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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (25)transporters (13) Show 38 proteins XML

enzymes (25)transporters (13) Show 38 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:36 UTC

Update Date

2021-09-14 14:59:06 UTC

HMDB ID

HMDB0013961

Secondary Accession Numbers

HMDB0060539
HMDB13961
HMDB60539

Metabolite Identification

Common Name

O-Desmethylverapamil (D-702)

Description

O-Desmethylverapamil (D-702) 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. O-Desmethylverapamil (D-702) is a very strong basic compound (based on its pKa).

Structure

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

[NO NAME]
  Mrv0541 09021220312D          
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
    3.7935   -2.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    1.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8062    2.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2686    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    0.4273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0936    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5061    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3311    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7436    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7436    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5686    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5686    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2187    3.2853    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
  2 31  1  0  0  0  0
  3 27  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

HMDB0013961
     RDKit          3D
O-Desmethylverapamil (D-702)
 68 69  0  0  0  0  0  0  0  0999 V2000
    9.3127    0.4486   -1.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1298    0.0678   -1.7463 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8655    0.4216   -1.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6334    1.1794   -0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3451    1.5162    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    1.0849   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590    1.4183   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146    0.2845    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699    0.4090    1.3630 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0455    1.4477    2.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854   -0.9011    1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -1.1056    2.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8561   -0.7427    1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3027   -1.2855    0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168   -0.9323   -0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982   -0.6527   -1.3659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4652   -0.4931   -0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714   -1.0411   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7432   -0.2671   -0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6320    1.0907   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6996    1.8863   -1.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9092    1.2610   -1.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4241    1.6549   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897    3.0235   -0.7756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1191    3.7374   -0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3756    0.8963   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5335   -2.7365    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -3.6027    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5544   -3.2709    1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798    0.3238   -1.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7661   -0.0107   -2.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550   -0.7761   -3.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2194    0.5087    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1490   -0.2802   -1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6504    1.4716   -1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4949    1.5245    0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2189    2.1141    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235    2.3354    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845    1.5092   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971   -0.7171    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1040    0.2768    1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    2.3982    1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0752    1.6993    2.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403    1.3626    3.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -1.2113    2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8553   -1.5851    0.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850   -0.5347    3.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367   -2.1653    2.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971    0.3954    1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -0.8782    2.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197   -2.1217   -0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6585   -0.7586   -1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1976    0.5658   -0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7366    2.0109   -1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8086    0.6907   -2.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    4.8039   -0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3048    3.2295   -1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094    3.6649    0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235    1.3551    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -2.9331   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512   -4.5762   -0.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718   -3.1237   -0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0959   -3.9543    1.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286   -2.5068    1.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2318   -4.0252    0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582   -3.8582    2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6126   -0.0057   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -1.0153   -3.4556 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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 14 27  1  0
 27 28  1  0
 27 29  1  0
  6 30  1  0
 30 31  2  0
 31 32  1  0
 31  3  1  0
 26 17  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
 10 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
 13 49  1  0
 13 50  1  0
 18 51  1  0
 19 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 25 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  0
 32 68  1  0
M  END

[NO NAME]
  Mrv0541 09021220312D          
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
    3.7935   -2.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    1.1418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8062    2.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2686    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    0.4273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0936    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5061    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3311    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7436    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7436    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5686    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5686    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9812    2.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2187    3.2853    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
  2 31  1  0  0  0  0
  3 27  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>
HMDB0013961

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1

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

> <INCHI_KEY>
OAAPYTCHFIIVON-UHFFFAOYSA-N

> <FORMULA>
C26H36N2O4

> <MOLECULAR_WEIGHT>
440.575

> <EXACT_MASS>
440.26750765

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
50.79955008872245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
4.408625715808291

> <ALOGPS_LOGS>
-4.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.268739644861553

> <JCHEM_PKA_STRONGEST_BASIC>
9.438919752206088

> <JCHEM_POLAR_SURFACE_AREA>
74.95

> <JCHEM_REFRACTIVITY>
128.16559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.62e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013961
     RDKit          3D
O-Desmethylverapamil (D-702)
 68 69  0  0  0  0  0  0  0  0999 V2000
    9.3127    0.4486   -1.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1298    0.0678   -1.7463 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8655    0.4216   -1.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6334    1.1794   -0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3451    1.5162    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    1.0849   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590    1.4183   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146    0.2845    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699    0.4090    1.3630 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0455    1.4477    2.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854   -0.9011    1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -1.1056    2.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8561   -0.7427    1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3027   -1.2855    0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168   -0.9323   -0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982   -0.6527   -1.3659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4652   -0.4931   -0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714   -1.0411   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7432   -0.2671   -0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6320    1.0907   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6996    1.8863   -1.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9092    1.2610   -1.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4241    1.6549   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897    3.0235   -0.7756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1191    3.7374   -0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3756    0.8963   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5335   -2.7365    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -3.6027    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5544   -3.2709    1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798    0.3238   -1.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7661   -0.0107   -2.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550   -0.7761   -3.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2194    0.5087    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1490   -0.2802   -1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6504    1.4716   -1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4949    1.5245    0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2189    2.1141    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235    2.3354    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845    1.5092   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971   -0.7171    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1040    0.2768    1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    2.3982    1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0752    1.6993    2.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403    1.3626    3.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -1.2113    2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8553   -1.5851    0.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850   -0.5347    3.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367   -2.1653    2.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971    0.3954    1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -0.8782    2.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197   -2.1217   -0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6585   -0.7586   -1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1976    0.5658   -0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7366    2.0109   -1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8086    0.6907   -2.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    4.8039   -0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3048    3.2295   -1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094    3.6649    0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235    1.3551    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -2.9331   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512   -4.5762   -0.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718   -3.1237   -0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0959   -3.9543    1.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286   -2.5068    1.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2318   -4.0252    0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582   -3.8582    2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6126   -0.0057   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -1.0153   -3.4556 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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 14 27  1  0
 27 28  1  0
 27 29  1  0
  6 30  1  0
 30 31  2  0
 31 32  1  0
 31  3  1  0
 26 17  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
 10 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
 13 49  1  0
 13 50  1  0
 18 51  1  0
 19 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 25 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 29 64  1  0
 29 65  1  0
 29 66  1  0
 30 67  1  0
 32 68  1  0
M  END

HEADER    PROTEIN                                 02-SEP-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-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      10.931   4.799   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415  -3.053   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.011   4.799   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081  -3.823   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.551   4.799   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.321   3.465   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.321   6.133   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.861   3.465   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.080  -3.053   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.861   6.133   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.632   4.799   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.415  -6.133   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   28                                                       
CONECT    2   23   31                                                       
CONECT    3   27                                                            
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    2                                                            
CONECT   32    4                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0013961
HETATM    1  C1  UNL     1       9.313   0.449  -1.101  1.00  0.00           C  
HETATM    2  O1  UNL     1       8.130   0.068  -1.746  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.866   0.422  -1.298  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.633   1.179  -0.173  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.345   1.516   0.247  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.257   1.085  -0.473  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.859   1.418  -0.030  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.415   0.285   0.828  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.070   0.409   1.363  1.00  0.00           N  
HETATM   10  C8  UNL     1       1.046   1.448   2.311  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.685  -0.901   1.755  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.625  -1.106   2.380  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.856  -0.743   1.701  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.303  -1.285   0.423  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.217  -0.932  -0.582  1.00  0.00           C  
HETATM   16  N2  UNL     1      -0.398  -0.653  -1.366  1.00  0.00           N  
HETATM   17  C14 UNL     1      -3.465  -0.493  -0.089  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.671  -1.041  -0.438  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.743  -0.267  -0.890  1.00  0.00           C  
HETATM   20  C17 UNL     1      -5.632   1.091  -1.007  1.00  0.00           C  
HETATM   21  O2  UNL     1      -6.700   1.886  -1.458  1.00  0.00           O  
HETATM   22  C18 UNL     1      -7.909   1.261  -1.791  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.424   1.655  -0.662  1.00  0.00           C  
HETATM   24  O3  UNL     1      -4.290   3.023  -0.776  1.00  0.00           O  
HETATM   25  C20 UNL     1      -3.119   3.737  -0.467  1.00  0.00           C  
HETATM   26  C21 UNL     1      -3.376   0.896  -0.219  1.00  0.00           C  
HETATM   27  C22 UNL     1      -2.533  -2.737   0.267  1.00  0.00           C  
HETATM   28  C23 UNL     1      -1.284  -3.603   0.411  1.00  0.00           C  
HETATM   29  C24 UNL     1      -3.554  -3.271   1.280  1.00  0.00           C  
HETATM   30  C25 UNL     1       4.480   0.324  -1.604  1.00  0.00           C  
HETATM   31  C26 UNL     1       5.766  -0.011  -2.023  1.00  0.00           C  
HETATM   32  O4  UNL     1       5.955  -0.776  -3.161  1.00  0.00           O  
HETATM   33  H1  UNL     1       9.219   0.509   0.002  1.00  0.00           H  
HETATM   34  H2  UNL     1      10.149  -0.280  -1.293  1.00  0.00           H  
HETATM   35  H3  UNL     1       9.650   1.472  -1.447  1.00  0.00           H  
HETATM   36  H4  UNL     1       7.495   1.525   0.400  1.00  0.00           H  
HETATM   37  H5  UNL     1       5.219   2.114   1.136  1.00  0.00           H  
HETATM   38  H6  UNL     1       2.924   2.335   0.566  1.00  0.00           H  
HETATM   39  H7  UNL     1       2.184   1.509  -0.915  1.00  0.00           H  
HETATM   40  H8  UNL     1       2.597  -0.717   0.362  1.00  0.00           H  
HETATM   41  H9  UNL     1       3.104   0.277   1.729  1.00  0.00           H  
HETATM   42  H10 UNL     1       0.733   2.398   1.786  1.00  0.00           H  
HETATM   43  H11 UNL     1       2.075   1.699   2.699  1.00  0.00           H  
HETATM   44  H12 UNL     1       0.340   1.363   3.156  1.00  0.00           H  
HETATM   45  H13 UNL     1       1.459  -1.211   2.545  1.00  0.00           H  
HETATM   46  H14 UNL     1       0.855  -1.585   0.927  1.00  0.00           H  
HETATM   47  H15 UNL     1      -0.585  -0.535   3.391  1.00  0.00           H  
HETATM   48  H16 UNL     1      -0.637  -2.165   2.773  1.00  0.00           H  
HETATM   49  H17 UNL     1      -1.897   0.395   1.601  1.00  0.00           H  
HETATM   50  H18 UNL     1      -2.696  -0.878   2.495  1.00  0.00           H  
HETATM   51  H19 UNL     1      -4.820  -2.122  -0.391  1.00  0.00           H  
HETATM   52  H20 UNL     1      -6.659  -0.759  -1.147  1.00  0.00           H  
HETATM   53  H21 UNL     1      -8.198   0.566  -0.977  1.00  0.00           H  
HETATM   54  H22 UNL     1      -8.737   2.011  -1.927  1.00  0.00           H  
HETATM   55  H23 UNL     1      -7.809   0.691  -2.729  1.00  0.00           H  
HETATM   56  H24 UNL     1      -3.258   4.804  -0.807  1.00  0.00           H  
HETATM   57  H25 UNL     1      -2.305   3.230  -1.060  1.00  0.00           H  
HETATM   58  H26 UNL     1      -2.909   3.665   0.617  1.00  0.00           H  
HETATM   59  H27 UNL     1      -2.424   1.355   0.034  1.00  0.00           H  
HETATM   60  H28 UNL     1      -2.954  -2.933  -0.727  1.00  0.00           H  
HETATM   61  H29 UNL     1      -1.451  -4.576  -0.179  1.00  0.00           H  
HETATM   62  H30 UNL     1      -0.472  -3.124  -0.133  1.00  0.00           H  
HETATM   63  H31 UNL     1      -1.096  -3.954   1.423  1.00  0.00           H  
HETATM   64  H32 UNL     1      -4.129  -2.507   1.784  1.00  0.00           H  
HETATM   65  H33 UNL     1      -4.232  -4.025   0.846  1.00  0.00           H  
HETATM   66  H34 UNL     1      -2.958  -3.858   2.047  1.00  0.00           H  
HETATM   67  H35 UNL     1       3.613  -0.006  -2.155  1.00  0.00           H  
HETATM   68  H36 UNL     1       6.888  -1.015  -3.456  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    6   37
CONECT    6    7   30
CONECT    7    8   38   39
CONECT    8    9   40   41
CONECT    9   10   11
CONECT   10   42   43   44
CONECT   11   12   45   46
CONECT   12   13   47   48
CONECT   13   14   49   50
CONECT   14   15   17   27
CONECT   15   16   16   16
CONECT   17   18   18   26
CONECT   18   19   51
CONECT   19   20   20   52
CONECT   20   21   23
CONECT   21   22
CONECT   22   53   54   55
CONECT   23   24   26   26
CONECT   24   25
CONECT   25   56   57   58
CONECT   26   59
CONECT   27   28   29   60
CONECT   28   61   62   63
CONECT   29   64   65   66
CONECT   30   31   31   67
CONECT   31   32
CONECT   32   68
END

HMDB0013961
     RDKit          3D
O-Desmethylverapamil (D-702)
 68 69  0  0  0  0  0  0  0  0999 V2000
    9.3127    0.4486   -1.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1298    0.0678   -1.7463 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8655    0.4216   -1.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6334    1.1794   -0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3451    1.5162    0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2570    1.0849   -0.4731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8590    1.4183   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146    0.2845    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699    0.4090    1.3630 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0455    1.4477    2.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854   -0.9011    1.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6250   -1.1056    2.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8561   -0.7427    1.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3027   -1.2855    0.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168   -0.9323   -0.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3982   -0.6527   -1.3659 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4652   -0.4931   -0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6714   -1.0411   -0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7432   -0.2671   -0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6320    1.0907   -1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6996    1.8863   -1.4579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9092    1.2610   -1.7911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4241    1.6549   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2897    3.0235   -0.7756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1191    3.7374   -0.4670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3756    0.8963   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5335   -2.7365    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -3.6027    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5544   -3.2709    1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798    0.3238   -1.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7661   -0.0107   -2.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550   -0.7761   -3.1610 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2194    0.5087    0.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1490   -0.2802   -1.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6504    1.4716   -1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4949    1.5245    0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2189    2.1141    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235    2.3354    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845    1.5092   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971   -0.7171    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1040    0.2768    1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    2.3982    1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0752    1.6993    2.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3403    1.3626    3.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -1.2113    2.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8553   -1.5851    0.9273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5850   -0.5347    3.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6367   -2.1653    2.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971    0.3954    1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -0.8782    2.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197   -2.1217   -0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6585   -0.7586   -1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1976    0.5658   -0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7366    2.0109   -1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8086    0.6907   -2.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    4.8039   -0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3048    3.2295   -1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9094    3.6649    0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4235    1.3551    0.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9545   -2.9331   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512   -4.5762   -0.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718   -3.1237   -0.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0959   -3.9543    1.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286   -2.5068    1.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2318   -4.0252    0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582   -3.8582    2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6126   -0.0057   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -1.0153   -3.4556 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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  3  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 14 27  1  0
 27 28  1  0
 27 29  1  0
  6 30  1  0
 30 31  2  0
 31 32  1  0
 31  3  1  0
 26 17  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
 10 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
 13 49  1  0
 13 50  1  0
 18 51  1  0
 19 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 25 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  0
 27 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 29 64  1  0
 29 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

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1

InChI Identifier

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

InChI Key

OAAPYTCHFIIVON-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
Methoxyphenol
Phenylpropane
Phenethylamine
Phenol ether
Phenoxy compound
Methoxybenzene
Anisole
Aralkylamine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Tertiary aliphatic amine
Tertiary amine
Ether
Carbonitrile
Nitrile
Organic oxygen compound
Amine
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Liver (HMDB: HMDB0013961)
Kidney (HMDB: HMDB0013961)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

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	0.0086 g/L	ALOGPS
logP	4.57	ALOGPS
logP	4.41	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	9.44	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	50.8 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]+	204.976	31661259
DarkChem	[M-H]-	207.221	31661259
DeepCCS	[M+H]+	211.637	30932474
DeepCCS	[M-H]-	209.279	30932474
DeepCCS	[M-2H]-	242.62	30932474
DeepCCS	[M+Na]+	217.849	30932474
AllCCS	[M+H]+	211.4	32859911
AllCCS	[M+H-H2O]+	209.2	32859911
AllCCS	[M+NH4]+	213.4	32859911
AllCCS	[M+Na]+	214.0	32859911
AllCCS	[M-H]-	212.1	32859911
AllCCS	[M+Na-2H]-	213.5	32859911
AllCCS	[M+HCOO]-	215.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethylverapamil (D-702)	COC1=C(O)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1	3969.1	Standard polar	33892256
O-Desmethylverapamil (D-702)	COC1=C(O)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1	3068.6	Standard non polar	33892256
O-Desmethylverapamil (D-702)	COC1=C(O)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1	3197.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethylverapamil (D-702),1TMS,isomer #1	COC1=CC=C(C(C#N)(CCCN(C)CCC2=CC=C(OC)C(O[Si](C)(C)C)=C2)C(C)C)C=C1OC	3119.2	Semi standard non polar	33892256
O-Desmethylverapamil (D-702),1TBDMS,isomer #1	COC1=CC=C(C(C#N)(CCCN(C)CCC2=CC=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2)C(C)C)C=C1OC	3324.8	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-702) GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-6896300000-58f7a61a50f3b7247ea5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylverapamil (D-702) GC-MS (1 TMS) - 70eV, Positive	splash10-05mk-6091600000-24afe6aead6bb47ed327	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylverapamil (D-702) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylverapamil (D-702) 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-702) 10V, Positive-QTOF	splash10-0006-0101900000-370d6f3bbeae9ce80c2c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 20V, Positive-QTOF	splash10-0uk9-0885900000-2742c7b0dd554dc42090	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 40V, Positive-QTOF	splash10-0udi-2961000000-f1e6da54d14d6c755124	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 10V, Negative-QTOF	splash10-000i-0000900000-6f141a7eb3d926d1b76f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 20V, Negative-QTOF	splash10-0079-0132900000-0ff8902f6a18559bc506	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 40V, Negative-QTOF	splash10-00e9-0392100000-b7b26c285bf28998b88c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 10V, Negative-QTOF	splash10-000i-0000900000-f40cd4fbfec76fb6436f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 20V, Negative-QTOF	splash10-0a4r-0223900000-b0be793ca65b5346fb93	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 40V, Negative-QTOF	splash10-000i-0932400000-557df004a6b823bb6aad	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 10V, Positive-QTOF	splash10-0006-0100900000-9cc4ee8ba37d45bd37ea	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 20V, Positive-QTOF	splash10-0h2f-2490300000-d169555f5ce9f7012f82	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylverapamil (D-702) 40V, Positive-QTOF	splash10-0udi-0980000000-d83c07cf84cc7e8b161b	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Verapamil Action Pathway		Not Available

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750721

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

Only showing the first 10 proteins. There are 38 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

6. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

9. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

10. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Oostendorp RL, van de Steeg E, van der Kruijssen CM, Beijnen JH, Kenworthy KE, Schinkel AH, Schellens JH: Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors. Drug Metab Dispos. 2009 Apr;37(4):917-23. doi: 10.1124/dmd.108.024901. Epub 2009 Jan 12. [PubMed:19139163 ]

Enzyme Details

2. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]
Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]

Enzyme Details

3. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MRP2 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):773-9. [PubMed:12134946 ]

Enzyme Details

4. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Lespine A, Dupuy J, Orlowski S, Nagy T, Glavinas H, Krajcsi P, Alvinerie M: Interaction of ivermectin with multidrug resistance proteins (MRP1, 2 and 3). Chem Biol Interact. 2006 Feb 25;159(3):169-79. Epub 2005 Dec 27. [PubMed:16384552 ]

Enzyme Details

5. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

References

Zeng H, Chen ZS, Belinsky MG, Rea PA, Kruh GD: Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32. [PubMed:11585759 ]

Enzyme Details

6. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]

Enzyme Details

7. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Perloff MD, von Moltke LL, Fahey JM, Daily JP, Greenblatt DJ: Induction of P-glycoprotein expression by HIV protease inhibitors in cell culture. AIDS. 2000 Jun 16;14(9):1287-9. [PubMed:10894301 ]
Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [PubMed:12387747 ]
Choo EF, Leake B, Wandel C, Imamura H, Wood AJ, Wilkinson GR, Kim RB: Pharmacological inhibition of P-glycoprotein transport enhances the distribution of HIV-1 protease inhibitors into brain and testes. Drug Metab Dispos. 2000 Jun;28(6):655-60. [PubMed:10820137 ]
Kawahara I, Kato Y, Suzuki H, Achira M, Ito K, Crespi CL, Sugiyama Y: Selective inhibition of human cytochrome P450 3A4 by N-[2(R)-hydroxy-1(S)-indanyl]-5-[2(S)-(1, 1-dimethylethylaminocarbonyl)-4-[(furo[2, 3-b]pyridin-5-yl)methyl]piperazin-1-yl]-4(S)-hydroxy-2(R)-phenylmethy lpentanamide and P-glycoprotein by valspodar in gene transfectant systems. Drug Metab Dispos. 2000 Oct;28(10):1238-43. [PubMed:10997946 ]
Fujita R, Ishikawa M, Takayanagi M, Takayanagi Y, Sasaki K: Enhancement of doxorubicin activity in multidrug-resistant cells by mefloquine. Methods Find Exp Clin Pharmacol. 2000 Jun;22(5):281-4. [PubMed:11031728 ]
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Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
Leonessa F, Kim JH, Ghiorghis A, Kulawiec RJ, Hammer C, Talebian A, Clarke R: C-7 analogues of progesterone as potent inhibitors of the P-glycoprotein efflux pump. J Med Chem. 2002 Jan 17;45(2):390-8. [PubMed:11784143 ]
Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MDR1 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):765-72. [PubMed:12134945 ]
Zhang S, Morris ME: Effects of the flavonoids biochanin A, morin, phloretin, and silymarin on P-glycoprotein-mediated transport. J Pharmacol Exp Ther. 2003 Mar;304(3):1258-67. [PubMed:12604704 ]
Horie K, Tang F, Borchardt RT: Isolation and characterization of Caco-2 subclones expressing high levels of multidrug resistance protein efflux transporter. Pharm Res. 2003 Feb;20(2):161-8. [PubMed:12636153 ]
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van der Sandt IC, Blom-Roosemalen MC, de Boer AG, Breimer DD: Specificity of doxorubicin versus rhodamine-123 in assessing P-glycoprotein functionality in the LLC-PK1, LLC-PK1:MDR1 and Caco-2 cell lines. Eur J Pharm Sci. 2000 Sep;11(3):207-14. [PubMed:11042226 ]
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Hait WN, Gesmonde JF, Murren JR, Yang JM, Chen HX, Reiss M: Terfenadine (Seldane): a new drug for restoring sensitivity to multidrug resistant cancer cells. Biochem Pharmacol. 1993 Jan 26;45(2):401-6. [PubMed:8094615 ]
Pouliot JF, L'Heureux F, Liu Z, Prichard RK, Georges E: Reversal of P-glycoprotein-associated multidrug resistance by ivermectin. Biochem Pharmacol. 1997 Jan 10;53(1):17-25. [PubMed:8960059 ]
Kuhnel JM, Perrot JY, Faussat AM, Marie JP, Schwaller MA: Functional assay of multidrug resistant cells using JC-1, a carbocyanine fluorescent probe. Leukemia. 1997 Jul;11(7):1147-55. [PubMed:9205004 ]
Kim AE, Dintaman JM, Waddell DS, Silverman JA: Saquinavir, an HIV protease inhibitor, is transported by P-glycoprotein. J Pharmacol Exp Ther. 1998 Sep;286(3):1439-45. [PubMed:9732409 ]
Bebawy M, Morris MB, Roufogalis BD: A continuous fluorescence assay for the study of P-glycoprotein-mediated drug efflux using inside-out membrane vesicles. Anal Biochem. 1999 Mar 15;268(2):270-7. [PubMed:10075817 ]
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Baltes S, Gastens AM, Fedrowitz M, Potschka H, Kaever V, Loscher W: Differences in the transport of the antiepileptic drugs phenytoin, levetiracetam and carbamazepine by human and mouse P-glycoprotein. Neuropharmacology. 2007 Feb;52(2):333-46. Epub 2006 Oct 10. [PubMed:17045309 ]
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Chiu LY, Ko JL, Lee YJ, Yang TY, Tee YT, Sheu GT: L-type calcium channel blockers reverse docetaxel and vincristine-induced multidrug resistance independent of ABCB1 expression in human lung cancer cell lines. Toxicol Lett. 2010 Feb 15;192(3):408-18. doi: 10.1016/j.toxlet.2009.11.018. Epub 2009 Nov 26. [PubMed:19944135 ]
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Dahan A, Amidon GL: Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G371-7. doi: 10.1152/ajpgi.00102.2009. Epub 2009 Jun 18. [PubMed:19541926 ]
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Dahan A, Sabit H, Amidon GL: The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009 Jun;11(2):205-13. doi: 10.1208/s12248-009-9092-5. Epub 2009 Mar 25. [PubMed:19319690 ]
Pauli-Magnus C, von Richter O, Burk O, Ziegler A, Mettang T, Eichelbaum M, Fromm MF: Characterization of the major metabolites of verapamil as substrates and inhibitors of P-glycoprotein. J Pharmacol Exp Ther. 2000 May;293(2):376-82. [PubMed:10773005 ]
Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [PubMed:11785684 ]
Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]
Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [PubMed:12954186 ]
Dagenais C, Graff CL, Pollack GM: Variable modulation of opioid brain uptake by P-glycoprotein in mice. Biochem Pharmacol. 2004 Jan 15;67(2):269-76. [PubMed:14698039 ]
Borgnia MJ, Eytan GD, Assaraf YG: Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71. [PubMed:8621716 ]
Collett A, Tanianis-Hughes J, Hallifax D, Warhurst G: Predicting P-glycoprotein effects on oral absorption: correlation of transport in Caco-2 with drug pharmacokinetics in wild-type and mdr1a(-/-) mice in vivo. Pharm Res. 2004 May;21(5):819-26. [PubMed:15180340 ]
Tfelt-Hansen P, Tfelt-Hansen J: Verapamil for cluster headache. Clinical pharmacology and possible mode of action. Headache. 2009 Jan;49(1):117-25. doi: 10.1111/j.1526-4610.2008.01298.x. [PubMed:19125880 ]

Enzyme Details

8. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
Brown NL, Sirugue O, Worcel M: The effects of some slow channel blocking drugs on high affinity serotonin uptake by rat brain synaptosomes. Eur J Pharmacol. 1986 Apr 9;123(1):161-5. [PubMed:2940099 ]

Enzyme Details

9. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Ozvegy-Laczka C, Hegedus T, Varady G, Ujhelly O, Schuetz JD, Varadi A, Keri G, Orfi L, Nemet K, Sarkadi B: High-affinity interaction of tyrosine kinase inhibitors with the ABCG2 multidrug transporter. Mol Pharmacol. 2004 Jun;65(6):1485-95. [PubMed:15155841 ]

Enzyme Details

10. Solute carrier family 22 member 4

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:: SLC22A4
Uniprot ID:: Q9H015
Molecular weight:: 62154.5

References

Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]
Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [PubMed:10825452 ]

Only showing the first 10 proteins. There are 38 proteins in total.

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Showing metabocard for O-Desmethylverapamil (D-702) (HMDB0013961)

MOL for HMDB0013961 (O-Desmethylverapamil (D-702))

3D MOL for HMDB0013961 (O-Desmethylverapamil (D-702))

3D SDF for HMDB0013961 (O-Desmethylverapamil (D-702))

3D-SDF for HMDB0013961 (O-Desmethylverapamil (D-702))

PDB for HMDB0013961 (O-Desmethylverapamil (D-702))

3D PDB for HMDB0013961 (O-Desmethylverapamil (D-702))

SMILES for HMDB0013961 (O-Desmethylverapamil (D-702))

INCHI for HMDB0013961 (O-Desmethylverapamil (D-702))

Structure for HMDB0013961 (O-Desmethylverapamil (D-702))

3D Structure for HMDB0013961 (O-Desmethylverapamil (D-702))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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