ChemFOnt: Showing chemical card for Cycloserine (CFc000008796)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:43 UTC

Chemfont ID

CFc000008796

Molecule Identification

Common Name

Cycloserine

Definition

Cycloserine is only found in individuals that have used or taken this drug. It is an antibiotic substance produced by Streptomyces garyphalus. [PubChem]Cycloserine is an analog of the amino acid D-alanine. It interferes with an early step in bacterial cell wall synthesis in the cytoplasm by competitive inhibition of two enzymes, L-alanine racemase, which forms D-alanine from L-alanine, and D-alanylalanine synthetase, which incorporates D-alanine into the pentapeptide necessary for peptidoglycan formation and bacterial cell wall synthesis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-4-Amino-3-isoxazolidinone	ChEBI
(+)-Cycloserine	ChEBI
(R)-4-AMINO-isoxazolidin-3-one	ChEBI
alpha-Cycloserine	ChEBI
Cicloserina	ChEBI
Cyclo-D-serine	ChEBI
Cycloserinum	ChEBI
D-(+)-Cycloserine	ChEBI
D-4-Amino-3-isoxazolidinone	ChEBI
D-4-Amino-3-isoxazolidone	ChEBI
DCS	ChEBI
Orientomycin	ChEBI
PA 94	ChEBI
PA-94	ChEBI
Ro-1-9213	ChEBI
Seromycin	ChEBI
D-Cycloserine	Kegg
ABBR DCS	Kegg
a-Cycloserine	Generator
Α-cycloserine	Generator
D-CS	HMDB
D-Cycloserine synth. BP 88	HMDB
D-Cycloserine, synthetic	HMDB
D-Oxamicina	HMDB
D-Oxamycin	HMDB
DL-Cycloserine	HMDB
L-Cycloserine	HMDB
R-4-Amino-3-isoxazolidinone	HMDB

Chemical Formula

C₃H₆N₂O₂

Average Molecular Weight

102.0919

Monoisotopic Molecular Weight

102.042927446

IUPAC Name

(4R)-4-amino-1,2-oxazolidin-3-one

Traditional Name

cycloserine

CAS Registry Number

68-41-7

SMILES

[H][C@@]1(N)CON=C1O

InChI Identifier

InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

InChI Key

DYDCUQKUCUHJBH-UWTATZPHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoxazolines. Isoxazolines are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolines

Sub Class

Isoxazolines

Direct Parent

Isoxazolines

Alternative Parents

Substituents

Isoxazoline
Oxacycle
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organooxygen heterocyclic antibiotic (CHEBI:40009 )
organonitrogen heterocyclic antibiotic (CHEBI:40009 )
4-amino-1,2-oxazolidin-3-one (CHEBI:40009 )
Non-ribosomal peptide/polyketide hybrids (C08057 )
Non-ribosomal peptide/polyketide hybrids (LMPK14000007 )

Functional Ontology

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	71.9 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.4	ChemAxon
logS	-0.15	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.35 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	21.85 m³·mol⁻¹	ChemAxon
Polarizability	8.87 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