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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:47:17 UTC

Update Date

2021-09-14 15:40:14 UTC

HMDB ID

HMDB0041908

Secondary Accession Numbers

HMDB41908

Metabolite Identification

Common Name

Imidaprilat

Description

Imidaprilat, is the active metabolite of Imidapril. Imidapril is a prodrug used to treat hypertension, chronic congestive heart failure (CHF), acute myocardial infarction (AMI), and diabetic nephropathy (PMID: 17547476 ,18192036 ,12177688 , 17094051 ). Imidapril belongs to a class of long-acting, non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitors (PMID: 8851752 , 12177688 ). Imidaprilat competitively binds and inhibits the catalytic activity of ACE, which results in a reduction of peripheral resistance and a reduction in systemic blood pressure (BP) (PMID: 17547476 ). Imidaprilat is only found in individuals that have used or taken imidapril.

Structure

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


  Mrv0541 09131211472D          

 30 31  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9445   -0.0957    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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    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
    1.4289    1.6500    0.0000 C   0  0  0  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
    7.0215    1.3725    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4694    1.9856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6410    2.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8020    0.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6090    0.6580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    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
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0279    3.3446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4256    3.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889    0.2775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2663    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 11  1  1  6  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  1  0  0  0  0
 14 17  1  6  0  0  0
 19 11  1  0  0  0  0
 13 19  1  1  0  0  0
 20  2  1  0  0  0  0
 20 10  1  0  0  0  0
 20 18  1  0  0  0  0
 21 14  1  0  0  0  0
 21 15  1  0  0  0  0
 21 18  1  0  0  0  0
 22 15  2  0  0  0  0
 23 16  2  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26 17  1  0  0  0  0
 27 18  2  0  0  0  0
 11 28  1  1  0  0  0
 13 29  1  1  0  0  0
 14 30  1  1  0  0  0
M  END

HMDB0041908
     RDKit          3D
Imidaprilat
 50 51  0  0  0  0  0  0  0  0999 V2000
   -1.2593    1.2430    0.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246    0.6668   -0.4635 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2049    1.5185   -1.1443 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564    2.1441   -0.7819 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5534    1.3220   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4647    0.3522    0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7899   -0.3620    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376    0.1371    1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550   -0.5105    1.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227   -1.6650    1.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2583   -2.1748    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0567   -1.5052    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7865    3.0719   -1.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    3.1304   -2.9835 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156    3.8583   -1.8037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    0.3969   -1.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508    1.0341   -2.4304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001   -0.5849   -1.0357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -1.4208    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467   -1.6217    0.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0101   -2.1113    0.1354 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6737   -2.5925    1.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -2.2158   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852   -0.9042   -1.7984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9989    0.1403   -1.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1465    0.1083   -1.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7419    1.1721   -0.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3209    0.9753    0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    2.3385    0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    0.7893    1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2581   -0.3325   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1981    1.8456   -2.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2689    2.8201    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714    0.8235   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109    2.0197   -0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353    0.9401    1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -0.4173    0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5771    1.0293    2.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7063   -0.1259    2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1333   -2.2232    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4207   -3.0766   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857   -1.8787   -0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842    4.8726   -1.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2419   -3.5461    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7401   -1.8439    2.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7294   -2.8386    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8663   -3.0137   -1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5359   -2.3799   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7885   -0.9427   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4616    1.5378    0.0537 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  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 12  7  1  0
 24 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  1
  3 32  1  0
  4 33  1  1
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 15 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  6
 27 50  1  0
M  END


  Mrv0541 09131211472D          

 30 31  0  0  0  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9445   -0.0957    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
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    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
    1.4289    1.6500    0.0000 C   0  0  0  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
    7.0215    1.3725    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4694    1.9856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6410    2.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8020    0.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6090    0.6580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    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
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0279    3.3446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4256    3.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1889    0.2775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2663    2.1991    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 11  1  1  6  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  1  0  0  0  0
 14 17  1  6  0  0  0
 19 11  1  0  0  0  0
 13 19  1  1  0  0  0
 20  2  1  0  0  0  0
 20 10  1  0  0  0  0
 20 18  1  0  0  0  0
 21 14  1  0  0  0  0
 21 15  1  0  0  0  0
 21 18  1  0  0  0  0
 22 15  2  0  0  0  0
 23 16  2  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26 17  1  0  0  0  0
 27 18  2  0  0  0  0
 11 28  1  1  0  0  0
 13 29  1  1  0  0  0
 14 30  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0041908

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1C(=O)N(C)C[C@@]1([H])C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H23N3O6/c1-11(15(22)21-14(17(25)26)10-20(2)18(21)27)19-13(16(23)24)9-8-12-6-4-3-5-7-12/h3-7,11,13-14,19H,8-10H2,1-2H3,(H,23,24)(H,25,26)/t11-,13-,14-/m0/s1

> <INCHI_KEY>
VFAVNRVDTAPBNR-UBHSHLNASA-N

> <FORMULA>
C18H23N3O6

> <MOLECULAR_WEIGHT>
377.3917

> <EXACT_MASS>
377.158685483

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
37.899500444964815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.04

> <JCHEM_LOGP>
-1.6827117906227724

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.772431291779487

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9826483365792225

> <JCHEM_PKA_STRONGEST_BASIC>
7.830791912429779

> <JCHEM_POLAR_SURFACE_AREA>
127.25

> <JCHEM_REFRACTIVITY>
93.68619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-3-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-1-methyl-2-oxoimidazolidine-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041908
     RDKit          3D
Imidaprilat
 50 51  0  0  0  0  0  0  0  0999 V2000
   -1.2593    1.2430    0.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246    0.6668   -0.4635 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2049    1.5185   -1.1443 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564    2.1441   -0.7819 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5534    1.3220   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4647    0.3522    0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7899   -0.3620    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376    0.1371    1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550   -0.5105    1.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227   -1.6650    1.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2583   -2.1748    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0567   -1.5052    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7865    3.0719   -1.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    3.1304   -2.9835 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156    3.8583   -1.8037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    0.3969   -1.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508    1.0341   -2.4304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001   -0.5849   -1.0357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -1.4208    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467   -1.6217    0.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0101   -2.1113    0.1354 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6737   -2.5925    1.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -2.2158   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852   -0.9042   -1.7984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9989    0.1403   -1.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1465    0.1083   -1.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7419    1.1721   -0.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3209    0.9753    0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    2.3385    0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    0.7893    1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2581   -0.3325   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1981    1.8456   -2.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2689    2.8201    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714    0.8235   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109    2.0197   -0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353    0.9401    1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -0.4173    0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5771    1.0293    2.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7063   -0.1259    2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1333   -2.2232    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4207   -3.0766   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857   -1.8787   -0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842    4.8726   -1.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2419   -3.5461    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7401   -1.8439    2.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7294   -2.8386    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8663   -3.0137   -1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5359   -2.3799   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7885   -0.9427   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4616    1.5378    0.0537 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  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 12  7  1  0
 24 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  1
  3 32  1  0
  4 33  1  1
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 15 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  6
 27 50  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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.963  -0.179   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.107   2.562   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.076   3.706   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.397   5.213   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.830   1.548   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      12.337   1.228   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      10.669   3.080   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       9.336   5.390   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      11.252   6.243   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.861   5.689   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.686   0.518   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0       9.336   2.310   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.001   2.310   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      13.564   4.105   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10   14   20                                                       
CONECT   11    1   15   19   28                                             
CONECT   12    6    7    8                                                  
CONECT   13    9   16   19   29                                             
CONECT   14   10   17   21   30                                             
CONECT   15   11   21   22                                                  
CONECT   16   13   23   24                                                  
CONECT   17   14   25   26                                                  
CONECT   18   20   21   27                                                  
CONECT   19   11   13                                                       
CONECT   20    2   10   18                                                  
CONECT   21   14   15   18                                                  
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26   17                                                            
CONECT   27   18                                                            
CONECT   28   11                                                            
CONECT   29   13                                                            
CONECT   30   14                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

COMPND    HMDB0041908
HETATM    1  C1  UNL     1      -1.259   1.243   0.788  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.625   0.667  -0.464  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.205   1.519  -1.144  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.356   2.144  -0.782  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.553   1.322  -0.507  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.465   0.352   0.608  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.790  -0.362   0.751  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.738   0.137   1.591  1.00  0.00           C  
HETATM    9  C8  UNL     1       5.955  -0.511   1.737  1.00  0.00           C  
HETATM   10  C9  UNL     1       6.223  -1.665   1.035  1.00  0.00           C  
HETATM   11  C10 UNL     1       5.258  -2.175   0.178  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.057  -1.505   0.057  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.786   3.072  -1.930  1.00  0.00           C  
HETATM   14  O1  UNL     1       1.131   3.130  -2.984  1.00  0.00           O  
HETATM   15  O2  UNL     1       2.916   3.858  -1.804  1.00  0.00           O  
HETATM   16  C13 UNL     1      -1.821   0.397  -1.374  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.951   1.034  -2.430  1.00  0.00           O  
HETATM   18  N2  UNL     1      -2.800  -0.585  -1.036  1.00  0.00           N  
HETATM   19  C14 UNL     1      -2.749  -1.421   0.091  1.00  0.00           C  
HETATM   20  O4  UNL     1      -1.847  -1.622   0.963  1.00  0.00           O  
HETATM   21  N3  UNL     1      -4.010  -2.111   0.135  1.00  0.00           N  
HETATM   22  C15 UNL     1      -4.674  -2.592   1.311  1.00  0.00           C  
HETATM   23  C16 UNL     1      -4.456  -2.216  -1.240  1.00  0.00           C  
HETATM   24  C17 UNL     1      -3.985  -0.904  -1.798  1.00  0.00           C  
HETATM   25  C18 UNL     1      -4.999   0.140  -1.464  1.00  0.00           C  
HETATM   26  O5  UNL     1      -6.147   0.108  -1.996  1.00  0.00           O  
HETATM   27  O6  UNL     1      -4.742   1.172  -0.577  1.00  0.00           O  
HETATM   28  H1  UNL     1      -2.321   0.975   0.853  1.00  0.00           H  
HETATM   29  H2  UNL     1      -1.092   2.339   0.865  1.00  0.00           H  
HETATM   30  H3  UNL     1      -0.738   0.789   1.648  1.00  0.00           H  
HETATM   31  H4  UNL     1      -0.258  -0.333  -0.245  1.00  0.00           H  
HETATM   32  H5  UNL     1      -0.198   1.846  -2.072  1.00  0.00           H  
HETATM   33  H6  UNL     1       1.269   2.820   0.138  1.00  0.00           H  
HETATM   34  H7  UNL     1       2.871   0.824  -1.472  1.00  0.00           H  
HETATM   35  H8  UNL     1       3.411   2.020  -0.253  1.00  0.00           H  
HETATM   36  H9  UNL     1       2.335   0.940   1.559  1.00  0.00           H  
HETATM   37  H10 UNL     1       1.708  -0.417   0.571  1.00  0.00           H  
HETATM   38  H11 UNL     1       4.577   1.029   2.158  1.00  0.00           H  
HETATM   39  H12 UNL     1       6.706  -0.126   2.400  1.00  0.00           H  
HETATM   40  H13 UNL     1       7.133  -2.223   1.095  1.00  0.00           H  
HETATM   41  H14 UNL     1       5.421  -3.077  -0.395  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.286  -1.879  -0.605  1.00  0.00           H  
HETATM   43  H16 UNL     1       2.884   4.873  -1.782  1.00  0.00           H  
HETATM   44  H17 UNL     1      -4.242  -3.546   1.689  1.00  0.00           H  
HETATM   45  H18 UNL     1      -4.740  -1.844   2.142  1.00  0.00           H  
HETATM   46  H19 UNL     1      -5.729  -2.839   1.025  1.00  0.00           H  
HETATM   47  H20 UNL     1      -3.866  -3.014  -1.778  1.00  0.00           H  
HETATM   48  H21 UNL     1      -5.536  -2.380  -1.356  1.00  0.00           H  
HETATM   49  H22 UNL     1      -3.788  -0.943  -2.887  1.00  0.00           H  
HETATM   50  H23 UNL     1      -5.462   1.538   0.054  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   16   31
CONECT    3    4   32
CONECT    4    5   13   33
CONECT    5    6   34   35
CONECT    6    7   36   37
CONECT    7    8    8   12
CONECT    8    9   38
CONECT    9   10   10   39
CONECT   10   11   40
CONECT   11   12   12   41
CONECT   12   42
CONECT   13   14   14   15
CONECT   15   43
CONECT   16   17   17   18
CONECT   18   19   24
CONECT   19   20   20   21
CONECT   21   22   23
CONECT   22   44   45   46
CONECT   23   24   47   48
CONECT   24   25   49
CONECT   25   26   26   27
CONECT   27   50
END

HMDB0041908
     RDKit          3D
Imidaprilat
 50 51  0  0  0  0  0  0  0  0999 V2000
   -1.2593    1.2430    0.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6246    0.6668   -0.4635 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2049    1.5185   -1.1443 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564    2.1441   -0.7819 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5534    1.3220   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4647    0.3522    0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7899   -0.3620    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376    0.1371    1.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550   -0.5105    1.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227   -1.6650    1.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2583   -2.1748    0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0567   -1.5052    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7865    3.0719   -1.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1312    3.1304   -2.9835 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9156    3.8583   -1.8037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209    0.3969   -1.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9508    1.0341   -2.4304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8001   -0.5849   -1.0357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -1.4208    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467   -1.6217    0.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0101   -2.1113    0.1354 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6737   -2.5925    1.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559   -2.2158   -1.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9852   -0.9042   -1.7984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9989    0.1403   -1.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1465    0.1083   -1.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7419    1.1721   -0.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3209    0.9753    0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    2.3385    0.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    0.7893    1.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2581   -0.3325   -0.2455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1981    1.8456   -2.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2689    2.8201    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714    0.8235   -1.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109    2.0197   -0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353    0.9401    1.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -0.4173    0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5771    1.0293    2.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7063   -0.1259    2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1333   -2.2232    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4207   -3.0766   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2857   -1.8787   -0.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842    4.8726   -1.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2419   -3.5461    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7401   -1.8439    2.1422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7294   -2.8386    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8663   -3.0137   -1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5359   -2.3799   -1.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7885   -0.9427   -2.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4616    1.5378    0.0537 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  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 12  7  1  0
 24 18  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  1
  3 32  1  0
  4 33  1  1
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 12 42  1  0
 15 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  6
 27 50  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(4S)-1-Methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid	ChEBI
Imidaprilate	ChEBI
Imidaprilatum	ChEBI
(4S)-1-Methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate	Generator
Imidaprilic acid	Generator
6366a	HMDB
Imidaprilat, (4S-(3(R(r)),4R))-isomer	HMDB
Imidaprilat, monosodium salt, (4S-(3(r(r)),4R*))-isomer	HMDB
3-(2-(N-(1-Carboxy-3-phenylpropyl)amino)propionyl)-1-methyl-2-oxoimidazolidine-4-carboxylic acid	HMDB
Imidaprilat hydrochloride, (4S-(3(r(r)),4R*))	HMDB
Imidaprilat hydrochloride, (4S-(3(s(r)),4R*))-isomer	HMDB

Chemical Formula

C₁₈H₂₃N₃O₆

Average Molecular Weight

377.3917

Monoisotopic Molecular Weight

377.158685483

IUPAC Name

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

Traditional Name

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

CAS Registry Number

89371-44-8

SMILES

[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1C(=O)N(C)C[C@@]1([H])C(O)=O

InChI Identifier

InChI=1S/C18H23N3O6/c1-11(15(22)21-14(17(25)26)10-20(2)18(21)27)19-13(16(23)24)9-8-12-6-4-3-5-7-12/h3-7,11,13-14,19H,8-10H2,1-2H3,(H,23,24)(H,25,26)/t11-,13-,14-/m0/s1

InChI Key

VFAVNRVDTAPBNR-UBHSHLNASA-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
L-alpha-amino acid
N-acyl urea
Aralkylamine
Ureide
Imidazolidinone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Dicarboximide
Imidazolidine
Urea
Amino acid
Amino acid or derivatives
Carbonic acid derivative
Carboxylic acid
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0041908)

Process

Not Available

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	1.06 g/L	ALOGPS
logP	-0.04	ALOGPS
logP	-1.7	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.98	ChemAxon
pKa (Strongest Basic)	7.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	127.25 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	93.69 m³·mol⁻¹	ChemAxon
Polarizability	37.9 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	185.667	31661259
DarkChem	[M-H]-	179.769	31661259
DeepCCS	[M+H]+	176.004	30932474
DeepCCS	[M-H]-	173.608	30932474
DeepCCS	[M-2H]-	206.492	30932474
DeepCCS	[M+Na]+	181.916	30932474
AllCCS	[M+H]+	189.4	32859911
AllCCS	[M+H-H2O]+	186.7	32859911
AllCCS	[M+NH4]+	192.0	32859911
AllCCS	[M+Na]+	192.7	32859911
AllCCS	[M-H]-	187.8	32859911
AllCCS	[M+Na-2H]-	188.2	32859911
AllCCS	[M+HCOO]-	188.9	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.	3.21 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3133 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.09 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	153.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1571.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	202.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	128.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	92.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	351.2 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	415.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	323.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	844.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	411.9 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	1367.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	261.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	329.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	175.4 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	130.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Imidaprilat	[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1C(=O)N(C)C[C@@]1([H])C(O)=O	4703.0	Standard polar	33892256
Imidaprilat	[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1C(=O)N(C)C[C@@]1([H])C(O)=O	3031.0	Standard non polar	33892256
Imidaprilat	[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1C(=O)N(C)C[C@@]1([H])C(O)=O	3078.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Imidaprilat,1TMS,isomer #1	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1C(=O)N(C)C[C@H]1C(=O)O	2923.4	Semi standard non polar	33892256
Imidaprilat,1TMS,isomer #2	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1C(=O)N(C)C[C@H]1C(=O)O[Si](C)(C)C	2945.3	Semi standard non polar	33892256
Imidaprilat,1TMS,isomer #3	C[C@@H](C(=O)N1C(=O)N(C)C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2970.8	Semi standard non polar	33892256
Imidaprilat,2TMS,isomer #1	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1C(=O)N(C)C[C@H]1C(=O)O[Si](C)(C)C	2890.6	Semi standard non polar	33892256
Imidaprilat,2TMS,isomer #2	C[C@@H](C(=O)N1C(=O)N(C)C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2902.9	Semi standard non polar	33892256
Imidaprilat,2TMS,isomer #3	C[C@@H](C(=O)N1C(=O)N(C)C[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C	2907.8	Semi standard non polar	33892256
Imidaprilat,3TMS,isomer #1	C[C@@H](C(=O)N1C(=O)N(C)C[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	2903.3	Semi standard non polar	33892256
Imidaprilat,3TMS,isomer #1	C[C@@H](C(=O)N1C(=O)N(C)C[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	2908.8	Standard non polar	33892256
Imidaprilat,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)N1C(=O)N(C)C[C@H]1C(=O)O	3152.0	Semi standard non polar	33892256
Imidaprilat,1TBDMS,isomer #2	C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1C(=O)N(C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3174.8	Semi standard non polar	33892256
Imidaprilat,1TBDMS,isomer #3	C[C@@H](C(=O)N1C(=O)N(C)C[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C	3187.4	Semi standard non polar	33892256
Imidaprilat,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)N1C(=O)N(C)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3310.7	Semi standard non polar	33892256
Imidaprilat,2TBDMS,isomer #2	C[C@@H](C(=O)N1C(=O)N(C)C[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	3374.0	Semi standard non polar	33892256
Imidaprilat,2TBDMS,isomer #3	C[C@@H](C(=O)N1C(=O)N(C)C[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	3374.5	Semi standard non polar	33892256
Imidaprilat,3TBDMS,isomer #1	C[C@@H](C(=O)N1C(=O)N(C)C[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	3554.9	Semi standard non polar	33892256
Imidaprilat,3TBDMS,isomer #1	C[C@@H](C(=O)N1C(=O)N(C)C[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	3492.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Imidaprilat GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r6-9333000000-0342cc7c97fb89e1eed0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imidaprilat GC-MS (2 TMS) - 70eV, Positive	splash10-06yc-9220210000-78ec36f997b709bf0ace	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Imidaprilat 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 - Imidaprilat 10V, Positive-QTOF	splash10-002b-0914000000-099f0a02b987aabfaa0f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 20V, Positive-QTOF	splash10-06tb-2921000000-6f70e3b444c1e977d053	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 40V, Positive-QTOF	splash10-0007-9410000000-08630f8b3a5958164079	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 10V, Negative-QTOF	splash10-0059-0109000000-85019522c786c8c76d13	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 20V, Negative-QTOF	splash10-0006-8539000000-b8655b8f422e331f5618	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 40V, Negative-QTOF	splash10-0006-9500000000-cdf7c5bfaad296576300	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 10V, Positive-QTOF	splash10-004i-0009000000-2346205b5410c69c549b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 20V, Positive-QTOF	splash10-03e9-1925000000-c0b2ed0519bf2dc40b71	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 40V, Positive-QTOF	splash10-016s-3900000000-c9e8c6e9815a4c714364	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 10V, Negative-QTOF	splash10-004i-0009000000-be90e2b489daf582f2f1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 20V, Negative-QTOF	splash10-0059-2639000000-c8bc49157fba0a601caa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Imidaprilat 40V, Negative-QTOF	splash10-0006-5900000000-8a33c559ab9193f1b173	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

4576629

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Imidapril

METLIN ID

Not Available

PubChem Compound

5464344

PDB ID

Not Available

ChEBI ID

141520

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

Yamanaka K, Morikawa S, Murata K, Banno K, Sato T, Takai T, Suzuki T, Mizobe M, Ito M, Ishibashi K: Radioimmunoassay for imidapril, a new angiotensin-converting enzyme inhibitor, and imidaprilat, its active metabolite, in human plasma and urine. J Pharm Biomed Anal. 1996 Jan;14(3):281-7. [PubMed:8851752 ]
Hosoya K, Ishimitsu T: Protection of the cardiovascular system by imidapril, a versatile angiotensin-converting enzyme inhibitor. Cardiovasc Drug Rev. 2002 Summer;20(2):93-110. doi: 10.1111/j.1527-3466.2002.tb00185.x. [PubMed:12177688 ]
Robinson DM, Curran MP, Lyseng-Williamson KA: Imidapril: a review of its use in essential hypertension, Type 1 diabetic nephropathy and chronic heart failure. Drugs. 2007;67(9):1359-78. doi: 10.2165/00003495-200767090-00008. [PubMed:17547476 ]
Dolezal T: Imidapril in heart failure. J Renin Angiotensin Aldosterone Syst. 2006 Sep;7(3):146-54. doi: 10.3317/jraas.2006.024. [PubMed:17094051 ]
Guo XG, Uzui H, Mizuguchi T, Ueda T, Chen JZ, Lee JD: Imidaprilat inhibits matrix metalloproteinase-2 activity in human cardiac fibroblasts induced by interleukin-1beta via NO-dependent pathway. Int J Cardiol. 2008 Jun 6;126(3):414-20. doi: 10.1016/j.ijcard.2007.08.134. Epub 2008 Jan 14. [PubMed:18192036 ]

Showing metabocard for Imidaprilat (HMDB0041908)

MOL for HMDB0041908 (Imidaprilat)

3D MOL for HMDB0041908 (Imidaprilat)

3D SDF for HMDB0041908 (Imidaprilat)

3D-SDF for HMDB0041908 (Imidaprilat)

PDB for HMDB0041908 (Imidaprilat)

3D PDB for HMDB0041908 (Imidaprilat)

SMILES for HMDB0041908 (Imidaprilat)

INCHI for HMDB0041908 (Imidaprilat)

Structure for HMDB0041908 (Imidaprilat)

3D Structure for HMDB0041908 (Imidaprilat)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra