCCS	[M+Na]+	213.6	32859911
AllCCS	[M-H]-	211.5	32859911
AllCCS	[M+Na-2H]-	212.9	32859911
AllCCS	[M+HCOO]-	214.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norverapamil	COC1=C(OC)C=C(CCNCCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1	3731.1	Standard polar	33892256
Norverapamil	COC1=C(OC)C=C(CCNCCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1	3224.6	Standard non polar	33892256
Norverapamil	COC1=C(OC)C=C(CCNCCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1	3206.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norverapamil,1TMS,isomer #1	COC1=CC=C(CCN(CCCC(C#N)(C2=CC=C(OC)C(OC)=C2)C(C)C)[Si](C)(C)C)C=C1OC	3236.1	Semi standard non polar	33892256
Norverapamil,1TMS,isomer #1	COC1=CC=C(CCN(CCCC(C#N)(C2=CC=C(OC)C(OC)=C2)C(C)C)[Si](C)(C)C)C=C1OC	3477.2	Standard non polar	33892256
Norverapamil,1TMS,isomer #1	COC1=CC=C(CCN(CCCC(C#N)(C2=CC=C(OC)C(OC)=C2)C(C)C)[Si](C)(C)C)C=C1OC	4483.1	Standard polar	33892256
Norverapamil,1TBDMS,isomer #1	COC1=CC=C(CCN(CCCC(C#N)(C2=CC=C(OC)C(OC)=C2)C(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	3490.1	Semi standard non polar	33892256
Norverapamil,1TBDMS,isomer #1	COC1=CC=C(CCN(CCCC(C#N)(C2=CC=C(OC)C(OC)=C2)C(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	3608.9	Standard non polar	33892256
Norverapamil,1TBDMS,isomer #1	COC1=CC=C(CCN(CCCC(C#N)(C2=CC=C(OC)C(OC)=C2)C(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	4481.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norverapamil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5894400000-1905d27fda526950b48a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norverapamil 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 - Norverapamil 10V, Positive-QTOF	splash10-0006-0111900000-f6499f82af6436a7ffeb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 20V, Positive-QTOF	splash10-02t9-0792400000-08e2f7e8c53985c53cee	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 40V, Positive-QTOF	splash10-014i-0972000000-08658a08d28032cd18b1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 10V, Negative-QTOF	splash10-000i-0000900000-7ffe5e7bd99bb75f243a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 20V, Negative-QTOF	splash10-0080-0013900000-eca8291f2c7f6c6a2e58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 40V, Negative-QTOF	splash10-00nf-0559300000-ff37eccd07a8565257b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 10V, Positive-QTOF	splash10-0006-0100900000-49dae5e8c26055f14dfe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 20V, Positive-QTOF	splash10-0006-3573900000-30f9b8c1942de6e2b083	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 40V, Positive-QTOF	splash10-0i09-0791100000-38ab31d93b0b16941a6b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 10V, Negative-QTOF	splash10-000i-0000900000-252ab6672a823d321850	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 20V, Negative-QTOF	splash10-057i-0009700000-66c7a6d4b2381a3754e1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norverapamil 40V, Negative-QTOF	splash10-029l-0519200000-bab1f58bc74b461d1d19	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norverapamil

METLIN ID

Not Available

PubChem Compound

104972

PDB ID

Not Available

ChEBI ID

134080

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Norverapamil (HMDB0060540)

MOL for HMDB0060540 (Norverapamil)

3D MOL for HMDB0060540 (Norverapamil)

3D SDF for HMDB0060540 (Norverapamil)

3D-SDF for HMDB0060540 (Norverapamil)

PDB for HMDB0060540 (Norverapamil)

3D PDB for HMDB0060540 (Norverapamil)

SMILES for HMDB0060540 (Norverapamil)

INCHI for HMDB0060540 (Norverapamil)

Structure for HMDB0060540 (Norverapamil)

3D Structure for HMDB0060540 (Norverapamil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra