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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (3) Show 5 proteins XML

enzymes (2)transporters (3) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014928

Secondary Accession Numbers

HMDB14928

Metabolite Identification

Common Name

Perindopril

Description

Perindopril is a nonsulfhydryl prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly metabolized in the liver to perindoprilat, its active metabolite, following oral administration. Perindoprilat 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). Perindopril may be used to treat mild to moderate essential hypertension, mild to moderate congestive heart failure, and to reduce the cardiovascular risk of individuals with hypertension or post-myocardial infarction and stable coronary disease.

Structure

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

790
  Mrv0541 02231215002D          

 28 29  0  0  1  0            999 V2000
    5.4686   -1.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1240   -3.4305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1240   -2.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    2.1428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4050   -2.0521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666    0.1304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243   -3.1285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6243   -2.3035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4050   -3.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -2.7160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9099   -3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -1.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1953   -3.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1953   -2.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613   -1.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7115   -2.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -0.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3030   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8157    0.7445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0083    0.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0719    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501    1.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7772    2.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2263    3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6942   -3.7848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6942   -1.6472    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  2  0  0  0  0
  2 17  1  0  0  0  0
  3 17  2  0  0  0  0
  4 22  1  0  0  0  0
  4 25  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 16  1  0  0  0  0
 18  7  1  6  0  0  0
 20  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  8 27  1  1  0  0  0
  9 13  1  0  0  0  0
  9 28  1  1  0  0  0
 10 11  1  0  0  0  0
 11 17  1  6  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0014928
     RDKit          3D
Perindopril
 58 59  0  0  0  0  0  0  0  0999 V2000
    4.0927   -2.1787   -3.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -0.9241   -3.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061    0.0826   -2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8991   -0.4351   -1.0054 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5532   -0.7784   -0.8903 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    0.1600   -0.8937 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4243    0.9280   -2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797   -0.6000   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7823   -1.8039   -1.0766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679   -0.0116   -0.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109    1.3183    0.2617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6239    1.5269    1.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0628    0.5883    2.2292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    2.7351    2.2564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    1.6596    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2369    0.3217    0.1317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0709    0.1649    1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6339   -1.2612    1.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4706   -2.1544    1.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -1.8553    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153   -0.7049   -0.0657 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3864    0.4602    0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117    0.8426    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    0.8378    0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896    1.6807    1.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2085    1.1883    2.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888   -2.7177   -4.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9548   -1.9584   -2.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -2.8564   -2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622   -0.5401   -4.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -1.2847   -3.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5201    0.2447   -2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    1.0389   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4973   -1.3940   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3410   -1.5767   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5791    0.9300   -0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.1577   -2.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920    1.9381   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723    0.3850   -3.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236    1.9783   -0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283    2.8489    2.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    2.2779    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619    2.2255   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9913    0.3463   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4899    0.1841    2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8387    0.9311    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9995   -1.3725    0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4142   -1.4421    2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8334   -3.2062    1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266   -2.0553    2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036   -1.6812    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8881   -2.8048    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931   -1.1635   -1.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3807    1.7548    0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8473    2.6846    0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0282    1.6636    3.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2576    1.5766    2.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    0.1001    2.5764 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  4 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 21 10  1  0
 21 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  1
  5 35  1  0
  6 36  1  1
  7 37  1  0
  7 38  1  0
  7 39  1  0
 11 40  1  6
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  6
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  6
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
M  END

790
  Mrv0541 02231215002D          

 28 29  0  0  1  0            999 V2000
    5.4686   -1.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1240   -3.4305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1240   -2.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5210    2.1428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4050   -2.0521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666    0.1304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243   -3.1285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6243   -2.3035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4050   -3.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -2.7160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9099   -3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -1.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1953   -3.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1953   -2.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613   -1.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7115   -2.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -0.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3030   -0.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8157    0.7445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0083    0.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0719    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4573    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501    1.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7772    2.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2263    3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6942   -3.7848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6942   -1.6472    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  2  0  0  0  0
  2 17  1  0  0  0  0
  3 17  2  0  0  0  0
  4 22  1  0  0  0  0
  4 25  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 16  1  0  0  0  0
 18  7  1  6  0  0  0
 20  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  8 27  1  1  0  0  0
  9 13  1  0  0  0  0
  9 28  1  1  0  0  0
 10 11  1  0  0  0  0
 11 17  1  6  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014928

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H32N2O5/c1-4-8-14(19(25)26-5-2)20-12(3)17(22)21-15-10-7-6-9-13(15)11-16(21)18(23)24/h12-16,20H,4-11H2,1-3H3,(H,23,24)/t12-,13-,14-,15-,16-/m0/s1

> <INCHI_KEY>
IPVQLZZIHOAWMC-QXKUPLGCSA-N

> <FORMULA>
C19H32N2O5

> <MOLECULAR_WEIGHT>
368.4678

> <EXACT_MASS>
368.231122144

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.9984417915483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
0.6307438391420584

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7860549560034094

> <JCHEM_PKA_STRONGEST_BASIC>
5.480288012911529

> <JCHEM_POLAR_SURFACE_AREA>
95.93999999999998

> <JCHEM_REFRACTIVITY>
95.69279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
perindopril

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014928
     RDKit          3D
Perindopril
 58 59  0  0  0  0  0  0  0  0999 V2000
    4.0927   -2.1787   -3.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -0.9241   -3.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061    0.0826   -2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8991   -0.4351   -1.0054 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5532   -0.7784   -0.8903 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    0.1600   -0.8937 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4243    0.9280   -2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797   -0.6000   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7823   -1.8039   -1.0766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679   -0.0116   -0.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109    1.3183    0.2617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6239    1.5269    1.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0628    0.5883    2.2292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    2.7351    2.2564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    1.6596    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2369    0.3217    0.1317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0709    0.1649    1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6339   -1.2612    1.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4706   -2.1544    1.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -1.8553    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153   -0.7049   -0.0657 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3864    0.4602    0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117    0.8426    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    0.8378    0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896    1.6807    1.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2085    1.1883    2.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888   -2.7177   -4.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9548   -1.9584   -2.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -2.8564   -2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622   -0.5401   -4.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -1.2847   -3.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5201    0.2447   -2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    1.0389   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4973   -1.3940   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3410   -1.5767   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5791    0.9300   -0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.1577   -2.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920    1.9381   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723    0.3850   -3.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236    1.9783   -0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283    2.8489    2.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    2.2779    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619    2.2255   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9913    0.3463   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4899    0.1841    2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8387    0.9311    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9995   -1.3725    0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4142   -1.4421    2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8334   -3.2062    1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266   -2.0553    2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036   -1.6812    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8881   -2.8048    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931   -1.1635   -1.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3807    1.7548    0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8473    2.6846    0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0282    1.6636    3.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2576    1.5766    2.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    0.1001    2.5764 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  4 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 21 10  1  0
 21 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  1
  5 35  1  0
  6 36  1  1
  7 37  1  0
  7 38  1  0
  7 39  1  0
 11 40  1  6
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  6
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  6
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 790                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      10.208  -2.049   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.431  -6.404   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.431  -3.736   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.573   4.000   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.108   3.171   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       8.223  -3.831   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.151   0.243   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.765  -5.840   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.765  -4.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.223  -6.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.121  -5.070   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.432  -6.610   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.432  -3.530   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.098  -5.840   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.098  -4.300   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.701  -2.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.661  -5.070   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.673  -1.220   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.166  -1.538   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.123   1.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.615   1.072   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.601   2.854   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.587   2.218   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080   1.901   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.051   5.464   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.022   6.610   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       6.896  -7.065   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.896  -3.075   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4   22   25                                                       
CONECT    5   22                                                            
CONECT    6    9   11   16                                                  
CONECT    7   18   20                                                       
CONECT    8    9   10   12   27                                             
CONECT    9    6    8   13   28                                             
CONECT   10    8   11                                                       
CONECT   11    6   10   17                                                  
CONECT   12    8   14                                                       
CONECT   13    9   15                                                       
CONECT   14   12   15                                                       
CONECT   15   13   14                                                       
CONECT   16    1    6   18                                                  
CONECT   17    2    3   11                                                  
CONECT   18    7   16   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21   22                                                  
CONECT   21   20   23                                                       
CONECT   22    4    5   20                                                  
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25    4   26                                                       
CONECT   26   25                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0014928
HETATM    1  C1  UNL     1       4.093  -2.179  -3.120  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.280  -0.924  -3.434  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.406   0.083  -2.318  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.899  -0.435  -1.005  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.553  -0.778  -0.890  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.516   0.160  -0.894  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.424   0.928  -2.181  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.780  -0.600  -0.731  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.782  -1.804  -1.077  1.00  0.00           O  
HETATM   10  N2  UNL     1      -1.968  -0.012  -0.207  1.00  0.00           N  
HETATM   11  C8  UNL     1      -2.111   1.318   0.262  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.624   1.527   1.641  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.063   0.588   2.229  1.00  0.00           O  
HETATM   14  O3  UNL     1      -1.792   2.735   2.256  1.00  0.00           O  
HETATM   15  C10 UNL     1      -3.558   1.660   0.091  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.237   0.322   0.132  1.00  0.00           C  
HETATM   17  C12 UNL     1      -5.071   0.165   1.380  1.00  0.00           C  
HETATM   18  C13 UNL     1      -5.634  -1.261   1.271  1.00  0.00           C  
HETATM   19  C14 UNL     1      -4.471  -2.154   1.594  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.208  -1.855   0.881  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.215  -0.705  -0.066  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.386   0.460   0.090  1.00  0.00           C  
HETATM   23  O4  UNL     1       2.612   0.843   0.971  1.00  0.00           O  
HETATM   24  O5  UNL     1       4.703   0.838   0.084  1.00  0.00           O  
HETATM   25  C18 UNL     1       5.290   1.681   1.047  1.00  0.00           C  
HETATM   26  C19 UNL     1       5.208   1.188   2.454  1.00  0.00           C  
HETATM   27  H1  UNL     1       4.389  -2.718  -4.040  1.00  0.00           H  
HETATM   28  H2  UNL     1       4.955  -1.958  -2.468  1.00  0.00           H  
HETATM   29  H3  UNL     1       3.429  -2.856  -2.551  1.00  0.00           H  
HETATM   30  H4  UNL     1       3.662  -0.540  -4.380  1.00  0.00           H  
HETATM   31  H5  UNL     1       2.253  -1.285  -3.595  1.00  0.00           H  
HETATM   32  H6  UNL     1       4.520   0.245  -2.194  1.00  0.00           H  
HETATM   33  H7  UNL     1       3.016   1.039  -2.648  1.00  0.00           H  
HETATM   34  H8  UNL     1       3.497  -1.394  -0.834  1.00  0.00           H  
HETATM   35  H9  UNL     1       1.341  -1.577  -0.276  1.00  0.00           H  
HETATM   36  H10 UNL     1       0.579   0.930  -0.081  1.00  0.00           H  
HETATM   37  H11 UNL     1      -0.652   1.158  -2.417  1.00  0.00           H  
HETATM   38  H12 UNL     1       0.892   1.938  -2.059  1.00  0.00           H  
HETATM   39  H13 UNL     1       0.772   0.385  -3.071  1.00  0.00           H  
HETATM   40  H14 UNL     1      -1.524   1.978  -0.450  1.00  0.00           H  
HETATM   41  H15 UNL     1      -2.528   2.849   2.953  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.832   2.278   0.993  1.00  0.00           H  
HETATM   43  H17 UNL     1      -3.762   2.226  -0.842  1.00  0.00           H  
HETATM   44  H18 UNL     1      -4.991   0.346  -0.714  1.00  0.00           H  
HETATM   45  H19 UNL     1      -4.490   0.184   2.309  1.00  0.00           H  
HETATM   46  H20 UNL     1      -5.839   0.931   1.401  1.00  0.00           H  
HETATM   47  H21 UNL     1      -6.000  -1.373   0.219  1.00  0.00           H  
HETATM   48  H22 UNL     1      -6.414  -1.442   2.016  1.00  0.00           H  
HETATM   49  H23 UNL     1      -4.833  -3.206   1.438  1.00  0.00           H  
HETATM   50  H24 UNL     1      -4.327  -2.055   2.708  1.00  0.00           H  
HETATM   51  H25 UNL     1      -2.404  -1.681   1.623  1.00  0.00           H  
HETATM   52  H26 UNL     1      -2.888  -2.805   0.354  1.00  0.00           H  
HETATM   53  H27 UNL     1      -3.393  -1.164  -1.094  1.00  0.00           H  
HETATM   54  H28 UNL     1       6.381   1.755   0.781  1.00  0.00           H  
HETATM   55  H29 UNL     1       4.847   2.685   0.923  1.00  0.00           H  
HETATM   56  H30 UNL     1       6.028   1.664   3.066  1.00  0.00           H  
HETATM   57  H31 UNL     1       4.258   1.577   2.916  1.00  0.00           H  
HETATM   58  H32 UNL     1       5.200   0.100   2.576  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   22   34
CONECT    5    6   35
CONECT    6    7    8   36
CONECT    7   37   38   39
CONECT    8    9    9   10
CONECT   10   11   21
CONECT   11   12   15   40
CONECT   12   13   13   14
CONECT   14   41
CONECT   15   16   42   43
CONECT   16   17   21   44
CONECT   17   18   45   46
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   51   52
CONECT   21   53
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   54   55
CONECT   26   56   57   58
END

HMDB0014928
     RDKit          3D
Perindopril
 58 59  0  0  0  0  0  0  0  0999 V2000
    4.0927   -2.1787   -3.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -0.9241   -3.4341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061    0.0826   -2.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8991   -0.4351   -1.0054 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5532   -0.7784   -0.8903 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    0.1600   -0.8937 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4243    0.9280   -2.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7797   -0.6000   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7823   -1.8039   -1.0766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679   -0.0116   -0.2072 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1109    1.3183    0.2617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6239    1.5269    1.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0628    0.5883    2.2292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    2.7351    2.2564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579    1.6596    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2369    0.3217    0.1317 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0709    0.1649    1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6339   -1.2612    1.2709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4706   -2.1544    1.5938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -1.8553    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2153   -0.7049   -0.0657 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3864    0.4602    0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6117    0.8426    0.9711 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7034    0.8378    0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896    1.6807    1.0471 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2085    1.1883    2.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888   -2.7177   -4.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9548   -1.9584   -2.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4291   -2.8564   -2.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622   -0.5401   -4.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -1.2847   -3.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5201    0.2447   -2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0155    1.0389   -2.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4973   -1.3940   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3410   -1.5767   -0.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5791    0.9300   -0.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.1577   -2.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920    1.9381   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7723    0.3850   -3.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236    1.9783   -0.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283    2.8489    2.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    2.2779    0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619    2.2255   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9913    0.3463   -0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4899    0.1841    2.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8387    0.9311    1.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9995   -1.3725    0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4142   -1.4421    2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8334   -3.2062    1.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266   -2.0553    2.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4036   -1.6812    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8881   -2.8048    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931   -1.1635   -1.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3807    1.7548    0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8473    2.6846    0.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0282    1.6636    3.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2576    1.5766    2.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    0.1001    2.5764 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  4 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 21 10  1  0
 21 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  1
  5 35  1  0
  6 36  1  1
  7 37  1  0
  7 38  1  0
  7 39  1  0
 11 40  1  6
 14 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  6
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  6
 25 54  1  0
 25 55  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3AS,7as)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylic acid	ChEBI
Perindoprilum	ChEBI
(2S,3AS,7as)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]octahydro-1H-indole-2-carboxylate	Generator
Perindopril erbumine	HMDB
Erbumine, perindopril	HMDB
Perstarium	HMDB
Pirindopril	HMDB

Chemical Formula

C₁₉H₃₂N₂O₅

Average Molecular Weight

368.4678

Monoisotopic Molecular Weight

368.231122144

IUPAC Name

(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid

Traditional Name

perindopril

CAS Registry Number

107133-36-8

SMILES

[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O

InChI Identifier

InChI=1S/C19H32N2O5/c1-4-8-14(19(25)26-5-2)20-12(3)17(22)21-15-10-7-6-9-13(15)11-16(21)18(23)24/h12-16,20H,4-11H2,1-3H3,(H,23,24)/t12-,13-,14-,15-,16-/m0/s1

InChI Key

IPVQLZZIHOAWMC-QXKUPLGCSA-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
Alpha-amino acid ester
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Indole or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Amino acid
Azacycle
Secondary aliphatic amine
Carboxylic acid
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

dicarboxylic acid monoester (CHEBI:8024 )
ethyl ester (CHEBI:8024 )
alpha-amino acid ester (CHEBI:8024 )
organic heterobicyclic compound (CHEBI:8024 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014928)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Perindopril Action Pathway (PathBank: SMP0000152)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.22 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	188.771	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001290

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.22 g/L	ALOGPS
logP	0.56	ALOGPS
logP	0.63	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	5.48	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	9	ChemAxon
Refractivity	95.69 m³·mol⁻¹	ChemAxon
Polarizability	40 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]+	188.751	31661259
DarkChem	[M-H]-	184.536	31661259
DeepCCS	[M-2H]-	228.008	30932474
DeepCCS	[M+Na]+	203.431	30932474
AllCCS	[M+H]+	191.3	32859911
AllCCS	[M+H-H2O]+	188.9	32859911
AllCCS	[M+NH4]+	193.4	32859911
AllCCS	[M+Na]+	194.0	32859911
AllCCS	[M-H]-	189.9	32859911
AllCCS	[M+Na-2H]-	190.5	32859911
AllCCS	[M+HCOO]-	191.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.46 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7364 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.09 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	111.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2242.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	186.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	131.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	491.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	498.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	154.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1026.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	479.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1493.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	265.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	152.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	80.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Perindopril	[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O	3582.5	Standard polar	33892256
Perindopril	[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O	2511.1	Standard non polar	33892256
Perindopril	[H][C@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O	2643.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Perindopril,1TMS,isomer #1	CCC[C@H](N[C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCCC[C@@H]21)C(=O)OCC	2502.7	Semi standard non polar	33892256
Perindopril,1TMS,isomer #2	CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C	2559.8	Semi standard non polar	33892256
Perindopril,2TMS,isomer #1	CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C	2584.6	Semi standard non polar	33892256
Perindopril,2TMS,isomer #1	CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C	2626.8	Standard non polar	33892256
Perindopril,2TMS,isomer #1	CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C	3568.4	Standard polar	33892256
Perindopril,1TBDMS,isomer #1	CCC[C@H](N[C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCCC[C@@H]21)C(=O)OCC	2732.6	Semi standard non polar	33892256
Perindopril,1TBDMS,isomer #2	CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C	2801.4	Semi standard non polar	33892256
Perindopril,2TBDMS,isomer #1	CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C	3034.6	Semi standard non polar	33892256
Perindopril,2TBDMS,isomer #1	CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C	3015.9	Standard non polar	33892256
Perindopril,2TBDMS,isomer #1	CCC[C@@H](C(=O)OCC)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C	3687.2	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Perindopril Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00790	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00790	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00790

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

96956

KEGG Compound ID

C07706

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Perindopril

METLIN ID

Not Available

PubChem Compound

107807

PDB ID

Not Available

ChEBI ID

8024

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

Yoshiji H, Kuriyama S, Kawata M, Yoshii J, Ikenaka Y, Noguchi R, Nakatani T, Tsujinoue H, Fukui H: The angiotensin-I-converting enzyme inhibitor perindopril suppresses tumor growth and angiogenesis: possible role of the vascular endothelial growth factor. Clin Cancer Res. 2001 Apr;7(4):1073-8. [PubMed:11309359 ]
Hurst M, Jarvis B: Perindopril: an updated review of its use in hypertension. Drugs. 2001;61(6):867-96. [PubMed:11398915 ]
Simpson D, Noble S, Goa KL: Perindopril: in congestive heart failure. Drugs. 2002;62(9):1367-77; discussion 1378-9. [PubMed:12076191 ]
Yasumatsu R, Nakashima T, Masuda M, Ito A, Kuratomi Y, Nakagawa T, Komune S: Effects of the angiotensin-I converting enzyme inhibitor perindopril on tumor growth and angiogenesis in head and neck squamous cell carcinoma cells. J Cancer Res Clin Oncol. 2004 Oct;130(10):567-73. Epub 2004 Jul 27. [PubMed:15449186 ]
Jastrzebskal M, Widecka K, Naruszewicz M, Ciechanowicz A, Janczak-Bazan A, Foltynska A, Goracy I, Chetstowski K, Wesotowska T: Effects of perindopril treatment on hemostatic function in patients with essential hypertension in relation to angiotensin converting enzyme (ACE) and plasminogen activator inhibitor-1 (PAI-1) gene polymorphisms. Nutr Metab Cardiovasc Dis. 2004 Oct;14(5):259-69. [PubMed:15673060 ]
Parker E, Aarons L, Rowland M, Resplandy G: The pharmacokinetics of perindoprilat in normal volunteers and patients: influence of age and disease state. Eur J Pharm Sci. 2005 Sep;26(1):104-13. [PubMed:15982858 ]

Enzymes

Enzyme Details

1. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Mehta A, Iyer L, Parmar S, Shah G, Goyal R: Oculohypotensive effect of perindopril in acute and chronic models of glaucoma in rabbits. Can J Physiol Pharmacol. 2010 May;88(5):595-600. doi: 10.1139/y10-026. [PubMed:20555429 ]

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

Alfakih K, Hall AS: Perindopril. Expert Opin Pharmacother. 2006 Jan;7(1):63-71. [PubMed:16370923 ]
Brugts JJ, Ferrari R, Simoons ML: Angiotensin-converting enzyme inhibition by perindopril in the treatment of cardiovascular disease. Expert Rev Cardiovasc Ther. 2009 Apr;7(4):345-60. doi: 10.1586/erc.09.2. [PubMed:19379059 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [PubMed:11929321 ]

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 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

Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951 ]

Enzyme Details

3. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951 ]

Showing metabocard for Perindopril (HMDB0014928)

MOL for HMDB0014928 (Perindopril)

3D MOL for HMDB0014928 (Perindopril)

3D SDF for HMDB0014928 (Perindopril)

3D-SDF for HMDB0014928 (Perindopril)

PDB for HMDB0014928 (Perindopril)

3D PDB for HMDB0014928 (Perindopril)

SMILES for HMDB0014928 (Perindopril)

INCHI for HMDB0014928 (Perindopril)

Structure for HMDB0014928 (Perindopril)

3D Structure for HMDB0014928 (Perindopril)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

Transporters

References

References

References