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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (2) Show 3 proteins XML

enzymes (1)transporters (2) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014660

Secondary Accession Numbers

HMDB14660

Metabolite Identification

Common Name

Trandolapril

Description

Trandolapril is a non-sulhydryl prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is metabolized to its biologically active diacid form, trandolaprilat, in the liver. Trandolaprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Trandolapril may be used to treat mild to moderate hypertension, to improve survival following myocardial infarction in clinically stable patients with left ventricular dysfunction, as an adjunct treatment for congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.

Structure

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

519
  Mrv0541 02231214442D          

 33 35  0  0  1  0            999 V2000
    7.0831   -1.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7385   -3.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7385   -2.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1355    2.1427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4937    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0195   -2.0521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811    0.1304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389   -3.1285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2389   -2.3035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0195   -3.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5010   -2.7160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5244   -3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5244   -1.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099   -3.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099   -2.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2758   -1.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3260   -2.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7248   -0.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9175   -0.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302    0.7445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6229    0.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6864    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0719    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2646    1.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917    2.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136    1.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083    0.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9064    1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    0.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408    3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3087   -3.7848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3087   -1.6471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  2  0  0  0  0
  2 17  1  0  0  0  0
  3 17  2  0  0  0  0
  4 22  1  0  0  0  0
  4 25  1  0  0  0  0
  5 22  2  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
 18  7  1  6  0  0  0
 20  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  8 32  1  6  0  0  0
  9 13  1  0  0  0  0
  9 33  1  1  0  0  0
 10 11  1  0  0  0  0
 11 17  1  6  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 25 30  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  2  0  0  0  0
 28 31  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

HMDB0014660
     RDKit          3D
Trandolapril
 65 67  0  0  0  0  0  0  0  0999 V2000
    4.5316   -3.4637   -1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146   -2.8360   -2.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0620   -1.6305   -2.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -1.5976   -0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317   -2.6651   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277   -0.3210   -0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7876    0.5673    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8770    0.8820   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8325    1.7755   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499    3.1345   -0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5498    3.9785    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6115    3.4561    1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7726    2.1065    1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8813    1.2427    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256   -0.4726    0.3890 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780   -0.6379   -0.1674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9530   -1.7664   -1.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961   -0.7238    1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.3117    2.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8949   -0.2687    1.1692 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367   -0.6103    2.3441 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4946   -1.9405    2.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666   -2.8755    2.3841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0549   -2.1886    4.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1615   -0.5752    1.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9753   -0.2222    0.2777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1021    0.6136   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6253    1.9870   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4312    1.9347   -1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2784    1.1408   -0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7325    0.6385    0.4243 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5592   -3.4813   -1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -4.4637   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5043   -2.8256   -0.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -3.5637   -2.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1739   -2.5746   -3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    0.2624   -1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847    0.0113    0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642    1.5430    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4225   -0.0439   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3909    1.3556   -1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363    3.5811   -0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467    5.0465    0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3332    4.1110    1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6009    1.6692    1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438    0.1698    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7431   -1.2571    1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315    0.2993   -0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963   -1.3736   -2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809   -2.4647   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384   -2.3793   -1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5933    0.2230    3.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5636   -2.7793    4.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204   -1.5923    1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7821    0.1077    2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7239   -1.0905   -0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8472    0.7584    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6614    0.1153   -1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4891    2.6612    0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4527    2.4338   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0616    2.9707   -1.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6944    1.5221   -2.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347    1.8641   -0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0538    0.3431   -1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0649    1.4901    1.1162 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
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14  9  1  0
 31 20  1  0
 31 26  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  6 37  1  6
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  6
 17 49  1  0
 17 50  1  0
 17 51  1  0
 21 52  1  1
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  6
 27 57  1  0
 27 58  1  0
 28 59  1  0
 28 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  1
M  END

519
  Mrv0541 02231214442D          

 33 35  0  0  1  0            999 V2000
    7.0831   -1.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7385   -3.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7385   -2.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1355    2.1427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4937    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0195   -2.0521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811    0.1304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2389   -3.1285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2389   -2.3035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0195   -3.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5010   -2.7160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5244   -3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5244   -1.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099   -3.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099   -2.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2758   -1.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3260   -2.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7248   -0.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9175   -0.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302    0.7445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6229    0.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6864    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0719    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2646    1.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917    2.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136    1.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0083    0.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9064    1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2010    0.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408    3.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3087   -3.7848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3087   -1.6471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  2  0  0  0  0
  2 17  1  0  0  0  0
  3 17  2  0  0  0  0
  4 22  1  0  0  0  0
  4 25  1  0  0  0  0
  5 22  2  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 16  1  0  0  0  0
 18  7  1  6  0  0  0
 20  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 12  1  0  0  0  0
  8 32  1  6  0  0  0
  9 13  1  0  0  0  0
  9 33  1  1  0  0  0
 10 11  1  0  0  0  0
 11 17  1  6  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 25 30  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  2  0  0  0  0
 28 31  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014660

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H34N2O5/c1-3-31-24(30)19(14-13-17-9-5-4-6-10-17)25-16(2)22(27)26-20-12-8-7-11-18(20)15-21(26)23(28)29/h4-6,9-10,16,18-21,25H,3,7-8,11-15H2,1-2H3,(H,28,29)/t16-,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
VXFJYXUZANRPDJ-WTNASJBWSA-N

> <FORMULA>
C24H34N2O5

> <MOLECULAR_WEIGHT>
430.5372

> <EXACT_MASS>
430.246772208

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
46.7908268482963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3aR,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
1.9473587942916133

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.799917848495624

> <JCHEM_PKA_STRONGEST_BASIC>
5.2056489674218

> <JCHEM_POLAR_SURFACE_AREA>
95.93999999999998

> <JCHEM_REFRACTIVITY>
115.78779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trandolapril

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014660
     RDKit          3D
Trandolapril
 65 67  0  0  0  0  0  0  0  0999 V2000
    4.5316   -3.4637   -1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146   -2.8360   -2.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0620   -1.6305   -2.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -1.5976   -0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317   -2.6651   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277   -0.3210   -0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7876    0.5673    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8770    0.8820   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8325    1.7755   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499    3.1345   -0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5498    3.9785    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6115    3.4561    1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7726    2.1065    1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8813    1.2427    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256   -0.4726    0.3890 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780   -0.6379   -0.1674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9530   -1.7664   -1.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961   -0.7238    1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.3117    2.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8949   -0.2687    1.1692 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367   -0.6103    2.3441 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4946   -1.9405    2.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666   -2.8755    2.3841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0549   -2.1886    4.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1615   -0.5752    1.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9753   -0.2222    0.2777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1021    0.6136   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6253    1.9870   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4312    1.9347   -1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2784    1.1408   -0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7325    0.6385    0.4243 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5592   -3.4813   -1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -4.4637   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5043   -2.8256   -0.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -3.5637   -2.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1739   -2.5746   -3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    0.2624   -1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847    0.0113    0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642    1.5430    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4225   -0.0439   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3909    1.3556   -1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363    3.5811   -0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467    5.0465    0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3332    4.1110    1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6009    1.6692    1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438    0.1698    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7431   -1.2571    1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315    0.2993   -0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963   -1.3736   -2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809   -2.4647   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384   -2.3793   -1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5933    0.2230    3.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5636   -2.7793    4.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204   -1.5923    1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7821    0.1077    2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7239   -1.0905   -0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8472    0.7584    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6614    0.1153   -1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4891    2.6612    0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4527    2.4338   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0616    2.9707   -1.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6944    1.5221   -2.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347    1.8641   -0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0538    0.3431   -1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0649    1.4901    1.1162 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
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14  9  1  0
 31 20  1  0
 31 26  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  6 37  1  6
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  6
 17 49  1  0
 17 50  1  0
 17 51  1  0
 21 52  1  1
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  6
 27 57  1  0
 27 58  1  0
 28 59  1  0
 28 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 519                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      13.222  -2.049   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      14.445  -6.403   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.445  -3.736   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.586   4.000   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      12.122   3.171   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      11.236  -3.831   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      11.165   0.243   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.779  -5.840   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.779  -4.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.236  -6.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.135  -5.070   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.446  -6.610   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.446  -3.530   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.112  -5.840   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.112  -4.300   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.715  -2.367   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.675  -5.070   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.686  -1.220   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.179  -1.538   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.136   1.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.629   1.072   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.615   2.854   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.601   2.218   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.094   1.901   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.065   5.464   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.065   3.047   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.615   0.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.559   2.729   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.109   0.119   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.036   6.610   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.080   1.266   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       9.910  -7.065   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       9.910  -3.075   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4   22   25                                                       
CONECT    5   22                                                            
CONECT    6    9   11   16                                                  
CONECT    7   18   20                                                       
CONECT    8    9   10   12   32                                             
CONECT    9    6    8   13   33                                             
CONECT   10    8   11                                                       
CONECT   11    6   10   17                                                  
CONECT   12    8   14                                                       
CONECT   13    9   15                                                       
CONECT   14   12   15                                                       
CONECT   15   13   14                                                       
CONECT   16    1    6   18                                                  
CONECT   17    2    3   11                                                  
CONECT   18    7   16   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21   22                                                  
CONECT   21   20   23                                                       
CONECT   22    4    5   20                                                  
CONECT   23   21   24                                                       
CONECT   24   23   26   27                                                  
CONECT   25    4   30                                                       
CONECT   26   24   28                                                       
CONECT   27   24   29                                                       
CONECT   28   26   31                                                       
CONECT   29   27   31                                                       
CONECT   30   25                                                            
CONECT   31   28   29                                                       
CONECT   32    8                                                            
CONECT   33    9                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

COMPND    HMDB0014660
HETATM    1  C1  UNL     1       4.532  -3.464  -1.572  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.615  -2.836  -2.585  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.062  -1.630  -2.081  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.264  -1.598  -0.945  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.032  -2.665  -0.363  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.728  -0.321  -0.469  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.788   0.567   0.166  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.877   0.882  -0.863  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.832   1.775  -0.187  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.650   3.134  -0.267  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.550   3.978   0.380  1.00  0.00           C  
HETATM   12  C10 UNL     1       6.612   3.456   1.094  1.00  0.00           C  
HETATM   13  C11 UNL     1       6.773   2.107   1.159  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.881   1.243   0.516  1.00  0.00           C  
HETATM   15  N1  UNL     1       0.626  -0.473   0.389  1.00  0.00           N  
HETATM   16  C13 UNL     1      -0.678  -0.638  -0.167  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.953  -1.766  -1.080  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.596  -0.724   1.039  1.00  0.00           C  
HETATM   19  O3  UNL     1      -1.061  -1.312   2.058  1.00  0.00           O  
HETATM   20  N2  UNL     1      -2.895  -0.269   1.169  1.00  0.00           N  
HETATM   21  C16 UNL     1      -3.737  -0.610   2.344  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.495  -1.940   2.888  1.00  0.00           C  
HETATM   23  O4  UNL     1      -2.867  -2.875   2.384  1.00  0.00           O  
HETATM   24  O5  UNL     1      -4.055  -2.189   4.159  1.00  0.00           O  
HETATM   25  C18 UNL     1      -5.162  -0.575   1.753  1.00  0.00           C  
HETATM   26  C19 UNL     1      -4.975  -0.222   0.278  1.00  0.00           C  
HETATM   27  C20 UNL     1      -6.102   0.614  -0.224  1.00  0.00           C  
HETATM   28  C21 UNL     1      -5.625   1.987  -0.606  1.00  0.00           C  
HETATM   29  C22 UNL     1      -4.431   1.935  -1.514  1.00  0.00           C  
HETATM   30  C23 UNL     1      -3.278   1.141  -0.871  1.00  0.00           C  
HETATM   31  C24 UNL     1      -3.732   0.639   0.424  1.00  0.00           C  
HETATM   32  H1  UNL     1       5.559  -3.481  -2.000  1.00  0.00           H  
HETATM   33  H2  UNL     1       4.173  -4.464  -1.301  1.00  0.00           H  
HETATM   34  H3  UNL     1       4.504  -2.826  -0.643  1.00  0.00           H  
HETATM   35  H4  UNL     1       2.830  -3.564  -2.880  1.00  0.00           H  
HETATM   36  H5  UNL     1       4.174  -2.575  -3.498  1.00  0.00           H  
HETATM   37  H6  UNL     1       1.406   0.262  -1.420  1.00  0.00           H  
HETATM   38  H7  UNL     1       3.285   0.011   0.985  1.00  0.00           H  
HETATM   39  H8  UNL     1       2.364   1.543   0.466  1.00  0.00           H  
HETATM   40  H9  UNL     1       4.423  -0.044  -1.130  1.00  0.00           H  
HETATM   41  H10 UNL     1       3.391   1.356  -1.728  1.00  0.00           H  
HETATM   42  H11 UNL     1       3.836   3.581  -0.809  1.00  0.00           H  
HETATM   43  H12 UNL     1       5.447   5.047   0.343  1.00  0.00           H  
HETATM   44  H13 UNL     1       7.333   4.111   1.608  1.00  0.00           H  
HETATM   45  H14 UNL     1       7.601   1.669   1.709  1.00  0.00           H  
HETATM   46  H15 UNL     1       6.044   0.170   0.587  1.00  0.00           H  
HETATM   47  H16 UNL     1       0.743  -1.257   1.100  1.00  0.00           H  
HETATM   48  H17 UNL     1      -0.931   0.299  -0.692  1.00  0.00           H  
HETATM   49  H18 UNL     1      -1.496  -1.374  -2.012  1.00  0.00           H  
HETATM   50  H19 UNL     1      -1.681  -2.465  -0.590  1.00  0.00           H  
HETATM   51  H20 UNL     1      -0.138  -2.379  -1.445  1.00  0.00           H  
HETATM   52  H21 UNL     1      -3.593   0.223   3.054  1.00  0.00           H  
HETATM   53  H22 UNL     1      -3.564  -2.779   4.829  1.00  0.00           H  
HETATM   54  H23 UNL     1      -5.620  -1.592   1.756  1.00  0.00           H  
HETATM   55  H24 UNL     1      -5.782   0.108   2.312  1.00  0.00           H  
HETATM   56  H25 UNL     1      -4.724  -1.090  -0.332  1.00  0.00           H  
HETATM   57  H26 UNL     1      -6.847   0.758   0.617  1.00  0.00           H  
HETATM   58  H27 UNL     1      -6.661   0.115  -1.042  1.00  0.00           H  
HETATM   59  H28 UNL     1      -5.489   2.661   0.246  1.00  0.00           H  
HETATM   60  H29 UNL     1      -6.453   2.434  -1.225  1.00  0.00           H  
HETATM   61  H30 UNL     1      -4.062   2.971  -1.651  1.00  0.00           H  
HETATM   62  H31 UNL     1      -4.694   1.522  -2.501  1.00  0.00           H  
HETATM   63  H32 UNL     1      -2.435   1.864  -0.679  1.00  0.00           H  
HETATM   64  H33 UNL     1      -3.054   0.343  -1.558  1.00  0.00           H  
HETATM   65  H34 UNL     1      -4.065   1.490   1.116  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3   35   36
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   15   37
CONECT    7    8   38   39
CONECT    8    9   40   41
CONECT    9   10   10   14
CONECT   10   11   42
CONECT   11   12   12   43
CONECT   12   13   44
CONECT   13   14   14   45
CONECT   14   46
CONECT   15   16   47
CONECT   16   17   18   48
CONECT   17   49   50   51
CONECT   18   19   19   20
CONECT   20   21   31
CONECT   21   22   25   52
CONECT   22   23   23   24
CONECT   24   53
CONECT   25   26   54   55
CONECT   26   27   31   56
CONECT   27   28   57   58
CONECT   28   29   59   60
CONECT   29   30   61   62
CONECT   30   31   63   64
CONECT   31   65
END

HMDB0014660
     RDKit          3D
Trandolapril
 65 67  0  0  0  0  0  0  0  0999 V2000
    4.5316   -3.4637   -1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6146   -2.8360   -2.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0620   -1.6305   -2.0811 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -1.5976   -0.9448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317   -2.6651   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277   -0.3210   -0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7876    0.5673    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8770    0.8820   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8325    1.7755   -0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6499    3.1345   -0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5498    3.9785    0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6115    3.4561    1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7726    2.1065    1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8813    1.2427    0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256   -0.4726    0.3890 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6780   -0.6379   -0.1674 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9530   -1.7664   -1.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961   -0.7238    1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.3117    2.0579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8949   -0.2687    1.1692 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7367   -0.6103    2.3441 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4946   -1.9405    2.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666   -2.8755    2.3841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0549   -2.1886    4.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1615   -0.5752    1.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9753   -0.2222    0.2777 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1021    0.6136   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6253    1.9870   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4312    1.9347   -1.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2784    1.1408   -0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7325    0.6385    0.4243 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5592   -3.4813   -1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -4.4637   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5043   -2.8256   -0.6428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -3.5637   -2.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1739   -2.5746   -3.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4056    0.2624   -1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847    0.0113    0.9853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642    1.5430    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4225   -0.0439   -1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3909    1.3556   -1.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363    3.5811   -0.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467    5.0465    0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3332    4.1110    1.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6009    1.6692    1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438    0.1698    0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7431   -1.2571    1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9315    0.2993   -0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4963   -1.3736   -2.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809   -2.4647   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1384   -2.3793   -1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5933    0.2230    3.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5636   -2.7793    4.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204   -1.5923    1.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7821    0.1077    2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7239   -1.0905   -0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8472    0.7584    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6614    0.1153   -1.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4891    2.6612    0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4527    2.4338   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0616    2.9707   -1.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6944    1.5221   -2.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347    1.8641   -0.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0538    0.3431   -1.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0649    1.4901    1.1162 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
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14  9  1  0
 31 20  1  0
 31 26  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  6 37  1  6
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
 10 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  6
 17 49  1  0
 17 50  1  0
 17 51  1  0
 21 52  1  1
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  6
 27 57  1  0
 27 58  1  0
 28 59  1  0
 28 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Mavik	Kegg
Abbott brand OF trandolapril	HMDB
Aventis brand OF trandolapril	HMDB
Gopten	HMDB
Alter brand OF trandolapril	HMDB
1-(2-((1-(Ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydro-1H-indol-2-carboxylic acid	HMDB
Aventis pharma brand OF trandolapril	HMDB
Hoechst brand OF trandolapril	HMDB
Odrik	HMDB
Udrik	HMDB
Knoll brand OF trandolapril	HMDB

Chemical Formula

C₂₄H₃₄N₂O₅

Average Molecular Weight

430.5372

Monoisotopic Molecular Weight

430.246772208

IUPAC Name

(2S,3aR,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid

Traditional Name

trandolapril

CAS Registry Number

87679-37-6

SMILES

[H][C@@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O

InChI Identifier

InChI=1S/C24H34N2O5/c1-3-31-24(30)19(14-13-17-9-5-4-6-10-17)25-16(2)22(27)26-20-12-8-7-11-18(20)15-21(26)23(28)29/h4-6,9-10,16,18-21,25H,3,7-8,11-15H2,1-2H3,(H,28,29)/t16-,18+,19-,20-,21-/m0/s1

InChI Key

VXFJYXUZANRPDJ-WTNASJBWSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Alpha-amino acid ester
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Indole or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Fatty acid ester
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Fatty acyl
Pyrrolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Amino acid
Azacycle
Secondary aliphatic amine
Carboxylic acid
Organoheterocyclic compound
Secondary amine
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
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

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014660)
Membrane (HMDB: HMDB0014660)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Trandolapril Action Pathway (PathBank: SMP0000157)

Metabolic pathway

Trandolapril Metabolism Pathway (PathBank: SMP0000599)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	119 - 123 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.021 g/L	Not Available
LogP	3.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	203.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	1.31	ALOGPS
logP	1.95	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	5.21	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.94 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	115.79 m³·mol⁻¹	ChemAxon
Polarizability	46.79 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]+	199.982	31661259
DarkChem	[M-H]-	194.468	31661259
DeepCCS	[M-2H]-	236.001	30932474
DeepCCS	[M+Na]+	211.074	30932474
AllCCS	[M+H]+	206.2	32859911
AllCCS	[M+H-H2O]+	204.2	32859911
AllCCS	[M+NH4]+	208.2	32859911
AllCCS	[M+Na]+	208.7	32859911
AllCCS	[M-H]-	198.2	32859911
AllCCS	[M+Na-2H]-	199.2	32859911
AllCCS	[M+HCOO]-	200.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trandolapril	[H][C@@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O	4178.2	Standard polar	33892256
Trandolapril	[H][C@@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O	3018.7	Standard non polar	33892256
Trandolapril	[H][C@@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(=O)OCC)[C@@]1([H])CCCC2)C(O)=O	3244.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trandolapril,1TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@H]2CCCC[C@@H]21	3086.3	Semi standard non polar	33892256
Trandolapril,1TMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@H]2CCCC[C@@H]21)[Si](C)(C)C	3126.4	Semi standard non polar	33892256
Trandolapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@H]2CCCC[C@@H]21)[Si](C)(C)C	3121.4	Semi standard non polar	33892256
Trandolapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@H]2CCCC[C@@H]21)[Si](C)(C)C	3112.6	Standard non polar	33892256
Trandolapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C)C[C@H]2CCCC[C@@H]21)[Si](C)(C)C	4195.9	Standard polar	33892256
Trandolapril,1TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2CCCC[C@@H]21	3315.0	Semi standard non polar	33892256
Trandolapril,1TBDMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C	3365.1	Semi standard non polar	33892256
Trandolapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C	3559.5	Semi standard non polar	33892256
Trandolapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C	3505.2	Standard non polar	33892256
Trandolapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C[C@H]2CCCC[C@@H]21)[Si](C)(C)C(C)(C)C	4313.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trandolapril GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9134000000-c52f8386e44b6f3e4183	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trandolapril GC-MS (1 TMS) - 70eV, Positive	splash10-004i-4112900000-5696f5c17973fe4d225b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trandolapril 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 - Trandolapril 10V, Positive-QTOF	splash10-001i-0344900000-99ab1a9e9945717fb390	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 20V, Positive-QTOF	splash10-001l-3892000000-2c1c412e4f9f90ca78ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 40V, Positive-QTOF	splash10-01wf-2920000000-549eb411c184d9623926	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 10V, Negative-QTOF	splash10-005i-1009500000-13932e1c6beeefa44a68	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 20V, Negative-QTOF	splash10-00ks-2529200000-a0a12c08cda6be722cf4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 40V, Negative-QTOF	splash10-01ba-3911000000-6f9e1a5a81f4539f8f44	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 10V, Negative-QTOF	splash10-004i-0001900000-1d6328b40cc6fc4cd692	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 20V, Negative-QTOF	splash10-014i-2966200000-6647aa4aadfe2af7c9d3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 40V, Negative-QTOF	splash10-0329-0900100000-32685cedae485e671c9f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 10V, Positive-QTOF	splash10-053r-0115900000-e1046071e0edb6b7cd2d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 20V, Positive-QTOF	splash10-03dl-2933100000-1522daaf764576e88653	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trandolapril 40V, Positive-QTOF	splash10-00kf-5900000000-b61562d820bcec79a11c	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
Trandolapril Action Pathway		Not Available
Trandolapril 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 DB00519	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00519	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00519

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4588590

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trandolapril

METLIN ID

Not Available

PubChem Compound

5484727

PDB ID

Not Available

ChEBI ID

521317

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

Zannad F: Trandolapril. How does it differ from other angiotensin converting enzyme inhibitors? Drugs. 1993;46 Suppl 2:172-81; discussion 182. [PubMed:7512472 ]
Wiseman LR, McTavish D: Trandolapril. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in essential hypertension. Drugs. 1994 Jul;48(1):71-90. [PubMed:7525196 ]
Jouquey S, Stepniewski JP, Hamon G: Trandolapril dose-response in spontaneously hypertensive rats: effects on ACE activity, blood pressure, and cardiac hypertrophy. J Cardiovasc Pharmacol. 1994;23 Suppl 4:S16-8. [PubMed:7527096 ]
Conen H, Brunner HR: Pharmacologic profile of trandolapril, a new angiotensin-converting enzyme inhibitor. Am Heart J. 1993 May;125(5 Pt 2):1525-31. [PubMed:8480624 ]
Sanbe A, Tanonaka K, Kobayasi R, Takeo S: Effects of long-term therapy with ACE inhibitors, captopril, enalapril and trandolapril, on myocardial energy metabolism in rats with heart failure following myocardial infarction. J Mol Cell Cardiol. 1995 Oct;27(10):2209-22. [PubMed:8576937 ]
Authors unspecified: Trandolapril: an ACE inhibitor for treatment of hypertension. Med Lett Drugs Ther. 1996 Nov 22;38(988):104-5. [PubMed:8941256 ]
Torp-Pedersen C, Kober L: Effect of ACE inhibitor trandolapril on life expectancy of patients with reduced left-ventricular function after acute myocardial infarction. TRACE Study Group. Trandolapril Cardiac Evaluation. Lancet. 1999 Jul 3;354(9172):9-12. [PubMed:10406358 ]
Guay DR: Trandolapril: a newer angiotensin-converting enzyme inhibitor. Clin Ther. 2003 Mar;25(3):713-75. [PubMed:12852701 ]
Reynolds NA, Wagstaff AJ, Keam SJ: Trandolapril/verapamil sustained release: a review of its use in the treatment of essential hypertension. Drugs. 2005;65(13):1893-914. [PubMed:16114984 ]
Rubio-Guerra AF, Vargas-Robles H, Vargas-Ayala G, Rodriguez-Lopez L, Escalante-Acosta BA: The effect of trandolapril and its fixed-dose combination with verapamil on circulating adhesion molecules levels in hypertensive patients with type 2 diabetes. Clin Exp Hypertens. 2008 Oct;30(7):682-8. doi: 10.1080/10641960802251941. [PubMed:18855271 ]
Berl T: Review: renal protection by inhibition of the renin-angiotensin-aldosterone system. J Renin Angiotensin Aldosterone Syst. 2009 Mar;10(1):1-8. doi: 10.1177/1470320309102747. [PubMed:19286752 ]
Diaz A, Ducharme A: Update on the use of trandolapril in the management of cardiovascular disorders. Vasc Health Risk Manag. 2008;4(6):1147-58. [PubMed:19337528 ]

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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [PubMed:11030016 ]
Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [PubMed:11929321 ]

Transporters

Enzyme Details

1. 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

2. 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 Trandolapril (HMDB0014660)

MOL for HMDB0014660 (Trandolapril)

3D MOL for HMDB0014660 (Trandolapril)

3D SDF for HMDB0014660 (Trandolapril)

3D-SDF for HMDB0014660 (Trandolapril)

PDB for HMDB0014660 (Trandolapril)

3D PDB for HMDB0014660 (Trandolapril)

SMILES for HMDB0014660 (Trandolapril)

INCHI for HMDB0014660 (Trandolapril)

Structure for HMDB0014660 (Trandolapril)

3D Structure for HMDB0014660 (Trandolapril)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References