Cyclacillin (CED0018322)

Record Information

Version

1.0

Creation Date

2016-05-22 03:39:17 UTC

Update Date

2026-08-19 12:23:29 UTC

Accession Number

CHEM016645

Identification

Common Name

Cyclacillin

Class

Small Molecule

Description

Cyclacillin is an organic compound with the chemical formula C15H23N3O4S and an average molecular weight of 341.43 g/mol. Cyclacillin belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified within the superclass of organoheterocyclic compounds. The compound is found in or released from two recorded sources: antennas, which are categorized under electrical and electronic equipment, and antibiotics, which are categorized under healthcare, pharmaceuticals and veterinary products. Recorded routes of exposure for this substance include oral and inhalation. In terms of biological activity, cyclacillin has ten recorded protein targets. It acts as an inhibitor of several proteins, including Penicillin-binding protein 1A (pbpA), Penicillin-binding protein 1A (mrcA), Penicillin binding protein 2a (mecA), and serine-type D-Ala-D-Ala carboxypeptidase (pbp3), along with six other proteins.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1-Aminocyclohexyl)penicillin	ChEBI
(2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
6-(1-Aminocyclohexanecarboxamido)penicillanic acid	ChEBI
6-(1-Aminocyclohexylcarboxamido)penicillanic acid	ChEBI
Bastcillin	ChEBI
Calthor	ChEBI
Ciclacilina	ChEBI
Ciclacillin	ChEBI
Ciclacilline	ChEBI
Ciclacillinum	ChEBI
Citosarin	ChEBI
Cyclapen	ChEBI
Cyclapen-W	ChEBI
Syngacillin	ChEBI
Ultracillin	ChEBI
Vastcillin	ChEBI
Vipicil	ChEBI
Wyvital	ChEBI
ACPC	Kegg
(2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6-(1-Aminocyclohexanecarboxamido)penicillanate	Generator
6-(1-Aminocyclohexylcarboxamido)penicillanate	Generator
Aminocyclohexylpenicillin	HMDB
Ciclacillum	HMDB

Chemical Formula

C₁₅H₂₃N₃O₄S

Average Molecular Mass

341.426 g/mol

Monoisotopic Mass

341.141 g/mol

CAS Registry Number

3485-14-1

IUPAC Name

(2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

cyclacillin

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O

InChI Identifier

InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1

InChI Key

HGBLNBBNRORJKI-WCABBAIRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Penicillins

Alternative Parents

Substituents

Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Cyclohexylamine
Thiazolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Azetidine
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Dialkylthioether
Hemithioaminal
Thioether
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Primary amine
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:31444 )

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	1.9 g/L	ALOGPS
logP	0.56	ALOGPS
logP	-1.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	8.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.73 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.22 m³·mol⁻¹	ChemAxon
Polarizability	34.81 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0002-9110000000-880dc522fc28c1bba7cb	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0002-9000000000-68fd157b54c0f0c04c1a	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03ea-3913000000-e1b225a6069c25031e80	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01pk-6900000000-9015a0229a34616fbc41	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05u5-9100000000-ebbfbef8f7baae6dadba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0911000000-0b9e6a3d9d3b19d46cac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-0930000000-738172cee45fa138ecea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002b-9400000000-e5e5efd7b191cd291cea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0009000000-f94d572cb27dd62c4495	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004l-4529000000-90a2bebebc953a6db79c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a59-7922000000-40fa844297d16d9e505b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0019000000-02832c883fa4bd6dfa39	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0007-9834000000-12493a6db58de235a70b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-8901000000-5c2d54fc89ea21fd80a1	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H 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
6292.0	Log mg/kg	[3500:11000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available

Pathways

2 pathways

Cyclacillin Drug Metabolism Action Pathway

Cyclacillin Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Beta-lactamase ACC-4	A4ZYU9	Escherichia coli	Predicted (SEA)	0.233548
Click to view 3D structure	Beta-lactamase	P00811	Escherichia coli (strain K12)	Predicted (SEA)	3.19182
Click to view 3D structure	Extended-spectrum beta-lactamase PER-6	D5HSX5	Aeromonas allosaccharophila	Predicted (SEA)	0.856341
Click to view 3D structure	ADC-14 protein	Q0VTR6	Acinetobacter genomosp. 3	Predicted (SEA)	0.856341
Click to view 3D structure	Beta-lactamase SHV-11	Q7X575	Escherichia coli	Predicted (SEA)	0.856341
Click to view 3D structure	ADC-16 protein	Q0VTR8	Acinetobacter genomosp. 3	Predicted (SEA)	0.856341
Click to view 3D structure	Efflux transporter	Q3S5C3	Salmonella newport	Predicted (SEA)	0.233548
Click to view 3D structure	Class C beta-lactamase CMY-36	Q48435	Klebsiella pneumoniae	Predicted (SEA)	0.233548
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	277.143
Click to view 3D structure	Beta-lactamase TEM	P62593	Escherichia coli	Predicted (SEA)	1.71268
Click to view 3D structure	Hemagglutinin	P03438	Influenza A virus (strain A/X-31 H3N2)	Predicted (SEA)	1.47914
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	338.099
Click to view 3D structure	Metallo-beta-lactamase type 2	P14488	Bacillus cereus	Predicted (SEA)	1.32344
Click to view 3D structure	PER-2 beta-lactamase	A2RP81	Citrobacter freundii	Predicted (SEA)	0.544945
Click to view 3D structure	Beta-lactamase	P05364	Enterobacter cloacae	Predicted (SEA)	3.19182
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	2450.15
Click to view 3D structure	Beta-lactamase bla(BEL1)	Q3SAW3	Pseudomonas aeruginosa	Predicted (SEA)	1.16774
Click to view 3D structure	Beta-lactamase	A8RR46	Bacillus clausii	Predicted (SEA)	1.16774
Click to view 3D structure	Beta-lactamase	D2SSQ3	Pseudomonas aeruginosa	Predicted (SEA)	1.16774
Click to view 3D structure	Beta-lactamase SCO-1	A1E3K9	Escherichia coli	Predicted (SEA)	1.16774
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	1222.0
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	1077.51
Click to view 3D structure	PenB class A beta-lactamase	B8R6A5	Burkholderia cenocepacia	Predicted (SEA)	1.71268
Click to view 3D structure	Beta-lactamase	P94958	Morganella morganii	Predicted (SEA)	1.71268
Click to view 3D structure	Carbapenem-hydrolizing beta-lactamase SFC-1	Q6JP75	Serratia fonticola	Predicted (SEA)	1.71268