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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-18 09:03:34 UTC

Update Date

2022-03-07 02:49:11 UTC

HMDB ID

HMDB0001938

Secondary Accession Numbers

HMDB01938

Metabolite Identification

Common Name

Lisinopril

Description

One of the Angiotensin-converting enzyme inhibitors (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure. -- Pubchem; Lisinopril is a drug of the angiotensin converting enzyme (ACE) inhibitor class that is primarily used in treatment of hypertension, congestive heart failure and heart attacks. Historically, lisinopril was the third ACE inhibitor, after captopril and enalapril that was introduced into therapy in early 1990s. Lisinopril has a number of properties that distinguish it from other ACE inhibitors: it is hydrophilic, has long half life and tissue penetration and is not metabolized by the liver. -- Wikipedia ; Lisinopril is solely excreted in urine in the unchanged form. Elimination of the drug depends on glomerular filtration and tubular excretion. Rate of lisinopril elimination decreases with old age and kidney or heart failure. There is a relation between creatinine and lisinopril clearance. With prolonged therapy dose reduction can be necessary to avoid accumulation. -- Wikipedia .

Structure

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

722
  Mrv1652305271900192D          

 29 30  0  0  1  0            999 V2000
    5.6655    0.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0162    2.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5746    1.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.0130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    3.6631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6185    2.4980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3634    3.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2835    2.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5384    3.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.7755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9509    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.4620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4030    2.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  2  0  0  0  0
  2 18  1  0  0  0  0
  3 18  2  0  0  0  0
  4 22  1  0  0  0  0
  5 22  2  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 14  1  0  0  0  0
 13  7  1  1  0  0  0
 16  7  1  1  0  0  0
  8 23  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  1  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
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 17 20  1  0  0  0  0
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 24 25  2  0  0  0  0
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 25 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END

HMDB0001938
     RDKit          3D
Lisinopril
 60 61  0  0  0  0  0  0  0  0999 V2000
   -2.7561   -0.9468   -4.2713 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6945   -2.2268   -3.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3754   -2.5009   -2.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.4890   -1.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2704   -1.7963   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204   -0.7273   -0.1493 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7780   -0.9852    0.4773 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9621   -0.9932   -0.2366 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9747    0.0226    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366    1.4594   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    2.1789    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244    2.6195    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844    3.3122    0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9530    3.5713    2.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639    3.1303    2.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    2.4512    2.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368   -2.3366    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765   -3.1729    0.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8630   -2.5948   -0.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5142   -1.0740    0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776   -2.0774    1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201   -0.4403    1.1198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6935   -0.8738    2.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842   -0.2077    1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7531    0.2920    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2894    0.7465    0.4987 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2738    1.8491    1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7817    1.6601    2.6524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126    3.0706    1.2031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -0.4907   -4.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929   -0.3045   -3.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4781   -2.3450   -2.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8883   -3.0690   -4.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8412    1.8109   -1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378    1.9111    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4128    3.3169    3.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    2.1186    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0975   -3.5197   -0.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -0.5755    3.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0930    0.6728    2.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494   -0.5339   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    1.1555    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8474    1.0269   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904    3.9044    1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  2  0
 17 19  1  0
  6 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 16 11  1  0
 26 22  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
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  4 36  1  0
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  5 38  1  0
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  6 40  1  6
  7 41  1  0
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 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  6
 29 60  1  0
M  END

722
  Mrv1652305271900192D          

 29 30  0  0  1  0            999 V2000
    5.6655    0.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0162    2.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5746    1.4360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.0130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    3.6631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6185    2.4980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3634    3.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2835    2.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5384    3.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.7755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9509    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.4620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5220    2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4030    2.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -4.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  2  0  0  0  0
  2 18  1  0  0  0  0
  3 18  2  0  0  0  0
  4 22  1  0  0  0  0
  5 22  2  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 14  1  0  0  0  0
 13  7  1  1  0  0  0
 16  7  1  1  0  0  0
  8 23  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  1  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 16 22  1  0  0  0  0
 17 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  2  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001938

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1

> <INCHI_KEY>
RLAWWYSOJDYHDC-BZSNNMDCSA-N

> <FORMULA>
C21H31N3O5

> <MOLECULAR_WEIGHT>
405.4879

> <EXACT_MASS>
405.226371117

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
43.63788919658357

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-1.23

> <JCHEM_LOGP>
-3.102603245726448

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.850622320338458

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1725657699887164

> <JCHEM_PKA_STRONGEST_BASIC>
10.208230835264743

> <JCHEM_POLAR_SURFACE_AREA>
132.95999999999998

> <JCHEM_REFRACTIVITY>
107.3691

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lisinopril

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001938
     RDKit          3D
Lisinopril
 60 61  0  0  0  0  0  0  0  0999 V2000
   -2.7561   -0.9468   -4.2713 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6945   -2.2268   -3.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3754   -2.5009   -2.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.4890   -1.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2704   -1.7963   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204   -0.7273   -0.1493 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7780   -0.9852    0.4773 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9621   -0.9932   -0.2366 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9747    0.0226    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366    1.4594   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    2.1789    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244    2.6195    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844    3.3122    0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9530    3.5713    2.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639    3.1303    2.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    2.4512    2.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368   -2.3366    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765   -3.1729    0.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8630   -2.5948   -0.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5142   -1.0740    0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776   -2.0774    1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201   -0.4403    1.1198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6935   -0.8738    2.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842   -0.2077    1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7531    0.2920    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2894    0.7465    0.4987 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2738    1.8491    1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7817    1.6601    2.6524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126    3.0706    1.2031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -0.4907   -4.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929   -0.3045   -3.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4781   -2.3450   -2.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8883   -3.0690   -4.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -2.5028   -3.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4443   -3.4960   -2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177   -0.4861   -2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8981   -1.5800   -1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -2.7477   -0.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181   -1.7762   -2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4347    0.2689   -0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7924   -0.5143    1.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -1.0103   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9958   -0.3231   -0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2845   -0.1752    1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412    1.8109   -1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378    1.9111    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215    2.4146   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307    3.6411    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3031    4.0929    2.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    3.3169    3.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    2.1186    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0975   -3.5197   -0.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -0.5755    3.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196   -1.9691    2.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8872   -0.8361    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0930    0.6728    2.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494   -0.5339   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    1.1555    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8474    1.0269   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904    3.9044    1.7906 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  2  0
 17 19  1  0
  6 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 16 11  1  0
 26 22  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  6
  7 41  1  0
  8 42  1  6
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 19 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  6
 29 60  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 722                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      10.576   1.448   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      13.097   5.218   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.273   2.681   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.241   1.448   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.907  -0.862   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       9.242   3.758   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.908  -0.092   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       3.907   6.838   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      10.488   4.663   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.012   6.128   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.996   4.663   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.472   6.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.908   1.448   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.242   2.218   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.574   2.218   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -0.862   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.574   3.758   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.952   4.187   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.574  -2.402   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.241   4.528   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.241  -3.172   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.241  -0.092   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.241   6.068   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.241  -4.713   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.574  -5.483   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.907  -5.483   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.574  -7.023   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.907  -7.023   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.241  -7.793   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   18                                                            
CONECT    3   18                                                            
CONECT    4   22                                                            
CONECT    5   22                                                            
CONECT    6    9   11   14                                                  
CONECT    7   13   16                                                       
CONECT    8   23                                                            
CONECT    9    6   10   18                                                  
CONECT   10    9   12                                                       
CONECT   11    6   12                                                       
CONECT   12   10   11                                                       
CONECT   13    7   14   15                                                  
CONECT   14    1    6   13                                                  
CONECT   15   13   17                                                       
CONECT   16    7   19   22                                                  
CONECT   17   15   20                                                       
CONECT   18    2    3    9                                                  
CONECT   19   16   21                                                       
CONECT   20   17   23                                                       
CONECT   21   19   24                                                       
CONECT   22    4    5   16                                                  
CONECT   23    8   20                                                       
CONECT   24   21   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24   28                                                       
CONECT   27   25   29                                                       
CONECT   28   26   29                                                       
CONECT   29   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

COMPND    HMDB0001938
HETATM    1  N1  UNL     1      -2.756  -0.947  -4.271  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.694  -2.227  -3.632  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.375  -2.501  -2.961  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.061  -1.489  -1.870  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.270  -1.796  -1.232  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.520  -0.727  -0.149  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.778  -0.985   0.477  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.962  -0.993  -0.237  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.975   0.023   0.067  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.837   1.459  -0.065  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.826   2.179   0.704  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.624   2.620   0.200  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.684   3.312   0.968  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.953   3.571   2.277  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.164   3.130   2.796  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.086   2.451   2.043  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.637  -2.337   0.048  1.00  0.00           C  
HETATM   18  O1  UNL     1       3.077  -3.173   0.783  1.00  0.00           O  
HETATM   19  O2  UNL     1       4.863  -2.595  -0.523  1.00  0.00           O  
HETATM   20  C16 UNL     1      -0.514  -1.074   0.894  1.00  0.00           C  
HETATM   21  O3  UNL     1      -0.178  -2.077   1.618  1.00  0.00           O  
HETATM   22  N3  UNL     1      -1.720  -0.440   1.120  1.00  0.00           N  
HETATM   23  C17 UNL     1      -2.693  -0.874   2.136  1.00  0.00           C  
HETATM   24  C18 UNL     1      -3.984  -0.208   1.787  1.00  0.00           C  
HETATM   25  C19 UNL     1      -3.753   0.292   0.381  1.00  0.00           C  
HETATM   26  C20 UNL     1      -2.289   0.746   0.499  1.00  0.00           C  
HETATM   27  C21 UNL     1      -2.274   1.849   1.524  1.00  0.00           C  
HETATM   28  O4  UNL     1      -1.782   1.660   2.652  1.00  0.00           O  
HETATM   29  O5  UNL     1      -2.813   3.071   1.203  1.00  0.00           O  
HETATM   30  H1  UNL     1      -1.824  -0.491  -4.203  1.00  0.00           H  
HETATM   31  H2  UNL     1      -3.493  -0.305  -3.910  1.00  0.00           H  
HETATM   32  H3  UNL     1      -3.478  -2.345  -2.826  1.00  0.00           H  
HETATM   33  H4  UNL     1      -2.888  -3.069  -4.333  1.00  0.00           H  
HETATM   34  H5  UNL     1      -0.554  -2.503  -3.731  1.00  0.00           H  
HETATM   35  H6  UNL     1      -1.444  -3.496  -2.457  1.00  0.00           H  
HETATM   36  H7  UNL     1      -1.118  -0.486  -2.306  1.00  0.00           H  
HETATM   37  H8  UNL     1      -1.898  -1.580  -1.135  1.00  0.00           H  
HETATM   38  H9  UNL     1       0.249  -2.748  -0.667  1.00  0.00           H  
HETATM   39  H10 UNL     1       1.018  -1.776  -2.027  1.00  0.00           H  
HETATM   40  H11 UNL     1       0.435   0.269  -0.521  1.00  0.00           H  
HETATM   41  H12 UNL     1       1.792  -0.514   1.391  1.00  0.00           H  
HETATM   42  H13 UNL     1       2.764  -1.010  -1.385  1.00  0.00           H  
HETATM   43  H14 UNL     1       4.996  -0.323  -0.403  1.00  0.00           H  
HETATM   44  H15 UNL     1       4.285  -0.175   1.185  1.00  0.00           H  
HETATM   45  H16 UNL     1       3.841   1.811  -1.150  1.00  0.00           H  
HETATM   46  H17 UNL     1       4.838   1.911   0.293  1.00  0.00           H  
HETATM   47  H18 UNL     1       1.422   2.415  -0.848  1.00  0.00           H  
HETATM   48  H19 UNL     1      -0.231   3.641   0.538  1.00  0.00           H  
HETATM   49  H20 UNL     1       0.303   4.093   2.964  1.00  0.00           H  
HETATM   50  H21 UNL     1       2.413   3.317   3.842  1.00  0.00           H  
HETATM   51  H22 UNL     1       4.015   2.119   2.458  1.00  0.00           H  
HETATM   52  H23 UNL     1       5.097  -3.520  -0.856  1.00  0.00           H  
HETATM   53  H24 UNL     1      -2.298  -0.576   3.133  1.00  0.00           H  
HETATM   54  H25 UNL     1      -2.820  -1.969   2.114  1.00  0.00           H  
HETATM   55  H26 UNL     1      -4.887  -0.836   1.901  1.00  0.00           H  
HETATM   56  H27 UNL     1      -4.093   0.673   2.485  1.00  0.00           H  
HETATM   57  H28 UNL     1      -3.849  -0.534  -0.313  1.00  0.00           H  
HETATM   58  H29 UNL     1      -4.422   1.156   0.190  1.00  0.00           H  
HETATM   59  H30 UNL     1      -1.847   1.027  -0.449  1.00  0.00           H  
HETATM   60  H31 UNL     1      -2.690   3.904   1.791  1.00  0.00           H  
CONECT    1    2   30   31
CONECT    2    3   32   33
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6   38   39
CONECT    6    7   20   40
CONECT    7    8   41
CONECT    8    9   17   42
CONECT    9   10   43   44
CONECT   10   11   45   46
CONECT   11   12   12   16
CONECT   12   13   47
CONECT   13   14   14   48
CONECT   14   15   49
CONECT   15   16   16   50
CONECT   16   51
CONECT   17   18   18   19
CONECT   19   52
CONECT   20   21   21   22
CONECT   22   23   26
CONECT   23   24   53   54
CONECT   24   25   55   56
CONECT   25   26   57   58
CONECT   26   27   59
CONECT   27   28   28   29
CONECT   29   60
END

HMDB0001938
     RDKit          3D
Lisinopril
 60 61  0  0  0  0  0  0  0  0999 V2000
   -2.7561   -0.9468   -4.2713 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6945   -2.2268   -3.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3754   -2.5009   -2.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.4890   -1.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2704   -1.7963   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5204   -0.7273   -0.1493 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7780   -0.9852    0.4773 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9621   -0.9932   -0.2366 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9747    0.0226    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366    1.4594   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8261    2.1789    0.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244    2.6195    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844    3.3122    0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9530    3.5713    2.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639    3.1303    2.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860    2.4512    2.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368   -2.3366    0.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765   -3.1729    0.7829 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8630   -2.5948   -0.5233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5142   -1.0740    0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776   -2.0774    1.6181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201   -0.4403    1.1198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6935   -0.8738    2.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842   -0.2077    1.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7531    0.2920    0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2894    0.7465    0.4987 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2738    1.8491    1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7817    1.6601    2.6524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8126    3.0706    1.2031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -0.4907   -4.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929   -0.3045   -3.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4781   -2.3450   -2.8257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8883   -3.0690   -4.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -2.5028   -3.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4443   -3.4960   -2.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177   -0.4861   -2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8981   -1.5800   -1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490   -2.7477   -0.6672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181   -1.7762   -2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4347    0.2689   -0.5211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7924   -0.5143    1.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7639   -1.0103   -1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9958   -0.3231   -0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2845   -0.1752    1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412    1.8109   -1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8378    1.9111    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4215    2.4146   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307    3.6411    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3031    4.0929    2.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    3.3169    3.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    2.1186    2.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0975   -3.5197   -0.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -0.5755    3.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196   -1.9691    2.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8872   -0.8361    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0930    0.6728    2.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8494   -0.5339   -0.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    1.1555    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8474    1.0269   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904    3.9044    1.7906 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  2  0
 17 19  1  0
  6 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 16 11  1  0
 26 22  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  5 38  1  0
  5 39  1  0
  6 40  1  6
  7 41  1  0
  8 42  1  6
  9 43  1  0
  9 44  1  0
 10 45  1  0
 10 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 15 50  1  0
 16 51  1  0
 19 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  6
 29 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-1-(N(2)-(1-Carboxy-3-phenylpropyl)-L-lysyl)-L-proline	ChEBI
[N2-[(S)-1-CARBOXY-3-phenylpropyl]-L-lysyl-L-proline	ChEBI
Lisinopril anhydrous	ChEBI
Zestril	Kegg
Acerbon	HMDB
Acercomp	HMDB
Alapril	HMDB
Carace	HMDB
Cipral	HMDB
Cipril	HMDB
Coric	HMDB
Inhibril	HMDB
Inopril	HMDB
Linopril	HMDB
Linvas	HMDB
Lipril	HMDB
Lisinal	HMDB
Lisinoprilum	HMDB
Lisipril	HMDB
Lisoril	HMDB
Lispril	HMDB
Loril	HMDB
LPR	HMDB
Lysinopril	HMDB
Noperten	HMDB
Novatec	HMDB
Presiten	HMDB
Prinil	HMDB
Prinivil	HMDB
Sinopril	HMDB
Sinopryl	HMDB
Tensopril	HMDB
Tensyn	HMDB
Tersif	HMDB
Vivatec	HMDB
Lisinopril maleate (1:1)	HMDB
Lisinopril sulfate (1:2)	HMDB

Chemical Formula

C₂₁H₃₁N₃O₅

Average Molecular Weight

405.4879

Monoisotopic Molecular Weight

405.226371117

IUPAC Name

(2S)-1-[(2S)-6-amino-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

lisinopril

CAS Registry Number

83915-83-7

SMILES

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

InChI Identifier

InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:43755 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0001938)
Skeletal muscle (HMDB: HMDB0001938)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0001938)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Lisinopril Action Pathway (HMDB: HMDB0001938)
Lisinopril Action Pathway (PathBank: SMP0000150)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001938)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	97 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	189.656	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001275

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-3.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.17	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.96 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	107.37 m³·mol⁻¹	ChemAxon
Polarizability	43.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	194.779	31661259
DarkChem	[M-H]-	191.46	31661259
AllCCS	[M+H]+	195.598	32859911
AllCCS	[M-H]-	195.504	32859911
DeepCCS	[M+H]+	196.773	30932474
DeepCCS	[M-H]-	194.377	30932474
DeepCCS	[M-2H]-	227.642	30932474
DeepCCS	[M+Na]+	202.706	30932474
AllCCS	[M+H]+	195.6	32859911
AllCCS	[M+H-H2O]+	193.3	32859911
AllCCS	[M+NH4]+	197.7	32859911
AllCCS	[M+Na]+	198.3	32859911
AllCCS	[M-H]-	195.5	32859911
AllCCS	[M+Na-2H]-	196.1	32859911
AllCCS	[M+HCOO]-	197.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lisinopril	NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O	4336.1	Standard polar	33892256
Lisinopril	NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O	3389.8	Standard non polar	33892256
Lisinopril	NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O	3430.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lisinopril,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O	3337.1	Semi standard non polar	33892256
Lisinopril,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N[C@@H](CCC1=CC=CC=C1)C(=O)O	3396.6	Semi standard non polar	33892256
Lisinopril,1TMS,isomer #3	C[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O	3549.8	Semi standard non polar	33892256
Lisinopril,1TMS,isomer #4	C[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O	3366.3	Semi standard non polar	33892256
Lisinopril,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	3300.6	Semi standard non polar	33892256
Lisinopril,2TMS,isomer #2	C[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3407.0	Semi standard non polar	33892256
Lisinopril,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	3256.6	Semi standard non polar	33892256
Lisinopril,2TMS,isomer #4	C[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	3443.5	Semi standard non polar	33892256
Lisinopril,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3264.7	Semi standard non polar	33892256
Lisinopril,2TMS,isomer #6	C[Si](C)(C)N(CCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	3565.4	Semi standard non polar	33892256
Lisinopril,2TMS,isomer #7	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3422.6	Semi standard non polar	33892256
Lisinopril,3TMS,isomer #1	C[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	3379.5	Semi standard non polar	33892256
Lisinopril,3TMS,isomer #1	C[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	3347.0	Standard non polar	33892256
Lisinopril,3TMS,isomer #1	C[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	4153.2	Standard polar	33892256
Lisinopril,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3233.8	Semi standard non polar	33892256
Lisinopril,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3215.6	Standard non polar	33892256
Lisinopril,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	4580.6	Standard polar	33892256
Lisinopril,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3483.7	Semi standard non polar	33892256
Lisinopril,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3406.4	Standard non polar	33892256
Lisinopril,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	4353.1	Standard polar	33892256
Lisinopril,3TMS,isomer #4	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3338.3	Semi standard non polar	33892256
Lisinopril,3TMS,isomer #4	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3338.2	Standard non polar	33892256
Lisinopril,3TMS,isomer #4	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	4304.5	Standard polar	33892256
Lisinopril,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N[C@@H](CCC1=CC=CC=C1)C(=O)O	3525.3	Semi standard non polar	33892256
Lisinopril,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N[C@@H](CCC1=CC=CC=C1)C(=O)O	3406.0	Standard non polar	33892256
Lisinopril,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N[C@@H](CCC1=CC=CC=C1)C(=O)O	4359.2	Standard polar	33892256
Lisinopril,3TMS,isomer #6	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3350.6	Semi standard non polar	33892256
Lisinopril,3TMS,isomer #6	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3364.6	Standard non polar	33892256
Lisinopril,3TMS,isomer #6	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	4274.6	Standard polar	33892256
Lisinopril,3TMS,isomer #7	C[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3551.2	Semi standard non polar	33892256
Lisinopril,3TMS,isomer #7	C[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3429.7	Standard non polar	33892256
Lisinopril,3TMS,isomer #7	C[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	4496.8	Standard polar	33892256
Lisinopril,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	3490.5	Semi standard non polar	33892256
Lisinopril,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	3422.5	Standard non polar	33892256
Lisinopril,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	4012.4	Standard polar	33892256
Lisinopril,4TMS,isomer #2	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3335.2	Semi standard non polar	33892256
Lisinopril,4TMS,isomer #2	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3356.1	Standard non polar	33892256
Lisinopril,4TMS,isomer #2	C[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3936.4	Standard polar	33892256
Lisinopril,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	3527.6	Semi standard non polar	33892256
Lisinopril,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	3427.9	Standard non polar	33892256
Lisinopril,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C	4155.9	Standard polar	33892256
Lisinopril,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3536.1	Semi standard non polar	33892256
Lisinopril,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3442.7	Standard non polar	33892256
Lisinopril,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	4125.9	Standard polar	33892256
Lisinopril,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3573.3	Semi standard non polar	33892256
Lisinopril,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3438.8	Standard non polar	33892256
Lisinopril,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3837.2	Standard polar	33892256
Lisinopril,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O	3605.0	Semi standard non polar	33892256
Lisinopril,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N[C@@H](CCC1=CC=CC=C1)C(=O)O	3661.7	Semi standard non polar	33892256
Lisinopril,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O	3746.9	Semi standard non polar	33892256
Lisinopril,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O	3629.7	Semi standard non polar	33892256
Lisinopril,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3807.7	Semi standard non polar	33892256
Lisinopril,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3875.8	Semi standard non polar	33892256
Lisinopril,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	3820.6	Semi standard non polar	33892256
Lisinopril,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3916.1	Semi standard non polar	33892256
Lisinopril,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3840.3	Semi standard non polar	33892256
Lisinopril,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(CCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	4034.3	Semi standard non polar	33892256
Lisinopril,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3934.9	Semi standard non polar	33892256
Lisinopril,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4052.6	Semi standard non polar	33892256
Lisinopril,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3868.2	Standard non polar	33892256
Lisinopril,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCC[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4307.2	Standard polar	33892256
Lisinopril,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4040.9	Semi standard non polar	33892256
Lisinopril,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3741.1	Standard non polar	33892256
Lisinopril,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4587.7	Standard polar	33892256
Lisinopril,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	4194.0	Semi standard non polar	33892256
Lisinopril,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3921.6	Standard non polar	33892256
Lisinopril,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	4442.0	Standard polar	33892256
Lisinopril,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4114.3	Semi standard non polar	33892256
Lisinopril,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3852.7	Standard non polar	33892256
Lisinopril,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4426.1	Standard polar	33892256
Lisinopril,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[C@@H](CCC1=CC=CC=C1)C(=O)O	4219.0	Semi standard non polar	33892256
Lisinopril,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[C@@H](CCC1=CC=CC=C1)C(=O)O	3909.6	Standard non polar	33892256
Lisinopril,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N[C@@H](CCC1=CC=CC=C1)C(=O)O	4439.9	Standard polar	33892256
Lisinopril,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	4127.2	Semi standard non polar	33892256
Lisinopril,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3859.9	Standard non polar	33892256
Lisinopril,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	4394.1	Standard polar	33892256
Lisinopril,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	4272.1	Semi standard non polar	33892256
Lisinopril,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	3926.2	Standard non polar	33892256
Lisinopril,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	4544.9	Standard polar	33892256
Lisinopril,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4380.4	Semi standard non polar	33892256
Lisinopril,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4055.4	Standard non polar	33892256
Lisinopril,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4194.3	Standard polar	33892256
Lisinopril,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4302.1	Semi standard non polar	33892256
Lisinopril,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3992.5	Standard non polar	33892256
Lisinopril,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4174.1	Standard polar	33892256
Lisinopril,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	4461.9	Semi standard non polar	33892256
Lisinopril,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	4061.7	Standard non polar	33892256
Lisinopril,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O)[Si](C)(C)C(C)(C)C	4305.3	Standard polar	33892256
Lisinopril,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	4459.3	Semi standard non polar	33892256
Lisinopril,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	4051.3	Standard non polar	33892256
Lisinopril,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	4273.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lisinopril GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9344000000-3673a7191e97a0ee02e0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lisinopril GC-MS (2 TMS) - 70eV, Positive	splash10-0f6x-9201340000-bc9644b3a3a4109f3722	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lisinopril 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 - Lisinopril 10V, Negative-QTOF	splash10-0ik9-0900500000-85d2bfa23ac02fce017d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril 40V, Negative-QTOF	splash10-03di-0900000000-b4cd463dbaeec149b805	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril 20V, Negative-QTOF	splash10-03di-0900000000-c2a4ab9f5fb48e5480bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4r-0194100000-d9a47a283478b88bb101	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-9040000000-8d6d4ae6ba18da11e336	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-001i-9000000000-77e20f7eb799eea58ab0	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril LC-ESI-qTof , Positive-QTOF	splash10-01q0-0940000000-116994867a4e2c649c00	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril LC-ESI-qTof , Positive-QTOF	splash10-01q0-0940000000-116994867a4e2c649c00	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril 40V, Positive-QTOF	splash10-001i-9120000000-fd2acaa1eae37a6f7ba6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril 10V, Positive-QTOF	splash10-0a4i-2010900000-67e85126826eedd63b6c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lisinopril 20V, Positive-QTOF	splash10-053r-9052300000-d651e557fe1ae7eac452	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 10V, Negative-QTOF	splash10-0w29-0119600000-219bea00e0a247bc0888	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 20V, Negative-QTOF	splash10-03di-2429100000-404746794cb47e7eb6fc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 40V, Negative-QTOF	splash10-03di-3920000000-b1093c7b1913ec8ec8d0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 10V, Negative-QTOF	splash10-0udi-0002900000-ce436e39fbead59af3f2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 20V, Negative-QTOF	splash10-0ik9-3933500000-a236ac37e133779ee0ac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 40V, Negative-QTOF	splash10-03dj-8910000000-db165b4504f7321c51e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 10V, Positive-QTOF	splash10-06ri-0229300000-236b576cdfc8112530c7	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 20V, Positive-QTOF	splash10-03xu-4497000000-ad2ca7e02728a51b0051	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 40V, Positive-QTOF	splash10-014i-9760000000-517501fe175444669d72	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 10V, Positive-QTOF	splash10-0a4i-0002900000-a76c25515295bb79175b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 20V, Positive-QTOF	splash10-0901-2395300000-cc32f663c74e5f0f3306	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lisinopril 40V, Positive-QTOF	splash10-001i-9110000000-ccd25ccd5c2ff94948b4	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
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

Kidney
Pancreas
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Lisinopril 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

DB00722

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022753

KNApSAcK ID

Not Available

Chemspider ID

4514933

KEGG Compound ID

D00362

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lisinopril

METLIN ID

1009

PubChem Compound

5362119

PDB ID

Not Available

ChEBI ID

43755

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

Corradi HR, Schwager SL, Nchinda AT, Sturrock ED, Acharya KR: Crystal structure of the N domain of human somatic angiotensin I-converting enzyme provides a structural basis for domain-specific inhibitor design. J Mol Biol. 2006 Mar 31;357(3):964-74. Epub 2006 Jan 31. [PubMed:16476442 ]
Alves MF, Araujo MC, Juliano MA, Oliveira EM, Krieger JE, Casarini DE, Juliano L, Carmona AK: A continuous fluorescent assay for the determination of plasma and tissue angiotensin I-converting enzyme activity. Braz J Med Biol Res. 2005 Jun;38(6):861-8. Epub 2005 Jun 1. [PubMed:15933779 ]
Tashtoush BM, Alali FQ, Najib NM: Liquid chromatographic-mass spectrometric method for quantitative determination of lisinopril in human plasma. Pharmazie. 2004 Jan;59(1):21-4. [PubMed:14964416 ]
Swaisland AJ: The pharmacokinetics of co-administered lisinopril and hydrochlorothiazide. J Hum Hypertens. 1991 Dec;5 Suppl 2:69-71. [PubMed:1665181 ]
Lanzillo JJ, Stevens J, Dasarathy Y, Yotsumoto H, Fanburg BL: Angiotensin-converting enzyme from human tissues. Physicochemical, catalytic, and immunological properties. J Biol Chem. 1985 Dec 5;260(28):14938-44. [PubMed:2999099 ]
Huang J, Xu Y, Liu F, Gao S, Guo Q: Development of a liquid chromatography/tandem mass spectrometry assay for the quantification of lisinopril in human plasma. Rapid Commun Mass Spectrom. 2006;20(2):248-52. [PubMed:16345121 ]
Sudoh T, Fujimura A, Shiga T, Tateishi T, Sunaga K, Ohashi K, Ebihara A: Influence of lisinopril on urinary electrolytes excretion after furosemide in healthy subjects. J Clin Pharmacol. 1993 Jul;33(7):640-3. [PubMed:8396158 ]
Ranieri G, Andriani A, Lamontanara G, De Cesaris R: Effects of lisinopril and amlodipine on microalbuminuria and renal function in patients with hypertension. Clin Pharmacol Ther. 1994 Sep;56(3):323-30. [PubMed:7924128 ]
Haenni A, Reneland R, Andersson PE, Lind L, Lithell H: Skeletal muscle magnesium content is correlated with plasma glucose concentration in patients with essential hypertension treated with lisinopril or bendrofluazide. Am J Hypertens. 2002 Aug;15(8):735-8. [PubMed:12160198 ]
Arakawa M, Murata Y, Rikimaru Y, Sasaki Y: Drug-induced isolated visceral angioneurotic edema. Intern Med. 2005 Sep;44(9):975-8. [PubMed:16258215 ]
Donohoe JF, Kelly J, Laher MS, Doyle GD: Lisinopril in the treatment of hypertensive patients with renal impairment. Am J Med. 1988 Sep 23;85(3B):31-4. [PubMed:2844084 ]
Donohoe JF, Laher M, Doyle GD, Long C, Glover DR, Cooper WD: Lisinopril treatment of hypertension in patients with impaired renal function. Gerontology. 1987;33 Suppl 1:36-41. [PubMed:2831115 ]
Yuan AS, Gilbert JD: Time-resolved fluoroimmunoassay for the determination of lisinopril and enalaprilat in human serum. J Pharm Biomed Anal. 1996 May;14(7):773-81. [PubMed:8809701 ]
Araujo MC, Melo RI, Del Nery E, Alves MF, Juliano MA, Casarini DE, Juliano L, Carmona AK: Internally quenched fluorogenic substrates for angiotensin I-converting enzyme. J Hypertens. 1999 May;17(5):665-72. [PubMed:10403610 ]
Shionoiri H, Shigemasa T, Takasaki I: [Angiotensin-converting enzyme inhibitors: recent therapeutic aspect]. Nihon Rinsho. 1997 Aug;55(8):2067-74. [PubMed:9284425 ]

Enzymes

Enzyme Details

1. 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

Enzyme Details

2. Angiotensinogen

General function:: Involved in serine-type endopeptidase inhibitor activity
Specific function:: Angiotensin 1-7 is a ligand for the G-protein coupled receptor MAS1. Has vasodilator and antidiuretic effects. Has an antithrombotic effect that involves MAS1-mediated release of nitric oxide from platelets
Gene Name:: AGT
Uniprot ID:: P01019
Molecular weight:: 53153.7

Showing metabocard for Lisinopril (HMDB0001938)

MOL for HMDB0001938 (Lisinopril)

3D MOL for HMDB0001938 (Lisinopril)

3D SDF for HMDB0001938 (Lisinopril)

3D-SDF for HMDB0001938 (Lisinopril)

PDB for HMDB0001938 (Lisinopril)

3D PDB for HMDB0001938 (Lisinopril)

SMILES for HMDB0001938 (Lisinopril)

INCHI for HMDB0001938 (Lisinopril)

Structure for HMDB0001938 (Lisinopril)

3D Structure for HMDB0001938 (Lisinopril)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes