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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-06-23 10:26:39 UTC

Update Date

2021-09-14 15:47:06 UTC

HMDB ID

HMDB0061720

Secondary Accession Numbers

HMDB61720

Metabolite Identification

Common Name

Temocapril

Description

Temocapril 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. Temocapril is a very strong basic compound (based on its pKa). In humans, temocapril is involved in temocapril metabolism pathway. Temocapril can also be used in hemodialysis patients without risk of serious accumulation. When compared with other Angiotensin-converting Enzyme Inhibitors, temocapril's advantages include a rapid onset of action and what research suggests is tighter vascular ACE binding than enalaprilat. ACE inhibitors exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. Temocaprilat has slightly higher potency than enalaprilat in ACE inhibition isolated from rabbit lung. Temocapril is a prodrug-type angiotensin-I converting enzyme (ACE) inhibitor not approved for use in the United States, but is approved in Japan and South Korea. Temocapril is a prodrug of its active metabolite (and diacid form) temocaprilat which contains a thiazepine ring. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis.

Structure

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


  Mrv0541 06231403282D          

 32 34  0  0  0  0            999 V2000
    1.8832    0.8598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7020    1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353   -0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    1.2536    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748    2.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3804    0.7974    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4855   -0.5985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977    0.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7547    2.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0393    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785   -0.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8325   -1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833    0.1111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2534   -1.2885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5029   -0.2866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -0.6686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0373   -2.1073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125    0.1189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9416   -0.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125    0.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629    0.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9143    1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5029    1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726   -0.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928    0.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726   -1.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1017    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3024    1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1017   -1.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7996   -0.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7996   -1.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 11 14  2  0  0  0  0
 11 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  1  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  1  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 25 27  2  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  1  0  0  0  0
 28 31  2  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END

HMDB0061720
     RDKit          3D
Temocapril
 60 62  0  0  0  0  0  0  0  0999 V2000
   -4.5684   -2.5701    3.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3011   -1.9119    3.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2555   -1.6403    1.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -1.0850    1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1762   -0.9095    2.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198   -0.7480   -0.1556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7678   -1.4101   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -1.0308   -0.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3831    0.4503   -1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5359    1.0677   -2.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    2.4300   -2.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7783    3.1752   -1.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6212    2.5468    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4216    1.1714    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -0.7293   -0.6110 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554    0.2143   -0.3240 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9693    0.5026    1.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314    1.4917    0.8719 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631    0.2874    1.0724 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1701    1.0005    1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0084    1.2266    2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1419    1.9094    1.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3634    2.3182    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9925    1.7443   -0.2223 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341   -0.7902    0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623   -0.6321   -1.0480 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3143   -1.3253   -2.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0811   -0.3581   -3.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496    0.8543   -2.7938 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7444   -0.7862   -4.2723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289    0.0002   -1.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    0.4726   -2.4151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0689   -1.9736    4.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3096   -3.5345    4.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2406   -2.8195    2.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168   -2.5251    3.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -0.9325    3.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298    0.3683   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283   -1.1072   -2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298   -2.5050   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6452   -1.4004   -0.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7945   -1.4791   -1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092    0.5319   -3.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8540    2.9541   -3.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9289    4.2499   -1.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548    3.1304    0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3126    0.7609    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5148   -0.9195   -1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0502    1.2356   -0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674   -0.3752    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    1.1611    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826   -0.1938    2.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7430    0.8609    3.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9046    2.1590    2.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2427    2.8869    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -1.7886    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7844   -0.9213   -0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0278   -2.1406   -2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.7225   -2.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093   -0.8970   -5.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 26 31  1  0
 31 32  2  0
 14  9  1  0
 31 16  1  0
 24 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  6 38  1  1
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  6
 17 50  1  0
 17 51  1  0
 19 52  1  1
 21 53  1  0
 22 54  1  0
 23 55  1  0
 25 56  1  0
 25 57  1  0
 27 58  1  0
 27 59  1  0
 30 60  1  0
M  END


  Mrv0541 06231403282D          

 32 34  0  0  0  0            999 V2000
    1.8832    0.8598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7020    1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353   -0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    1.2536    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748    2.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3804    0.7974    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4855   -0.5985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977    0.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7547    2.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0393    1.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6785   -0.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8325   -1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833    0.1111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2534   -1.2885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -1.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5029   -0.2866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567   -0.6686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0373   -2.1073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125    0.1189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9416   -0.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125    0.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6629    0.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9143    1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5029    1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726   -0.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5928    0.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726   -1.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1017    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3024    1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1017   -1.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7996   -0.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7996   -1.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 11 14  2  0  0  0  0
 11 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  1  0  0  0
 15 17  1  0  0  0  0
 15 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  1  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 25 27  2  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  1  0  0  0  0
 28 31  2  0  0  0  0
 30 32  2  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061720

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C23H28N2O5S2/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27)/t17-,18-,20-/m0/s1

> <INCHI_KEY>
FIQOFIRCTOWDOW-BJLQDIEVSA-N

> <FORMULA>
C23H28N2O5S2

> <MOLECULAR_WEIGHT>
476.609

> <EXACT_MASS>
476.143963396

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
49.28480295353984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
2.0427770619041414

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.877209787584375

> <JCHEM_PKA_STRONGEST_BASIC>
5.143176481174263

> <JCHEM_POLAR_SURFACE_AREA>
95.94000000000003

> <JCHEM_REFRACTIVITY>
124.09989999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061720
     RDKit          3D
Temocapril
 60 62  0  0  0  0  0  0  0  0999 V2000
   -4.5684   -2.5701    3.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3011   -1.9119    3.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2555   -1.6403    1.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -1.0850    1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1762   -0.9095    2.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198   -0.7480   -0.1556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7678   -1.4101   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -1.0308   -0.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3831    0.4503   -1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5359    1.0677   -2.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    2.4300   -2.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7783    3.1752   -1.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6212    2.5468    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4216    1.1714    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -0.7293   -0.6110 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554    0.2143   -0.3240 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9693    0.5026    1.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314    1.4917    0.8719 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631    0.2874    1.0724 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1701    1.0005    1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0084    1.2266    2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1419    1.9094    1.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3634    2.3182    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9925    1.7443   -0.2223 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341   -0.7902    0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623   -0.6321   -1.0480 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3143   -1.3253   -2.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0811   -0.3581   -3.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496    0.8543   -2.7938 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7444   -0.7862   -4.2723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289    0.0002   -1.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    0.4726   -2.4151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0689   -1.9736    4.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3096   -3.5345    4.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2406   -2.8195    2.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168   -2.5251    3.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -0.9325    3.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298    0.3683   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283   -1.1072   -2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298   -2.5050   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6452   -1.4004   -0.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7945   -1.4791   -1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092    0.5319   -3.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8540    2.9541   -3.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9289    4.2499   -1.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548    3.1304    0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3126    0.7609    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5148   -0.9195   -1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0502    1.2356   -0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674   -0.3752    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    1.1611    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826   -0.1938    2.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7430    0.8609    3.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9046    2.1590    2.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2427    2.8869    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -1.7886    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7844   -0.9213   -0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0278   -2.1406   -2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.7225   -2.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093   -0.8970   -5.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 26 31  1  0
 31 32  2  0
 14  9  1  0
 31 16  1  0
 24 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  6 38  1  1
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  6
 17 50  1  0
 17 51  1  0
 19 52  1  1
 21 53  1  0
 22 54  1  0
 23 55  1  0
 25 56  1  0
 25 57  1  0
 27 58  1  0
 27 59  1  0
 30 60  1  0
M  END

HEADER    PROTEIN                                 23-JUN-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-14         0                                  
HETATM    1  C   UNK     0       3.515   1.605   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.044   2.551   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.799  -0.062   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       2.132   2.340   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       5.553   3.934   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       6.310   1.488   0.000  0.00  0.00           S+0
HETATM    7  N   UNK     0       2.773  -1.117   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.742   1.605   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.009   3.934   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.540   2.456   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.267  -1.117   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.421  -2.609   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.342   0.207   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.473  -2.405   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.007  -2.609   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.939  -0.535   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       5.706  -1.248   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.670  -3.934   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.263   0.222   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.624  -0.535   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.263   1.816   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.971   0.207   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.573   2.551   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.939   2.551   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.296  -0.535   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.840   1.816   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.296  -2.121   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.657   0.186   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.164   2.551   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -7.657  -2.915   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.959  -0.535   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.959  -2.121   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11   12                                                  
CONECT    8    4   13                                                       
CONECT    9    5   10                                                       
CONECT   10    6    9                                                       
CONECT   11    7   14   13                                                  
CONECT   12    7   15                                                       
CONECT   13    8   11   16                                                  
CONECT   14   11                                                            
CONECT   15   12   17   18                                                  
CONECT   16   13   19                                                       
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19   23   24                                                  
CONECT   22   20   25                                                       
CONECT   23   21   26                                                       
CONECT   24   21                                                            
CONECT   25   22   27   28                                                  
CONECT   26   23   29                                                       
CONECT   27   25   30                                                       
CONECT   28   25   31                                                       
CONECT   29   26                                                            
CONECT   30   27   32                                                       
CONECT   31   28   32                                                       
CONECT   32   30   31                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

COMPND    HMDB0061720
HETATM    1  C1  UNL     1      -4.568  -2.570   3.565  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.301  -1.912   3.110  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.256  -1.640   1.729  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.047  -1.085   1.242  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.176  -0.910   2.114  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.820  -0.748  -0.156  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.768  -1.410  -1.141  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.189  -1.031  -0.935  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.383   0.450  -1.050  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.536   1.068  -2.249  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.734   2.430  -2.304  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.778   3.175  -1.168  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.621   2.547   0.048  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.422   1.171   0.112  1.00  0.00           C  
HETATM   15  N1  UNL     1      -0.504  -0.729  -0.611  1.00  0.00           N  
HETATM   16  C13 UNL     1       0.455   0.214  -0.324  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.969   0.503   1.030  1.00  0.00           C  
HETATM   18  S1  UNL     1       2.531   1.492   0.872  1.00  0.00           S  
HETATM   19  C15 UNL     1       3.863   0.287   1.072  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.170   1.001   1.074  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.008   1.227   2.134  1.00  0.00           C  
HETATM   22  C18 UNL     1       7.142   1.909   1.884  1.00  0.00           C  
HETATM   23  C19 UNL     1       7.363   2.318   0.604  1.00  0.00           C  
HETATM   24  S2  UNL     1       5.993   1.744  -0.222  1.00  0.00           S  
HETATM   25  C20 UNL     1       3.734  -0.790   0.064  1.00  0.00           C  
HETATM   26  N2  UNL     1       2.862  -0.632  -1.048  1.00  0.00           N  
HETATM   27  C21 UNL     1       3.314  -1.325  -2.291  1.00  0.00           C  
HETATM   28  C22 UNL     1       4.081  -0.358  -3.114  1.00  0.00           C  
HETATM   29  O3  UNL     1       4.150   0.854  -2.794  1.00  0.00           O  
HETATM   30  O4  UNL     1       4.744  -0.786  -4.272  1.00  0.00           O  
HETATM   31  C23 UNL     1       1.629   0.000  -1.281  1.00  0.00           C  
HETATM   32  O5  UNL     1       1.398   0.473  -2.415  1.00  0.00           O  
HETATM   33  H1  UNL     1      -5.069  -1.974   4.338  1.00  0.00           H  
HETATM   34  H2  UNL     1      -4.310  -3.534   4.070  1.00  0.00           H  
HETATM   35  H3  UNL     1      -5.241  -2.819   2.739  1.00  0.00           H  
HETATM   36  H4  UNL     1      -2.417  -2.525   3.379  1.00  0.00           H  
HETATM   37  H5  UNL     1      -3.158  -0.932   3.639  1.00  0.00           H  
HETATM   38  H6  UNL     1      -2.230   0.368  -0.209  1.00  0.00           H  
HETATM   39  H7  UNL     1      -2.428  -1.107  -2.158  1.00  0.00           H  
HETATM   40  H8  UNL     1      -2.630  -2.505  -0.992  1.00  0.00           H  
HETATM   41  H9  UNL     1      -4.645  -1.400  -0.007  1.00  0.00           H  
HETATM   42  H10 UNL     1      -4.794  -1.479  -1.772  1.00  0.00           H  
HETATM   43  H11 UNL     1      -4.509   0.532  -3.179  1.00  0.00           H  
HETATM   44  H12 UNL     1      -4.854   2.954  -3.243  1.00  0.00           H  
HETATM   45  H13 UNL     1      -4.929   4.250  -1.153  1.00  0.00           H  
HETATM   46  H14 UNL     1      -4.655   3.130   0.952  1.00  0.00           H  
HETATM   47  H15 UNL     1      -4.313   0.761   1.094  1.00  0.00           H  
HETATM   48  H16 UNL     1      -0.515  -0.919  -1.661  1.00  0.00           H  
HETATM   49  H17 UNL     1       0.050   1.236  -0.706  1.00  0.00           H  
HETATM   50  H18 UNL     1       1.267  -0.375   1.621  1.00  0.00           H  
HETATM   51  H19 UNL     1       0.316   1.161   1.636  1.00  0.00           H  
HETATM   52  H20 UNL     1       3.783  -0.194   2.110  1.00  0.00           H  
HETATM   53  H21 UNL     1       5.743   0.861   3.142  1.00  0.00           H  
HETATM   54  H22 UNL     1       7.905   2.159   2.670  1.00  0.00           H  
HETATM   55  H23 UNL     1       8.243   2.887   0.224  1.00  0.00           H  
HETATM   56  H24 UNL     1       3.588  -1.789   0.576  1.00  0.00           H  
HETATM   57  H25 UNL     1       4.784  -0.921  -0.373  1.00  0.00           H  
HETATM   58  H26 UNL     1       4.028  -2.141  -2.050  1.00  0.00           H  
HETATM   59  H27 UNL     1       2.475  -1.723  -2.849  1.00  0.00           H  
HETATM   60  H28 UNL     1       4.209  -0.897  -5.114  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3   36   37
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   15   38
CONECT    7    8   39   40
CONECT    8    9   41   42
CONECT    9   10   10   14
CONECT   10   11   43
CONECT   11   12   12   44
CONECT   12   13   45
CONECT   13   14   14   46
CONECT   14   47
CONECT   15   16   48
CONECT   16   17   31   49
CONECT   17   18   50   51
CONECT   18   19
CONECT   19   20   25   52
CONECT   20   21   21   24
CONECT   21   22   53
CONECT   22   23   23   54
CONECT   23   24   55
CONECT   25   26   56   57
CONECT   26   27   31
CONECT   27   28   58   59
CONECT   28   29   29   30
CONECT   30   60
CONECT   31   32   32
END

HMDB0061720
     RDKit          3D
Temocapril
 60 62  0  0  0  0  0  0  0  0999 V2000
   -4.5684   -2.5701    3.5648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3011   -1.9119    3.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2555   -1.6403    1.7292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474   -1.0850    1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1762   -0.9095    2.1142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8198   -0.7480   -0.1556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7678   -1.4101   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -1.0308   -0.9352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3831    0.4503   -1.0498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5359    1.0677   -2.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    2.4300   -2.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7783    3.1752   -1.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6212    2.5468    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4216    1.1714    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5039   -0.7293   -0.6110 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554    0.2143   -0.3240 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9693    0.5026    1.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314    1.4917    0.8719 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8631    0.2874    1.0724 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1701    1.0005    1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0084    1.2266    2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1419    1.9094    1.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3634    2.3182    0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9925    1.7443   -0.2223 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7341   -0.7902    0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623   -0.6321   -1.0480 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3143   -1.3253   -2.2913 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0811   -0.3581   -3.1137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1496    0.8543   -2.7938 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7444   -0.7862   -4.2723 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6289    0.0002   -1.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    0.4726   -2.4151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0689   -1.9736    4.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3096   -3.5345    4.0703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2406   -2.8195    2.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4168   -2.5251    3.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1578   -0.9325    3.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298    0.3683   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283   -1.1072   -2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298   -2.5050   -0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6452   -1.4004   -0.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7945   -1.4791   -1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092    0.5319   -3.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8540    2.9541   -3.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9289    4.2499   -1.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6548    3.1304    0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3126    0.7609    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5148   -0.9195   -1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0502    1.2356   -0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674   -0.3752    1.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3156    1.1611    1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826   -0.1938    2.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7430    0.8609    3.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9046    2.1590    2.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2427    2.8869    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875   -1.7886    0.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7844   -0.9213   -0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0278   -2.1406   -2.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.7225   -2.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093   -0.8970   -5.1145 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  6 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 26 31  1  0
 31 32  2  0
 14  9  1  0
 31 16  1  0
 24 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  6 38  1  1
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  0
 15 48  1  0
 16 49  1  6
 17 50  1  0
 17 51  1  0
 19 52  1  1
 21 53  1  0
 22 54  1  0
 23 55  1  0
 25 56  1  0
 25 57  1  0
 27 58  1  0
 27 59  1  0
 30 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-((2S,6R)-6-((1S)-1-Ethoxycarbonyl-3-phenylpropyl)amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl)acetic acid.hcl	HMDB
Temocapril hydrochloride	HMDB

Chemical Formula

C₂₃H₂₈N₂O₅S₂

Average Molecular Weight

476.609

Monoisotopic Molecular Weight

476.143963396

IUPAC Name

2-[(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid

Traditional Name

[(2S,6R)-6-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS1

InChI Identifier

InChI=1S/C23H28N2O5S2/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27)/t17-,18-,20-/m0/s1

InChI Key

FIQOFIRCTOWDOW-BJLQDIEVSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Alpha-amino acid ester
Alpha-amino acid or derivatives
Fatty acid ester
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Tertiary carboxylic acid amide
Heteroaromatic compound
Thiophene
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Amino acid
Lactam
Secondary amine
Dialkylthioether
Organoheterocyclic compound
Azacycle
Thioether
Carboxylic acid
Secondary aliphatic amine
Organooxygen compound
Organic oxide
Amine
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0034 g/L	ALOGPS
logP	2.46	ALOGPS
logP	2.04	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	5.14	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	11	ChemAxon
Refractivity	124.1 m³·mol⁻¹	ChemAxon
Polarizability	49.28 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]+	205.029	31661259
DarkChem	[M-H]-	196.903	31661259
DeepCCS	[M+H]+	200.637	30932474
DeepCCS	[M-H]-	198.241	30932474
DeepCCS	[M-2H]-	231.125	30932474
DeepCCS	[M+Na]+	206.55	30932474
AllCCS	[M+H]+	210.1	32859911
AllCCS	[M+H-H2O]+	208.2	32859911
AllCCS	[M+NH4]+	211.8	32859911
AllCCS	[M+Na]+	212.3	32859911
AllCCS	[M-H]-	201.4	32859911
AllCCS	[M+Na-2H]-	202.4	32859911
AllCCS	[M+HCOO]-	203.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.79 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7036 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.47 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2366.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	251.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	196.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	165.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	580.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	578.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	139.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1241.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	576.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1660.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	361.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	401.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	196.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	108.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Temocapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS1	5465.2	Standard polar	33892256
Temocapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS1	3208.5	Standard non polar	33892256
Temocapril	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@@H](CN(CC(O)=O)C1=O)C1=CC=CS1	3728.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Temocapril,1TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O	3803.4	Semi standard non polar	33892256
Temocapril,1TMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O)C1=O)[Si](C)(C)C	3787.8	Semi standard non polar	33892256
Temocapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C	3731.9	Semi standard non polar	33892256
Temocapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C	3516.8	Standard non polar	33892256
Temocapril,2TMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C)C1=O)[Si](C)(C)C	4878.1	Standard polar	33892256
Temocapril,1TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O	4037.4	Semi standard non polar	33892256
Temocapril,1TBDMS,isomer #2	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O)C1=O)[Si](C)(C)C(C)(C)C	3969.8	Semi standard non polar	33892256
Temocapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C	4111.3	Semi standard non polar	33892256
Temocapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C	3935.0	Standard non polar	33892256
Temocapril,2TBDMS,isomer #1	CCOC(=O)[C@H](CCC1=CC=CC=C1)N([C@H]1CS[C@H](C2=CC=CS2)CN(CC(=O)O[Si](C)(C)C(C)(C)C)C1=O)[Si](C)(C)C(C)(C)C	4887.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Temocapril GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-3300900000-07c0bde728f9e7cad38a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Temocapril GC-MS (1 TMS) - 70eV, Positive	splash10-004i-3200910000-b52f07bd2a96ae84f2c2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Temocapril 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 - Temocapril 10V, Positive-QTOF	splash10-0fmi-2900400000-06af7a1143b5abccba26	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 20V, Positive-QTOF	splash10-003u-4362900000-0743a982c0ed45c1affb	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 40V, Positive-QTOF	splash10-00du-9300000000-2585084c57fba4d3130f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 10V, Negative-QTOF	splash10-004i-2921400000-ea6d0202eb7b0a7b86b4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 20V, Negative-QTOF	splash10-004i-3953400000-eea8b567695e04163132	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 40V, Negative-QTOF	splash10-00ej-9430000000-053ca4271d92f5f59f9d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 10V, Positive-QTOF	splash10-004i-0000900000-55f39eb3922a0c1c8f26	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 20V, Positive-QTOF	splash10-004i-0511900000-9d098ce150dd0dd4ee3e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 40V, Positive-QTOF	splash10-08ir-0790000000-ef9ad031ca41af6d886f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 10V, Negative-QTOF	splash10-004i-0000900000-2c8feffe734e85cdc085	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 20V, Negative-QTOF	splash10-00fr-1091400000-22c4735d269f91570e2a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Temocapril 40V, Negative-QTOF	splash10-01zi-1490100000-9fff467ed2cf416a6dce	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08836

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Temocapril

METLIN ID

Not Available

PubChem Compound

443874

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Temocapril (HMDB0061720)

MOL for HMDB0061720 (Temocapril)

3D MOL for HMDB0061720 (Temocapril)

3D SDF for HMDB0061720 (Temocapril)

3D-SDF for HMDB0061720 (Temocapril)

PDB for HMDB0061720 (Temocapril)

3D PDB for HMDB0061720 (Temocapril)

SMILES for HMDB0061720 (Temocapril)

INCHI for HMDB0061720 (Temocapril)

Structure for HMDB0061720 (Temocapril)

3D Structure for HMDB0061720 (Temocapril)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra