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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 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015438

Secondary Accession Numbers

HMDB15438

Metabolite Identification

Common Name

Spirapril

Description

Spirapril, also known as quadropril or renpress, 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. Spirapril is a very strong basic compound (based on its pKa). In humans, spirapril is involved in spirapril action pathway. Unlike other members of the group, it is eliminated both by renal and hepatic routes, which may allow for greater use in patients with renal impairment. However, data on its effect upon the renal function are conflicting. It belongs to dicarboxy group of ACE inhibitors. It was patented in 1980 and approved for medical use in 1995. Spirapril, sold under the brand name Renormax among others, is an ACE inhibitor antihypertensive drug used to treat hypertension. Like many ACE inhibitors, this prodrug is converted to the active metabolite spiraprilat following oral administration.

Structure

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

1348
  Mrv0541 02231215232D          

 31 33  0  0  1  0            999 V2000
    6.6536   -1.7767    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9885   -1.7767    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7592    1.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0390    0.5590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8829    1.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922    1.7214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483    2.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -0.0222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1182    1.2265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3211   -1.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9885   -0.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7336   -0.0222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6536   -0.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4236    0.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -2.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7336   -2.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2185    0.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6032    0.5590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2977    1.1402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2675   -0.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621    0.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416    0.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8128    1.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910   -1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5074    2.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9554   -1.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -1.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868    2.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 15  1  0  0  0  0
  2 10  1  0  0  0  0
  2 16  1  0  0  0  0
  3 14  2  0  0  0  0
  4 17  1  0  0  0  0
  5 17  2  0  0  0  0
  6 23  1  0  0  0  0
  6 27  1  0  0  0  0
  7 23  2  0  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
 18  9  1  6  0  0  0
 19  9  1  1  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 17  1  6  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  2  0  0  0  0
 27 31  1  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END

HMDB0015438
     RDKit          3D
Spirapril
 61 63  0  0  0  0  0  0  0  0999 V2000
   -1.8948   -4.4411    2.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6286   -3.8936    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960   -2.4770    1.3315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335   -1.6086    1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848   -2.1651    1.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7742   -0.1424    1.4980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6757    0.4890    0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1433    0.0544    0.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8663    0.8073   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4009    2.0554   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0629    2.7259   -1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2059    2.1792   -2.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6717    0.9328   -2.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0086    0.2625   -1.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5276    0.4924    1.5839 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394    0.4298    0.5790 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0798    1.0828   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6639    1.1608    1.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101    1.7529    2.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769    1.2320    0.3632 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660    0.6259   -0.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5372    0.0274   -0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266    1.1513    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032    1.9051    0.7368 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1455    3.3033    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537    3.9955    0.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    3.8624   -0.4243 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3893   -0.4850   -2.1389 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657   -1.9055   -1.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3986   -2.6958   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4476   -1.4967    0.3097 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886   -3.8217    3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8204   -4.3673    2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2441   -5.4676    2.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -4.2026    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6792   -4.3045    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968    0.1323    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7087    1.5873    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356    0.2063   -0.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4830    0.4277    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2465   -1.0226    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2898    2.4946    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4846    3.7037   -1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7273    2.7188   -3.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7664    0.4757   -3.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5820   -0.7238   -1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1102    0.5329    2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759   -0.6289    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1811    0.3319   -1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719    1.6574   -1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959    1.8576   -0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367    1.3582   -1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4769   -0.2077   -1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8972    0.6902    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8347    1.7798   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2696    1.9105    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624    4.3620   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6694   -2.4852   -2.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2541   -1.5530   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7332   -3.2560   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9539   -3.4035   -0.0279 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  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14  9  1  0
 24 20  1  0
 31 22  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  1
  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  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  1
 27 57  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  0
 30 61  1  0
M  END

1348
  Mrv0541 02231215232D          

 31 33  0  0  1  0            999 V2000
    6.6536   -1.7767    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9885   -1.7767    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7592    1.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0390    0.5590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8829    1.3989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9922    1.7214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1483    2.5613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -0.0222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1182    1.2265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3211   -1.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9885   -0.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7336   -0.0222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6536   -0.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4236    0.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -2.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7336   -2.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2185    0.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6032    0.5590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2977    1.1402    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2675   -0.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621    0.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1416    0.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8128    1.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8061   -0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9856   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910   -1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5074    2.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9554   -1.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -1.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868    2.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  1 15  1  0  0  0  0
  2 10  1  0  0  0  0
  2 16  1  0  0  0  0
  3 14  2  0  0  0  0
  4 17  1  0  0  0  0
  5 17  2  0  0  0  0
  6 23  1  0  0  0  0
  6 27  1  0  0  0  0
  7 23  2  0  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  0  0  0  0
 18  9  1  6  0  0  0
 19  9  1  1  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 17  1  6  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  2  0  0  0  0
 27 31  1  0  0  0  0
 28 30  2  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015438

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2(C[C@H]1C(O)=O)SCCS2

> <INCHI_IDENTIFIER>
InChI=1S/C22H30N2O5S2/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27)/t15-,17-,18-/m0/s1

> <INCHI_KEY>
HRWCVUIFMSZDJS-SZMVWBNQSA-N

> <FORMULA>
C22H30N2O5S2

> <MOLECULAR_WEIGHT>
466.614

> <EXACT_MASS>
466.15961346

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
48.74005483504923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8S)-7-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.6036345915656902

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6249575075648437

> <JCHEM_PKA_STRONGEST_BASIC>
5.199901730998292

> <JCHEM_POLAR_SURFACE_AREA>
95.93999999999998

> <JCHEM_REFRACTIVITY>
121.93960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
spirapril

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015438
     RDKit          3D
Spirapril
 61 63  0  0  0  0  0  0  0  0999 V2000
   -1.8948   -4.4411    2.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6286   -3.8936    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960   -2.4770    1.3315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335   -1.6086    1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848   -2.1651    1.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7742   -0.1424    1.4980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6757    0.4890    0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1433    0.0544    0.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8663    0.8073   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4009    2.0554   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0629    2.7259   -1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2059    2.1792   -2.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6717    0.9328   -2.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0086    0.2625   -1.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5276    0.4924    1.5839 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394    0.4298    0.5790 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0798    1.0828   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6639    1.1608    1.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101    1.7529    2.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769    1.2320    0.3632 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660    0.6259   -0.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5372    0.0274   -0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266    1.1513    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032    1.9051    0.7368 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1455    3.3033    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537    3.9955    0.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    3.8624   -0.4243 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3893   -0.4850   -2.1389 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657   -1.9055   -1.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3986   -2.6958   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4476   -1.4967    0.3097 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886   -3.8217    3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8204   -4.3673    2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2441   -5.4676    2.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -4.2026    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6792   -4.3045    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968    0.1323    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7087    1.5873    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356    0.2063   -0.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4830    0.4277    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2465   -1.0226    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2898    2.4946    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4846    3.7037   -1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7273    2.7188   -3.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7664    0.4757   -3.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5820   -0.7238   -1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1102    0.5329    2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759   -0.6289    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1811    0.3319   -1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719    1.6574   -1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959    1.8576   -0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367    1.3582   -1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4769   -0.2077   -1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8972    0.6902    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8347    1.7798   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2696    1.9105    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624    4.3620   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6694   -2.4852   -2.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2541   -1.5530   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7332   -3.2560   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9539   -3.4035   -0.0279 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  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14  9  1  0
 24 20  1  0
 31 22  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  1
  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  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  1
 27 57  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  0
 30 61  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1348                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      12.420  -3.317   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      14.912  -3.317   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      12.617   2.611   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.873   1.043   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      14.715   2.611   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.585   3.213   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.743   4.781   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      12.896  -0.041   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.554   2.289   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      13.666  -2.411   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.912  -1.506   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.436  -0.041   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.420  -1.506   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.991   1.204   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.896  -4.781   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.436  -4.781   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.341   1.204   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.459   1.043   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.022   2.128   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.833  -0.363   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.396   0.721   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.864   0.561   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.117   3.374   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.238  -0.846   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.706  -1.007   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.143  -2.092   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.680   4.459   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.080  -2.414   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.517  -3.499   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.985  -3.660   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.149   4.298   0.000  0.00  0.00           C+0
CONECT    1   10   15                                                       
CONECT    2   10   16                                                       
CONECT    3   14                                                            
CONECT    4   17                                                            
CONECT    5   17                                                            
CONECT    6   23   27                                                       
CONECT    7   23                                                            
CONECT    8   12   13   14                                                  
CONECT    9   18   19                                                       
CONECT   10    1    2   11   13                                             
CONECT   11   10   12                                                       
CONECT   12    8   11   17                                                  
CONECT   13    8   10                                                       
CONECT   14    3    8   18                                                  
CONECT   15    1   16                                                       
CONECT   16    2   15                                                       
CONECT   17    4    5   12                                                  
CONECT   18    9   14   20                                                  
CONECT   19    9   21   23                                                  
CONECT   20   18                                                            
CONECT   21   19   22                                                       
CONECT   22   21   24                                                       
CONECT   23    6    7   19                                                  
CONECT   24   22   25   26                                                  
CONECT   25   24   28                                                       
CONECT   26   24   29                                                       
CONECT   27    6   31                                                       
CONECT   28   25   30                                                       
CONECT   29   26   30                                                       
CONECT   30   28   29                                                       
CONECT   31   27                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

COMPND    HMDB0015438
HETATM    1  C1  UNL     1      -1.895  -4.441   2.441  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.629  -3.894   1.248  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.796  -2.477   1.332  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.733  -1.609   1.406  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.585  -2.165   1.394  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.774  -0.142   1.498  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.676   0.489   0.476  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.143   0.054   0.616  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.866   0.807  -0.466  1.00  0.00           C  
HETATM   10  C8  UNL     1      -5.401   2.055  -0.234  1.00  0.00           C  
HETATM   11  C9  UNL     1      -6.063   2.726  -1.257  1.00  0.00           C  
HETATM   12  C10 UNL     1      -6.206   2.179  -2.513  1.00  0.00           C  
HETATM   13  C11 UNL     1      -5.672   0.933  -2.743  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.009   0.262  -1.717  1.00  0.00           C  
HETATM   15  N1  UNL     1      -0.528   0.492   1.584  1.00  0.00           N  
HETATM   16  C13 UNL     1       0.439   0.430   0.579  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.080   1.083  -0.746  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.664   1.161   1.071  1.00  0.00           C  
HETATM   19  O3  UNL     1       1.610   1.753   2.198  1.00  0.00           O  
HETATM   20  N2  UNL     1       2.877   1.232   0.363  1.00  0.00           N  
HETATM   21  C16 UNL     1       3.166   0.626  -0.918  1.00  0.00           C  
HETATM   22  C17 UNL     1       4.537   0.027  -0.621  1.00  0.00           C  
HETATM   23  C18 UNL     1       5.227   1.151   0.074  1.00  0.00           C  
HETATM   24  C19 UNL     1       4.103   1.905   0.737  1.00  0.00           C  
HETATM   25  C20 UNL     1       4.145   3.303   0.272  1.00  0.00           C  
HETATM   26  O4  UNL     1       5.154   3.995   0.514  1.00  0.00           O  
HETATM   27  O5  UNL     1       3.096   3.862  -0.424  1.00  0.00           O  
HETATM   28  S1  UNL     1       5.389  -0.485  -2.139  1.00  0.00           S  
HETATM   29  C21 UNL     1       6.366  -1.906  -1.516  1.00  0.00           C  
HETATM   30  C22 UNL     1       5.399  -2.696  -0.679  1.00  0.00           C  
HETATM   31  S2  UNL     1       4.448  -1.497   0.310  1.00  0.00           S  
HETATM   32  H1  UNL     1      -2.189  -3.822   3.335  1.00  0.00           H  
HETATM   33  H2  UNL     1      -0.820  -4.367   2.247  1.00  0.00           H  
HETATM   34  H3  UNL     1      -2.244  -5.468   2.618  1.00  0.00           H  
HETATM   35  H4  UNL     1      -2.221  -4.203   0.284  1.00  0.00           H  
HETATM   36  H5  UNL     1      -3.679  -4.304   1.302  1.00  0.00           H  
HETATM   37  H6  UNL     1      -2.297   0.132   2.513  1.00  0.00           H  
HETATM   38  H7  UNL     1      -2.709   1.587   0.547  1.00  0.00           H  
HETATM   39  H8  UNL     1      -2.336   0.206  -0.567  1.00  0.00           H  
HETATM   40  H9  UNL     1      -4.483   0.428   1.599  1.00  0.00           H  
HETATM   41  H10 UNL     1      -4.247  -1.023   0.464  1.00  0.00           H  
HETATM   42  H11 UNL     1      -5.290   2.495   0.762  1.00  0.00           H  
HETATM   43  H12 UNL     1      -6.485   3.704  -1.084  1.00  0.00           H  
HETATM   44  H13 UNL     1      -6.727   2.719  -3.301  1.00  0.00           H  
HETATM   45  H14 UNL     1      -5.766   0.476  -3.717  1.00  0.00           H  
HETATM   46  H15 UNL     1      -4.582  -0.724  -1.888  1.00  0.00           H  
HETATM   47  H16 UNL     1      -0.110   0.533   2.538  1.00  0.00           H  
HETATM   48  H17 UNL     1       0.776  -0.629   0.368  1.00  0.00           H  
HETATM   49  H18 UNL     1      -0.181   0.332  -1.492  1.00  0.00           H  
HETATM   50  H19 UNL     1       0.972   1.657  -1.159  1.00  0.00           H  
HETATM   51  H20 UNL     1      -0.696   1.858  -0.666  1.00  0.00           H  
HETATM   52  H21 UNL     1       3.237   1.358  -1.751  1.00  0.00           H  
HETATM   53  H22 UNL     1       2.477  -0.208  -1.096  1.00  0.00           H  
HETATM   54  H23 UNL     1       5.897   0.690   0.857  1.00  0.00           H  
HETATM   55  H24 UNL     1       5.835   1.780  -0.608  1.00  0.00           H  
HETATM   56  H25 UNL     1       4.270   1.910   1.826  1.00  0.00           H  
HETATM   57  H26 UNL     1       3.262   4.362  -1.308  1.00  0.00           H  
HETATM   58  H27 UNL     1       6.669  -2.485  -2.402  1.00  0.00           H  
HETATM   59  H28 UNL     1       7.254  -1.553  -0.944  1.00  0.00           H  
HETATM   60  H29 UNL     1       4.733  -3.256  -1.384  1.00  0.00           H  
HETATM   61  H30 UNL     1       5.954  -3.404  -0.028  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   24
CONECT   21   22   52   53
CONECT   22   23   28   31
CONECT   23   24   54   55
CONECT   24   25   56
CONECT   25   26   26   27
CONECT   27   57
CONECT   28   29
CONECT   29   30   58   59
CONECT   30   31   60   61
END

HMDB0015438
     RDKit          3D
Spirapril
 61 63  0  0  0  0  0  0  0  0999 V2000
   -1.8948   -4.4411    2.4410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6286   -3.8936    1.2477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960   -2.4770    1.3315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7335   -1.6086    1.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848   -2.1651    1.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7742   -0.1424    1.4980 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6757    0.4890    0.4760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1433    0.0544    0.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8663    0.8073   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4009    2.0554   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0629    2.7259   -1.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2059    2.1792   -2.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6717    0.9328   -2.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0086    0.2625   -1.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5276    0.4924    1.5839 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4394    0.4298    0.5790 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0798    1.0828   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6639    1.1608    1.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6101    1.7529    2.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8769    1.2320    0.3632 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660    0.6259   -0.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5372    0.0274   -0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266    1.1513    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1032    1.9051    0.7368 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1455    3.3033    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537    3.9955    0.5142 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    3.8624   -0.4243 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3893   -0.4850   -2.1389 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3657   -1.9055   -1.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3986   -2.6958   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4476   -1.4967    0.3097 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886   -3.8217    3.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8204   -4.3673    2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2441   -5.4676    2.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2206   -4.2026    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6792   -4.3045    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2968    0.1323    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7087    1.5873    0.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3356    0.2063   -0.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4830    0.4277    1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2465   -1.0226    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2898    2.4946    0.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4846    3.7037   -1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7273    2.7188   -3.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7664    0.4757   -3.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5820   -0.7238   -1.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1102    0.5329    2.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7759   -0.6289    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1811    0.3319   -1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719    1.6574   -1.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6959    1.8576   -0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2367    1.3582   -1.7505 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4769   -0.2077   -1.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8972    0.6902    0.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8347    1.7798   -0.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2696    1.9105    1.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624    4.3620   -1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6694   -2.4852   -2.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2541   -1.5530   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7332   -3.2560   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9539   -3.4035   -0.0279 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  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 14  9  1  0
 24 20  1  0
 31 22  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  1
  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  0
 21 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  1
 27 57  1  0
 29 58  1  0
 29 59  1  0
 30 60  1  0
 30 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Quadropril	HMDB
Renpress	HMDB
Spirapril hydrochloride	HMDB
Renormax	HMDB

Chemical Formula

C₂₂H₃₀N₂O₅S₂

Average Molecular Weight

466.614

Monoisotopic Molecular Weight

466.15961346

IUPAC Name

(8S)-7-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid

Traditional Name

spirapril

CAS Registry Number

83647-97-6

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2(C[C@H]1C(O)=O)SCCS2

InChI Identifier

InChI=1S/C22H30N2O5S2/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27)/t15-,17-,18-/m0/s1

InChI Key

HRWCVUIFMSZDJS-SZMVWBNQSA-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-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Fatty acid ester
Aralkylamine
Dithioketal
Monocyclic benzene moiety
Fatty acyl
Dicarboxylic acid or derivatives
Benzenoid
Pyrrolidine
Dithiolane
Tertiary carboxylic acid amide
Thioacetal
1,3-dithiolane
Amino acid or derivatives
Carboxylic acid ester
Amino acid
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid
Secondary aliphatic amine
Dialkylthioether
Thioether
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Amine
Organic oxide
Hydrocarbon derivative
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: HMDB0015438)
Membrane (HMDB: HMDB0015438)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Spirapril Action Pathway (PathBank: SMP0000156)

Metabolic pathway

Spirapril Metabolism Pathway (PathBank: SMP0000598)

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	0.029 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.6	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.62	ChemAxon
pKa (Strongest Basic)	5.2	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	121.94 m³·mol⁻¹	ChemAxon
Polarizability	48.74 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]+	201.044	31661259
DarkChem	[M-H]-	195.006	31661259
DeepCCS	[M+H]+	203.097	30932474
DeepCCS	[M-H]-	200.701	30932474
DeepCCS	[M-2H]-	233.586	30932474
DeepCCS	[M+Na]+	209.009	30932474
AllCCS	[M+H]+	207.2	32859911
AllCCS	[M+H-H2O]+	205.4	32859911
AllCCS	[M+NH4]+	208.9	32859911
AllCCS	[M+Na]+	209.4	32859911
AllCCS	[M-H]-	199.5	32859911
AllCCS	[M+Na-2H]-	200.6	32859911
AllCCS	[M+HCOO]-	202.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Spirapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2(C[C@H]1C(O)=O)SCCS2	4698.7	Standard polar	33892256
Spirapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2(C[C@H]1C(O)=O)SCCS2	3203.8	Standard non polar	33892256
Spirapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2(C[C@H]1C(O)=O)SCCS2	3577.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Spirapril,1TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O[Si](C)(C)C)SCCS2	3650.2	Semi standard non polar	33892256
Spirapril,1TMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2)[Si](C)(C)C	3642.4	Semi standard non polar	33892256
Spirapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O[Si](C)(C)C)SCCS2)[Si](C)(C)C	3610.4	Semi standard non polar	33892256
Spirapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O[Si](C)(C)C)SCCS2)[Si](C)(C)C	3358.3	Standard non polar	33892256
Spirapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O[Si](C)(C)C)SCCS2)[Si](C)(C)C	4596.8	Standard polar	33892256
Spirapril,1TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)SCCS2	3842.1	Semi standard non polar	33892256
Spirapril,1TBDMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2)[Si](C)(C)C(C)(C)C	3834.6	Semi standard non polar	33892256
Spirapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)SCCS2)[Si](C)(C)C(C)(C)C	3999.0	Semi standard non polar	33892256
Spirapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)SCCS2)[Si](C)(C)C(C)(C)C	3765.2	Standard non polar	33892256
Spirapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)SCCS2)[Si](C)(C)C(C)(C)C	4703.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Spirapril GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2329000000-e6426e1f4b1766007fb1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Spirapril GC-MS (1 TMS) - 70eV, Positive	splash10-014i-3020900000-bae90ea325c8ab017203	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Spirapril GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Spirapril 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 - Spirapril 10V, Positive-QTOF	splash10-014i-0151900000-794ab140bd7377bee543	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 20V, Positive-QTOF	splash10-001i-2492200000-3e1605fcedb193a44513	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 40V, Positive-QTOF	splash10-08gu-3940000000-8cfd8a9e4db6203ffd42	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 10V, Negative-QTOF	splash10-052f-9001400000-c0d3ef34b28403d583fb	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 20V, Negative-QTOF	splash10-0a4i-9000000000-e68f2dc1894747d86885	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 40V, Negative-QTOF	splash10-0a4i-9101000000-99d2254d32243752bbac	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 10V, Positive-QTOF	splash10-014i-0021900000-9d3ec1b110ee9ea14e5f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 20V, Positive-QTOF	splash10-00r6-0425900000-4de98c170e5f68982b37	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 40V, Positive-QTOF	splash10-014i-3920000000-554f8dbc645d0b1dd714	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 10V, Negative-QTOF	splash10-014i-0000900000-438d7bc3c320eca0298a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 20V, Negative-QTOF	splash10-014l-3135900000-a3b59b47cb7d860d17d6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Spirapril 40V, Negative-QTOF	splash10-0nmi-3921000000-2906c69550f813e0c035	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Spirapril Action Pathway		Not Available
Spirapril 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 DB01348	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01348	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01348

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4470933

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Spirapril

METLIN ID

Not Available

PubChem Compound

5311447

PDB ID

Not Available

ChEBI ID

101967

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

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 ]
Noble S, Sorkin EM: Spirapril. A preliminary review of its pharmacology and therapeutic efficacy in the treatment of hypertension. Drugs. 1995 May;49(5):750-66. [PubMed:7601014 ]
Shohat J, Wittenberg C, Erman A, Rosenfeld J, Boner G: Acute and chronic effects of spirapril, alone or in combination with isradipine on kidney function and blood pressure in patients with reduced kidney function and hypertension. Scand J Urol Nephrol. 1999 Feb;33(1):57-62. [PubMed:10100366 ]

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

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 ]
Maul B, Krause W, Pankow K, Becker M, Gembardt F, Alenina N, Walther T, Bader M, Siems WE: Central angiotensin II controls alcohol consumption via its AT1 receptor. FASEB J. 2005 Sep;19(11):1474-81. [PubMed:16126915 ]
Hermida RC, Ayala DE, Fontao MJ, Mojon A, Alonso I, Fernandez JR: Administration-time-dependent effects of spirapril on ambulatory blood pressure in uncomplicated essential hypertension. Chronobiol Int. 2010 May;27(3):560-74. doi: 10.3109/07420528.2010.485411. [PubMed:20524801 ]
Arend U, Albrecht S, Meisel E, Schmidt J: [Influence of ACE inhibitor spirapril on left ventricular hypertrophy]. Fortschr Med Orig. 2002 Dec 5;120(4):147-50. [PubMed:12613273 ]
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. 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 Spirapril (HMDB0015438)

MOL for HMDB0015438 (Spirapril)

3D MOL for HMDB0015438 (Spirapril)

3D SDF for HMDB0015438 (Spirapril)

3D-SDF for HMDB0015438 (Spirapril)

PDB for HMDB0015438 (Spirapril)

3D PDB for HMDB0015438 (Spirapril)

SMILES for HMDB0015438 (Spirapril)

INCHI for HMDB0015438 (Spirapril)

Structure for HMDB0015438 (Spirapril)

3D Structure for HMDB0015438 (Spirapril)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Transporters

References

References