NP-MRD: Showing NP-Card for (2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid (NP0186909)

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Record Information

Version

2.0

Created at

2022-09-04 02:54:27 UTC

Updated at

2022-09-04 02:54:28 UTC

NP-MRD ID

NP0186909

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid

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. (2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid is found in Apis cerana. (2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid was first documented in 1987 (PMID: 3495664). 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 (PMID: 7492120).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 50  0  0  0  0  0  0  0  0999 V2000
   -5.0672    2.8791   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7884    1.5201    0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1538    1.5576    1.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8067    0.4771   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3550    0.3946   -0.7015 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5495   -0.7113   -0.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6421   -0.9810    1.1001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6630   -1.4904   -0.9162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951   -2.5462   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5736   -2.4623   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1130   -1.3235   -1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9681   -0.6477   -0.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7378    0.5278   -0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7214    0.1449   -1.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9232   -1.0382   -1.1165 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0633   -0.5370    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1671    0.3956   -0.2161 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9314    0.6274    1.0513 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8327    1.7043   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506    1.8843   -1.9323 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8097    2.8247    0.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5243   -3.6928    0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7702   -3.7460    0.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7680   -4.7018    0.8136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2406    3.2573   -1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2447    3.5935    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9844    2.8960   -1.0461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7419    0.9754    2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1495    2.5977    1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858    1.2449    1.5210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5865    0.7161   -0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0680   -0.2464    0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2567    0.6127   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5533   -1.3049   -1.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0069   -3.2777   -0.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694   -0.6001   -1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7990   -1.7615   -1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3172   -0.2906    0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -1.3568    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3045    1.0047    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0253    1.2464   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1150    1.0689   -2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0734   -0.3053   -2.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5435   -1.4824    0.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025   -0.1342    1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9365   -0.1006   -0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2398    0.8924    1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5718    1.4207    0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0100    2.7884    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9191   -4.5144    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  9 22  1  0
 22 23  2  0
 22 24  1  0
 17 19  1  0
 19 20  2  0
 19 21  1  0
  2  5  1  0
 18 47  1  0
 18 48  1  0
 17 46  1  6
 16 44  1  0
 16 45  1  0
 14 42  1  0
 14 43  1  0
 13 40  1  0
 13 41  1  0
 12 38  1  0
 12 39  1  0
 11 36  1  0
 11 37  1  0
 10 35  1  0
  8 34  1  0
  5 33  1  6
  4 31  1  0
  4 32  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
 24 50  1  0
 21 49  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>
NP0186909

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

358.4530 Da

Monoisotopic Mass

358.15624 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0015535

DrugBank ID

DB01597

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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. doi: 10.1128/AAC.39.7.1629. [PubMed:7492120 ]
Graham DW, Ashton WT, Barash L, Brown JE, Brown RD, Canning LF, Chen A, Springer JP, Rogers EF: Inhibition of the mammalian beta-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-(acylamino)-3-substituted-propenoic acids. J Med Chem. 1987 Jun;30(6):1074-90. doi: 10.1021/jm00389a018. [PubMed:3495664 ]
LOTUS database [Link]

Showing NP-Card for (2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid (NP0186909)

MOL for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)

3D MOL for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)

3D SDF for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)

3D-SDF for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)

PDB for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)

3D PDB for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)

SMILES for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)

INCHI for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)

Structure for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)

3D Structure for NP0186909 ((2z)-7-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}-2-({[(1s)-2,2-dimethylcyclopropyl](hydroxy)methylidene}amino)hept-2-enoic acid)