ChemFOnt: Showing chemical card for 3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (CFc000227220)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:52:06 UTC

Chemfont ID

CFc000227220

Molecule Identification

Common Name

3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Definition

3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain. Based on a literature review very few articles have been published on 3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulphanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	Generator
3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulphanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid	Generator
3-{[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	HMDB
3-{[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulphanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	HMDB
3-{[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulphanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid	HMDB

Chemical Formula

C₁₇H₂₅N₃O₅S

Average Molecular Weight

383.46

Monoisotopic Molecular Weight

383.151492091

IUPAC Name

3-{[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Traditional Name

3-{[5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(O)C1C2C(C)C(SC3CNC(C3)C(=O)N(C)C)=C(N2C1=O)C(O)=O

InChI Identifier

InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)

InChI Key

DMJNNHOOLUXYBV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Thienamycins

Alternative Parents

Substituents

Thienamycin
Proline or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Azepine
Vinylogous thioester
Pyrrolidine
Pyrroline
Tertiary carboxylic acid amide
Amino acid or derivatives
Azetidine
Carboxamide group
Amino acid
Thioenolether
Secondary alcohol
Secondary amine
Sulfenyl compound
Azacycle
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Amine
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organic oxide
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.63 g/L	ALOGPS
logP	-0.69	ALOGPS
logP	-4.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.18 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.89 m³·mol⁻¹	ChemAxon
Polarizability	39.43 Å³	ChemAxon
Number of Rings	3	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

HMDB0247684

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3099076

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3874387

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (CFc000227220)

MOL for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D MOL for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D SDF for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D-SDF for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

PDB for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D PDB for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

SMILES for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

INCHI for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

Structure for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D Structure for CFc000227220 (3-[5-(Dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)