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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-10-17 08:50:19 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005018

Secondary Accession Numbers

HMDB05018

Metabolite Identification

Common Name

Amlodipine

Description

Amlodipine is a long-acting calcium channel blocker used as an anti-hypertensive and in the treatment of angina. As other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance and hence improving blood pressure; in angina it improves blood flow to the myocardium. It was developed under the direction of Dr. Simon Campbell; A long acting dihydropyridine calcium channel blocker. It is effective in the treatment of angina pectoris and hypertension; in angina it improves blood flow to the myocardium. Amlodipine (as besylate, mesylate or maleate) is a long-acting calcium channel blocker used as an anti hypertensive and in the treatment of angina. Amlodipine is marketed as Norvasc in North America and as Istin in the United Kingdom as well as under various other names. As other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance and hence improving blood pressure; Amlodipine (as besylate, mesylate or maleate) is a long-acting calcium channel blocker used as an anti-hypertensive and in the treatment of angina. Amlodipine is marketed as Norvasc in North America and as Istin in the United Kingdom as well as under various other names. As other calcium channel blockers, amlodipine acts by relaxing the smooth muscle in the arterial wall, decreasing peripheral resistance and hence improving blood pressure; in angina it improves blood flow to the myocardium. It was developed under the direction of Dr. Simon Campbell.

Structure

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

381
  Mrv1652305271900022D          

 28 29  0  0  1  0            999 V2000
    6.7495    2.4615    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1818    1.7127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.0443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 15  1  0  0  0  0
  2 24  1  0  0  0  0
  3 16  1  0  0  0  0
  3 25  1  0  0  0  0
  4 18  1  0  0  0  0
  4 27  1  0  0  0  0
  5 16  2  0  0  0  0
  6 18  2  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 26  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  2  0  0  0  0
 10 16  1  0  0  0  0
 11 13  2  0  0  0  0
 11 18  1  0  0  0  0
 12 15  1  0  0  0  0
 13 17  1  0  0  0  0
 14 19  1  0  0  0  0
 14 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
 24 26  1  0  0  0  0
 25 28  1  0  0  0  0
M  END

HMDB0243718
     RDKit          3D
Levamlodipine
 53 54  0  0  0  0  0  0  0  0999 V2000
    0.7025    4.7485   -1.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0775    4.2285   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3640    2.8644   -0.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    1.8610   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7817    2.3419   -0.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728    0.4567   -0.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065   -0.4639   -0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6635   -0.1991   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2936   -0.8207    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6453   -0.5115    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4402   -1.1357    1.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2549   -2.5791    1.3015 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990   -1.8673   -0.7970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -2.2449   -0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -3.7065   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682   -1.3140   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9060   -1.6644   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7888   -0.7723   -0.6017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3337   -2.9792   -0.7265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7246   -3.2234   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1949    0.1605   -0.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    0.7680    0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7662    1.8402    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864    2.4064    1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603    1.9130    2.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017    0.8382    2.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7826    0.2693    1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7113   -1.0732    2.0992 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3646    5.7854   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4561    4.1019   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    4.7135   -1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4846    4.5045    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0482    4.7614   -0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9982    0.7906   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096   -0.7775   -1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8017    0.5976    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9930   -0.9051   -0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781   -0.7917    2.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5182   -0.9419    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315   -2.9723    0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8535   -3.0332    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -2.5934   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0302   -4.2833   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905   -3.8995   -1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4427   -4.0439    0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2447   -2.8240   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9096   -4.3195   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1826   -2.8014    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6334    0.5729   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8880    2.2204   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1495    3.2426    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043    2.3239    3.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3837    0.4308    3.7894 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 21  6  1  0
 27 22  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
M  END

381
  Mrv1652305271900022D          

 28 29  0  0  1  0            999 V2000
    6.7495    2.4615    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.9058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1818    1.7127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.5693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.0443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 15  1  0  0  0  0
  2 24  1  0  0  0  0
  3 16  1  0  0  0  0
  3 25  1  0  0  0  0
  4 18  1  0  0  0  0
  4 27  1  0  0  0  0
  5 16  2  0  0  0  0
  6 18  2  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 26  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  1  0  0  0  0
 10 12  2  0  0  0  0
 10 16  1  0  0  0  0
 11 13  2  0  0  0  0
 11 18  1  0  0  0  0
 12 15  1  0  0  0  0
 13 17  1  0  0  0  0
 14 19  1  0  0  0  0
 14 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  2  0  0  0  0
 24 26  1  0  0  0  0
 25 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005018

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3

> <INCHI_KEY>
HTIQEAQVCYTUBX-UHFFFAOYSA-N

> <FORMULA>
C20H25ClN2O5

> <MOLECULAR_WEIGHT>
408.876

> <EXACT_MASS>
408.145199627

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.31141604801554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
1.6355954516666678

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.12333262212675

> <JCHEM_PKA_STRONGEST_BASIC>
9.445646936621939

> <JCHEM_POLAR_SURFACE_AREA>
99.88

> <JCHEM_REFRACTIVITY>
108.63810000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-amlodipine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0243718
     RDKit          3D
Levamlodipine
 53 54  0  0  0  0  0  0  0  0999 V2000
    0.7025    4.7485   -1.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0775    4.2285   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3640    2.8644   -0.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    1.8610   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7817    2.3419   -0.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728    0.4567   -0.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065   -0.4639   -0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6635   -0.1991   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2936   -0.8207    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6453   -0.5115    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4402   -1.1357    1.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2549   -2.5791    1.3015 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990   -1.8673   -0.7970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -2.2449   -0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -3.7065   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682   -1.3140   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9060   -1.6644   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7888   -0.7723   -0.6017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3337   -2.9792   -0.7265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7246   -3.2234   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1949    0.1605   -0.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    0.7680    0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7662    1.8402    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864    2.4064    1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603    1.9130    2.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017    0.8382    2.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7826    0.2693    1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7113   -1.0732    2.0992 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3646    5.7854   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4561    4.1019   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    4.7135   -1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4846    4.5045    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0482    4.7614   -0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9982    0.7906   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096   -0.7775   -1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8017    0.5976    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9930   -0.9051   -0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781   -0.7917    2.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5182   -0.9419    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315   -2.9723    0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8535   -3.0332    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -2.5934   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0302   -4.2833   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905   -3.8995   -1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4427   -4.0439    0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2447   -2.8240   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9096   -4.3195   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1826   -2.8014    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6334    0.5729   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8880    2.2204   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1495    3.2426    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043    2.3239    3.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3837    0.4308    3.7894 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 21  6  1  0
 27 22  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 381                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1 Cl   UNK     0      12.599   4.595   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.081  -2.603   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.748   1.247   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.750   1.247   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.081   3.557   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.406   3.197   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       9.748  -1.063   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.414  -5.683   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.748   2.017   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   1.247   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082   1.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -0.293   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082  -0.293   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   3.557   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -1.063   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   2.017   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416  -1.063   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.416   2.017   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082   4.327   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   4.327   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082   5.867   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415   5.867   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748   6.637   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.748  -3.373   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414   2.017   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.748  -4.913   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.083   2.017   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.080   1.247   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   15   24                                                       
CONECT    3   16   25                                                       
CONECT    4   18   27                                                       
CONECT    5   16                                                            
CONECT    6   18                                                            
CONECT    7   12   13                                                       
CONECT    8   26                                                            
CONECT    9   10   11   14                                                  
CONECT   10    9   12   16                                                  
CONECT   11    9   13   18                                                  
CONECT   12    7   10   15                                                  
CONECT   13    7   11   17                                                  
CONECT   14    9   19   20                                                  
CONECT   15    2   12                                                       
CONECT   16    3    5   10                                                  
CONECT   17   13                                                            
CONECT   18    4    6   11                                                  
CONECT   19    1   14   21                                                  
CONECT   20   14   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   23                                                       
CONECT   23   21   22                                                       
CONECT   24    2   26                                                       
CONECT   25    3   28                                                       
CONECT   26    8   24                                                       
CONECT   27    4                                                            
CONECT   28   25                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0243718
HETATM    1  C1  UNL     1       0.703   4.748  -1.597  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.078   4.229  -0.424  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.364   2.864  -0.503  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.636   1.861  -0.577  1.00  0.00           C  
HETATM    5  O2  UNL     1       1.782   2.342  -0.564  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.273   0.457  -0.658  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.206  -0.464  -0.735  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.663  -0.199  -0.753  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.294  -0.821   0.345  1.00  0.00           O  
HETATM   10  C7  UNL     1       4.645  -0.512   0.232  1.00  0.00           C  
HETATM   11  C8  UNL     1       5.440  -1.136   1.376  1.00  0.00           C  
HETATM   12  N1  UNL     1       5.255  -2.579   1.302  1.00  0.00           N  
HETATM   13  N2  UNL     1       0.799  -1.867  -0.797  1.00  0.00           N  
HETATM   14  C9  UNL     1      -0.560  -2.245  -0.776  1.00  0.00           C  
HETATM   15  C10 UNL     1      -0.934  -3.706  -0.840  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.468  -1.314  -0.701  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.906  -1.664  -0.674  1.00  0.00           C  
HETATM   18  O4  UNL     1      -3.789  -0.772  -0.602  1.00  0.00           O  
HETATM   19  O5  UNL     1      -3.334  -2.979  -0.727  1.00  0.00           O  
HETATM   20  C13 UNL     1      -4.725  -3.223  -0.695  1.00  0.00           C  
HETATM   21  C14 UNL     1      -1.195   0.161  -0.658  1.00  0.00           C  
HETATM   22  C15 UNL     1      -1.911   0.768   0.500  1.00  0.00           C  
HETATM   23  C16 UNL     1      -2.766   1.840   0.240  1.00  0.00           C  
HETATM   24  C17 UNL     1      -3.486   2.406   1.270  1.00  0.00           C  
HETATM   25  C18 UNL     1      -3.360   1.913   2.547  1.00  0.00           C  
HETATM   26  C19 UNL     1      -2.502   0.838   2.797  1.00  0.00           C  
HETATM   27  C20 UNL     1      -1.783   0.269   1.786  1.00  0.00           C  
HETATM   28 CL1  UNL     1      -0.711  -1.073   2.099  1.00  0.00          CL  
HETATM   29  H1  UNL     1       0.365   5.785  -1.798  1.00  0.00           H  
HETATM   30  H2  UNL     1       0.456   4.102  -2.468  1.00  0.00           H  
HETATM   31  H3  UNL     1       1.796   4.713  -1.363  1.00  0.00           H  
HETATM   32  H4  UNL     1       0.485   4.505   0.495  1.00  0.00           H  
HETATM   33  H5  UNL     1      -1.048   4.761  -0.369  1.00  0.00           H  
HETATM   34  H6  UNL     1       2.998   0.791  -0.934  1.00  0.00           H  
HETATM   35  H7  UNL     1       3.010  -0.778  -1.700  1.00  0.00           H  
HETATM   36  H8  UNL     1       4.802   0.598   0.300  1.00  0.00           H  
HETATM   37  H9  UNL     1       4.993  -0.905  -0.727  1.00  0.00           H  
HETATM   38  H10 UNL     1       5.078  -0.792   2.346  1.00  0.00           H  
HETATM   39  H11 UNL     1       6.518  -0.942   1.254  1.00  0.00           H  
HETATM   40  H12 UNL     1       5.531  -2.972   0.391  1.00  0.00           H  
HETATM   41  H13 UNL     1       5.853  -3.033   2.036  1.00  0.00           H  
HETATM   42  H14 UNL     1       1.537  -2.593  -0.858  1.00  0.00           H  
HETATM   43  H15 UNL     1       0.030  -4.283  -0.983  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.491  -3.899  -1.779  1.00  0.00           H  
HETATM   45  H17 UNL     1      -1.443  -4.044   0.076  1.00  0.00           H  
HETATM   46  H18 UNL     1      -5.245  -2.824  -1.591  1.00  0.00           H  
HETATM   47  H19 UNL     1      -4.910  -4.319  -0.648  1.00  0.00           H  
HETATM   48  H20 UNL     1      -5.183  -2.801   0.238  1.00  0.00           H  
HETATM   49  H21 UNL     1      -1.633   0.573  -1.584  1.00  0.00           H  
HETATM   50  H22 UNL     1      -2.888   2.220  -0.777  1.00  0.00           H  
HETATM   51  H23 UNL     1      -4.149   3.243   1.053  1.00  0.00           H  
HETATM   52  H24 UNL     1      -3.904   2.324   3.387  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.384   0.431   3.789  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   32   33
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   21
CONECT    7    8   13
CONECT    8    9   34   35
CONECT    9   10
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   40   41
CONECT   13   14   42
CONECT   14   15   16   16
CONECT   15   43   44   45
CONECT   16   17   21
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   46   47   48
CONECT   21   22   49
CONECT   22   23   23   27
CONECT   23   24   50
CONECT   24   25   25   51
CONECT   25   26   52
CONECT   26   27   27   53
CONECT   27   28
END

HMDB0243718
     RDKit          3D
Levamlodipine
 53 54  0  0  0  0  0  0  0  0999 V2000
    0.7025    4.7485   -1.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0775    4.2285   -0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3640    2.8644   -0.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    1.8610   -0.5774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7817    2.3419   -0.5642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728    0.4567   -0.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065   -0.4639   -0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6635   -0.1991   -0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2936   -0.8207    0.3445 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6453   -0.5115    0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4402   -1.1357    1.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2549   -2.5791    1.3015 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990   -1.8673   -0.7970 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603   -2.2449   -0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -3.7065   -0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4682   -1.3140   -0.7010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9060   -1.6644   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7888   -0.7723   -0.6017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3337   -2.9792   -0.7265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7246   -3.2234   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1949    0.1605   -0.6575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9106    0.7680    0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7662    1.8402    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864    2.4064    1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603    1.9130    2.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017    0.8382    2.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7826    0.2693    1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7113   -1.0732    2.0992 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3646    5.7854   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4561    4.1019   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    4.7135   -1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4846    4.5045    0.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0482    4.7614   -0.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9982    0.7906   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096   -0.7775   -1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8017    0.5976    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9930   -0.9051   -0.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0781   -0.7917    2.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5182   -0.9419    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5315   -2.9723    0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8535   -3.0332    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -2.5934   -0.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0302   -4.2833   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905   -3.8995   -1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4427   -4.0439    0.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2447   -2.8240   -1.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9096   -4.3195   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1826   -2.8014    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6334    0.5729   -1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8880    2.2204   -0.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1495    3.2426    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043    2.3239    3.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3837    0.4308    3.7894 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 21  6  1  0
 27 22  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  0
 26 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate	ChEBI
Amlodipine free base	ChEBI
Amlodipino	ChEBI
Amlodipinum	ChEBI
Norvasc	Kegg
3-Ethyl-5-methyl (+-)-2-(2-aminoethoxymethyl)-4-(O-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid	Generator
Amlodipine besilate	HMDB
Amlodipine besylate	HMDB
AMVAZ	HMDB
Istin	HMDB
Pelmec	HMDB
Racemic amlodipine	HMDB
Amlodipine, (+-)-isomer	HMDB
Amlodipine, (+-)-isomer, maleate (1:1)	HMDB
Amlodipine, (S)-isomer, maleate (1:1)	HMDB
Amlor	HMDB
Amlodipine, (R)-isomer	HMDB
Pfizer brand OF amlodipine besilate	HMDB
Amlodipine maleate	HMDB
Amlodipine maleate (1:1)	HMDB
Amlodis	HMDB
Astudal	HMDB
Mack brand OF amlodipine besilate	HMDB
Almirall brand OF amlodipine besilate	HMDB
Eczacibasi brand OF amlodipine besilate	HMDB

Chemical Formula

C₂₀H₂₅ClN₂O₅

Average Molecular Weight

408.876

Monoisotopic Molecular Weight

408.145199627

IUPAC Name

3-ethyl 5-methyl 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Traditional Name

(+-)-amlodipine

CAS Registry Number

88150-42-9

SMILES

CCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC

InChI Identifier

InChI=1S/C20H25ClN2O5/c1-4-28-20(25)18-15(11-27-10-9-22)23-12(2)16(19(24)26-3)17(18)13-7-5-6-8-14(13)21/h5-8,17,23H,4,9-11,22H2,1-3H3

InChI Key

HTIQEAQVCYTUBX-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
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
Dialkyl ether
Secondary aliphatic amine
Azacycle
Enamine
Ether
Secondary amine
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Amine
Primary amine
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Primary aliphatic amine
Organohalogen compound
Organochloride
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

ethyl ester (CHEBI:2668 )
primary amino compound (CHEBI:2668 )
methyl ester (CHEBI:2668 )
monochlorobenzenes (CHEBI:2668 )
dihydropyridine (CHEBI:2668 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0243718)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.00	AUSTIN,RP ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	188.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0074 g/L	ALOGPS
logP	2.22	ALOGPS
logP	1.64	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	19.12	ChemAxon
pKa (Strongest Basic)	9.45	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.88 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108.64 m³·mol⁻¹	ChemAxon
Polarizability	42.31 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]+	202.75	30932474
DeepCCS	[M-H]-	200.21	30932474
DeepCCS	[M-2H]-	234.483	30932474
DeepCCS	[M+Na]+	210.773	30932474
AllCCS	[M+H]+	194.3	32859911
AllCCS	[M+H-H2O]+	191.7	32859911
AllCCS	[M+NH4]+	196.6	32859911
AllCCS	[M+Na]+	197.3	32859911
AllCCS	[M-H]-	195.8	32859911
AllCCS	[M+Na-2H]-	196.5	32859911
AllCCS	[M+HCOO]-	197.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amlodipine	CCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC	4272.2	Standard polar	33892256
Amlodipine	CCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC	2879.7	Standard non polar	33892256
Amlodipine	CCOC(=O)C1=C(COCCN)NC(C)=C(C1C1=CC=CC=C1Cl)C(=O)OC	2919.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amlodipine,1TMS,isomer #1	CCOC(=O)C1=C(COCCN[Si](C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	2981.4	Semi standard non polar	33892256
Amlodipine,1TMS,isomer #1	CCOC(=O)C1=C(COCCN[Si](C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	2883.3	Standard non polar	33892256
Amlodipine,1TMS,isomer #1	CCOC(=O)C1=C(COCCN[Si](C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	4398.8	Standard polar	33892256
Amlodipine,1TMS,isomer #2	CCOC(=O)C1=C(COCCN)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	2845.0	Semi standard non polar	33892256
Amlodipine,1TMS,isomer #2	CCOC(=O)C1=C(COCCN)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	2769.0	Standard non polar	33892256
Amlodipine,1TMS,isomer #2	CCOC(=O)C1=C(COCCN)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	4315.0	Standard polar	33892256
Amlodipine,2TMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C)[Si](C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3091.0	Semi standard non polar	33892256
Amlodipine,2TMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C)[Si](C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	2984.2	Standard non polar	33892256
Amlodipine,2TMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C)[Si](C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	4201.1	Standard polar	33892256
Amlodipine,2TMS,isomer #2	CCOC(=O)C1=C(COCCN[Si](C)(C)C)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	2865.5	Semi standard non polar	33892256
Amlodipine,2TMS,isomer #2	CCOC(=O)C1=C(COCCN[Si](C)(C)C)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	2879.8	Standard non polar	33892256
Amlodipine,2TMS,isomer #2	CCOC(=O)C1=C(COCCN[Si](C)(C)C)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3839.5	Standard polar	33892256
Amlodipine,3TMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3029.2	Semi standard non polar	33892256
Amlodipine,3TMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	2994.0	Standard non polar	33892256
Amlodipine,3TMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3695.8	Standard polar	33892256
Amlodipine,1TBDMS,isomer #1	CCOC(=O)C1=C(COCCN[Si](C)(C)C(C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3161.4	Semi standard non polar	33892256
Amlodipine,1TBDMS,isomer #1	CCOC(=O)C1=C(COCCN[Si](C)(C)C(C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3048.9	Standard non polar	33892256
Amlodipine,1TBDMS,isomer #1	CCOC(=O)C1=C(COCCN[Si](C)(C)C(C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	4383.6	Standard polar	33892256
Amlodipine,1TBDMS,isomer #2	CCOC(=O)C1=C(COCCN)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3064.1	Semi standard non polar	33892256
Amlodipine,1TBDMS,isomer #2	CCOC(=O)C1=C(COCCN)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	2928.8	Standard non polar	33892256
Amlodipine,1TBDMS,isomer #2	CCOC(=O)C1=C(COCCN)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	4258.9	Standard polar	33892256
Amlodipine,2TBDMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3509.5	Semi standard non polar	33892256
Amlodipine,2TBDMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3312.3	Standard non polar	33892256
Amlodipine,2TBDMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	4194.6	Standard polar	33892256
Amlodipine,2TBDMS,isomer #2	CCOC(=O)C1=C(COCCN[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3262.5	Semi standard non polar	33892256
Amlodipine,2TBDMS,isomer #2	CCOC(=O)C1=C(COCCN[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3199.0	Standard non polar	33892256
Amlodipine,2TBDMS,isomer #2	CCOC(=O)C1=C(COCCN[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3910.5	Standard polar	33892256
Amlodipine,3TBDMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3625.6	Semi standard non polar	33892256
Amlodipine,3TBDMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3477.4	Standard non polar	33892256
Amlodipine,3TBDMS,isomer #1	CCOC(=O)C1=C(COCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl	3821.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amlodipine GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-9008000000-1fbca2d37d687cf7db0b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amlodipine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amlodipine 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 - Amlodipine LC-ESI-QTOF , positive-QTOF	splash10-0a4u-0192000000-988fbef9dd83defbfbe0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amlodipine , positive-QTOF	splash10-002o-1392000000-3e9bc5dcf61b0f4cae6a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amlodipine 35V, Negative-QTOF	splash10-0002-0092000000-ee62f2bc59215356e927	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amlodipine 35V, Positive-QTOF	splash10-052r-0191000000-f2696d00f557899608c4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amlodipine -1V, Positive-QTOF	splash10-0a4u-0192000000-dbb503bf75ac45992a8c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 10V, Positive-QTOF	splash10-0a4j-2029500000-6f84285a27a09d3975ad	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 20V, Positive-QTOF	splash10-0gw3-3189000000-2934b69ddcfba1ecb708	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 40V, Positive-QTOF	splash10-0ffx-3293000000-4459172f2e0c2c8495ef	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 10V, Negative-QTOF	splash10-0a4i-3007900000-5363cd8b8ca60ece4eea	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 20V, Negative-QTOF	splash10-08fr-4029200000-2a9e3badde424295bb13	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 40V, Negative-QTOF	splash10-03dl-9085000000-7db6de7520133d8f4045	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 10V, Negative-QTOF	splash10-0a4i-1033900000-377f5862d692ece9b8b3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 20V, Negative-QTOF	splash10-001i-6019200000-246c2de5f16d1f940e93	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 40V, Negative-QTOF	splash10-001i-7093000000-e5145c0579c14e90d8d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 10V, Positive-QTOF	splash10-0lxw-0049100000-fa18ab567110013335f8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 20V, Positive-QTOF	splash10-0zor-0029100000-79f4e839da15602ebfb0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amlodipine 40V, Positive-QTOF	splash10-004l-3495000000-4c7c1402fa10dd2c0919	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Epidermis

Pathways

Name	SMPDB/PathBank	KEGG
Amlodipine Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00381

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023590

KNApSAcK ID

Not Available

Chemspider ID

2077

KEGG Compound ID

C06825

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amlodipine

METLIN ID

955

PubChem Compound

2162

PDB ID

Not Available

ChEBI ID

2668

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kim, Seok-Chan; Choi, Kwan-Min; Cheong, Chan-Seong. Synthesis of amlodipine using aza Diels-Alder reaction. Bulletin of the Korean Chemical Society (2002), 23(1), 143-144.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Iabichella ML, Dell'Omo G, Melillo E, Pedrinelli R: Calcium channel blockers blunt postural cutaneous vasoconstriction in hypertensive patients. Hypertension. 1997 Mar;29(3):751-6. [PubMed:9052891 ]
Pedrinelli R, Dell'Omo G, Nuti M, Menegato A, Balbarini A, Mariani M: Heterogeneous effect of calcium antagonists on leg oedema: a comparison of amlodipine versus lercanidipine in hypertensive patients. J Hypertens. 2003 Oct;21(10):1969-73. [PubMed:14508205 ]

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

Enzyme Details

2. Carbonic anhydrase 1

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:: CA1
Uniprot ID:: P00915
Molecular weight:: 28870.0

Enzyme Details

3. Voltage-dependent N-type calcium channel subunit alpha-1B

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-1B gives rise to N-type calcium currents. N-type calcium channels belong to the 'high-voltage activated' (HVA) group and are blocked by omega-conotoxin-GVIA (omega-CTx-GVIA) and by omega-agatoxin- IIIA (omega-Aga-IIIA). They are however insensitive to dihydropyridines (DHP), and omega-agatoxin-IVA (omega-Aga-IVA). Calcium channels containing alpha-1B subunit may play a role in directed migration of immature neurons
Gene Name:: CACNA1B
Uniprot ID:: Q00975
Molecular weight:: 262493.8

Enzyme Details

4. Voltage-dependent calcium channel gamma-1 subunit

General function:: Involved in voltage-gated calcium channel activity
Specific function:: This protein is a subunit of the dihydropyridine (DHP) sensitive calcium channel. Plays a role in excitation-contraction coupling. The skeletal muscle DHP-sensitive Ca(2+) channel may function only as a multiple subunit complex
Gene Name:: CACNG1
Uniprot ID:: Q06432
Molecular weight:: 25028.1

Showing metabocard for Amlodipine (HMDB0005018)

MOL for HMDB0005018 (Amlodipine)

3D MOL for HMDB0005018 (Amlodipine)

3D SDF for HMDB0005018 (Amlodipine)

3D-SDF for HMDB0005018 (Amlodipine)

PDB for HMDB0005018 (Amlodipine)

3D PDB for HMDB0005018 (Amlodipine)

SMILES for HMDB0005018 (Amlodipine)

INCHI for HMDB0005018 (Amlodipine)

Structure for HMDB0005018 (Amlodipine)

3D Structure for HMDB0005018 (Amlodipine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes