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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2018-05-20 20:49:01 UTC
HMDB IDHMDB0014405
Secondary Accession Numbers
  • HMDB14405
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
a-CycloserineGenerator
α-cycloserineGenerator
D-CSHMDB
D-CycloserineHMDB
D-Cycloserine synth. BP 88HMDB
D-Cycloserine, syntheticHMDB
D-OxamicinaHMDB
D-OxamycinHMDB
DL-CycloserineHMDB
L-CycloserineHMDB
R-4-amino-3-IsoxazolidinoneMeSH
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 KeyDYDCUQKUCUHJBH-UWTATZPHSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as isoxazolines. These are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolines
Sub ClassIsoxazolines
Direct ParentIsoxazolines
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility877 g/LNot Available
LogP-0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility877 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.85 m³·mol⁻¹ChemAxon
Polarizability8.87 ųChemAxon
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
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uy0-5900000000-06bce0b228f324fe49b4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-0e7a5a8b0f7ce48e4509View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-4900000000-f1c1692f9e6318f52377View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-9300000000-45585d9e68724372ca94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9000000000-bac95a810bc34e20e690View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-5babaf58090cc358ab6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6x-9300000000-0ff851b2ef4ce71985ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9000000000-8a39f19e4a34080991d1View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00260 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00260 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00260
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5998
KEGG Compound IDC08057
BioCyc IDCPD-2482
BiGG IDNot Available
Wikipedia LinkCycloserine
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. [PubMed:13885421 ]