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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (3) Show 4 proteins XML

enzymes (1)transporters (3) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015433

Secondary Accession Numbers

HMDB15433

Metabolite Identification

Common Name

Cilazapril

Description

Cilazapril is only found in individuals that have used or taken this drug. It is one of the angiotensin-converting enzyme inhibitors (ACE inhibitors) used for hypertension. It is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat. [PubChem]Cilazapri, as a pyridazine ACE inhibitor, competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. As angiotensin II is a vasoconstrictor and a negative feedback mediator for renin activity, lower angiotensin II levels results in a decrease in blood pressure, an increase in renin activity, and stimulation of baroreceptor reflex mechanisms. Kininase II, an enzyme which degrades the vasodilator bradykinin, is identical to ACE and may also be inhibited.

Structure

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

1340
  Mrv0541 02231215232D          

 30 32  0  0  1  0            999 V2000
    5.8928    2.0873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4004    0.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0055    1.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5264    5.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8443    3.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7611    2.6017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5044    2.2437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2356    3.5896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5818    1.3878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4313    3.4060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0436    2.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5775    3.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9169    4.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013    1.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0919    4.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2478    2.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4788    4.3779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3293    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9177    4.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1609    5.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2832    4.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997    6.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7954    6.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8428    7.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3307    5.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2342    6.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2817    7.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5738    6.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4774    7.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
  2 19  1  0  0  0  0
  3 19  2  0  0  0  0
  4 22  1  0  0  0  0
  4 26  1  0  0  0  0
  5 22  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  7 17  1  0  0  0  0
 10  8  1  6  0  0  0
 18  8  1  1  0  0  0
  9 13  1  0  0  0  0
  9 19  1  6  0  0  0
 10 14  1  0  0  0  0
 10 17  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 18 20  1  0  0  0  0
 18 22  1  0  0  0  0
 20 21  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 30  1  0  0  0  0
M  END

HMDB0015433
     RDKit          3D
Cilazapril
 61 63  0  0  0  0  0  0  0  0999 V2000
    2.6271   -0.6341    5.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2869    0.2672    4.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867   -0.2296    2.8943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.3485    2.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.0134    3.2222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157   -0.8563    1.0896 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1236   -0.3473   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -0.6954    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078   -0.0952   -1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642   -0.8669   -2.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009   -0.3481   -3.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2770    0.9312   -3.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249    1.7059   -2.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889    1.1963   -1.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0509   -0.8967    0.8197 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933    0.2029    0.8110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6905    1.3109   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7940    0.8931   -1.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    1.1438   -2.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2431    0.4798   -1.6483 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911   -0.4130   -2.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2734   -0.8335   -1.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2618   -1.1412   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6204    0.0865    0.2430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7054    0.1857    1.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781    0.6057    2.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8775   -0.1997    2.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    0.1167   -0.3317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -0.2918    0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -1.2653    1.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -0.1653    5.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214   -0.7520    6.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -1.6397    4.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955    0.2743    4.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239    1.3161    4.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6214   -1.9973    1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7683   -0.9205   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0134    0.7235   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -0.2502    0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -1.7951   -0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -1.8864   -2.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8424   -0.9613   -4.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013    1.3541   -4.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6153    2.7311   -2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6272    1.7691   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4552   -1.8175    0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294    0.6738    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1455    1.9952    0.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058    1.9917   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4352   -0.1487   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731    1.5405   -2.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3256    2.2586   -2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050    0.9563   -3.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2361    0.1774   -3.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675   -1.2684   -2.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6025   -1.7786   -2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0869   -0.0905   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3065   -1.2346   -0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7204   -2.0611   -0.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2268    0.9409   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6914    0.3882    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 24 28  1  0
 28 29  1  0
 29 30  2  0
 14  9  1  0
 29 16  1  0
 28 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  6 36  1  1
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  1
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  6
 27 61  1  0
M  END

1340
  Mrv0541 02231215232D          

 30 32  0  0  1  0            999 V2000
    5.8928    2.0873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4004    0.2166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0055    1.5111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5264    5.3499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8443    3.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7611    2.6017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5044    2.2437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2356    3.5896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5818    1.3878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4313    3.4060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0436    2.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5775    3.4060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    0.8984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9169    4.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1013    1.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0919    4.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2478    2.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4788    4.3779    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3293    1.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9177    4.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1609    5.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2832    4.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5997    6.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7954    6.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8428    7.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3307    5.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2342    6.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2817    7.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5738    6.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4774    7.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  2  0  0  0  0
  2 19  1  0  0  0  0
  3 19  2  0  0  0  0
  4 22  1  0  0  0  0
  4 26  1  0  0  0  0
  5 22  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  7 17  1  0  0  0  0
 10  8  1  6  0  0  0
 18  8  1  1  0  0  0
  9 13  1  0  0  0  0
  9 19  1  6  0  0  0
 10 14  1  0  0  0  0
 10 17  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 18 20  1  0  0  0  0
 18 22  1  0  0  0  0
 20 21  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015433

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCCN2CCC[C@H](N2C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H31N3O5/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28)/t17-,18-,19-/m0/s1

> <INCHI_KEY>
HHHKFGXWKKUNCY-FHWLQOOXSA-N

> <FORMULA>
C22H31N3O5

> <MOLECULAR_WEIGHT>
417.4986

> <EXACT_MASS>
417.226371117

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
44.72753415687893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S)-9-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-0.007882287847574103

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.409948821751159

> <JCHEM_PKA_STRONGEST_BASIC>
5.352254250776891

> <JCHEM_POLAR_SURFACE_AREA>
99.17999999999998

> <JCHEM_REFRACTIVITY>
110.56370000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
inhibace

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015433
     RDKit          3D
Cilazapril
 61 63  0  0  0  0  0  0  0  0999 V2000
    2.6271   -0.6341    5.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2869    0.2672    4.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867   -0.2296    2.8943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.3485    2.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.0134    3.2222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157   -0.8563    1.0896 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1236   -0.3473   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -0.6954    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078   -0.0952   -1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642   -0.8669   -2.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009   -0.3481   -3.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2770    0.9312   -3.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249    1.7059   -2.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889    1.1963   -1.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0509   -0.8967    0.8197 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933    0.2029    0.8110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6905    1.3109   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7940    0.8931   -1.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    1.1438   -2.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2431    0.4798   -1.6483 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911   -0.4130   -2.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2734   -0.8335   -1.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2618   -1.1412   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6204    0.0865    0.2430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7054    0.1857    1.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781    0.6057    2.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8775   -0.1997    2.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    0.1167   -0.3317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -0.2918    0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -1.2653    1.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -0.1653    5.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214   -0.7520    6.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -1.6397    4.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955    0.2743    4.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239    1.3161    4.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6214   -1.9973    1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7683   -0.9205   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0134    0.7235   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -0.2502    0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -1.7951   -0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -1.8864   -2.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8424   -0.9613   -4.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013    1.3541   -4.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6153    2.7311   -2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6272    1.7691   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4552   -1.8175    0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294    0.6738    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1455    1.9952    0.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058    1.9917   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4352   -0.1487   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731    1.5405   -2.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3256    2.2586   -2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050    0.9563   -3.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2361    0.1774   -3.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675   -1.2684   -2.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6025   -1.7786   -2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0869   -0.0905   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3065   -1.2346   -0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7204   -2.0611   -0.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2268    0.9409   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6914    0.3882    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 24 28  1  0
 28 29  1  0
 29 30  2  0
 14  9  1  0
 29 16  1  0
 28 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  6 36  1  1
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  1
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  6
 27 61  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1340                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.000   3.896   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.081   0.404   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.210   2.821   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.049   9.986   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      14.643   7.386   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.021   4.857   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       8.408   4.188   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      11.640   6.701   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.553   2.591   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.138   6.358   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.681   3.973   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.678   6.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.234   1.677   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.178   7.562   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.789   2.373   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.638   7.562   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.796   4.857   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.094   8.172   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.948   1.939   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.046   9.301   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.500  10.773   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.595   8.515   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.453  11.902   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.951  11.559   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.907  13.373   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.551  10.329   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.904  12.688   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.859  14.502   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.004  11.801   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.358  14.159   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4   22   26                                                       
CONECT    5   22                                                            
CONECT    6    7   11   12                                                  
CONECT    7    6    9   17                                                  
CONECT    8   10   18                                                       
CONECT    9    7   13   19                                                  
CONECT   10    8   14   17                                                  
CONECT   11    6   15                                                       
CONECT   12    6   16                                                       
CONECT   13    9   15                                                       
CONECT   14   10   16                                                       
CONECT   15   11   13                                                       
CONECT   16   12   14                                                       
CONECT   17    1    7   10                                                  
CONECT   18    8   20   22                                                  
CONECT   19    2    3    9                                                  
CONECT   20   18   21                                                       
CONECT   21   20   23                                                       
CONECT   22    4    5   18                                                  
CONECT   23   21   24   25                                                  
CONECT   24   23   27                                                       
CONECT   25   23   28                                                       
CONECT   26    4   29                                                       
CONECT   27   24   30                                                       
CONECT   28   25   30                                                       
CONECT   29   26                                                            
CONECT   30   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0015433
HETATM    1  C1  UNL     1       2.627  -0.634   5.199  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.287   0.267   4.192  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.987  -0.230   2.894  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.692  -0.349   2.423  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.788   0.013   3.222  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.316  -0.856   1.090  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.124  -0.347  -0.054  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.611  -0.695   0.040  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.208  -0.095  -1.212  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.264  -0.867  -2.353  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.801  -0.348  -3.505  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.277   0.931  -3.515  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.225   1.706  -2.385  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.689   1.196  -1.224  1.00  0.00           C  
HETATM   15  N1  UNL     1      -0.051  -0.897   0.820  1.00  0.00           N  
HETATM   16  C13 UNL     1      -0.893   0.203   0.811  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.691   1.311  -0.153  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.794   0.893  -1.593  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.150   1.144  -2.179  1.00  0.00           C  
HETATM   20  N2  UNL     1      -3.243   0.480  -1.648  1.00  0.00           N  
HETATM   21  C17 UNL     1      -3.991  -0.413  -2.500  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.273  -0.833  -1.894  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.262  -1.141  -0.412  1.00  0.00           C  
HETATM   24  C20 UNL     1      -4.620   0.086   0.243  1.00  0.00           C  
HETATM   25  C21 UNL     1      -4.705   0.186   1.666  1.00  0.00           C  
HETATM   26  O3  UNL     1      -3.778   0.606   2.384  1.00  0.00           O  
HETATM   27  O4  UNL     1      -5.877  -0.200   2.328  1.00  0.00           O  
HETATM   28  N3  UNL     1      -3.297   0.117  -0.332  1.00  0.00           N  
HETATM   29  C22 UNL     1      -2.313  -0.292   0.558  1.00  0.00           C  
HETATM   30  O5  UNL     1      -2.577  -1.265   1.343  1.00  0.00           O  
HETATM   31  H1  UNL     1       1.658  -0.165   5.494  1.00  0.00           H  
HETATM   32  H2  UNL     1       3.321  -0.752   6.048  1.00  0.00           H  
HETATM   33  H3  UNL     1       2.410  -1.640   4.808  1.00  0.00           H  
HETATM   34  H4  UNL     1       4.396   0.274   4.297  1.00  0.00           H  
HETATM   35  H5  UNL     1       2.924   1.316   4.236  1.00  0.00           H  
HETATM   36  H6  UNL     1       1.621  -1.997   1.110  1.00  0.00           H  
HETATM   37  H7  UNL     1       1.768  -0.920  -0.961  1.00  0.00           H  
HETATM   38  H8  UNL     1       2.013   0.724  -0.240  1.00  0.00           H  
HETATM   39  H9  UNL     1       4.105  -0.250   0.901  1.00  0.00           H  
HETATM   40  H10 UNL     1       3.742  -1.795  -0.016  1.00  0.00           H  
HETATM   41  H11 UNL     1       3.900  -1.886  -2.394  1.00  0.00           H  
HETATM   42  H12 UNL     1       4.842  -0.961  -4.400  1.00  0.00           H  
HETATM   43  H13 UNL     1       5.701   1.354  -4.409  1.00  0.00           H  
HETATM   44  H14 UNL     1       5.615   2.731  -2.422  1.00  0.00           H  
HETATM   45  H15 UNL     1       4.627   1.769  -0.312  1.00  0.00           H  
HETATM   46  H16 UNL     1      -0.455  -1.818   0.558  1.00  0.00           H  
HETATM   47  H17 UNL     1      -0.929   0.674   1.834  1.00  0.00           H  
HETATM   48  H18 UNL     1       0.146   1.995   0.035  1.00  0.00           H  
HETATM   49  H19 UNL     1      -1.606   1.992  -0.005  1.00  0.00           H  
HETATM   50  H20 UNL     1      -0.435  -0.149  -1.765  1.00  0.00           H  
HETATM   51  H21 UNL     1      -0.073   1.541  -2.162  1.00  0.00           H  
HETATM   52  H22 UNL     1      -2.326   2.259  -2.054  1.00  0.00           H  
HETATM   53  H23 UNL     1      -2.105   0.956  -3.282  1.00  0.00           H  
HETATM   54  H24 UNL     1      -4.236   0.177  -3.426  1.00  0.00           H  
HETATM   55  H25 UNL     1      -3.368  -1.268  -2.871  1.00  0.00           H  
HETATM   56  H26 UNL     1      -5.602  -1.779  -2.398  1.00  0.00           H  
HETATM   57  H27 UNL     1      -6.087  -0.090  -2.105  1.00  0.00           H  
HETATM   58  H28 UNL     1      -6.306  -1.235  -0.092  1.00  0.00           H  
HETATM   59  H29 UNL     1      -4.720  -2.061  -0.197  1.00  0.00           H  
HETATM   60  H30 UNL     1      -5.227   0.941  -0.261  1.00  0.00           H  
HETATM   61  H31 UNL     1      -6.691   0.388   2.198  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   34   35
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   15   36
CONECT    7    8   37   38
CONECT    8    9   39   40
CONECT    9   10   10   14
CONECT   10   11   41
CONECT   11   12   12   42
CONECT   12   13   43
CONECT   13   14   14   44
CONECT   14   45
CONECT   15   16   46
CONECT   16   17   29   47
CONECT   17   18   48   49
CONECT   18   19   50   51
CONECT   19   20   52   53
CONECT   20   21   28
CONECT   21   22   54   55
CONECT   22   23   56   57
CONECT   23   24   58   59
CONECT   24   25   28   60
CONECT   25   26   26   27
CONECT   27   61
CONECT   28   29
CONECT   29   30   30
END

HMDB0015433
     RDKit          3D
Cilazapril
 61 63  0  0  0  0  0  0  0  0999 V2000
    2.6271   -0.6341    5.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2869    0.2672    4.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867   -0.2296    2.8943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -0.3485    2.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.0134    3.2222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157   -0.8563    1.0896 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1236   -0.3473   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -0.6954    0.0402 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078   -0.0952   -1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2642   -0.8669   -2.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009   -0.3481   -3.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2770    0.9312   -3.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2249    1.7059   -2.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889    1.1963   -1.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0509   -0.8967    0.8197 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8933    0.2029    0.8110 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6905    1.3109   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7940    0.8931   -1.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    1.1438   -2.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2431    0.4798   -1.6483 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9911   -0.4130   -2.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2734   -0.8335   -1.8938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2618   -1.1412   -0.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6204    0.0865    0.2430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7054    0.1857    1.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781    0.6057    2.3835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8775   -0.1997    2.3284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2973    0.1167   -0.3317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -0.2918    0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -1.2653    1.3431 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -0.1653    5.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214   -0.7520    6.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4095   -1.6397    4.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955    0.2743    4.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239    1.3161    4.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6214   -1.9973    1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7683   -0.9205   -0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0134    0.7235   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1055   -0.2502    0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -1.7951   -0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995   -1.8864   -2.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8424   -0.9613   -4.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013    1.3541   -4.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6153    2.7311   -2.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6272    1.7691   -0.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4552   -1.8175    0.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294    0.6738    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1455    1.9952    0.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6058    1.9917   -0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4352   -0.1487   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0731    1.5405   -2.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3256    2.2586   -2.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050    0.9563   -3.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2361    0.1774   -3.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675   -1.2684   -2.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6025   -1.7786   -2.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0869   -0.0905   -2.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3065   -1.2346   -0.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7204   -2.0611   -0.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2268    0.9409   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6914    0.3882    2.1981 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 24 28  1  0
 28 29  1  0
 29 30  2  0
 14  9  1  0
 29 16  1  0
 28 20  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  6 36  1  1
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 16 47  1  1
 17 48  1  0
 17 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  6
 27 61  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Cilazapril anhydrous	ChEBI
Cilazaprilum	ChEBI
Dynorm	ChEBI
Inhibace	ChEBI
Ro 34-2848	ChEBI
Vascace	ChEBI
Vascase	ChEBI
Monohydrate, cilazapril	HMDB
Cilazapril monohydrate	HMDB
Cilazapril, (s*)-isomer	HMDB
Hydrate, cilazapril	HMDB
Anhydrous, cilazapril	HMDB
Cilazapril hydrate	HMDB
Cilazapril monohydrobromide	HMDB
Cilazapril, anhydrous	HMDB
Monohydrobromide, cilazapril	HMDB

Chemical Formula

C₂₂H₃₁N₃O₅

Average Molecular Weight

417.4986

Monoisotopic Molecular Weight

417.226371117

IUPAC Name

(1S,9S)-9-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

Traditional Name

inhibace

CAS Registry Number

92077-78-6

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCCN2CCC[C@H](N2C1=O)C(O)=O

InChI Identifier

InChI=1S/C22H31N3O5/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28)/t17-,18-,19-/m0/s1

InChI Key

HHHKFGXWKKUNCY-FHWLQOOXSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Alpha-amino acid ester
Alpha-amino acid or derivatives
1,2-diazepane
Fatty acid ester
Diazepane
Aralkylamine
Dicarboxylic acid or derivatives
1,2-diazinane
Pyridazine
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Carboxylic acid hydrazide
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015433)
Membrane (HMDB: HMDB0015433)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cilazapril Action Pathway (PathBank: SMP0000147)

Metabolic pathway

Cilazapril Metabolism Pathway (PathBank: SMP0000592)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.06 g/L	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	-0.2	ALOGPS
logP	-0.0079	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	5.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.18 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	110.56 m³·mol⁻¹	ChemAxon
Polarizability	44.73 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]+	193.669	31661259
DarkChem	[M-H]-	191.144	31661259
DeepCCS	[M+H]+	199.661	30932474
DeepCCS	[M-H]-	197.266	30932474
DeepCCS	[M-2H]-	230.147	30932474
DeepCCS	[M+Na]+	205.677	30932474
AllCCS	[M+H]+	200.0	32859911
AllCCS	[M+H-H2O]+	197.7	32859911
AllCCS	[M+NH4]+	202.1	32859911
AllCCS	[M+Na]+	202.8	32859911
AllCCS	[M-H]-	196.2	32859911
AllCCS	[M+Na-2H]-	197.0	32859911
AllCCS	[M+HCOO]-	198.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cilazapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCCN2CCC[C@H](N2C1=O)C(O)=O	4294.6	Standard polar	33892256
Cilazapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCCN2CCC[C@H](N2C1=O)C(O)=O	3052.8	Standard non polar	33892256
Cilazapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCCN2CCC[C@H](N2C1=O)C(O)=O	3264.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cilazapril,1TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C)N2C1=O	3218.5	Semi standard non polar	33892256
Cilazapril,1TMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCCN2CCC[C@@H](C(=O)O)N2C1=O)[Si](C)(C)C	3246.6	Semi standard non polar	33892256
Cilazapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C)N2C1=O)[Si](C)(C)C	3208.7	Semi standard non polar	33892256
Cilazapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C)N2C1=O)[Si](C)(C)C	3099.1	Standard non polar	33892256
Cilazapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C)N2C1=O)[Si](C)(C)C	4502.7	Standard polar	33892256
Cilazapril,1TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N2C1=O	3439.7	Semi standard non polar	33892256
Cilazapril,1TBDMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCCN2CCC[C@@H](C(=O)O)N2C1=O)[Si](C)(C)C(C)(C)C	3463.7	Semi standard non polar	33892256
Cilazapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N2C1=O)[Si](C)(C)C(C)(C)C	3648.4	Semi standard non polar	33892256
Cilazapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N2C1=O)[Si](C)(C)C(C)(C)C	3482.3	Standard non polar	33892256
Cilazapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N2C1=O)[Si](C)(C)C(C)(C)C	4557.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cilazapril GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3119000000-cf816839d9e62aaeb51d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cilazapril GC-MS (1 TMS) - 70eV, Positive	splash10-014i-3100900000-8a98b7cfd4306c863f3b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cilazapril GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cilazapril 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 - Cilazapril 10V, Positive-QTOF	splash10-014i-0114900000-46b169656e56da84df00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 20V, Positive-QTOF	splash10-00r6-3339300000-597e65efc2ccd4259fc6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 40V, Positive-QTOF	splash10-0006-7930000000-01cd40a3307d1d9136e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 10V, Negative-QTOF	splash10-0100-2609400000-2b63f9aade5f2408e90c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 20V, Negative-QTOF	splash10-00fs-2029000000-ef46b50c866af838f6d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 40V, Negative-QTOF	splash10-000i-9413000000-bf81f08b26484eff95d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 10V, Positive-QTOF	splash10-014i-0001900000-2155fa52bd310940aaa1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 20V, Positive-QTOF	splash10-00kf-0129300000-d64d5ab791860881b405	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 40V, Positive-QTOF	splash10-0560-5901000000-8c919145e29e13e6d804	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 10V, Negative-QTOF	splash10-014i-0001900000-13fb2fadf7c261ea1f97	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 20V, Negative-QTOF	splash10-014l-3289700000-05092f6b096b7ae757aa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilazapril 40V, Negative-QTOF	splash10-0019-2982000000-4f5dadbd2ce238e96eef	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01340	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01340	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01340

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

50831

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cilazapril

METLIN ID

Not Available

PubChem Compound

56330

PDB ID

Not Available

ChEBI ID

553655

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

Not Available

Enzymes

Enzyme Details

1. Angiotensin-converting enzyme

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

References

Yoshiyama M, Takeuchi K, Omura T, Kim S, Yamagishi H, Toda I, Teragaki M, Akioka K, Iwao H, Yoshikawa J: Effects of candesartan and cilazapril on rats with myocardial infarction assessed by echocardiography. Hypertension. 1999 Apr;33(4):961-8. [PubMed:10205231 ]
Kihara M, Mitsui MK, Mitsui Y, Okuda K, Nakasaka Y, Takahashi M, Schmelzer JD: Altered vasoreactivity to angiotensin II in experimental diabetic neuropathy: role of nitric oxide. Muscle Nerve. 1999 Jul;22(7):920-5. [PubMed:10398211 ]
Mervaala E, Dehmel B, Gross V, Lippoldt A, Bohlender J, Milia AF, Ganten D, Luft FC: Angiotensin-converting enzyme inhibition and AT1 receptor blockade modify the pressure-natriuresis relationship by additive mechanisms in rats with human renin and angiotensinogen genes. J Am Soc Nephrol. 1999 Aug;10(8):1669-80. [PubMed:10446934 ]
Rosendorff C, Patton J, Radford HM, Kalliatakis B: Alpha-adrenergic and angiotensin II pressor sensitivity in hypertensive patients treated with an angiotensin-converting enzyme inhibitor. J Cardiovasc Pharmacol. 1992;19 Suppl 6:S105-9. [PubMed:1382157 ]
Hannedouche T, Ikeni A, Marques LP, Natov S, Dechaux M, Schmitt F, Lacour B, Grunfeld JP: Renal effects of angiotensin II in normotensive subjects on short-term cilazapril treatment. J Cardiovasc Pharmacol. 1992;19 Suppl 6:S25-7. [PubMed:1382161 ]
Tylicki L, Rutkowski P, Renke M, Larczynski W, Aleksandrowicz E, Lysiak-Szydlowska W, Rutkowski B: Triple pharmacological blockade of the renin-angiotensin-aldosterone system in nondiabetic CKD: an open-label crossover randomized controlled trial. Am J Kidney Dis. 2008 Sep;52(3):486-93. doi: 10.1053/j.ajkd.2008.02.297. Epub 2008 Apr 18. [PubMed:18423812 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

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

Enzyme Details

2. Solute carrier family 15 member 1

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

References

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

Enzyme Details

3. Solute carrier family 15 member 2

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

References

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

Showing metabocard for Cilazapril (HMDB0015433)

MOL for HMDB0015433 (Cilazapril)

3D MOL for HMDB0015433 (Cilazapril)

3D SDF for HMDB0015433 (Cilazapril)

3D-SDF for HMDB0015433 (Cilazapril)

PDB for HMDB0015433 (Cilazapril)

3D PDB for HMDB0015433 (Cilazapril)

SMILES for HMDB0015433 (Cilazapril)

INCHI for HMDB0015433 (Cilazapril)

Structure for HMDB0015433 (Cilazapril)

3D Structure for HMDB0015433 (Cilazapril)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References

References

References