ChemFOnt: Showing chemical card for 7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid (CFc000227319)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:52:17 UTC

Chemfont ID

CFc000227319

Molecule Identification

Common Name

7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid

Definition

7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid, also known as cilastatin or salt, cilastatin monosodium, 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. Based on a literature review very few articles have been published on 7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoate	Generator
Cilastatin	HMDB
Cilastatin monosodium salt	HMDB
Cilastatin sodium	HMDB
Monosodium salt, cilastatin	HMDB
Salt, cilastatin monosodium	HMDB
Sodium, cilastatin	HMDB

Chemical Formula

C₁₆H₂₆N₂O₅S

Average Molecular Weight

358.45

Monoisotopic Molecular Weight

358.156243119

IUPAC Name

7-[(2-amino-2-carboxyethyl)sulfanyl]-2-[(2,2-dimethylcyclopropyl)formamido]hept-2-enoic acid

Traditional Name

7-[(2-amino-2-carboxyethyl)sulfanyl]-2-[(2,2-dimethylcyclopropyl)formamido]hept-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CC1C(=O)NC(=CCCCCSCC(N)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)

InChI Key

DHSUYTOATWAVLW-UHFFFAOYSA-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
Cysteine or derivatives
Alpha-amino acid
Medium-chain fatty acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acid
Fatty acyl
Amino acid
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Carboximidic acid
Carboximidic acid derivative
Thioether
Carboxylic acid
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Primary aliphatic amine
Primary amine
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Amine
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

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	38.6 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

HMDB0247784

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

94653

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104867

PDB ID

Not Available

ChEBI ID

91950

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid (CFc000227319)

MOL for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)

3D MOL for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)

3D SDF for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)

3D-SDF for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)

PDB for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)

3D PDB for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)

SMILES for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)

INCHI for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)

Structure for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)

3D Structure for CFc000227319 (7-[[(2R)-2-Amino-2-carboxyethyl]thio]-2-[[[(1S)-2,2-dimethylcyclopropyl]-oxomethyl]amino]-2-heptenoic acid)