Showing metabocard for Cycloserine (BMDB0062042)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-06-25 21:46:12 UTC
Update Date2020-04-22 15:51:12 UTC
BMDB IDBMDB0062042
Secondary Accession Numbers
  • BMDB62042
Metabolite Identification
Common NameCycloserine
DescriptionCycloserine, also known as alpha-cycloserine or seromycin, 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. Thus, cycloserine is considered to be a non-ribosomal peptide/polyketide hybrid lipid molecule. Cycloserine is a drug which is used in combination with up to 5 other drugs as a treatment for mycobacterium avium complex (mac) and is also used to treat tuberculosis (tb). Cycloserine exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule.
Structure
Thumb
MOLSDFPDBSMILESInChI
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-CycloserineKegg
ABBR DCSKegg
a-CycloserineGenerator
Α-cycloserineGenerator
D-CSHMDB
D-Cycloserine synth. BP 88HMDB
D-Cycloserine, syntheticHMDB
D-OxamicinaHMDB
D-OxamycinHMDB
DL-CycloserineHMDB
L-CycloserineHMDB
R-4-Amino-3-isoxazolidinoneHMDB
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
[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 KeyDYDCUQKUCUHJBH-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.
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
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.3ALOGPS
logP-2.4ChemAxon
logS-0.15ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0014405
DrugBank IDDB00260
Phenol Explorer Compound IDNot Available
FooDB IDFDB098104
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)Not Available
General References
  1. Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. [PubMed:25599412 ]