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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:52:41 UTC

Update Date

2021-09-14 15:40:15 UTC

HMDB ID

HMDB0042005

Secondary Accession Numbers

HMDB42005

Metabolite Identification

Common Name

Quinaprilat

Description

Quinaprilat is the active metabolite of quinapril. Quinapril is a prodrug and is a long-acting, non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor used in the treatment of arterial hypertension or chronic heart failure (PMID: 19761414 ). Prodrugs are compounds that must be metabolized in the gut or liver before they can become active. Quinaprilat functions through blocking the conversion of angiotensin I to the vasoconstrictor angiotensin II, thereby inhibiting bradykinin degradation which reduces vascular oxidative stress and endothelial activity (PMID: 15223904 ). It is eliminated mainly in urine. It has no teratogenic, mutagenic or carcinogenic effect. Quinaprilat is only found in individuals who have taken or consumed the drug quinapril.

Structure

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


  Mrv0541 09131211522D          

 33 35  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 12 11  1  0  0  0  0
 15  1  1  6  0  0  0
 16  7  2  0  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
 17  9  2  0  0  0  0
 17 13  1  0  0  0  0
 18 10  2  0  0  0  0
 18 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 15  1  0  0  0  0
 22 19  1  0  0  0  0
 20 23  1  1  0  0  0
 24 15  1  0  0  0  0
 19 24  1  1  0  0  0
 25 14  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 21  2  0  0  0  0
 27 22  2  0  0  0  0
 28 22  1  0  0  0  0
 29 23  2  0  0  0  0
 30 23  1  0  0  0  0
 15 31  1  1  0  0  0
 19 32  1  1  0  0  0
 20 33  1  6  0  0  0
M  END

HMDB0042005
     RDKit          3D
Quinaprilat
 56 58  0  0  0  0  0  0  0  0999 V2000
    0.1154    1.3132    0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681    0.0095    0.2201 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0770   -0.6025   -0.3390 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625   -1.3774    0.3789 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4011   -1.2471   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8881    0.1521    0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2884    0.2862   -0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180    0.6550   -1.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9271    0.7574   -2.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9189    0.4689   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6366    0.0929    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    0.0060    0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9364   -1.4362    1.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180   -0.7619    2.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071   -2.3452    2.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586   -0.0573   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8682   -0.2524   -2.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236    0.0729   -0.4908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -0.0556   -1.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8715    0.2763   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9783   -0.1806   -1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2523    0.1323   -1.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4106    0.8991   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3569    1.3581    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0595    1.0395    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765    1.5082    0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414    0.2979    0.8811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6572   -0.9076    1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0916   -0.8417    2.5983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8625   -2.0531    0.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    1.3584    1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    2.0411    0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    1.8308    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503   -0.7568    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011   -0.0406   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170   -2.4955    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0470   -2.0086    0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -1.5290   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8232    0.3761    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2248    0.8516   -0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8534    0.8949   -2.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1206    1.0690   -3.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9549    0.5491   -1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4622   -0.1232    0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1025   -0.3011    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592   -2.2633    3.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2425    0.5961   -2.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -1.1159   -1.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7980   -0.7719   -2.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1275   -0.2170   -1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4081    1.1722    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4769    1.9729    1.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299    2.2883    0.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741    1.8307    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269    0.5261    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068   -2.9412    1.1108 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 12  7  1  0
 27 18  1  0
 25 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  1
  3 35  1  0
  4 36  1  6
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 15 46  1  0
 19 47  1  0
 19 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  1
 30 56  1  0
M  END


  Mrv0541 09131211522D          

 33 35  0  0  0  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 12 11  1  0  0  0  0
 15  1  1  6  0  0  0
 16  7  2  0  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
 17  9  2  0  0  0  0
 17 13  1  0  0  0  0
 18 10  2  0  0  0  0
 18 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 15  1  0  0  0  0
 22 19  1  0  0  0  0
 20 23  1  1  0  0  0
 24 15  1  0  0  0  0
 19 24  1  1  0  0  0
 25 14  1  0  0  0  0
 25 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 21  2  0  0  0  0
 27 22  2  0  0  0  0
 28 22  1  0  0  0  0
 29 23  2  0  0  0  0
 30 23  1  0  0  0  0
 15 31  1  1  0  0  0
 19 32  1  1  0  0  0
 20 33  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0042005

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N2O5/c1-15(24-19(22(27)28)12-11-16-7-3-2-4-8-16)21(26)25-14-18-10-6-5-9-17(18)13-20(25)23(29)30/h2-10,15,19-20,24H,11-14H2,1H3,(H,27,28)(H,29,30)/t15-,19-,20-/m0/s1

> <INCHI_KEY>
FLSLEGPOVLMJMN-YSSFQJQWSA-N

> <FORMULA>
C23H26N2O5

> <MOLECULAR_WEIGHT>
410.4629

> <EXACT_MASS>
410.184171952

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
42.759478698422015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
0.2992457205145838

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.9459627014064402

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.066926103007926

> <JCHEM_PKA_STRONGEST_BASIC>
7.799950567548593

> <JCHEM_POLAR_SURFACE_AREA>
106.94000000000001

> <JCHEM_REFRACTIVITY>
110.43809999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quinaprilat

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0042005
     RDKit          3D
Quinaprilat
 56 58  0  0  0  0  0  0  0  0999 V2000
    0.1154    1.3132    0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681    0.0095    0.2201 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0770   -0.6025   -0.3390 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625   -1.3774    0.3789 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4011   -1.2471   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8881    0.1521    0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2884    0.2862   -0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180    0.6550   -1.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9271    0.7574   -2.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9189    0.4689   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6366    0.0929    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    0.0060    0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9364   -1.4362    1.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180   -0.7619    2.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071   -2.3452    2.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586   -0.0573   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8682   -0.2524   -2.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236    0.0729   -0.4908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -0.0556   -1.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8715    0.2763   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9783   -0.1806   -1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2523    0.1323   -1.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4106    0.8991   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3569    1.3581    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0595    1.0395    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765    1.5082    0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414    0.2979    0.8811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6572   -0.9076    1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0916   -0.8417    2.5983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8625   -2.0531    0.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    1.3584    1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    2.0411    0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    1.8308    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503   -0.7568    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011   -0.0406   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170   -2.4955    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0470   -2.0086    0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -1.5290   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8232    0.3761    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2248    0.8516   -0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8534    0.8949   -2.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1206    1.0690   -3.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9549    0.5491   -1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4622   -0.1232    0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1025   -0.3011    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592   -2.2633    3.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2425    0.5961   -2.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -1.1159   -1.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7980   -0.7719   -2.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1275   -0.2170   -1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4081    1.1722    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4769    1.9729    1.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299    2.2883    0.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741    1.8307    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269    0.5261    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068   -2.9412    1.1108 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 12  7  1  0
 27 18  1  0
 25 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  1
  3 35  1  0
  4 36  1  6
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 15 46  1  0
 19 47  1  0
 19 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  1
 30 56  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337   7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.671   5.390   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       9.336   3.850   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      12.003   5.390   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0      13.337   3.080   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      16.004   6.160   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      14.671   3.850   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0      12.003   2.310   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.668   2.310   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      14.671   6.930   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    3   16                                                       
CONECT    8    4   16                                                       
CONECT    9    5   17                                                       
CONECT   10    6   18                                                       
CONECT   11   12   16                                                       
CONECT   12   11   19                                                       
CONECT   13   17   20                                                       
CONECT   14   18   25                                                       
CONECT   15    1   21   24   31                                             
CONECT   16    7    8   11                                                  
CONECT   17    9   13   18                                                  
CONECT   18   10   14   17                                                  
CONECT   19   12   22   24   32                                             
CONECT   20   13   23   25   33                                             
CONECT   21   15   25   26                                                  
CONECT   22   19   27   28                                                  
CONECT   23   20   29   30                                                  
CONECT   24   15   19                                                       
CONECT   25   14   20   21                                                  
CONECT   26   21                                                            
CONECT   27   22                                                            
CONECT   28   22                                                            
CONECT   29   23                                                            
CONECT   30   23                                                            
CONECT   31   15                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

COMPND    HMDB0042005
HETATM    1  C1  UNL     1       0.115   1.313   0.909  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.068   0.009   0.220  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.077  -0.602  -0.339  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.963  -1.377   0.379  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.401  -1.247  -0.116  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.888   0.152   0.056  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.288   0.286  -0.379  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.618   0.655  -1.647  1.00  0.00           C  
HETATM    9  C8  UNL     1       6.927   0.757  -2.073  1.00  0.00           C  
HETATM   10  C9  UNL     1       7.919   0.469  -1.171  1.00  0.00           C  
HETATM   11  C10 UNL     1       7.637   0.093   0.110  1.00  0.00           C  
HETATM   12  C11 UNL     1       6.312   0.006   0.494  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.936  -1.436   1.835  1.00  0.00           C  
HETATM   14  O1  UNL     1       1.218  -0.762   2.585  1.00  0.00           O  
HETATM   15  O2  UNL     1       2.807  -2.345   2.452  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.159  -0.057  -0.805  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.868  -0.252  -2.037  1.00  0.00           O  
HETATM   18  N2  UNL     1      -2.524   0.073  -0.491  1.00  0.00           N  
HETATM   19  C14 UNL     1      -3.512  -0.056  -1.551  1.00  0.00           C  
HETATM   20  C15 UNL     1      -4.872   0.276  -1.092  1.00  0.00           C  
HETATM   21  C16 UNL     1      -5.978  -0.181  -1.816  1.00  0.00           C  
HETATM   22  C17 UNL     1      -7.252   0.132  -1.419  1.00  0.00           C  
HETATM   23  C18 UNL     1      -7.411   0.899  -0.301  1.00  0.00           C  
HETATM   24  C19 UNL     1      -6.357   1.358   0.425  1.00  0.00           C  
HETATM   25  C20 UNL     1      -5.060   1.040   0.021  1.00  0.00           C  
HETATM   26  C21 UNL     1      -3.877   1.508   0.813  1.00  0.00           C  
HETATM   27  C22 UNL     1      -2.941   0.298   0.881  1.00  0.00           C  
HETATM   28  C23 UNL     1      -3.657  -0.908   1.397  1.00  0.00           C  
HETATM   29  O4  UNL     1      -4.092  -0.842   2.598  1.00  0.00           O  
HETATM   30  O5  UNL     1      -3.863  -2.053   0.647  1.00  0.00           O  
HETATM   31  H1  UNL     1       0.007   1.358   1.989  1.00  0.00           H  
HETATM   32  H2  UNL     1      -0.636   2.041   0.441  1.00  0.00           H  
HETATM   33  H3  UNL     1       1.096   1.831   0.666  1.00  0.00           H  
HETATM   34  H4  UNL     1      -0.450  -0.757   1.032  1.00  0.00           H  
HETATM   35  H5  UNL     1       1.501  -0.041  -1.134  1.00  0.00           H  
HETATM   36  H6  UNL     1       1.717  -2.495   0.013  1.00  0.00           H  
HETATM   37  H7  UNL     1       4.047  -2.009   0.366  1.00  0.00           H  
HETATM   38  H8  UNL     1       3.364  -1.529  -1.217  1.00  0.00           H  
HETATM   39  H9  UNL     1       3.823   0.376   1.157  1.00  0.00           H  
HETATM   40  H10 UNL     1       3.225   0.852  -0.475  1.00  0.00           H  
HETATM   41  H11 UNL     1       4.853   0.895  -2.390  1.00  0.00           H  
HETATM   42  H12 UNL     1       7.121   1.069  -3.100  1.00  0.00           H  
HETATM   43  H13 UNL     1       8.955   0.549  -1.498  1.00  0.00           H  
HETATM   44  H14 UNL     1       8.462  -0.123   0.784  1.00  0.00           H  
HETATM   45  H15 UNL     1       6.103  -0.301   1.521  1.00  0.00           H  
HETATM   46  H16 UNL     1       3.059  -2.263   3.400  1.00  0.00           H  
HETATM   47  H17 UNL     1      -3.242   0.596  -2.390  1.00  0.00           H  
HETATM   48  H18 UNL     1      -3.473  -1.116  -1.933  1.00  0.00           H  
HETATM   49  H19 UNL     1      -5.798  -0.772  -2.683  1.00  0.00           H  
HETATM   50  H20 UNL     1      -8.127  -0.217  -1.977  1.00  0.00           H  
HETATM   51  H21 UNL     1      -8.408   1.172   0.055  1.00  0.00           H  
HETATM   52  H22 UNL     1      -6.477   1.973   1.317  1.00  0.00           H  
HETATM   53  H23 UNL     1      -3.330   2.288   0.268  1.00  0.00           H  
HETATM   54  H24 UNL     1      -4.174   1.831   1.811  1.00  0.00           H  
HETATM   55  H25 UNL     1      -2.127   0.526   1.546  1.00  0.00           H  
HETATM   56  H26 UNL     1      -3.707  -2.941   1.111  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   16   34
CONECT    3    4   35
CONECT    4    5   13   36
CONECT    5    6   37   38
CONECT    6    7   39   40
CONECT    7    8    8   12
CONECT    8    9   41
CONECT    9   10   10   42
CONECT   10   11   43
CONECT   11   12   12   44
CONECT   12   45
CONECT   13   14   14   15
CONECT   15   46
CONECT   16   17   17   18
CONECT   18   19   27
CONECT   19   20   47   48
CONECT   20   21   21   25
CONECT   21   22   49
CONECT   22   23   23   50
CONECT   23   24   51
CONECT   24   25   25   52
CONECT   25   26
CONECT   26   27   53   54
CONECT   27   28   55
CONECT   28   29   29   30
CONECT   30   56
END

HMDB0042005
     RDKit          3D
Quinaprilat
 56 58  0  0  0  0  0  0  0  0999 V2000
    0.1154    1.3132    0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0681    0.0095    0.2201 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0770   -0.6025   -0.3390 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625   -1.3774    0.3789 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4011   -1.2471   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8881    0.1521    0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2884    0.2862   -0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6180    0.6550   -1.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9271    0.7574   -2.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9189    0.4689   -1.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6366    0.0929    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    0.0060    0.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9364   -1.4362    1.8352 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180   -0.7619    2.5850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071   -2.3452    2.4517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586   -0.0573   -0.8045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8682   -0.2524   -2.0371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5236    0.0729   -0.4908 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5118   -0.0556   -1.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8715    0.2763   -1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9783   -0.1806   -1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2523    0.1323   -1.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4106    0.8991   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3569    1.3581    0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0595    1.0395    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765    1.5082    0.8132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414    0.2979    0.8811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6572   -0.9076    1.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0916   -0.8417    2.5983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8625   -2.0531    0.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0070    1.3584    1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    2.0411    0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    1.8308    0.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4503   -0.7568    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011   -0.0406   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170   -2.4955    0.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0470   -2.0086    0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638   -1.5290   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8232    0.3761    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2248    0.8516   -0.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8534    0.8949   -2.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1206    1.0690   -3.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9549    0.5491   -1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4622   -0.1232    0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1025   -0.3011    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0592   -2.2633    3.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2425    0.5961   -2.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -1.1159   -1.9333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7980   -0.7719   -2.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1275   -0.2170   -1.9771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4081    1.1722    0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4769    1.9729    1.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299    2.2883    0.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741    1.8307    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1269    0.5261    1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068   -2.9412    1.1108 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 12  7  1  0
 27 18  1  0
 25 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  1
  3 35  1  0
  4 36  1  6
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 15 46  1  0
 19 47  1  0
 19 48  1  0
 21 49  1  0
 22 50  1  0
 23 51  1  0
 24 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  1
 30 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
CI 928	ChEBI
CI-928	ChEBI
CI928	ChEBI
CL-928	ChEBI
Quinaprilate	ChEBI
Quinaprilatum	ChEBI
Quinaprilic acid	Generator
CI-928quinaprilat	HMDB
2-(2-((1-Carboxy-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid	HMDB
Quinaprilat, (3S-(2(r(r)),3R*))-isomer	HMDB

Chemical Formula

C₂₃H₂₆N₂O₅

Average Molecular Weight

410.4629

Monoisotopic Molecular Weight

410.184171952

IUPAC Name

(3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Traditional Name

quinaprilat

CAS Registry Number

82768-85-2

SMILES

[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O

InChI Identifier

InChI=1S/C23H26N2O5/c1-15(24-19(22(27)28)12-11-16-7-3-2-4-8-16)21(26)25-14-18-10-6-5-9-17(18)13-20(25)23(29)30/h2-10,15,19-20,24H,11-14H2,1H3,(H,27,28)(H,29,30)/t15-,19-,20-/m0/s1

InChI Key

FLSLEGPOVLMJMN-YSSFQJQWSA-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-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid
Alpha-amino acid or derivatives
Tetrahydroisoquinoline
L-alpha-amino acid
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Organoheterocyclic compound
Azacycle
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0042005)

Endogenous

Endogenous (HMDB: HMDB0042005)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Quinapril Action Pathway (PathBank: SMP0000153)

Metabolic pathway

Quinapril Metabolism Pathway (PathBank: SMP0000596)

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.036 g/L	ALOGPS
logP	0.81	ALOGPS
logP	0.3	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.07	ChemAxon
pKa (Strongest Basic)	7.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.94 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	110.44 m³·mol⁻¹	ChemAxon
Polarizability	42.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.601	31661259
DarkChem	[M-H]-	189.339	31661259
DeepCCS	[M+H]+	183.913	30932474
DeepCCS	[M-H]-	181.518	30932474
DeepCCS	[M-2H]-	214.402	30932474
DeepCCS	[M+Na]+	189.826	30932474
AllCCS	[M+H]+	200.1	32859911
AllCCS	[M+H-H2O]+	197.7	32859911
AllCCS	[M+NH4]+	202.3	32859911
AllCCS	[M+Na]+	202.9	32859911
AllCCS	[M-H]-	195.3	32859911
AllCCS	[M+Na-2H]-	195.9	32859911
AllCCS	[M+HCOO]-	196.7	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.	4.36 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4729 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.39 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	101.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1855.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	213.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	128.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	448.7 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	454.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	259.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1003.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	509.8 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	1346.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	260.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	185.4 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	54.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quinaprilat	[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O	4863.0	Standard polar	33892256
Quinaprilat	[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O	3070.6	Standard non polar	33892256
Quinaprilat	[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CC2=CC=CC=C2C[C@@]1([H])C(O)=O	3476.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quinaprilat,1TMS,isomer #1	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O	3284.0	Semi standard non polar	33892256
Quinaprilat,1TMS,isomer #2	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C	3303.0	Semi standard non polar	33892256
Quinaprilat,1TMS,isomer #3	C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3293.6	Semi standard non polar	33892256
Quinaprilat,2TMS,isomer #1	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C	3223.8	Semi standard non polar	33892256
Quinaprilat,2TMS,isomer #2	C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3227.4	Semi standard non polar	33892256
Quinaprilat,2TMS,isomer #3	C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	3211.1	Semi standard non polar	33892256
Quinaprilat,3TMS,isomer #1	C[C@@H](C(=O)N1CC2=CC=CC=C2C[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	3223.7	Semi standard non polar	33892256
Quinaprilat,3TMS,isomer #1	C[C@@H](C(=O)N1CC2=CC=CC=C2C[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	3210.5	Standard non polar	33892256
Quinaprilat,1TBDMS,isomer #1	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O	3548.2	Semi standard non polar	33892256
Quinaprilat,1TBDMS,isomer #2	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3568.5	Semi standard non polar	33892256
Quinaprilat,1TBDMS,isomer #3	C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3578.0	Semi standard non polar	33892256
Quinaprilat,2TBDMS,isomer #1	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3721.7	Semi standard non polar	33892256
Quinaprilat,2TBDMS,isomer #2	C[C@@H](C(=O)N1CC2=CC=CC=C2C[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	3764.8	Semi standard non polar	33892256
Quinaprilat,2TBDMS,isomer #3	C[C@@H](C(=O)N1CC2=CC=CC=C2C[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	3761.7	Semi standard non polar	33892256
Quinaprilat,3TBDMS,isomer #1	C[C@@H](C(=O)N1CC2=CC=CC=C2C[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	3947.4	Semi standard non polar	33892256
Quinaprilat,3TBDMS,isomer #1	C[C@@H](C(=O)N1CC2=CC=CC=C2C[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	3812.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Quinaprilat GC-MS (Non-derivatized) - 70eV, Positive	splash10-0403-2925000000-e4de4c2b1f51a90ebc34	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinaprilat GC-MS (2 TMS) - 70eV, Positive	splash10-000i-9642440000-3935bd20baf3ed736d1d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinaprilat 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 10V, Positive-QTOF	splash10-03xu-0239400000-657f7ef4a13d754d6019	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 20V, Positive-QTOF	splash10-0a4i-1953000000-6560d0372a2a1dd70171	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 40V, Positive-QTOF	splash10-03ec-2900000000-89636c81c5cbbdc3ef6d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 10V, Negative-QTOF	splash10-0aor-0009500000-9c12c7c6c289ed26d187	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 20V, Negative-QTOF	splash10-0690-0529100000-5ebce1d9aed5907f8abf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 40V, Negative-QTOF	splash10-02e9-1910000000-df2dae9a4c8d21668f20	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 10V, Positive-QTOF	splash10-03di-0125900000-de537442df409f3872dc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 20V, Positive-QTOF	splash10-014i-0319100000-0d99754c5f3bea7a6b30	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 40V, Positive-QTOF	splash10-02u3-2900000000-67e4c42bed2130a5a52d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 10V, Negative-QTOF	splash10-0a4i-0114900000-c3d294563f563dcc6f6d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 20V, Negative-QTOF	splash10-057i-0911100000-7452d726559f5d57738a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinaprilat 40V, Negative-QTOF	splash10-0m0x-2910000000-ad031a0b0ef9b18dd397	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Quinapril Action Pathway		Not Available
Quinapril Metabolism Pathway		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

97106

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Quinaprilat

METLIN ID

Not Available

PubChem Compound

107994

PDB ID

Not Available

ChEBI ID

140296

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

Kieback AG, Felix SB, Reffelmann T: Quinaprilat: a review of its pharmacokinetics, pharmacodynamics, toxicological data and clinical application. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1337-47. doi: 10.1517/17425250903282773. [PubMed:19761414 ]
Steinhauff S, Pehlivanli S, Bakovic-Alt R, Meiser BM, Becker BF, von Scheidt W, Weis M: Beneficial effects of quinaprilat on coronary vasomotor function, endothelial oxidative stress, and endothelin activation after human heart transplantation. Transplantation. 2004 Jun 27;77(12):1859-65. doi: 10.1097/01.tp.0000131148.78203.b7. [PubMed:15223904 ]

Showing metabocard for Quinaprilat (HMDB0042005)

MOL for HMDB0042005 (Quinaprilat)

3D MOL for HMDB0042005 (Quinaprilat)

3D SDF for HMDB0042005 (Quinaprilat)

3D-SDF for HMDB0042005 (Quinaprilat)

PDB for HMDB0042005 (Quinaprilat)

3D PDB for HMDB0042005 (Quinaprilat)

SMILES for HMDB0042005 (Quinaprilat)

INCHI for HMDB0042005 (Quinaprilat)

Structure for HMDB0042005 (Quinaprilat)

3D Structure for HMDB0042005 (Quinaprilat)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra