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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (5) Show 7 proteins XML

enzymes (2)transporters (5) Show 7 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014722

Secondary Accession Numbers

HMDB14722

Metabolite Identification

Common Name

Enalapril

Description

Enalapril is a prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly metabolized in the liver to enalaprilat following oral administration. Enalaprilat is a potent, competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Enalapril may be used to treat essential or renovascular hypertension and symptomatic congestive heart failure.

Structure

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


  Mrv0541 04191212132D          

 27 28  0  0  1  0            999 V2000
    9.1805   -4.8012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4673   -5.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9336   -5.1331    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0381   -5.2203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512   -4.8054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1057   -5.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3219   -3.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3297   -4.8116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4675   -6.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4971   -6.4941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0252   -3.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166   -5.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2616   -3.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8928   -6.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6010   -3.5880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035   -4.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4815   -4.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1903   -5.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0667   -3.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512   -3.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5882   -2.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -4.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1903   -6.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -5.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772   -6.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -6.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8674   -2.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
 13  1  1  0  0  0  0
  5  2  1  0  0  0  0
  9  2  2  0  0  0  0
  3  6  1  1  0  0  0
 17  3  1  0  0  0  0
  5  4  1  0  0  0  0
  8  4  1  0  0  0  0
  5 20  1  1  0  0  0
 10  6  2  0  0  0  0
 14  6  1  0  0  0  0
  8  7  1  1  0  0  0
 11  7  2  0  0  0  0
 15  7  1  0  0  0  0
 12  8  1  0  0  0  0
 16 12  1  0  0  0  0
 19 13  1  0  0  0  0
 21 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 22 18  2  0  0  0  0
 23 18  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  2  0  0  0  0
 26 24  2  0  0  0  0
 26 25  1  0  0  0  0
 21 27  1  0  0  0  0
M  END

HMDB0014722
     RDKit          3D
Enalapril
 55 56  0  0  0  0  0  0  0  0999 V2000
    3.6024    3.5601    2.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5573    3.4973    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    2.1586    1.1407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440    1.7434    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    2.6028   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.3517    0.1945 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8128   -0.4951   -0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.3867    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1609   -1.2317   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315   -2.5158    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634   -3.2334   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1863   -2.6852   -1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0181   -1.3835   -1.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744   -0.6672   -1.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718    0.0406   -0.5232 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292    0.4876   -0.1204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0434    1.9344   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7508   -0.1927   -1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -0.4352   -2.1953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0370   -0.5466   -0.5902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0235   -1.1772   -1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2766   -0.3833   -1.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1770   -0.4338    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -0.4227    0.6830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3239   -1.6055    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7482   -1.7459    2.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5058   -2.5777    1.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694    2.9556    3.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596    3.1129    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    4.5991    2.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269    3.7689    0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7482    4.2178    1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703   -0.0138    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933   -0.1421   -1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557   -1.5493   -0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4646    0.6537    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637   -0.6416    1.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7142   -3.0100    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5108   -4.2575   -0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9956   -3.2735   -1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6429   -0.9105   -2.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8650    0.3598   -1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4168   -0.7112   -1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8975    0.1074    0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795    1.9996    0.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    2.5193    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    2.4725   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -1.0226   -2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1980   -2.2370   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1908   -0.8383   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1171    0.6647   -1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5955   -1.4383    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6949    0.3748    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4723    0.4882    1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1079   -2.5062    0.0864 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 14  9  1  0
 24 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  6 33  1  1
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  1
 17 45  1  0
 17 46  1  0
 17 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  1
 27 55  1  0
M  END


  Mrv0541 04191212132D          

 27 28  0  0  1  0            999 V2000
    9.1805   -4.8012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4673   -5.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9336   -5.1331    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0381   -5.2203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512   -4.8054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1057   -5.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3219   -3.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3297   -4.8116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4675   -6.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4971   -6.4941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0252   -3.5620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166   -5.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2616   -3.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8928   -6.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6010   -3.5880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035   -4.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4815   -4.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1903   -5.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0667   -3.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7512   -3.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5882   -2.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4742   -4.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1903   -6.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611   -5.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4772   -6.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -6.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8674   -2.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
 13  1  1  0  0  0  0
  5  2  1  0  0  0  0
  9  2  2  0  0  0  0
  3  6  1  1  0  0  0
 17  3  1  0  0  0  0
  5  4  1  0  0  0  0
  8  4  1  0  0  0  0
  5 20  1  1  0  0  0
 10  6  2  0  0  0  0
 14  6  1  0  0  0  0
  8  7  1  1  0  0  0
 11  7  2  0  0  0  0
 15  7  1  0  0  0  0
 12  8  1  0  0  0  0
 16 12  1  0  0  0  0
 19 13  1  0  0  0  0
 21 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 22 18  2  0  0  0  0
 23 18  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  2  0  0  0  0
 26 24  2  0  0  0  0
 26 25  1  0  0  0  0
 21 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014722

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1

> <INCHI_KEY>
GBXSMTUPTTWBMN-XIRDDKMYSA-N

> <FORMULA>
C20H28N2O5

> <MOLECULAR_WEIGHT>
376.4467

> <EXACT_MASS>
376.199822016

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.40726424198972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
0.5877766028820196

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.671330392672694

> <JCHEM_PKA_STRONGEST_BASIC>
5.201340771859483

> <JCHEM_POLAR_SURFACE_AREA>
95.94000000000001

> <JCHEM_REFRACTIVITY>
99.57460000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
enalapril

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014722
     RDKit          3D
Enalapril
 55 56  0  0  0  0  0  0  0  0999 V2000
    3.6024    3.5601    2.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5573    3.4973    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    2.1586    1.1407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440    1.7434    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    2.6028   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.3517    0.1945 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8128   -0.4951   -0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.3867    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1609   -1.2317   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315   -2.5158    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634   -3.2334   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1863   -2.6852   -1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0181   -1.3835   -1.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744   -0.6672   -1.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718    0.0406   -0.5232 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292    0.4876   -0.1204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0434    1.9344   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7508   -0.1927   -1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -0.4352   -2.1953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0370   -0.5466   -0.5902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0235   -1.1772   -1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2766   -0.3833   -1.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1770   -0.4338    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -0.4227    0.6830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3239   -1.6055    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7482   -1.7459    2.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5058   -2.5777    1.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694    2.9556    3.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596    3.1129    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    4.5991    2.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269    3.7689    0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7482    4.2178    1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703   -0.0138    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933   -0.1421   -1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557   -1.5493   -0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4646    0.6537    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637   -0.6416    1.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7142   -3.0100    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5108   -4.2575   -0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9956   -3.2735   -1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6429   -0.9105   -2.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8650    0.3598   -1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4168   -0.7112   -1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8975    0.1074    0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795    1.9996    0.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    2.5193    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    2.4725   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -1.0226   -2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1980   -2.2370   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1908   -0.8383   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1171    0.6647   -1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5955   -1.4383    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6949    0.3748    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4723    0.4882    1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1079   -2.5062    0.0864 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 14  9  1  0
 24 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  6 33  1  1
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  1
 17 45  1  0
 17 46  1  0
 17 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  1
 27 55  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  N   UNK     0      17.137  -8.962   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      15.806  -9.736   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.543  -9.582   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      13.138  -9.745   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      14.469  -8.970   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.864 -11.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.801  -7.446   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.816  -8.982   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      15.806 -11.269   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      17.728 -12.122   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      13.114  -6.649   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.484  -9.756   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.288  -7.425   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      20.333 -11.557   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.455  -6.698   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.153  -8.999   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.565  -8.441   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.822  -9.773   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.791  -7.109   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.469  -7.438   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.431  -5.156   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.485  -9.007   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.822 -11.305   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.154  -9.781   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.491 -12.079   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.159 -11.322   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.086  -4.408   0.000  0.00  0.00           C+0
CONECT    1    2    3   13                                                  
CONECT    2    1    5    9                                                  
CONECT    3    1    6   17                                                  
CONECT    4    5    8                                                       
CONECT    5    2    4   20                                                  
CONECT    6    3   10   14                                                  
CONECT    7    8   11   15                                                  
CONECT    8    4    7   12                                                  
CONECT    9    2                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8   16                                                       
CONECT   13    1   19                                                       
CONECT   14    6                                                            
CONECT   15    7   21                                                       
CONECT   16   12   18                                                       
CONECT   17    3   19                                                       
CONECT   18   16   22   23                                                  
CONECT   19   13   17                                                       
CONECT   20    5                                                            
CONECT   21   15   27                                                       
CONECT   22   18   24                                                       
CONECT   23   18   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   26                                                       
CONECT   26   24   25                                                       
CONECT   27   21                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

COMPND    HMDB0014722
HETATM    1  C1  UNL     1       3.602   3.560   2.323  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.557   3.497   1.211  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.107   2.159   1.141  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.144   1.743   0.230  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.685   2.603  -0.532  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.704   0.352   0.195  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.813  -0.495  -0.462  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.060  -0.387   0.333  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.161  -1.232  -0.247  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.332  -2.516   0.157  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.363  -3.233  -0.426  1.00  0.00           C  
HETATM   12  C10 UNL     1       6.186  -2.685  -1.374  1.00  0.00           C  
HETATM   13  C11 UNL     1       6.018  -1.384  -1.788  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.974  -0.667  -1.193  1.00  0.00           C  
HETATM   15  N1  UNL     1      -0.472   0.041  -0.523  1.00  0.00           N  
HETATM   16  C13 UNL     1      -1.729   0.488  -0.120  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.043   1.934  -0.103  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.751  -0.193  -1.004  1.00  0.00           C  
HETATM   19  O3  UNL     1      -2.353  -0.435  -2.195  1.00  0.00           O  
HETATM   20  N2  UNL     1      -4.037  -0.547  -0.590  1.00  0.00           N  
HETATM   21  C16 UNL     1      -5.023  -1.177  -1.459  1.00  0.00           C  
HETATM   22  C17 UNL     1      -6.277  -0.383  -1.074  1.00  0.00           C  
HETATM   23  C18 UNL     1      -6.177  -0.434   0.430  1.00  0.00           C  
HETATM   24  C19 UNL     1      -4.663  -0.423   0.683  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.324  -1.605   1.538  1.00  0.00           C  
HETATM   26  O4  UNL     1      -4.748  -1.746   2.706  1.00  0.00           O  
HETATM   27  O5  UNL     1      -3.506  -2.578   1.002  1.00  0.00           O  
HETATM   28  H1  UNL     1       3.269   2.956   3.192  1.00  0.00           H  
HETATM   29  H2  UNL     1       4.560   3.113   1.987  1.00  0.00           H  
HETATM   30  H3  UNL     1       3.728   4.599   2.705  1.00  0.00           H  
HETATM   31  H4  UNL     1       3.127   3.769   0.278  1.00  0.00           H  
HETATM   32  H5  UNL     1       1.748   4.218   1.377  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.570  -0.014   1.254  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.993  -0.142  -1.499  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.456  -1.549  -0.581  1.00  0.00           H  
HETATM   36  H9  UNL     1       3.465   0.654   0.271  1.00  0.00           H  
HETATM   37  H10 UNL     1       2.964  -0.642   1.388  1.00  0.00           H  
HETATM   38  H11 UNL     1       3.714  -3.010   0.904  1.00  0.00           H  
HETATM   39  H12 UNL     1       5.511  -4.257  -0.114  1.00  0.00           H  
HETATM   40  H13 UNL     1       6.996  -3.274  -1.821  1.00  0.00           H  
HETATM   41  H14 UNL     1       6.643  -0.910  -2.532  1.00  0.00           H  
HETATM   42  H15 UNL     1       4.865   0.360  -1.540  1.00  0.00           H  
HETATM   43  H16 UNL     1      -0.417  -0.711  -1.215  1.00  0.00           H  
HETATM   44  H17 UNL     1      -1.897   0.107   0.943  1.00  0.00           H  
HETATM   45  H18 UNL     1      -3.180   2.000   0.027  1.00  0.00           H  
HETATM   46  H19 UNL     1      -1.663   2.519   0.741  1.00  0.00           H  
HETATM   47  H20 UNL     1      -1.895   2.473  -1.061  1.00  0.00           H  
HETATM   48  H21 UNL     1      -4.784  -1.023  -2.531  1.00  0.00           H  
HETATM   49  H22 UNL     1      -5.198  -2.237  -1.197  1.00  0.00           H  
HETATM   50  H23 UNL     1      -7.191  -0.838  -1.463  1.00  0.00           H  
HETATM   51  H24 UNL     1      -6.117   0.665  -1.377  1.00  0.00           H  
HETATM   52  H25 UNL     1      -6.595  -1.438   0.729  1.00  0.00           H  
HETATM   53  H26 UNL     1      -6.695   0.375   0.944  1.00  0.00           H  
HETATM   54  H27 UNL     1      -4.472   0.488   1.248  1.00  0.00           H  
HETATM   55  H28 UNL     1      -3.108  -2.506   0.086  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   15   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10   10   14
CONECT   10   11   38
CONECT   11   12   12   39
CONECT   12   13   40
CONECT   13   14   14   41
CONECT   14   42
CONECT   15   16   43
CONECT   16   17   18   44
CONECT   17   45   46   47
CONECT   18   19   19   20
CONECT   20   21   24
CONECT   21   22   48   49
CONECT   22   23   50   51
CONECT   23   24   52   53
CONECT   24   25   54
CONECT   25   26   26   27
CONECT   27   55
END

HMDB0014722
     RDKit          3D
Enalapril
 55 56  0  0  0  0  0  0  0  0999 V2000
    3.6024    3.5601    2.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5573    3.4973    1.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072    2.1586    1.1407 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440    1.7434    0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    2.6028   -0.5321 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036    0.3517    0.1945 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8128   -0.4951   -0.4620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.3867    0.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1609   -1.2317   -0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315   -2.5158    0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634   -3.2334   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1863   -2.6852   -1.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0181   -1.3835   -1.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9744   -0.6672   -1.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718    0.0406   -0.5232 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292    0.4876   -0.1204 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0434    1.9344   -0.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7508   -0.1927   -1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -0.4352   -2.1953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0370   -0.5466   -0.5902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0235   -1.1772   -1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2766   -0.3833   -1.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1770   -0.4338    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6632   -0.4227    0.6830 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3239   -1.6055    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7482   -1.7459    2.7063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5058   -2.5777    1.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2694    2.9556    3.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5596    3.1129    1.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7280    4.5991    2.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269    3.7689    0.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7482    4.2178    1.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703   -0.0138    1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9933   -0.1421   -1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4557   -1.5493   -0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4646    0.6537    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637   -0.6416    1.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7142   -3.0100    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5108   -4.2575   -0.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9956   -3.2735   -1.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6429   -0.9105   -2.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8650    0.3598   -1.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4168   -0.7112   -1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8975    0.1074    0.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1795    1.9996    0.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6626    2.5193    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8953    2.4725   -1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7839   -1.0226   -2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1980   -2.2370   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1908   -0.8383   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1171    0.6647   -1.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5955   -1.4383    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6949    0.3748    0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4723    0.4882    1.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1079   -2.5062    0.0864 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 14  9  1  0
 24 20  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  6 33  1  1
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  1
 17 45  1  0
 17 46  1  0
 17 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  1
 27 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-1-(N-(1-(Ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline	ChEBI
(S)-1-{(S)-2-[1-((S)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid	ChEBI
1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester	ChEBI
Analapril	ChEBI
Enalaprila	ChEBI
Enalaprilum	ChEBI
(S)-1-{(S)-2-[1-((S)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylate	Generator
Enalapril maleate	HMDB
Enalaprilat	HMDB
Renitek	HMDB
Maleate, enalapril	HMDB
Renitec	HMDB

Chemical Formula

C₂₀H₂₈N₂O₅

Average Molecular Weight

376.4467

Monoisotopic Molecular Weight

376.199822016

IUPAC Name

(2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

enalapril

CAS Registry Number

75847-73-3

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1

InChI Key

GBXSMTUPTTWBMN-XIRDDKMYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
N-acyl-l-alpha-amino acid
Proline or derivatives
Alpha-amino acid ester
Alpha-amino acid amide
Alpha-amino acid or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
N-acylpyrrolidine
Fatty acid ester
Aralkylamine
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Amino acid
Azacycle
Secondary aliphatic amine
Carboxylic acid
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid monoester (CHEBI:4784 )
dipeptide (CHEBI:4784 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014722)
Membrane (HMDB: HMDB0014722)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Enalapril Action Pathway (PathBank: SMP0000148)

Metabolic pathway

Enalapril Metabolism Pathway (PathBank: SMP0000593)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	143 - 144.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.21 g/L	Not Available
LogP	2.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	187.2	30932474
[M+H]+	Not Available	186.622	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001273

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	0.19	ALOGPS
logP	0.59	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.94 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	99.57 m³·mol⁻¹	ChemAxon
Polarizability	40.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	185.555	31661259
DarkChem	[M-H]-	184.1	31661259
DeepCCS	[M+H]+	189.96	30932474
DeepCCS	[M-H]-	187.602	30932474
DeepCCS	[M-2H]-	220.533	30932474
DeepCCS	[M+Na]+	196.053	30932474
AllCCS	[M+H]+	192.1	32859911
AllCCS	[M+H-H2O]+	189.5	32859911
AllCCS	[M+NH4]+	194.5	32859911
AllCCS	[M+Na]+	195.2	32859911
AllCCS	[M-H]-	189.3	32859911
AllCCS	[M+Na-2H]-	190.0	32859911
AllCCS	[M+HCOO]-	190.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Enalapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O	4052.2	Standard polar	33892256
Enalapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O	2733.4	Standard non polar	33892256
Enalapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O	2836.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Enalapril,1TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2851.6	Semi standard non polar	33892256
Enalapril,1TMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	2822.5	Semi standard non polar	33892256
Enalapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)[Si](C)(C)C	2827.9	Semi standard non polar	33892256
Enalapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)[Si](C)(C)C	2778.1	Standard non polar	33892256
Enalapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)[Si](C)(C)C	3564.9	Standard polar	33892256
Enalapril,1TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3073.1	Semi standard non polar	33892256
Enalapril,1TBDMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	3080.9	Semi standard non polar	33892256
Enalapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3306.9	Semi standard non polar	33892256
Enalapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3165.0	Standard non polar	33892256
Enalapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3724.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Enalapril GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4329000000-0ccc991d6f82c8023381	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Enalapril GC-MS (1 TMS) - 70eV, Positive	splash10-004i-4139100000-e739549506767919633f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Enalapril 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 - Enalapril LC-ESI-QFT , negative-QTOF	splash10-004i-0809000000-0e192d1573028e60641c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril LC-ESI-QFT , positive-QTOF	splash10-003r-1859000000-8b202071e8860792a59f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril 40V, Positive-QTOF	splash10-02ai-0920000000-a43751d817c0f98bc5b6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril 30V, Positive-QTOF	splash10-001i-0591000000-1e07b9fe2aaace58211e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril 10V, Positive-QTOF	splash10-004i-0009000000-e737fba7359f446dfefa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril 20V, Positive-QTOF	splash10-001i-0096000000-f899a068af97bea539ac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril 35V, Positive-QTOF	splash10-003r-1859000000-a8e3ac5e4d170e35772c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril 50V, Positive-QTOF	splash10-02t9-0900000000-0f67eb2d8b2e7821015c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril 30V, Positive-QTOF	splash10-001i-0591000000-9695db764f080d9ae857	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril 35V, Negative-QTOF	splash10-004i-0809000000-0e192d1573028e60641c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Enalapril 20V, Positive-QTOF	splash10-001i-0095000000-f899a068af97bea539ac	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 10V, Positive-QTOF	splash10-0059-0239000000-feb01e2c02b331eea247	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 20V, Positive-QTOF	splash10-001i-5893000000-141cda4f7233f214c8dc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 40V, Positive-QTOF	splash10-0296-6910000000-189f3dddcaf5004e885f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 10V, Negative-QTOF	splash10-004i-1019000000-ae65ecb00dc3ab6e3701	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 20V, Negative-QTOF	splash10-03gs-5559000000-d8643ca2f50322b85449	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 40V, Negative-QTOF	splash10-01ot-8921000000-5383f963d934648ca615	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 10V, Positive-QTOF	splash10-004i-0129000000-f7705eec0d29efd988c2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 20V, Positive-QTOF	splash10-01sl-3944000000-04f3a7836b5b57821688	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 40V, Positive-QTOF	splash10-0903-3900000000-cb0bc55987e5b9460684	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 10V, Negative-QTOF	splash10-004i-0109000000-ec7a71512e90259b372c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 20V, Negative-QTOF	splash10-03di-3913000000-89b99fdc1118ca034b01	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Enalapril 40V, Negative-QTOF	splash10-03di-3900000000-294402e5b0098d7dc45e	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Enalapril Action Pathway		Not Available
Enalapril Metabolism 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
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00584	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00584	21059682	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

DB00584

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4534998

KEGG Compound ID

C06977

BioCyc ID

CPD0-2065

BiGG ID

Not Available

Wikipedia Link

Enalapril

METLIN ID

Not Available

PubChem Compound

40466924

PDB ID

Not Available

ChEBI ID

4784

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

(). D.P. Ip and G.S. Brenner, in K. Florey (Editor), Analytical Profiles of Drug Substances, Vol. 16, Aca- demic Press, London, 1987, pp. 207-243.. .

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

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

2. Angiotensin-converting enzyme

General function:: Involved in metallopeptidase activity
Specific function:: Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:: ACE
Uniprot ID:: P12821
Molecular weight:: 149713.7

References

Andujar-Sanchez M, Jara-Perez V, Camara-Artigas A: Thermodynamic determination of the binding constants of angiotensin-converting enzyme inhibitors by a displacement method. FEBS Lett. 2007 Jul 24;581(18):3449-54. Epub 2007 Jun 27. [PubMed:17618628 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Liu YH, Liu LY, Wu JX, Chen SX, Sun YX: Comparison of captopril and enalapril to study the role of the sulfhydryl-group in improvement of endothelial dysfunction with ACE inhibitors in high dieted methionine mice. J Cardiovasc Pharmacol. 2006 Jan;47(1):82-8. [PubMed:16424790 ]
Natesh R, Schwager SL, Evans HR, Sturrock ED, Acharya KR: Structural details on the binding of antihypertensive drugs captopril and enalaprilat to human testicular angiotensin I-converting enzyme. Biochemistry. 2004 Jul 13;43(27):8718-24. [PubMed:15236580 ]

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

Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [PubMed:11895100 ]

Enzyme Details

2. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Abu-Zahra TN, Wolkoff AW, Kim RB, Pang KS: Uptake of enalapril and expression of organic anion transporting polypeptide 1 in zonal, isolated rat hepatocytes. Drug Metab Dispos. 2000 Jul;28(7):801-6. [PubMed:10859154 ]
Pang KS, Wang PJ, Chung AY, Wolkoff AW: The modified dipeptide, enalapril, an angiotensin-converting enzyme inhibitor, is transported by the rat liver organic anion transport protein. Hepatology. 1998 Nov;28(5):1341-6. [PubMed:9794920 ]

Enzyme Details

3. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadee W, Amidon GL: 5'-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res. 1998 Aug;15(8):1154-9. [PubMed:9706043 ]
Han HK, Rhie JK, Oh DM, Saito G, Hsu CP, Stewart BH, Amidon GL: CHO/hPEPT1 cells overexpressing the human peptide transporter (hPEPT1) as an alternative in vitro model for peptidomimetic drugs. J Pharm Sci. 1999 Mar;88(3):347-50. [PubMed:10052994 ]
Temple CS, Boyd CA: Proton-coupled oligopeptide transport by rat renal cortical brush border membrane vesicles: a functional analysis using ACE inhibitors to determine the isoform of the transporter. Biochim Biophys Acta. 1998 Aug 14;1373(1):277-81. [PubMed:9733984 ]
Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677 ]

Enzyme Details

4. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [PubMed:9880528 ]

Enzyme Details

5. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

References

Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [PubMed:12065749 ]
Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [PubMed:9650585 ]

Showing metabocard for Enalapril (HMDB0014722)

MOL for HMDB0014722 (Enalapril)

3D MOL for HMDB0014722 (Enalapril)

3D SDF for HMDB0014722 (Enalapril)

3D-SDF for HMDB0014722 (Enalapril)

PDB for HMDB0014722 (Enalapril)

3D PDB for HMDB0014722 (Enalapril)

SMILES for HMDB0014722 (Enalapril)

INCHI for HMDB0014722 (Enalapril)

Structure for HMDB0014722 (Enalapril)

3D Structure for HMDB0014722 (Enalapril)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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