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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:01:35 UTC

Update Date

2021-09-14 14:57:29 UTC

HMDB ID

HMDB0014246

Secondary Accession Numbers

HMDB14246

Metabolite Identification

Common Name

O-Desmethylverapamil (D-703)

Description

O-Desmethylverapamil (D-703) is only found in individuals that have used or taken Verapamil. O-Desmethylverapamil (D-703) is a metabolite of Verapamil. O-desmethylverapamil (d-703) belongs to the family of Phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Structure

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


  Mrv0541 06191311032D          

 32 33  0  0  0  0            999 V2000
    4.8335   -6.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -6.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4500   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2750   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7375   -2.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125   -3.6829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4999   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3250   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481   -4.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770   -4.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5625   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481   -5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3250   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770   -5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9750   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -6.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7999   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2124   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2124   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0374   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1191   -5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0374   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4500   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2750   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6875   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 28  1  0  0  0  0
  2 23  1  0  0  0  0
  3 27  1  0  0  0  0
  3 31  1  0  0  0  0
  4 30  1  0  0  0  0
  4 32  1  0  0  0  0
  5 12  1  0  0  0  0
  5 18  1  0  0  0  0
  5 20  1  0  0  0  0
  6 15  3  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  7 15  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 16  2  0  0  0  0
 11 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 29  2  0  0  0  0
 27 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0014246
     RDKit          3D
O-Desmethylverapamil (D-703)
 68 69  0  0  0  0  0  0  0  0999 V2000
   -7.8326   -1.1186   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2195   -2.3032   -0.0303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885   -2.5468    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9660   -1.5228   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012   -1.7251    0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5852   -0.6186   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9035   -0.9256   -1.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3724   -1.1822   -2.4011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078   -0.7175    1.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    0.1667    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    0.1534    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626    1.1391    0.8064 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    0.8854    2.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5361    2.3632    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571    2.2907   -1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6590    1.8698   -0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5322    2.9113   -0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    2.6278   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3071    1.3129   -0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5465    1.0642    0.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7978    1.2070    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4040    0.2725   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9261   -0.9854   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576   -2.1618   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0891    0.5757   -0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137    0.6745   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    1.8798   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1181    0.9903    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012   -3.0142    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0757   -4.0379    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4190   -3.8075    0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3130   -4.8230    0.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2008   -1.1854   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2472   -0.1954   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7869   -0.9324    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3302   -0.5551   -0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028   -0.7407    1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -1.7692    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0896   -0.2331    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209    1.2082    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    0.2692   -0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -0.8532    0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    1.4133    2.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448    1.1545    2.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3655   -0.2047    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0819    3.0877    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127    2.7386   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493    1.5828   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2822    3.3150   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    3.9545   -0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5330    3.4136   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9929    1.9144    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4078    1.6694   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3466    0.2479    0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127   -2.2454   -0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -3.0267   -0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911   -2.3364   -1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -0.2533   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216    0.6376   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    2.5939   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871    2.5023    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5105    1.6410   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1129    1.4106    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2199    0.0691    1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052    1.7993    1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1312   -3.2355    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6635   -5.0059    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3035   -4.7449    0.5864 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  1  0
  6  7  1  0
  7  8  3  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 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  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
  6 26  1  0
 26 27  1  0
 26 28  1  0
  5 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31  3  1  0
 25 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 18 51  1  0
 21 52  1  0
 21 53  1  0
 21 54  1  0
 24 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
 32 68  1  0
M  END


  Mrv0541 06191311032D          

 32 33  0  0  0  0            999 V2000
    4.8335   -6.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -6.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4500   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2750   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7375   -2.2539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125   -3.6829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4999   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -4.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3250   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4375   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481   -4.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770   -4.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5625   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5481   -5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3250   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770   -5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9750   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -6.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7999   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2124   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2124   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0374   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1191   -5.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0374   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4500   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2750   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6875   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  1 28  1  0  0  0  0
  2 23  1  0  0  0  0
  3 27  1  0  0  0  0
  3 31  1  0  0  0  0
  4 30  1  0  0  0  0
  4 32  1  0  0  0  0
  5 12  1  0  0  0  0
  5 18  1  0  0  0  0
  5 20  1  0  0  0  0
  6 15  3  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
  7 15  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 16  2  0  0  0  0
 11 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 29  2  0  0  0  0
 27 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014246

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(=C1)C(CCCN(C)CCC1=CC(OC)=C(OC)C=C1)(C#N)C(C)C

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

> <INCHI_KEY>
WLKVZSXOMGNZLB-UHFFFAOYSA-N

> <FORMULA>
C26H36N2O4

> <MOLECULAR_WEIGHT>
440.575

> <EXACT_MASS>
440.26750765

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
49.54668765709338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
4.39999874488118

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.118505275513224

> <JCHEM_PKA_STRONGEST_BASIC>
9.482564955155757

> <JCHEM_POLAR_SURFACE_AREA>
74.95

> <JCHEM_REFRACTIVITY>
128.16559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(4-hydroxy-3-methoxyphenyl)-2-isopropylpentanenitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014246
     RDKit          3D
O-Desmethylverapamil (D-703)
 68 69  0  0  0  0  0  0  0  0999 V2000
   -7.8326   -1.1186   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2195   -2.3032   -0.0303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885   -2.5468    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9660   -1.5228   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012   -1.7251    0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5852   -0.6186   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9035   -0.9256   -1.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3724   -1.1822   -2.4011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078   -0.7175    1.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    0.1667    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    0.1534    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626    1.1391    0.8064 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    0.8854    2.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5361    2.3632    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571    2.2907   -1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6590    1.8698   -0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5322    2.9113   -0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    2.6278   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3071    1.3129   -0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5465    1.0642    0.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7978    1.2070    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4040    0.2725   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9261   -0.9854   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576   -2.1618   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0891    0.5757   -0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137    0.6745   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    1.8798   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1181    0.9903    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012   -3.0142    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0757   -4.0379    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4190   -3.8075    0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3130   -4.8230    0.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2008   -1.1854   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2472   -0.1954   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7869   -0.9324    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3302   -0.5551   -0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028   -0.7407    1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -1.7692    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0896   -0.2331    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209    1.2082    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    0.2692   -0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -0.8532    0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    1.4133    2.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448    1.1545    2.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3655   -0.2047    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0819    3.0877    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127    2.7386   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493    1.5828   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2822    3.3150   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    3.9545   -0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5330    3.4136   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9929    1.9144    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4078    1.6694   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3466    0.2479    0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127   -2.2454   -0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -3.0267   -0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911   -2.3364   -1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -0.2533   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216    0.6376   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    2.5939   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871    2.5023    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5105    1.6410   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1129    1.4106    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2199    0.0691    1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052    1.7993    1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1312   -3.2355    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6635   -5.0059    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3035   -4.7449    0.5864 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  1  0
  6  7  1  0
  7  8  3  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 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  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
  6 26  1  0
 26 27  1  0
 26 28  1  0
  5 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31  3  1  0
 25 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 18 51  1  0
 21 52  1  0
 21 53  1  0
 21 54  1  0
 24 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
 32 68  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1  O   UNK     0       9.023 -11.495   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.690 -13.035   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      23.240  -5.541   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      24.780  -2.874   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      16.310  -4.207   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.610  -6.875   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      11.690  -6.875   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.690  -5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.230  -6.875   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.000  -5.541   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.690  -8.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.540  -5.541   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.356  -4.565   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.024  -4.565   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.150  -6.875   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.356  -9.185   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.024  -9.185   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.850  -4.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.356 -10.725   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.540  -2.874   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.024 -10.725   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.620  -2.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.690 -11.495   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.160  -2.874   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.930  -4.207   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.930  -1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.470  -4.207   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.689 -10.725   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.470  -1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.240  -2.874   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.780  -5.541   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.550  -1.540   0.000  0.00  0.00           C+0
CONECT    1   19   28                                                       
CONECT    2   23                                                            
CONECT    3   27   31                                                       
CONECT    4   30   32                                                       
CONECT    5   12   18   20                                                  
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   21                                                       
CONECT   18    5   22                                                       
CONECT   19    1   16   23                                                  
CONECT   20    5                                                            
CONECT   21   17   23                                                       
CONECT   22   18   24                                                       
CONECT   23    2   19   21                                                  
CONECT   24   22   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24   29                                                       
CONECT   27    3   25   30                                                  
CONECT   28    1                                                            
CONECT   29   26   30                                                       
CONECT   30    4   27   29                                                  
CONECT   31    3                                                            
CONECT   32    4                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0014246
HETATM    1  C1  UNL     1      -7.833  -1.119  -0.367  1.00  0.00           C  
HETATM    2  O1  UNL     1      -7.220  -2.303  -0.030  1.00  0.00           O  
HETATM    3  C2  UNL     1      -5.889  -2.547   0.113  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.966  -1.523  -0.087  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.601  -1.725   0.049  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.585  -0.619  -0.146  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.903  -0.926  -1.382  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.372  -1.182  -2.401  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.708  -0.717   1.061  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.596   0.167   1.304  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.550   0.153   0.312  1.00  0.00           C  
HETATM   12  N2  UNL     1       1.463   1.139   0.806  1.00  0.00           N  
HETATM   13  C10 UNL     1       2.140   0.885   2.006  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.536   2.363   0.174  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.257   2.291  -1.167  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.659   1.870  -0.890  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.532   2.911  -0.580  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.820   2.628  -0.269  1.00  0.00           C  
HETATM   19  C16 UNL     1       6.307   1.313  -0.249  1.00  0.00           C  
HETATM   20  O2  UNL     1       7.546   1.064   0.054  1.00  0.00           O  
HETATM   21  C17 UNL     1       8.798   1.207   0.380  1.00  0.00           C  
HETATM   22  C18 UNL     1       5.404   0.273  -0.566  1.00  0.00           C  
HETATM   23  O3  UNL     1       5.926  -0.985  -0.532  1.00  0.00           O  
HETATM   24  C19 UNL     1       5.258  -2.162  -0.851  1.00  0.00           C  
HETATM   25  C20 UNL     1       4.089   0.576  -0.884  1.00  0.00           C  
HETATM   26  C21 UNL     1      -3.314   0.675  -0.257  1.00  0.00           C  
HETATM   27  C22 UNL     1      -2.417   1.880  -0.534  1.00  0.00           C  
HETATM   28  C23 UNL     1      -4.118   0.990   1.010  1.00  0.00           C  
HETATM   29  C24 UNL     1      -3.201  -3.014   0.394  1.00  0.00           C  
HETATM   30  C25 UNL     1      -4.076  -4.038   0.598  1.00  0.00           C  
HETATM   31  C26 UNL     1      -5.419  -3.808   0.458  1.00  0.00           C  
HETATM   32  O4  UNL     1      -6.313  -4.823   0.660  1.00  0.00           O  
HETATM   33  H1  UNL     1      -8.201  -1.185  -1.436  1.00  0.00           H  
HETATM   34  H2  UNL     1      -7.247  -0.195  -0.329  1.00  0.00           H  
HETATM   35  H3  UNL     1      -8.787  -0.932   0.206  1.00  0.00           H  
HETATM   36  H4  UNL     1      -5.330  -0.555  -0.378  1.00  0.00           H  
HETATM   37  H5  UNL     1      -2.403  -0.741   1.953  1.00  0.00           H  
HETATM   38  H6  UNL     1      -1.276  -1.769   1.054  1.00  0.00           H  
HETATM   39  H7  UNL     1      -0.090  -0.233   2.264  1.00  0.00           H  
HETATM   40  H8  UNL     1      -0.821   1.208   1.613  1.00  0.00           H  
HETATM   41  H9  UNL     1       0.280   0.269  -0.730  1.00  0.00           H  
HETATM   42  H10 UNL     1       1.054  -0.853   0.469  1.00  0.00           H  
HETATM   43  H11 UNL     1       3.112   1.413   2.033  1.00  0.00           H  
HETATM   44  H12 UNL     1       1.545   1.155   2.927  1.00  0.00           H  
HETATM   45  H13 UNL     1       2.366  -0.205   2.145  1.00  0.00           H  
HETATM   46  H14 UNL     1       2.082   3.088   0.829  1.00  0.00           H  
HETATM   47  H15 UNL     1       0.513   2.739  -0.071  1.00  0.00           H  
HETATM   48  H16 UNL     1       1.749   1.583  -1.840  1.00  0.00           H  
HETATM   49  H17 UNL     1       2.282   3.315  -1.595  1.00  0.00           H  
HETATM   50  H18 UNL     1       4.187   3.955  -0.578  1.00  0.00           H  
HETATM   51  H19 UNL     1       6.533   3.414  -0.024  1.00  0.00           H  
HETATM   52  H20 UNL     1       8.993   1.914   1.256  1.00  0.00           H  
HETATM   53  H21 UNL     1       9.408   1.669  -0.453  1.00  0.00           H  
HETATM   54  H22 UNL     1       9.347   0.248   0.684  1.00  0.00           H  
HETATM   55  H23 UNL     1       4.213  -2.245  -0.528  1.00  0.00           H  
HETATM   56  H24 UNL     1       5.855  -3.027  -0.409  1.00  0.00           H  
HETATM   57  H25 UNL     1       5.291  -2.336  -1.956  1.00  0.00           H  
HETATM   58  H26 UNL     1       3.414  -0.253  -1.129  1.00  0.00           H  
HETATM   59  H27 UNL     1      -4.022   0.638  -1.077  1.00  0.00           H  
HETATM   60  H28 UNL     1      -2.968   2.594  -1.242  1.00  0.00           H  
HETATM   61  H29 UNL     1      -2.287   2.502   0.366  1.00  0.00           H  
HETATM   62  H30 UNL     1      -1.510   1.641  -1.103  1.00  0.00           H  
HETATM   63  H31 UNL     1      -5.113   1.411   0.794  1.00  0.00           H  
HETATM   64  H32 UNL     1      -4.220   0.069   1.578  1.00  0.00           H  
HETATM   65  H33 UNL     1      -3.605   1.799   1.589  1.00  0.00           H  
HETATM   66  H34 UNL     1      -2.131  -3.236   0.489  1.00  0.00           H  
HETATM   67  H35 UNL     1      -3.664  -5.006   0.868  1.00  0.00           H  
HETATM   68  H36 UNL     1      -7.304  -4.745   0.586  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3
CONECT    3    4    4   31
CONECT    4    5   36
CONECT    5    6   29   29
CONECT    6    7    9   26
CONECT    7    8    8    8
CONECT    9   10   37   38
CONECT   10   11   39   40
CONECT   11   12   41   42
CONECT   12   13   14
CONECT   13   43   44   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   17   25
CONECT   17   18   50
CONECT   18   19   19   51
CONECT   19   20   22
CONECT   20   21
CONECT   21   52   53   54
CONECT   22   23   25   25
CONECT   23   24
CONECT   24   55   56   57
CONECT   25   58
CONECT   26   27   28   59
CONECT   27   60   61   62
CONECT   28   63   64   65
CONECT   29   30   66
CONECT   30   31   31   67
CONECT   31   32
CONECT   32   68
END

HMDB0014246
     RDKit          3D
O-Desmethylverapamil (D-703)
 68 69  0  0  0  0  0  0  0  0999 V2000
   -7.8326   -1.1186   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2195   -2.3032   -0.0303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885   -2.5468    0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9660   -1.5228   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012   -1.7251    0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5852   -0.6186   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9035   -0.9256   -1.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3724   -1.1822   -2.4011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7078   -0.7175    1.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    0.1667    1.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500    0.1534    0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4626    1.1391    0.8064 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405    0.8854    2.0059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5361    2.3632    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2571    2.2907   -1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6590    1.8698   -0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5322    2.9113   -0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8202    2.6278   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3071    1.3129   -0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5465    1.0642    0.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7978    1.2070    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4040    0.2725   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9261   -0.9854   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576   -2.1618   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0891    0.5757   -0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3137    0.6745   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    1.8798   -0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1181    0.9903    1.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2012   -3.0142    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0757   -4.0379    0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4190   -3.8075    0.4578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3130   -4.8230    0.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2008   -1.1854   -1.4363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2472   -0.1954   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7869   -0.9324    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3302   -0.5551   -0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028   -0.7407    1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -1.7692    1.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0896   -0.2331    2.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209    1.2082    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    0.2692   -0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -0.8532    0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115    1.4133    2.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448    1.1545    2.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3655   -0.2047    2.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0819    3.0877    0.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127    2.7386   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493    1.5828   -1.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2822    3.3150   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1867    3.9545   -0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5330    3.4136   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9929    1.9144    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4078    1.6694   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3466    0.2479    0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2127   -2.2454   -0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -3.0267   -0.4092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911   -2.3364   -1.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -0.2533   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216    0.6376   -1.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681    2.5939   -1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871    2.5023    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5105    1.6410   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1129    1.4106    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2199    0.0691    1.5777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6052    1.7993    1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1312   -3.2355    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6635   -5.0059    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3035   -4.7449    0.5864 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  1  0
  6  7  1  0
  7  8  3  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 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  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  2  0
  6 26  1  0
 26 27  1  0
 26 28  1  0
  5 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31  3  1  0
 25 16  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 13 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 18 51  1  0
 21 52  1  0
 21 53  1  0
 21 54  1  0
 24 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
 32 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆N₂O₄

Average Molecular Weight

440.575

Monoisotopic Molecular Weight

440.26750765

IUPAC Name

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

Traditional Name

5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(4-hydroxy-3-methoxyphenyl)-2-isopropylpentanenitrile

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C(CCCN(C)CCC1=CC(OC)=C(OC)C=C1)(C#N)C(C)C

InChI Identifier

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

InChI Key

WLKVZSXOMGNZLB-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
Methoxyphenol
Dimethoxybenzene
O-dimethoxybenzene
Phenethylamine
Phenylpropane
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Aralkylamine
Tertiary amine
Tertiary aliphatic amine
Nitrile
Carbonitrile
Ether
Organic oxygen compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0014246)
Kidney (HMDB: HMDB0014246)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014246)

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	0.0078 g/L	ALOGPS
logP	4.57	ALOGPS
logP	4.4	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.12	ChemAxon
pKa (Strongest Basic)	9.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.95 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	128.17 m³·mol⁻¹	ChemAxon
Polarizability	49.55 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]+	207.092	31661259
DarkChem	[M-H]-	204.59	31661259
DeepCCS	[M+H]+	207.723	30932474
DeepCCS	[M-H]-	205.365	30932474
DeepCCS	[M-2H]-	238.699	30932474
DeepCCS	[M+Na]+	213.895	30932474
AllCCS	[M+H]+	210.7	32859911
AllCCS	[M+H-H2O]+	208.4	32859911
AllCCS	[M+NH4]+	212.7	32859911
AllCCS	[M+Na]+	213.3	32859911
AllCCS	[M-H]-	212.4	32859911
AllCCS	[M+Na-2H]-	213.7	32859911
AllCCS	[M+HCOO]-	215.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethylverapamil (D-703)	COC1=C(O)C=CC(=C1)C(CCCN(C)CCC1=CC(OC)=C(OC)C=C1)(C#N)C(C)C	3956.2	Standard polar	33892256
O-Desmethylverapamil (D-703)	COC1=C(O)C=CC(=C1)C(CCCN(C)CCC1=CC(OC)=C(OC)C=C1)(C#N)C(C)C	3066.3	Standard non polar	33892256
O-Desmethylverapamil (D-703)	COC1=C(O)C=CC(=C1)C(CCCN(C)CCC1=CC(OC)=C(OC)C=C1)(C#N)C(C)C	3205.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethylverapamil (D-703),1TMS,isomer #1	COC1=CC=C(CCN(C)CCCC(C#N)(C2=CC=C(O[Si](C)(C)C)C(OC)=C2)C(C)C)C=C1OC	3128.3	Semi standard non polar	33892256
O-Desmethylverapamil (D-703),1TBDMS,isomer #1	COC1=CC=C(CCN(C)CCCC(C#N)(C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C(C)C)C=C1OC	3338.5	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 - O-Desmethylverapamil (D-703) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k97-4491100000-8f48234ef2ccfb67b52f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylverapamil (D-703) GC-MS (1 TMS) - 70eV, Positive	splash10-052e-6482900000-48f812b64d0bdb248ef0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylverapamil (D-703) 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 - O-Desmethylverapamil (D-703) 10V, Positive-QTOF	splash10-0006-0011900000-cce4cd8473843968605b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 20V, Positive-QTOF	splash10-01b9-0592700000-c027a5bbb46ab82816c1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 40V, Positive-QTOF	splash10-014i-1951100000-d24da5f3b85a660f31da	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 10V, Negative-QTOF	splash10-000i-0000900000-4e1c9414cbd447b18bb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 20V, Negative-QTOF	splash10-009i-0132900000-31c5a338136e3ba83ca5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 40V, Negative-QTOF	splash10-004i-0393100000-c509f5d20815fe8a23f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 10V, Positive-QTOF	splash10-0006-0011900000-c39dcd4b4e9f0e4f3f90	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 20V, Positive-QTOF	splash10-05mo-2292300000-f08792c746ac010960b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 40V, Positive-QTOF	splash10-0gb9-0981000000-346e126085e3120250df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 10V, Negative-QTOF	splash10-000i-0000900000-b7e50c6621dda369aa2d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 20V, Negative-QTOF	splash10-0a4r-0327900000-ddb0e037dbb2a8581c6b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-703) 40V, Negative-QTOF	splash10-014j-0309100000-2637f5063e5e2a83df50	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

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	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

543555

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

625729

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

Not Available

Showing metabocard for O-Desmethylverapamil (D-703) (HMDB0014246)

MOL for HMDB0014246 (O-Desmethylverapamil (D-703))

3D MOL for HMDB0014246 (O-Desmethylverapamil (D-703))

3D SDF for HMDB0014246 (O-Desmethylverapamil (D-703))

3D-SDF for HMDB0014246 (O-Desmethylverapamil (D-703))

PDB for HMDB0014246 (O-Desmethylverapamil (D-703))

3D PDB for HMDB0014246 (O-Desmethylverapamil (D-703))

SMILES for HMDB0014246 (O-Desmethylverapamil (D-703))

INCHI for HMDB0014246 (O-Desmethylverapamil (D-703))

Structure for HMDB0014246 (O-Desmethylverapamil (D-703))

3D Structure for HMDB0014246 (O-Desmethylverapamil (D-703))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra