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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:25 UTC
HMDB IDHMDB14405
Secondary Accession NumbersNone
Metabolite Identification
Common NameCycloserine
DescriptionCycloserine 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
Thumb
Synonyms
ValueSource
(+)-4-amino-3-IsoxazolidinoneChEBI
(+)-CycloserineChEBI
(R)-4-amino-ISOXAZOLIDIN-3-oneChEBI
alpha-CycloserineChEBI
CicloserinaChEBI
cyclo-D-SerineChEBI
CycloserinumChEBI
D-(+)-CycloserineChEBI
D-4-amino-3-IsoxazolidinoneChEBI
D-4-amino-3-IsoxazolidoneChEBI
DCSChEBI
OrientomycinChEBI
PA 94ChEBI
PA-94ChEBI
ro-1-9213ChEBI
SeromycinChEBI
D-CSHMDB
D-CycloserineHMDB
D-Cycloserine synth. BP 88HMDB
D-Cycloserine, syntheticHMDB
D-OxamicinaHMDB
D-OxamycinHMDB
DL-CycloserineHMDB
L-CycloserineHMDB
Chemical FormulaC3H6N2O2
Average Molecular Weight102.0919
Monoisotopic Molecular Weight102.042927446
IUPAC Name(4R)-4-amino-1,2-oxazolidin-3-one
Traditional Namecycloserine
CAS Registry Number68-41-7
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 KeyInChIKey=DYDCUQKUCUHJBH-UWTATZPHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Oxazolidinone
  • Isoxazolidine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents, Urinary
  • Antibiotics
  • Antibiotics, Antitubercular
  • Antimetabolites
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.77e+02 g/LNot Available
LogP-0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility877.0 mg/mLALOGPS
logP-2.3ALOGPS
logP-2.4ChemAxon
logS0.93ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.35 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.85 m3·mol-1ChemAxon
Polarizability8.87 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0uy0-5900000000-06bce0b228f324fe49b4View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00260
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00260
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00260
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5998
KEGG Compound IDC08057
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCycloserine
NuGOwiki LinkHMDB14405
Metagene LinkHMDB14405
METLIN IDNot Available
PubChem Compound6234
PDB ID4AX
ChEBI ID40009
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
References
  1. DENGLER HJ, RAUCHS E, RUMMEL W: [On the inhibition of L-glutamic acid and L-DOPA decarboxylase by D-cycloserine and other isoxazolidones]. Naunyn Schmiedebergs Arch Exp Pathol Pharmakol. 1962;243:366-81. [13885421 ]