Livestock Metabolome Database: Showing metabocard for Cycloserine (LMDB00645)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:54:32 UTC

Update Date

2016-07-20 21:02:22 UTC

Lmdb

LMDB00645

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cycloserine

Description

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

N[C@@H]1CONC1=O

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0uy0-5900000000-06bce0b228f324fe49b4	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0uy0-5900000000-06bce0b228f324fe49b4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-0e7a5a8b0f7ce48e4509	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-4900000000-f1c1692f9e6318f52377	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-9300000000-45585d9e68724372ca94	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-9000000000-bac95a810bc34e20e690	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-5babaf58090cc358ab6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6x-9300000000-0ff851b2ef4ce71985ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9000000000-8a39f19e4a34080991d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udl-9800000000-28ac2fbbebd31cc6100b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9200000000-739f88bc4c62ad6e99a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-940c87bcfe09a2af1fc9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w2c-9400000000-13b86532b272b0b5785d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a3d694a542f40615fe9e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum