ChemFOnt: Showing chemical card for Cyclacillin (CFc000009432)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:34 UTC

Chemfont ID

CFc000009432

Molecule Identification

Common Name

Cyclacillin

Definition

Cyclacillin is only found in individuals that have used or taken this drug. It is a cyclohexylamido analog of penicillanic acid. [PubChem]The bactericidal activity of cyclacillin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cyclacillin is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases.

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 Weight

341.426

Monoisotopic Molecular Weight

341.140926929

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

CAS Registry Number

3485-14-1

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015135)
Membrane (HMDB: HMDB0015135)

Source

Exogenous

Exogenous (HMDB: HMDB0015135)

Process

Not Available

Role

Not Available

Physical Properties

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