Cilastatin (CED0003616)

Record Information

Version

1.0

Creation Date

2016-05-25 18:27:59 UTC

Update Date

2026-08-19 17:29:11 UTC

Accession Number

CHEM022317

Identification

Common Name

Cilastatin

Class

Small Molecule

Description

Cilastatin is an organic compound with the formula C16H26N2O5S and an average molecular weight of 358.45 g/mol. Cilastatin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. In terms of biological activity, it acts as an inhibitor of the protein target Dipeptidase 1 (DPEP1). The compound has been found in or released from three recorded sources: household cleaning and consumer products (other smoking requisites), electrical and electronic equipment (video games), and healthcare, pharmaceuticals and veterinary products (beta-lactam antibacterials). Recorded routes of exposure for this substance include intravenous and intramuscular administration.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

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 Mass

358.453 g/mol

Monoisotopic Mass

358.156 g/mol

CAS Registry Number

82009-34-5

IUPAC Name

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

Traditional Name

cilastatin

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0007-9143000000-9267c830716476e05220	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-000j-9634300000-05e8bb2de2e0d6d642d3	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-ef2198c6225f95e6b765	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0092000000-f0483d6314128c99a866	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03fr-0089000000-e23865517b151264287c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-f94440db25517ee87789	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0193000000-9c52bb64f789ddf44d03	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01t9-0890000000-a16bc40171fdaad5d00f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01q9-0900000000-7f6fb4bc2c8d8b74669a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-f7395a558e6db43df825	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-65b5dae5f837cb16f232	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0093000000-f41454497f85c6c231e3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0890000000-2d4e1ce343461b9c33ff	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-f7395a558e6db43df825	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03fr-0079000000-f5a7ea868a31218529fb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-afc7a1706de335756516	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0uxr-0292000000-fc9fdc71c26de516aa47	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f89-0980000000-c7e9f3733dc9d5876f69	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f89-0940000000-5e461031ed3e8be30dce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udl-0197000000-ed9524572e0f6a20cf73	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-92adcd25c03169bce114	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9350000000-49e92e77b9da299b75c9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9100000000-93ce7c9a2d2ddb232af8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9100000000-a5fb73965dbd68cad5ca	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9000000000-314ddc83e7521820bbfc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9000000000-f4a4b127adc8552d8fff	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-ee64e7f7019c68d1b37c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9340000000-52a3fa17dbbe9e3a1655	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9100000000-455b80c43f8c12b3f0fc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9000000000-07045a080f03625d01af	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9000000000-8832abb1f60cae723d4a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00kb-9000000000-92b4d4d580bdc8669cd2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udl-0197000000-a5c912d56f6b1064113a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9100000000-6ba5521073c9de6e4bc3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9350000000-2683f9cc9dac75aeff4b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9100000000-5df1c972ffa12fb7216e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9000000000-2f2737fc28cb7482d10f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-4d5d15af9e3d436b910b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9340000000-b6b2d94e8bd520aac847	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-33affe65d35444af3629	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udl-0197000000-84a933499d987d8cab6b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9000000000-8832abb1f60cae723d4a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udl-0197000000-2ef082780971e803ac08	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-65b5dae5f837cb16f232	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-ef2198c6225f95e6b765	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0093000000-f41454497f85c6c231e3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0890000000-2d4e1ce343461b9c33ff	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0092000000-f0483d6314128c99a866	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-f7395a558e6db43df825	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01q9-0900000000-7f6fb4bc2c8d8b74669a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0193000000-9c52bb64f789ddf44d03	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01t9-0890000000-a16bc40171fdaad5d00f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f89-0980000000-c7e9f3733dc9d5876f69	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f89-0940000000-5e461031ed3e8be30dce	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0uxr-0292000000-fc9fdc71c26de516aa47	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-7a4bff045c2ceb8b75cc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9340000000-b0a37cd4fc61753eec56	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-c0c931dd58088136fa33	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fsi-0590000000-3703f2249ce3f6de5d50	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03fr-0079000000-af605e35a007f910c27a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-1000-0291000000-0b81f338edebc27dded5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03fr-0089000000-4cdea72946b910c0a75a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-056r-0069000000-21d76b98ff02ff1c25f0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0gb9-0292000000-abbc44cf333f2d303c8b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-98f6cd6b4943d95ad410	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9000000000-10951e2f4494aaf9e7b3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-9100000000-dec0b61abba30acb7e7e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0092000000-6f33a7a60f5f8589db45	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-08g3-3149000000-1697f40afdac95d9f1fb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ds-9262000000-2d286749c8bad80aca6c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9120000000-103a1c4913411a99597e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ab9-2359000000-4af9c04e6559117f7de8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-4493000000-902790a448dc5b5275ab	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-9210000000-68ca7d233d4d1846c27c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05n3-9385000000-bed05d9c78079ca425d6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00xs-9452000000-ac42f16b6392a8867405	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-06di-9100000000-206c1be30e979699df68	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0039000000-81e5b83aaf59d12c9457	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-2950000000-2712955c6d9732b0cca2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-8960000000-b238bc7372b10a93937b	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
4197.0	Log mg/kg	[2400:7500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
341	Beta-lactam antibacterials	Healthcare, pharmaceuticals & veterinary products	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available

Pathways

1 pathway

Cilastatin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Dipeptidase 1	P22412	Sus scrofa	Predicted (SEA)	1.01204
Click to view 3D structure	Betaine--homocysteine S-methyltransferase 1	Q93088	Humans	Predicted (SEA)	2.72472
Click to view 3D structure	S-ribosylhomocysteine lyase	P45578	Escherichia coli K-12	Predicted (SEA)	1.79053
Click to view 3D structure	S-ribosylhomocysteine lyase	Q9Z5X1	Vibrio campbellii	Predicted (SEA)	1.79053
Click to view 3D structure	Carboxypeptidase M	P14384	Humans	Predicted (SEA)	0.544945
Click to view 3D structure	S-methylmethionine--homocysteine S-methyltransferase BHMT2	Q9H2M3	Humans	Predicted (SEA)	3.89246
Click to view 3D structure	Aspartate-semialdehyde dehydrogenase	O25801	Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)	Predicted (SEA)	3.97031
Click to view 3D structure	S-ribosylhomocysteine lyase	O34667	Bacillus subtilis (strain 168)	Predicted (SEA)	2.10193
Click to view 3D structure	CD81 antigen	P60033	Humans	Predicted (SEA)	1.32344
Click to view 3D structure	Arginase-2, mitochondrial	P78540	Humans	Predicted (SEA)	6.69503
Click to view 3D structure	Arginase-1	P05089	Humans	Predicted (SEA)	5.83869
Click to view 3D structure	Glutamate receptor ionotropic, kainate 1	P39086	Humans	Predicted (SEA)	21.6421
Click to view 3D structure	Asc-type amino acid transporter 1	P63116	Rat	Predicted (SEA)	10.1982
Click to view 3D structure	Glutamate receptor 4	P48058	Humans	Predicted (SEA)	21.4085
Click to view 3D structure	Glutamate receptor ionotropic, kainate 1	P22756	Rattus norvegicus	Predicted (SEA)	99.3356
Click to view 3D structure	Glutamate receptor 1	P42261	Humans	Predicted (SEA)	81.586
Click to view 3D structure	Metabotropic glutamate receptor 2	P31421	Rattus norvegicus	Predicted (SEA)	693.948
Click to view 3D structure	Glutamate receptor ionotropic, kainate 5	Q16478	Humans	Predicted (SEA)	18.3724
Click to view 3D structure	Arginase	Q8I384	Plasmodium falciparum	Predicted (SEA)	10.5875
Click to view 3D structure	Glutamate receptor 2	P42262	Humans	Predicted (SEA)	62.2015
Click to view 3D structure	Metabotropic glutamate receptor 6	P35349	Rattus norvegicus	Predicted (SEA)	119.576
Click to view 3D structure	Glutamate receptor 1	P19490	Rattus norvegicus	Predicted (SEA)	276.053
Click to view 3D structure	Metabotropic glutamate receptor 2	Q14416	Humans	Predicted (SEA)	1273.92
Click to view 3D structure	Excitatory amino acid transporter 3	P43005	Humans	Predicted (SEA)	237.596
Click to view 3D structure	Glutamate receptor ionotropic, kainate 3	P42264	Rattus norvegicus	Predicted (SEA)	76.0587