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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (19)transporters (1) Show 20 proteins XML

enzymes (19)transporters (1) Show 20 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015158

Secondary Accession Numbers

HMDB15158

Metabolite Identification

Common Name

Felodipine

Description

Felodipine is a long-acting 1,4-dihydropyridine calcium channel blocker (CCB)b. It acts primarily on vascular smooth muscle cells by stabilizing voltage-gated L-type calcium channels in their inactive conformation. By inhibiting the influx of calcium in smooth muscle cells, felodipine prevents calcium-dependent myocyte contraction and vasoconstriction. Felodipine is the most potent CCB in use and is unique in that it exhibits fluorescent activity. In addition to binding to L-type calcium channels, felodipine binds to a number of calcium-binding proteins, exhibits competitive antagonism of the mineralcorticoid receptor, inhibits the activity of calmodulin-dependent cyclic nucleotide phosphodiesterase, and blocks calcium influx through voltage-gated T-type calcium channels. Felodipine is used to treat mild to moderate essential hypertension.

Structure

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

HMDB0015158
     RDKit          3D
Felodipine
 44 45  0  0  0  0  0  0  0  0999 V2000
    3.1015    3.3976    1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    3.7546    0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1885    2.5384   -0.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7934    1.4811   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    1.6694   -1.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    0.2384   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7147   -0.7011   -1.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1642   -0.4977   -2.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196   -1.9535   -1.9008 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2314   -2.1600   -1.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -3.5070   -1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078   -1.2432   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -1.5120   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -0.6237    0.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9282   -2.6835   -0.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598   -2.9745   -0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    0.0721   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634    0.5303    0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    1.7630    1.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807    2.2157    2.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709    1.4128    3.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    0.1537    3.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259   -0.8868    4.5759 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4623   -0.2622    1.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -1.8312    1.6722 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0376    3.3529    0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2421    4.1694    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306    2.4113    1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2805    4.1548   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    4.4253    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8348   -0.3732   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2112    0.2925   -2.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4952   -1.4895   -2.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -2.7194   -2.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7164   -3.3373   -2.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0899   -4.1275   -2.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561   -4.0040   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2169   -3.3210    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9438   -2.1268   -0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5758   -3.8642   -0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9139    0.7708   -1.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335    2.4205    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0172    3.1973    2.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526    1.7778    4.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 17  6  1  0
 24 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

1023
  Mrv0541 02231215112D          

 25 26  0  0  1  0            999 V2000
    6.7495    1.2240    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.3183    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.5693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1818    0.4752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2 20  1  0  0  0  0
  3 14  1  0  0  0  0
  3 23  1  0  0  0  0
  4 17  1  0  0  0  0
  4 24  1  0  0  0  0
  5 14  2  0  0  0  0
  6 17  2  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
  9 14  1  0  0  0  0
 10 13  2  0  0  0  0
 10 17  1  0  0  0  0
 11 18  2  0  0  0  0
 11 19  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015158

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1=C(C)NC(C)=C(C1C1=C(Cl)C(Cl)=CC=C1)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C18H19Cl2NO4/c1-5-25-18(23)14-10(3)21-9(2)13(17(22)24-4)15(14)11-7-6-8-12(19)16(11)20/h6-8,15,21H,5H2,1-4H3

> <INCHI_KEY>
RZTAMFZIAATZDJ-UHFFFAOYSA-N

> <FORMULA>
C18H19Cl2NO4

> <MOLECULAR_WEIGHT>
384.254

> <EXACT_MASS>
383.069113515

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.0448456046199

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

> <ALOGPS_LOGP>
4.36

> <JCHEM_LOGP>
3.4404073996666664

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.38827273418849

> <JCHEM_POLAR_SURFACE_AREA>
64.63

> <JCHEM_REFRACTIVITY>
99.19820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
felodipine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015158
     RDKit          3D
Felodipine
 44 45  0  0  0  0  0  0  0  0999 V2000
    3.1015    3.3976    1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    3.7546    0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1885    2.5384   -0.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7934    1.4811   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    1.6694   -1.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    0.2384   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7147   -0.7011   -1.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1642   -0.4977   -2.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196   -1.9535   -1.9008 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2314   -2.1600   -1.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -3.5070   -1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078   -1.2432   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -1.5120   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -0.6237    0.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9282   -2.6835   -0.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598   -2.9745   -0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    0.0721   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634    0.5303    0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    1.7630    1.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807    2.2157    2.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709    1.4128    3.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    0.1537    3.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259   -0.8868    4.5759 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4623   -0.2622    1.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -1.8312    1.6722 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0376    3.3529    0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2421    4.1694    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306    2.4113    1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2805    4.1548   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    4.4253    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8348   -0.3732   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2112    0.2925   -2.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4952   -1.4895   -2.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -2.7194   -2.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7164   -3.3373   -2.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0899   -4.1275   -2.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561   -4.0040   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2169   -3.3210    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9438   -2.1268   -0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5758   -3.8642   -0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9139    0.7708   -1.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335    2.4205    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0172    3.1973    2.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526    1.7778    4.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 17  6  1  0
 24 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1023                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      12.599   2.285   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0      12.416   4.327   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       5.748  -1.063   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.750  -1.063   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.081   1.247   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.406   0.887   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       9.748  -3.373   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.748  -0.293   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -1.063   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.082  -1.063   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748   1.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -2.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082  -2.603   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -0.293   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -3.373   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.416  -3.373   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416  -0.293   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   2.017   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415   2.017   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.082   3.557   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415   3.557   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.748   4.327   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -0.293   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.083  -0.293   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -1.063   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   20                                                            
CONECT    3   14   23                                                       
CONECT    4   17   24                                                       
CONECT    5   14                                                            
CONECT    6   17                                                            
CONECT    7   12   13                                                       
CONECT    8    9   10   11                                                  
CONECT    9    8   12   14                                                  
CONECT   10    8   13   17                                                  
CONECT   11    8   18   19                                                  
CONECT   12    7    9   15                                                  
CONECT   13    7   10   16                                                  
CONECT   14    3    5    9                                                  
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17    4    6   10                                                  
CONECT   18    1   11   20                                                  
CONECT   19   11   21                                                       
CONECT   20    2   18   22                                                  
CONECT   21   19   22                                                       
CONECT   22   20   21                                                       
CONECT   23    3   25                                                       
CONECT   24    4                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0015158
HETATM    1  C1  UNL     1       3.101   3.398   1.102  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.901   3.755   0.240  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.189   2.538  -0.032  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.793   1.481  -0.697  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.977   1.669  -1.030  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.045   0.238  -0.967  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.715  -0.701  -1.596  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.164  -0.498  -2.012  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.120  -1.953  -1.901  1.00  0.00           N  
HETATM   10  C7  UNL     1      -0.231  -2.160  -1.501  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.858  -3.507  -1.830  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.908  -1.243  -0.880  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.307  -1.512  -0.486  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.984  -0.624   0.123  1.00  0.00           O  
HETATM   15  O4  UNL     1      -2.928  -2.684  -0.742  1.00  0.00           O  
HETATM   16  C11 UNL     1      -4.260  -2.975  -0.380  1.00  0.00           C  
HETATM   17  C12 UNL     1      -0.335   0.072  -0.572  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.663   0.530   0.795  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.228   1.763   1.028  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.581   2.216   2.276  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.371   1.413   3.376  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.802   0.154   3.188  1.00  0.00           C  
HETATM   23 CL1  UNL     1      -0.526  -0.887   4.576  1.00  0.00          CL  
HETATM   24  C18 UNL     1      -0.462  -0.262   1.924  1.00  0.00           C  
HETATM   25 CL2  UNL     1       0.249  -1.831   1.672  1.00  0.00          CL  
HETATM   26  H1  UNL     1       4.038   3.353   0.490  1.00  0.00           H  
HETATM   27  H2  UNL     1       3.242   4.169   1.875  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.931   2.411   1.578  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.280   4.155  -0.711  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.235   4.425   0.792  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.835  -0.373  -1.171  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.211   0.292  -2.766  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.495  -1.490  -2.475  1.00  0.00           H  
HETATM   34  H9  UNL     1       1.638  -2.719  -2.404  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.716  -3.337  -2.477  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.090  -4.128  -2.385  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.156  -4.004  -0.902  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.217  -3.321   0.691  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.944  -2.127  -0.507  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.576  -3.864  -0.963  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.914   0.771  -1.265  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.434   2.421   0.197  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.017   3.197   2.365  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.653   1.778   4.360  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   17
CONECT    7    8    9
CONECT    8   31   32   33
CONECT    9   10   34
CONECT   10   11   12   12
CONECT   11   35   36   37
CONECT   12   13   17
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   38   39   40
CONECT   17   18   41
CONECT   18   19   19   24
CONECT   19   20   42
CONECT   20   21   21   43
CONECT   21   22   44
CONECT   22   23   24   24
CONECT   24   25
END

HMDB0015158
     RDKit          3D
Felodipine
 44 45  0  0  0  0  0  0  0  0999 V2000
    3.1015    3.3976    1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9015    3.7546    0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1885    2.5384   -0.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7934    1.4811   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9770    1.6694   -1.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0449    0.2384   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7147   -0.7011   -1.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1642   -0.4977   -2.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1196   -1.9535   -1.9008 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2314   -2.1600   -1.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8580   -3.5070   -1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9078   -1.2432   -0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3067   -1.5120   -0.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -0.6237    0.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9282   -2.6835   -0.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2598   -2.9745   -0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    0.0721   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634    0.5303    0.7953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    1.7630    1.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5807    2.2157    2.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709    1.4128    3.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    0.1537    3.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259   -0.8868    4.5759 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4623   -0.2622    1.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2491   -1.8312    1.6722 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0376    3.3529    0.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2421    4.1694    1.8755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9306    2.4113    1.5784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2805    4.1548   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    4.4253    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8348   -0.3732   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2112    0.2925   -2.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4952   -1.4895   -2.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -2.7194   -2.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7164   -3.3373   -2.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0899   -4.1275   -2.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1561   -4.0040   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2169   -3.3210    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9438   -2.1268   -0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5758   -3.8642   -0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9139    0.7708   -1.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4335    2.4205    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0172    3.1973    2.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526    1.7778    4.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 12 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 17  6  1  0
 24 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate	ChEBI
3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate	ChEBI
4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid ethyl methyl ester	ChEBI
Felodipina	ChEBI
Felodipinum	ChEBI
Plendil	Kegg
(+-)-Ethyl methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid	Generator
3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylic acid	Generator
4-(2,3-Dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate ethyl methyl ester	Generator
DL-Felodipine	HMDB
1a Brand OF felodipine	HMDB
Alpharma brand OF felodipine	HMDB
AstraZeneca brand OF felodipine	HMDB
Azupharma brand OF felodipine	HMDB
Felo biochemie	HMDB
Felo puren	HMDB
Felobeta	HMDB
Felodur	HMDB
Heumann brand OF felodipine	HMDB
Hoechst brand OF felodipine	HMDB
Pharmacia spain brand OF felodipine	HMDB
TheraPharm brand OF felodipine	HMDB
Felo-puren	HMDB
Felocor	HMDB
Felodipin heumann	HMDB
Felodipin stada	HMDB
Felodipin dura	HMDB
Munobal	HMDB
Pharmaceutica astra brand OF felodipine	HMDB
Wörwag brand OF felodipine	HMDB
CT Arzneimittel brand OF felodipine	HMDB
CT-Arzneimittel brand OF felodipine	HMDB
Aliud brand OF felodipine	HMDB
Alphapharm brand OF felodipine	HMDB
Astra brand OF felodipine	HMDB
BC Brand OF felodipine	HMDB
Felodipin al	HMDB
Felodipin azu	HMDB
Felodipin ratiopharm	HMDB
Merck dura brand OF felodipine	HMDB
Perfudal	HMDB
Promed brand OF felodipine	HMDB
Stadapharm brand OF felodipine	HMDB
Betapharm brand OF felodipine	HMDB
Felodipin von CT	HMDB
AbZ brand OF felodipine	HMDB
Agon	HMDB
Aventis brand OF felodipine	HMDB
Felodipin 1a pharma	HMDB
Felodipin abz	HMDB
Felodipin-ratiopharm	HMDB
Felogamma	HMDB
Fensel	HMDB
Flodil	HMDB
Heumann, felodipin	HMDB
Hexal brand OF felodipine	HMDB
Modip	HMDB
Renedil	HMDB
Ratiopharm brand OF felodipine	HMDB
Von CT, felodipin	HMDB

Chemical Formula

C₁₈H₁₉Cl₂NO₄

Average Molecular Weight

384.254

Monoisotopic Molecular Weight

383.069113515

IUPAC Name

3-ethyl 5-methyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Traditional Name

felodipine

CAS Registry Number

72509-76-3

SMILES

CCOC(=O)C1=C(C)NC(C)=C(C1C1=C(Cl)C(Cl)=CC=C1)C(=O)OC

InChI Identifier

InChI=1S/C18H19Cl2NO4/c1-5-25-18(23)14-10(3)21-9(2)13(17(22)24-4)15(14)11-7-6-8-12(19)16(11)20/h6-8,15,21H,5H2,1-4H3

InChI Key

RZTAMFZIAATZDJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyridinecarboxylic acids and derivatives. Dihydropyridinecarboxylic acids and derivatives are compounds containing a dihydropyridine moiety bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Dihydropyridinecarboxylic acids and derivatives

Alternative Parents

Substituents

Dihydropyridinecarboxylic acid derivative
1,2-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Enamine
Secondary amine
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Amine
Organohalogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organochloride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ethyl ester (CHEBI:585948 )
dichlorobenzene (CHEBI:585948 )
methyl ester (CHEBI:585948 )
dihydropyridine (CHEBI:585948 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	145 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0072 g/L	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0072 g/L	ALOGPS
logP	4.36	ALOGPS
logP	3.44	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	5.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.2 m³·mol⁻¹	ChemAxon
Polarizability	38.04 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
DeepCCS	[M+H]+	199.057	30932474
DeepCCS	[M-H]-	196.472	30932474
DeepCCS	[M-2H]-	231.468	30932474
DeepCCS	[M+Na]+	207.758	30932474
AllCCS	[M+H]+	184.1	32859911
AllCCS	[M+H-H2O]+	181.2	32859911
AllCCS	[M+NH4]+	186.7	32859911
AllCCS	[M+Na]+	187.5	32859911
AllCCS	[M-H]-	187.8	32859911
AllCCS	[M+Na-2H]-	187.8	32859911
AllCCS	[M+HCOO]-	188.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.2 minutes	32390414
Predicted by Siyang on May 30, 2022	18.1689 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.65 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2950.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	505.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	278.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	110.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	615.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	891.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1466.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	662.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1903.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	520.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	490.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	257.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	33.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Felodipine	CCOC(=O)C1=C(C)NC(C)=C(C1C1=C(Cl)C(Cl)=CC=C1)C(=O)OC	3861.1	Standard polar	33892256
Felodipine	CCOC(=O)C1=C(C)NC(C)=C(C1C1=C(Cl)C(Cl)=CC=C1)C(=O)OC	2456.4	Standard non polar	33892256
Felodipine	CCOC(=O)C1=C(C)NC(C)=C(C1C1=C(Cl)C(Cl)=CC=C1)C(=O)OC	2699.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Felodipine,1TMS,isomer #1	CCOC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl	2629.2	Semi standard non polar	33892256
Felodipine,1TMS,isomer #1	CCOC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl	2266.2	Standard non polar	33892256
Felodipine,1TMS,isomer #1	CCOC(=O)C1=C(C)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl	3365.5	Standard polar	33892256
Felodipine,1TBDMS,isomer #1	CCOC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl	2853.3	Semi standard non polar	33892256
Felodipine,1TBDMS,isomer #1	CCOC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl	2491.2	Standard non polar	33892256
Felodipine,1TBDMS,isomer #1	CCOC(=O)C1=C(C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC(Cl)=C1Cl	3396.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Felodipine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-3009000000-5b611cdc2d075de69610	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Felodipine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Felodipine LC-ESI-qTof , Positive-QTOF	splash10-000j-0922000000-9b26b987caa87b8a13af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Felodipine , positive-QTOF	splash10-0udu-0139000000-085071c20c5d0c134d8f	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 10V, Positive-QTOF	splash10-001r-0019000000-33bf0db3bf36f29993fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 20V, Positive-QTOF	splash10-0fe0-0095000000-c27a529dc8d62e0c3663	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 40V, Positive-QTOF	splash10-004i-0490000000-b027fd5c39a74d5a8983	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 10V, Negative-QTOF	splash10-001i-0009000000-74fea585f5eab97e301d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 20V, Negative-QTOF	splash10-01q9-0029000000-611d97581685b1d82833	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 40V, Negative-QTOF	splash10-0wbc-1095000000-178af93061f6d2ad0db1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 10V, Positive-QTOF	splash10-0019-0009000000-88f48d1738d7c1f69a11	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 20V, Positive-QTOF	splash10-0bu9-0129000000-d31431a7eda7ca7396bc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 40V, Positive-QTOF	splash10-0piu-0982000000-98f7be8fe67f962d9ef1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 10V, Negative-QTOF	splash10-001i-0009000000-e514f5ea1713c07d88b1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 20V, Negative-QTOF	splash10-001i-2009000000-409c00755f945e97a932	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Felodipine 40V, Negative-QTOF	splash10-001i-9280000000-97534f29e936d15877c7	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Felodipine Action Pathway		Not Available
Felodipine Metabolism 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 DB01023	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01023	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01023

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Felodipine

METLIN ID

Not Available

PubChem Compound

3333

PDB ID

Not Available

ChEBI ID

585948

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

Dunselman PH, Edgar B: Felodipine clinical pharmacokinetics. Clin Pharmacokinet. 1991 Dec;21(6):418-30. [PubMed:1782737 ]

Only showing the first 10 proteins. There are 20 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a higher affinity for cGMP than for cAMP.
Gene Name:: PDE1A
Uniprot ID:: P54750
Molecular weight:: 61251.38

References

Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. [PubMed:2933041 ]
Sharma RK, Wang JH, Wu Z: Mechanisms of inhibition of calmodulin-stimulated cyclic nucleotide phosphodiesterase by dihydropyridine calcium antagonists. J Neurochem. 1997 Aug;69(2):845-50. [PubMed:9231746 ]

Enzyme Details

2. Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1B

General function:: Involved in catalytic activity
Specific function:: Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a preference for cGMP as a substrate.
Gene Name:: PDE1B
Uniprot ID:: Q01064
Molecular weight:: 61379.235

References

Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. [PubMed:2933041 ]
Sharma RK, Wang JH, Wu Z: Mechanisms of inhibition of calmodulin-stimulated cyclic nucleotide phosphodiesterase by dihydropyridine calcium antagonists. J Neurochem. 1997 Aug;69(2):845-50. [PubMed:9231746 ]

Enzyme Details

3. 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

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 ]
Galetin A, Clarke SE, Houston JB: Quinidine and haloperidol as modifiers of CYP3A4 activity: multisite kinetic model approach. Drug Metab Dispos. 2002 Dec;30(12):1512-22. [PubMed:12433827 ]

Enzyme Details

4. 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

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 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

6. 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

Enzyme Details

7. 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

Enzyme Details

8. 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

Schoch GA, Yano JK, Sansen S, Dansette PM, Stout CD, Johnson EF: Determinants of cytochrome P450 2C8 substrate binding: structures of complexes with montelukast, troglitazone, felodipine, and 9-cis-retinoic acid. J Biol Chem. 2008 Jun 20;283(25):17227-37. doi: 10.1074/jbc.M802180200. Epub 2008 Apr 15. [PubMed:18413310 ]
Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
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. Calmodulin

General function:: Involved in calcium ion binding
Specific function:: Calmodulin mediates the control of a large number of enzymes and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CEP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis
Gene Name:: CALM1
Uniprot ID:: P62158
Molecular weight:: 16837.5

References

Bostrom SL, Westerlund C, Rochester S, Vogel HJ: Binding of a dihydropyridine felodipine-analogue to calmodulin and related calcium-binding proteins. Biochem Pharmacol. 1988 Oct 1;37(19):3723-8. [PubMed:3178884 ]
Johnson JD, Andrews CT, Khabbaza EJ, Mills JS: The interaction of felodipine with calcium-binding proteins. J Cardiovasc Pharmacol. 1987;10 Suppl 1:S53-9. [PubMed:2442519 ]
Lamers JM, Cysouw KJ, Verdouw PD: Slow calcium channel blockers and calmodulin. Effect of felodipine, nifedipine, prenylamine and bepridil on cardiac sarcolemmal calcium pumping ATPase. Biochem Pharmacol. 1985 Nov 1;34(21):3837-43. [PubMed:2933041 ]
Lamers JM, Verdouw PD, Mas-Oliva J: The effects of felodipine and bepridil on calcium-stimulated calmodulin binding and calcium pumping ATPase of cardiac sarcolemma before and after removal of endogenous calmodulin. Mol Cell Biochem. 1987 Dec;78(2):169-76. [PubMed:2964559 ]
Mills JS, Bailey BL, Johnson JD: Cooperativity among calmodulin's drug binding sites. Biochemistry. 1985 Aug 27;24(18):4897-902. [PubMed:4074665 ]
Walsh MP, Sutherland C, Scott-Woo GC: Effects of felodipine (a dihydropyridine calcium channel blocker) and analogues on calmodulin-dependent enzymes. Biochem Pharmacol. 1988 Apr 15;37(8):1569-80. [PubMed:2833901 ]

Enzyme Details

10. Voltage-dependent L-type calcium channel subunit alpha-1D

General function:: Involved in ion channel activity
Specific function:: Voltage-sensitive calcium channels (VSCC) mediate the entry of calcium ions into excitable cells and are also involved in a variety of calcium-dependent processes, including muscle contraction, hormone or neurotransmitter release, gene expression, cell motility, cell division and cell death. The isoform alpha-1D gives rise to L-type calcium currents. Long-lasting (L-type) calcium channels belong to the 'high-voltage activated' (HVA) group. They are blocked by dihydropyridines (DHP), phenylalkylamines, benzothiazepines, and by omega-agatoxin-IIIA (omega-Aga-IIIA). They are however insensitive to omega-conotoxin- GVIA (omega-CTx-GVIA) and omega-agatoxin-IVA (omega-Aga-IVA)
Gene Name:: CACNA1D
Uniprot ID:: Q01668
Molecular weight:: 245138.8

References

Sinnegger-Brauns MJ, Huber IG, Koschak A, Wild C, Obermair GJ, Einzinger U, Hoda JC, Sartori SB, Striessnig J: Expression and 1,4-dihydropyridine-binding properties of brain L-type calcium channel isoforms. Mol Pharmacol. 2009 Feb;75(2):407-14. doi: 10.1124/mol.108.049981. Epub 2008 Nov 24. [PubMed:19029287 ]

Transporters

Enzyme Details

1. 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

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 ]

Only showing the first 10 proteins. There are 20 proteins in total.

Show all enzymes and transporters

Showing metabocard for Felodipine (HMDB0015158)

MOL for HMDB0015158 (Felodipine)

3D MOL for HMDB0015158 (Felodipine)

3D SDF for HMDB0015158 (Felodipine)

3D-SDF for HMDB0015158 (Felodipine)

PDB for HMDB0015158 (Felodipine)

3D PDB for HMDB0015158 (Felodipine)

SMILES for HMDB0015158 (Felodipine)

INCHI for HMDB0015158 (Felodipine)

Structure for HMDB0015158 (Felodipine)

3D Structure for HMDB0015158 (Felodipine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

Transporters

References