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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 02:52:01 UTC

HMDB ID

HMDB0015535

Secondary Accession Numbers

HMDB15535

Metabolite Identification

Common Name

Cilastatin

Description

Cilastatin, also known as cilastatin sodium, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. The thioether resulting from the formal oxidative coupling of the thiol group of L-cysteine with the 7-position of (2Z)-2-({carbonyl}amino)hept-2-enoic acid. Cilastatin is a very strong basic compound (based on its pKa). Cilastatin also acts as a leukotriene D4 dipeptidase inhibitor, preventing the metabolism of leukotriene D4 to leukotriene E4. It is an inhibitor of dehydropeptidase I (membrane dipeptidase, 3.4.13.19), an enzyme found in the brush border of renal tubes and responsible for degrading the antibiotic imipenem. Cilastatin is therefore administered (as the sodium salt) with imipenem to prolong the antibacterial effect of the latter by preventing its renal metabolism to inactive and potentially nephrotoxic products.

Structure

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

HMDB0015535
     RDKit          3D
Cilastatin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -5.6916    0.7720   -2.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5550    0.9819   -1.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4421    2.3604   -1.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542   -0.1282   -0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4229    0.0228   -2.0688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0457    0.5114   -1.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671    0.1277   -2.7204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.3592   -0.7884 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110    1.7915   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    1.5206    0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    0.7470    1.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754   -0.4350    1.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555   -1.5156    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343   -1.2468   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -0.5781   -0.0288 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.5551    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3611   -1.8973    2.1748 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3080   -0.6704    2.9577 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184   -2.5964    2.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3452   -2.0747    3.4441 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0331   -3.7979    2.0277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993    2.5495   -1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5003    2.9695   -1.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3755    2.8624   -2.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524    0.2509   -3.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0658    1.7438   -3.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4531    0.0919   -2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5261    2.8501   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3023    2.9797   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5724    2.3741   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0985   -0.9401   -0.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0334    0.1761    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5037   -0.7105   -2.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    1.6571   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4082    1.8945    0.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    1.4805    2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.5529    1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517   -0.9265    2.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625   -0.1259    2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860   -2.3303    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -1.9331    0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678   -0.5969   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977   -2.2289   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4965   -1.0235    0.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684   -2.5019    0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -2.5833    2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2686   -0.3969    3.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9717    0.0808    2.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0806   -4.6009    2.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222    2.6859   -3.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
  9 22  1  0
 22 23  2  0
 22 24  1  0
  5  2  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  8 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 21 49  1  0
 24 50  1  0
M  END


  Mrv0541 02231215352D          

 24 24  0  0  1  0            999 V2000
    5.8263   -6.1809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4138   -6.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -6.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -5.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408   -4.9434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408   -4.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -3.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -3.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2566   -4.1184    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1118   -4.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.8809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -2.8809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552   -3.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2566   -4.9434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -4.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6855   -4.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -6.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8276   -4.1184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421   -3.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9697   -4.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131   -3.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6842   -3.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3986   -4.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  1  4  1  1  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  9  1  0  0  0  0
  9 20  1  0  0  0  0
 10  4  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  6  2  0  0  0  0
  9 14  1  1  0  0  0
 15  7  1  0  0  0  0
 16  8  1  0  0  0  0
 17  2  1  0  0  0  0
 18  2  1  0  0  0  0
 19 22  1  0  0  0  0
 20 19  1  0  0  0  0
 21 13  1  0  0  0  0
 22 24  1  0  0  0  0
 23 21  1  0  0  0  0
 24 23  1  0  0  0  0
  2  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015535

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CSCCCC\C=C(/NC(=O)[C@H]1CC1(C)C)C(=O)O)C(=O)O

> <INCHI_IDENTIFIER>
InChI=1S/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11+/m1/s1

> <INCHI_KEY>
DHSUYTOATWAVLW-WFVMDLQDSA-N

> <FORMULA>
C16H26N2O5S

> <MOLECULAR_WEIGHT>
358.453

> <EXACT_MASS>
358.156242642

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
38.28482513768682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1S)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acid

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
-1.2590919226410249

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.376665286734443

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.531970616604837

> <JCHEM_PKA_STRONGEST_BASIC>
9.142243765363126

> <JCHEM_POLAR_SURFACE_AREA>
129.72

> <JCHEM_REFRACTIVITY>
92.85069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cilastatin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015535
     RDKit          3D
Cilastatin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -5.6916    0.7720   -2.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5550    0.9819   -1.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4421    2.3604   -1.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542   -0.1282   -0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4229    0.0228   -2.0688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0457    0.5114   -1.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671    0.1277   -2.7204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.3592   -0.7884 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110    1.7915   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    1.5206    0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    0.7470    1.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754   -0.4350    1.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555   -1.5156    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343   -1.2468   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -0.5781   -0.0288 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.5551    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3611   -1.8973    2.1748 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3080   -0.6704    2.9577 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184   -2.5964    2.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3452   -2.0747    3.4441 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0331   -3.7979    2.0277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993    2.5495   -1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5003    2.9695   -1.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3755    2.8624   -2.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524    0.2509   -3.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0658    1.7438   -3.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4531    0.0919   -2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5261    2.8501   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3023    2.9797   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5724    2.3741   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0985   -0.9401   -0.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0334    0.1761    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5037   -0.7105   -2.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    1.6571   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4082    1.8945    0.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    1.4805    2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.5529    1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517   -0.9265    2.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625   -0.1259    2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860   -2.3303    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -1.9331    0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678   -0.5969   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977   -2.2289   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4965   -1.0235    0.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684   -2.5019    0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -2.5833    2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2686   -0.3969    3.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9717    0.0808    2.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0806   -4.6009    2.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222    2.6859   -3.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
  9 22  1  0
 22 23  2  0
 22 24  1  0
  5  2  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  8 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 21 49  1  0
 24 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      10.876 -11.538   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.106 -12.871   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.646 -12.871   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.876  -9.998   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      12.209  -9.228   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      12.209  -7.688   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.876  -6.918   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.213  -6.918   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.879  -7.688   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.542  -9.228   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      10.876  -5.378   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      24.213  -5.378   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.543  -6.918   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      22.879  -9.228   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       9.542  -7.688   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      25.546  -7.688   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.566 -12.871   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336 -14.205   0.000  0.00  0.00           C+0
HETATM   19  S   UNK     0      20.212  -7.688   0.000  0.00  0.00           S+0
HETATM   20  C   UNK     0      21.545  -6.918   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.877  -7.688   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.878  -6.918   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      16.211  -6.918   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.544  -7.688   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1   17   18    3                                             
CONECT    3    1    2                                                       
CONECT    4    1    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6   11   15                                                  
CONECT    8    9   12   16                                                  
CONECT    9    8   20   14                                                  
CONECT   10    4                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    6   21                                                       
CONECT   14    9                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    2                                                            
CONECT   18    2                                                            
CONECT   19   22   20                                                       
CONECT   20    9   19                                                       
CONECT   21   13   23                                                       
CONECT   22   19   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0015535
HETATM    1  C1  UNL     1      -5.692   0.772  -2.975  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.555   0.982  -1.983  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.442   2.360  -1.434  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.354  -0.128  -0.946  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.423   0.023  -2.069  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.046   0.511  -1.861  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.167   0.128  -2.720  1.00  0.00           O  
HETATM    8  N1  UNL     1      -1.646   1.359  -0.788  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.311   1.792  -0.640  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.412   1.521   0.463  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.202   0.747   1.561  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.575  -0.435   1.940  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.856  -1.516   0.997  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.634  -1.247  -0.230  1.00  0.00           C  
HETATM   15  S1  UNL     1       3.262  -0.578  -0.029  1.00  0.00           S  
HETATM   16  C13 UNL     1       4.508  -1.555   0.718  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.361  -1.897   2.175  1.00  0.00           C  
HETATM   18  N2  UNL     1       4.308  -0.670   2.958  1.00  0.00           N  
HETATM   19  C15 UNL     1       5.618  -2.596   2.572  1.00  0.00           C  
HETATM   20  O2  UNL     1       6.345  -2.075   3.444  1.00  0.00           O  
HETATM   21  O3  UNL     1       6.033  -3.798   2.028  1.00  0.00           O  
HETATM   22  C16 UNL     1       0.299   2.549  -1.720  1.00  0.00           C  
HETATM   23  O4  UNL     1       1.500   2.969  -1.647  1.00  0.00           O  
HETATM   24  O5  UNL     1      -0.376   2.862  -2.887  1.00  0.00           O  
HETATM   25  H1  UNL     1      -5.252   0.251  -3.856  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.066   1.744  -3.293  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.453   0.092  -2.537  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.526   2.850  -1.770  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.302   2.980  -1.844  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.572   2.374  -0.311  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.099  -0.940  -0.992  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.033   0.176   0.082  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.504  -0.710  -2.931  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.347   1.657  -0.098  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.408   1.894   0.468  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.242   1.481   2.431  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.279   0.553   1.359  1.00  0.00           H  
HETATM   38  H14 UNL     1       0.052  -0.927   2.833  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.563  -0.126   2.430  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.386  -2.330   1.576  1.00  0.00           H  
HETATM   41  H17 UNL     1      -0.154  -1.933   0.671  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.068  -0.597  -0.922  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.698  -2.229  -0.822  1.00  0.00           H  
HETATM   44  H20 UNL     1       5.496  -1.024   0.611  1.00  0.00           H  
HETATM   45  H21 UNL     1       4.668  -2.502   0.120  1.00  0.00           H  
HETATM   46  H22 UNL     1       3.549  -2.583   2.416  1.00  0.00           H  
HETATM   47  H23 UNL     1       5.269  -0.397   3.258  1.00  0.00           H  
HETATM   48  H24 UNL     1       3.972   0.081   2.315  1.00  0.00           H  
HETATM   49  H25 UNL     1       6.081  -4.601   2.672  1.00  0.00           H  
HETATM   50  H26 UNL     1       0.122   2.686  -3.765  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4    5
CONECT    3   28   29   30
CONECT    4    5   31   32
CONECT    5    6   33
CONECT    6    7    7    8
CONECT    8    9   34
CONECT    9   10   10   22
CONECT   10   11   35
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   42   43
CONECT   15   16
CONECT   16   17   44   45
CONECT   17   18   19   46
CONECT   18   47   48
CONECT   19   20   20   21
CONECT   21   49
CONECT   22   23   23   24
CONECT   24   50
END

HMDB0015535
     RDKit          3D
Cilastatin
 50 50  0  0  0  0  0  0  0  0999 V2000
   -5.6916    0.7720   -2.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5550    0.9819   -1.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4421    2.3604   -1.4340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3542   -0.1282   -0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4229    0.0228   -2.0688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0457    0.5114   -1.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671    0.1277   -2.7204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461    1.3592   -0.7884 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3110    1.7915   -0.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    1.5206    0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    0.7470    1.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754   -0.4350    1.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8555   -1.5156    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6343   -1.2468   -0.2304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -0.5781   -0.0288 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.5551    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3611   -1.8973    2.1748 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3080   -0.6704    2.9577 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184   -2.5964    2.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3452   -2.0747    3.4441 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0331   -3.7979    2.0277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993    2.5495   -1.7199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5003    2.9695   -1.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3755    2.8624   -2.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524    0.2509   -3.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0658    1.7438   -3.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4531    0.0919   -2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5261    2.8501   -1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3023    2.9797   -1.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5724    2.3741   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0985   -0.9401   -0.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0334    0.1761    0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5037   -0.7105   -2.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    1.6571   -0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4082    1.8945    0.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425    1.4805    2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    0.5529    1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517   -0.9265    2.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5625   -0.1259    2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3860   -2.3303    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1542   -1.9331    0.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678   -0.5969   -0.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977   -2.2289   -0.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4965   -1.0235    0.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6684   -2.5019    0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -2.5833    2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2686   -0.3969    3.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9717    0.0808    2.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0806   -4.6009    2.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1222    2.6859   -3.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
  9 22  1  0
 22 23  2  0
 22 24  1  0
  5  2  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  6
  8 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
 21 49  1  0
 24 50  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid	ChEBI
(Z)-(S)-6-Carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine	ChEBI
(Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid	ChEBI
Cilastatina	ChEBI
Cilastatine	ChEBI
Cilastatinum	ChEBI
(L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoate	Generator
(L)-7-(2-Amino-2-carboxy-ethylsulphanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoate	Generator
(L)-7-(2-Amino-2-carboxy-ethylsulphanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid	Generator
(Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoate	Generator
(Z)-7-((R)-2-Amino-2-carboxy-ethylsulphanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoate	Generator
(Z)-7-((R)-2-Amino-2-carboxy-ethylsulphanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid	Generator
Cilastatin sodium	HMDB
Monosodium salt, cilastatin	HMDB
Salt, cilastatin monosodium	HMDB
Cilastatin monosodium salt	HMDB
Sodium, cilastatin	HMDB

Chemical Formula

C₁₆H₂₆N₂O₅S

Average Molecular Weight

358.453

Monoisotopic Molecular Weight

358.156242642

IUPAC Name

(2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1S)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acid

Traditional Name

cilastatin

CAS Registry Number

82009-34-5

SMILES

N[C@@H](CSCCCC\C=C(/NC(=O)[C@H]1CC1(C)C)C(=O)O)C(=O)O

InChI Identifier

InChI=1S/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11+/m1/s1

InChI Key

DHSUYTOATWAVLW-WFVMDLQDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
L-cysteine-s-conjugate
Cysteine or derivatives
Alpha-amino acid
L-alpha-amino acid
Medium-chain fatty acid
Cyclopropanecarboxylic acid or derivatives
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acid
Fatty acyl
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Dialkylthioether
Sulfenyl compound
Carboxylic acid
Thioether
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Organic nitrogen compound
Organic oxide
Carbonyl group
Primary amine
Organopnictogen compound
Hydrocarbon derivative
Amine
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:3697 )
L-cysteine derivative (CHEBI:3697 )
organic sulfide (CHEBI:3697 )
carboxamide (CHEBI:3697 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015535)

Source

Exogenous

Exogenous (HMDB: HMDB0015535)

Process

Not Available

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	0.1 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	-0.29	ALOGPS
logP	-1.3	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.53	ChemAxon
pKa (Strongest Basic)	9.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	92.85 m³·mol⁻¹	ChemAxon
Polarizability	38.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	182.209	30932474
DeepCCS	[M-H]-	179.851	30932474
DeepCCS	[M-2H]-	213.514	30932474
DeepCCS	[M+Na]+	189.386	30932474
AllCCS	[M+H]+	181.3	32859911
AllCCS	[M+H-H2O]+	179.0	32859911
AllCCS	[M+NH4]+	183.4	32859911
AllCCS	[M+Na]+	184.0	32859911
AllCCS	[M-H]-	182.0	32859911
AllCCS	[M+Na-2H]-	182.9	32859911
AllCCS	[M+HCOO]-	184.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.29 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3379 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.17 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	131.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1953.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	211.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	119.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	382.7 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	489.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	384.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	906.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	393.3 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	1278.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	293.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	328.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	253.3 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	152.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cilastatin	N[C@@H](CSCCCC\C=C(/NC(=O)[C@H]1CC1(C)C)C(=O)O)C(=O)O	4267.0	Standard polar	33892256
Cilastatin	N[C@@H](CSCCCC\C=C(/NC(=O)[C@H]1CC1(C)C)C(=O)O)C(=O)O	2550.1	Standard non polar	33892256
Cilastatin	N[C@@H](CSCCCC\C=C(/NC(=O)[C@H]1CC1(C)C)C(=O)O)C(=O)O	3054.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cilastatin,1TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O[Si](C)(C)C	2929.8	Semi standard non polar	33892256
Cilastatin,1TMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O	2928.6	Semi standard non polar	33892256
Cilastatin,1TMS,isomer #3	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O	2977.7	Semi standard non polar	33892256
Cilastatin,1TMS,isomer #4	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O)[Si](C)(C)C	2874.6	Semi standard non polar	33892256
Cilastatin,2TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2877.9	Semi standard non polar	33892256
Cilastatin,2TMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C	2943.5	Semi standard non polar	33892256
Cilastatin,2TMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2777.8	Semi standard non polar	33892256
Cilastatin,2TMS,isomer #4	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	2932.5	Semi standard non polar	33892256
Cilastatin,2TMS,isomer #5	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2812.2	Semi standard non polar	33892256
Cilastatin,2TMS,isomer #6	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O)[Si](C)(C)C	2853.5	Semi standard non polar	33892256
Cilastatin,2TMS,isomer #7	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3041.8	Semi standard non polar	33892256
Cilastatin,3TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2890.9	Semi standard non polar	33892256
Cilastatin,3TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2859.0	Standard non polar	33892256
Cilastatin,3TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3841.4	Standard polar	33892256
Cilastatin,3TMS,isomer #2	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2734.1	Semi standard non polar	33892256
Cilastatin,3TMS,isomer #2	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2740.4	Standard non polar	33892256
Cilastatin,3TMS,isomer #2	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3922.1	Standard polar	33892256
Cilastatin,3TMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2802.9	Semi standard non polar	33892256
Cilastatin,3TMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2804.5	Standard non polar	33892256
Cilastatin,3TMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3665.9	Standard polar	33892256
Cilastatin,3TMS,isomer #4	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3000.9	Semi standard non polar	33892256
Cilastatin,3TMS,isomer #4	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2964.3	Standard non polar	33892256
Cilastatin,3TMS,isomer #4	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3934.3	Standard polar	33892256
Cilastatin,3TMS,isomer #5	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2807.9	Semi standard non polar	33892256
Cilastatin,3TMS,isomer #5	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2841.8	Standard non polar	33892256
Cilastatin,3TMS,isomer #5	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3636.8	Standard polar	33892256
Cilastatin,3TMS,isomer #6	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2979.6	Semi standard non polar	33892256
Cilastatin,3TMS,isomer #6	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	2980.1	Standard non polar	33892256
Cilastatin,3TMS,isomer #6	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O	3945.3	Standard polar	33892256
Cilastatin,3TMS,isomer #7	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2891.7	Semi standard non polar	33892256
Cilastatin,3TMS,isomer #7	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2946.7	Standard non polar	33892256
Cilastatin,3TMS,isomer #7	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3767.6	Standard polar	33892256
Cilastatin,4TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2771.6	Semi standard non polar	33892256
Cilastatin,4TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2823.9	Standard non polar	33892256
Cilastatin,4TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3238.3	Standard polar	33892256
Cilastatin,4TMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2956.1	Semi standard non polar	33892256
Cilastatin,4TMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2966.4	Standard non polar	33892256
Cilastatin,4TMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3572.6	Standard polar	33892256
Cilastatin,4TMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2899.6	Semi standard non polar	33892256
Cilastatin,4TMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2934.0	Standard non polar	33892256
Cilastatin,4TMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3377.5	Standard polar	33892256
Cilastatin,4TMS,isomer #4	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2877.0	Semi standard non polar	33892256
Cilastatin,4TMS,isomer #4	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	2954.7	Standard non polar	33892256
Cilastatin,4TMS,isomer #4	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O)[Si](C)(C)C	3407.6	Standard polar	33892256
Cilastatin,5TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2893.1	Semi standard non polar	33892256
Cilastatin,5TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2935.5	Standard non polar	33892256
Cilastatin,5TMS,isomer #1	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	3071.2	Standard polar	33892256
Cilastatin,1TBDMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	3195.1	Semi standard non polar	33892256
Cilastatin,1TBDMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3180.6	Semi standard non polar	33892256
Cilastatin,1TBDMS,isomer #3	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O	3200.2	Semi standard non polar	33892256
Cilastatin,1TBDMS,isomer #4	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	3097.4	Semi standard non polar	33892256
Cilastatin,2TBDMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3339.4	Semi standard non polar	33892256
Cilastatin,2TBDMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	3390.7	Semi standard non polar	33892256
Cilastatin,2TBDMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3266.2	Semi standard non polar	33892256
Cilastatin,2TBDMS,isomer #4	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	3390.0	Semi standard non polar	33892256
Cilastatin,2TBDMS,isomer #5	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3268.0	Semi standard non polar	33892256
Cilastatin,2TBDMS,isomer #6	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	3308.6	Semi standard non polar	33892256
Cilastatin,2TBDMS,isomer #7	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3520.6	Semi standard non polar	33892256
Cilastatin,3TBDMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3559.4	Semi standard non polar	33892256
Cilastatin,3TBDMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3331.7	Standard non polar	33892256
Cilastatin,3TBDMS,isomer #1	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3892.9	Standard polar	33892256
Cilastatin,3TBDMS,isomer #2	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3429.5	Semi standard non polar	33892256
Cilastatin,3TBDMS,isomer #2	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3199.3	Standard non polar	33892256
Cilastatin,3TBDMS,isomer #2	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3962.1	Standard polar	33892256
Cilastatin,3TBDMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3485.6	Semi standard non polar	33892256
Cilastatin,3TBDMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3250.0	Standard non polar	33892256
Cilastatin,3TBDMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3753.9	Standard polar	33892256
Cilastatin,3TBDMS,isomer #4	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3737.4	Semi standard non polar	33892256
Cilastatin,3TBDMS,isomer #4	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3417.8	Standard non polar	33892256
Cilastatin,3TBDMS,isomer #4	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3956.9	Standard polar	33892256
Cilastatin,3TBDMS,isomer #5	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3489.7	Semi standard non polar	33892256
Cilastatin,3TBDMS,isomer #5	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3299.8	Standard non polar	33892256
Cilastatin,3TBDMS,isomer #5	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3747.7	Standard polar	33892256
Cilastatin,3TBDMS,isomer #6	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3720.7	Semi standard non polar	33892256
Cilastatin,3TBDMS,isomer #6	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3471.8	Standard non polar	33892256
Cilastatin,3TBDMS,isomer #6	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O	3969.3	Standard polar	33892256
Cilastatin,3TBDMS,isomer #7	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3618.4	Semi standard non polar	33892256
Cilastatin,3TBDMS,isomer #7	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3397.5	Standard non polar	33892256
Cilastatin,3TBDMS,isomer #7	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3824.0	Standard polar	33892256
Cilastatin,4TBDMS,isomer #1	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3624.4	Semi standard non polar	33892256
Cilastatin,4TBDMS,isomer #1	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3398.8	Standard non polar	33892256
Cilastatin,4TBDMS,isomer #1	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3537.9	Standard polar	33892256
Cilastatin,4TBDMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3913.4	Semi standard non polar	33892256
Cilastatin,4TBDMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3549.0	Standard non polar	33892256
Cilastatin,4TBDMS,isomer #2	CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3750.8	Standard polar	33892256
Cilastatin,4TBDMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3823.1	Semi standard non polar	33892256
Cilastatin,4TBDMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3481.2	Standard non polar	33892256
Cilastatin,4TBDMS,isomer #3	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3586.4	Standard polar	33892256
Cilastatin,4TBDMS,isomer #4	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3808.0	Semi standard non polar	33892256
Cilastatin,4TBDMS,isomer #4	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3530.6	Standard non polar	33892256
Cilastatin,4TBDMS,isomer #4	CC1(C)C[C@@H]1C(=O)N(/C(=C\CCCCSC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	3627.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cilastatin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9143000000-9267c830716476e05220	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cilastatin GC-MS (2 TMS) - 70eV, Positive	splash10-000j-9634300000-05e8bb2de2e0d6d642d3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cilastatin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0009000000-ef2198c6225f95e6b765	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-QTOF , negative-QTOF	splash10-004i-0092000000-f0483d6314128c99a866	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-03fr-0089000000-e23865517b151264287c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0009000000-f94440db25517ee87789	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-004i-0193000000-9c52bb64f789ddf44d03	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-01t9-0890000000-a16bc40171fdaad5d00f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-01q9-0900000000-7f6fb4bc2c8d8b74669a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-001i-0900000000-f7395a558e6db43df825	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0009000000-65b5dae5f837cb16f232	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-004i-0093000000-f41454497f85c6c231e3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-004i-0890000000-2d4e1ce343461b9c33ff	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-001i-0900000000-f7395a558e6db43df825	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , negative-QTOF	splash10-03fr-0079000000-f5a7ea868a31218529fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0009000000-afc7a1706de335756516	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-QTOF , positive-QTOF	splash10-0uxr-0292000000-fc9fdc71c26de516aa47	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-QTOF , positive-QTOF	splash10-0f89-0980000000-c7e9f3733dc9d5876f69	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-QTOF , positive-QTOF	splash10-0f89-0940000000-5e461031ed3e8be30dce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , positive-QTOF	splash10-0udl-0197000000-ed9524572e0f6a20cf73	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cilastatin LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0009000000-92adcd25c03169bce114	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilastatin 10V, Positive-QTOF	splash10-08g3-3149000000-1697f40afdac95d9f1fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilastatin 20V, Positive-QTOF	splash10-00ds-9262000000-2d286749c8bad80aca6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilastatin 40V, Positive-QTOF	splash10-014i-9120000000-103a1c4913411a99597e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilastatin 10V, Negative-QTOF	splash10-0ab9-2359000000-4af9c04e6559117f7de8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilastatin 20V, Negative-QTOF	splash10-00di-4493000000-902790a448dc5b5275ab	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cilastatin 40V, Negative-QTOF	splash10-000i-9210000000-68ca7d233d4d1846c27c	2016-08-04	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB01597	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01597	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01597

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4940183

KEGG Compound ID

C01675

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cilastatin

METLIN ID

Not Available

PubChem Compound

6435415

PDB ID

Not Available

ChEBI ID

3697

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

Keynan S, Hooper NM, Felici A, Amicosante G, Turner AJ: The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-beta-lactamase enzyme CphA. Antimicrob Agents Chemother. 1995 Jul;39(7):1629-31. [PubMed:7492120 ]

Enzymes

Enzyme Details

1. Dipeptidase 1

General function:: Involved in metalloexopeptidase activity
Specific function:: Hydrolyzes a wide range of dipeptides. Implicated in the renal metabolism of glutathione and its conjugates. Converts leukotriene D4 to leukotriene E4; it may play an important role in the regulation of leukotriene activity
Gene Name:: DPEP1
Uniprot ID:: P16444
Molecular weight:: 45673.5

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Farrell CA, Allegretto NJ, Hitchcock MJ: Cilastatin-sensitive dehydropeptidase I enzymes from three sources all catalyze carbapenem hydrolysis and conversion of leukotriene D4 to leukotriene E4. Arch Biochem Biophys. 1987 Jul;256(1):253-9. [PubMed:3038022 ]
Kumon H, Nasu Y, Ohmori H, Kodama H, Konishi Y: [Effects of cilastatin sodium, an inhibitor of dehydropeptidase-I, on human urinary peptide excretion. Patients with renal insufficiency]. Jpn J Antibiot. 1987 Sep;40(9):1571-83. [PubMed:3480361 ]
Lin JH, Chen IW, Ulm EH: Dose-dependent kinetics of cilastatin in laboratory animals. Drug Metab Dispos. 1989 Jul-Aug;17(4):426-32. [PubMed:2571484 ]
Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. [PubMed:9573653 ]
Hirota T, Nishikawa Y, Tanaka M, Igarashi T, Kitagawa H: Characterization of dehydropeptidase I in the rat lung. Eur J Biochem. 1986 Nov 3;160(3):521-5. [PubMed:3780719 ]
Hirota T, Nishikawa Y, Komai T, Igarashi T, Kitagawa H: Role of dehydropeptidase-I in the metabolism of glutathione and its conjugates in the rat kidney. Res Commun Chem Pathol Pharmacol. 1987 May;56(2):235-42. [PubMed:3474745 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Keynan S, Hooper NM, Felici A, Amicosante G, Turner AJ: The renal membrane dipeptidase (dehydropeptidase I) inhibitor, cilastatin, inhibits the bacterial metallo-beta-lactamase enzyme CphA. Antimicrob Agents Chemother. 1995 Jul;39(7):1629-31. [PubMed:7492120 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Takeda M, Narikawa S, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of organic anion transport inhibitors using cells stably expressing human organic anion transporters. Eur J Pharmacol. 2001 May 11;419(2-3):113-20. [PubMed:11426832 ]
Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [PubMed:14978359 ]

Enzyme Details

2. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

References

Enomoto A, Takeda M, Shimoda M, Narikawa S, Kobayashi Y, Kobayashi Y, Yamamoto T, Sekine T, Cha SH, Niwa T, Endou H: Interaction of human organic anion transporters 2 and 4 with organic anion transport inhibitors. J Pharmacol Exp Ther. 2002 Jun;301(3):797-802. [PubMed:12023506 ]

Showing metabocard for Cilastatin (HMDB0015535)

MOL for HMDB0015535 (Cilastatin)

3D MOL for HMDB0015535 (Cilastatin)

3D SDF for HMDB0015535 (Cilastatin)

3D-SDF for HMDB0015535 (Cilastatin)

PDB for HMDB0015535 (Cilastatin)

3D PDB for HMDB0015535 (Cilastatin)

SMILES for HMDB0015535 (Cilastatin)

INCHI for HMDB0015535 (Cilastatin)

Structure for HMDB0015535 (Cilastatin)

3D Structure for HMDB0015535 (Cilastatin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

Transporters

References

References