Cycloserine (CED0002890)

Record Information
Version1.0
Creation Date2016-05-22 03:39:24 UTC
Update Date2026-08-22 13:22:33 UTC
Accession NumberCHEM016649
Identification
Common NameCycloserine
ClassSmall Molecule
Description
Cycloserine is an organic compound with the chemical formula C3H6N2O2 and an average molecular weight of 102.09 g/mol. Cycloserine belongs to the isoxazolines, a subclass of azolines within the organic compounds. This substance is categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from three recorded sources: amplifiers within electrical and electronic equipment, and antibiotics used as drugs for the treatment of tuberculosis within healthcare, pharmaceuticals, and veterinary products. Recorded exposure routes for this compound include oral and inhalation. In terms of biological activity, cycloserine acts on three recorded protein targets. It serves as an inhibitor of D-alanine--D-alanine ligase A (ddlA), Alanine racemase (alr), and Glutamate receptor ionotropic, NMDA 1 (GRIN1).
Contaminant TypeNot Available
Chemical Structure
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 Mass102.092 g/mol
Monoisotopic Mass102.043 g/mol
CAS Registry Number68-41-7
IUPAC Name(4R)-4-amino-1,2-oxazolidin-3-one
Traditional Namecycloserine
SMILESN[C@@H]1CONC1=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility71.9 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0uy0-5900000000-06bce0b228f324fe49b4Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0uy0-5900000000-06bce0b228f324fe49b4Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9000000000-0e7a5a8b0f7ce48e4509Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-4900000000-f1c1692f9e6318f52377Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f79-9300000000-45585d9e68724372ca94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-059f-9000000000-bac95a810bc34e20e690Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-5900000000-5babaf58090cc358ab6eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-9300000000-0ff851b2ef4ce71985ffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0596-9000000000-8a39f19e4a34080991d1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udl-9800000000-28ac2fbbebd31cc6100bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9200000000-739f88bc4c62ad6e99a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-90726b17dc36e29c5299Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-940c87bcfe09a2af1fc9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w2c-9400000000-13b86532b272b0b5785dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-a3d694a542f40615fe9eNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2216.0Log mg/kg[1200:3900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
349Drugs for treatment of tuberculosisHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
Pathways
2 pathways
Cycloserine Drug Metabolism
Cycloserine Drug Metabolism
Cycloserine Drug Metabolism Action Pathway
Cycloserine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSerine/threonine-protein phosphatase 2A 65 kDa regulatory subunit A alpha isoformQ76MZ3Mus musculusPredicted (SEA)3.65891
Protein cereblon structureClick to view 3D structureProtein cereblonQ96SW2HumansPredicted (SEA)1376.06
Click to view 3D structureZinc finger protein AiolosQ9UKT9HumansPredicted (SEA)448.1
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)7410.55
Kynurenine--oxoglutarate transaminase 1 structureClick to view 3D structureKynurenine--oxoglutarate transaminase 1Q16773HumansPredicted (SEA)704.535
Ornithine aminotransferase, mitochondrial structureClick to view 3D structureOrnithine aminotransferase, mitochondrialP04181HumansPredicted (SEA)101.438
Tumor necrosis factor structureClick to view 3D structureTumor necrosis factorP01375HumansPredicted (SEA)6714.81
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)7100.24
Amine oxidase [flavin-containing] A structureClick to view 3D structureAmine oxidase [flavin-containing] AP21397HumansPredicted (SEA)7023.63
Click to view 3D structureSerine-threonine protein phosphatase 2A regulatory subunitQ8AWE3Gallus gallusPredicted (SEA)190.497
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)7386.49
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)7726.61
Dipeptidyl peptidase 4 structureClick to view 3D structureDipeptidyl peptidase 4P27487HumansPredicted (SEA)6763.7
Click to view 3D structureAcetyl-CoA carboxylaseQ3V4E6Zea maysPredicted (SEA)490.917
Click to view 3D structureKynurenine/alpha-aminoadipate aminotransferase, mitochondrialQ64602Rattus norvegicusPredicted (SEA)265.544
Click to view 3D structureGlutamate receptor ionotropic, kainate 1P22756Rattus norvegicusPredicted (SEA)1849.54
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)7581.35
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial structureClick to view 3D structureKynurenine/alpha-aminoadipate aminotransferase, mitochondrialQ8N5Z0HumansPredicted (SEA)888.571
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)7628.37
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)7695.63
Interleukin-1 beta structureClick to view 3D structureInterleukin-1 betaP01584HumansPredicted (SEA)2573.7
Click to view 3D structureGlyceraldehyde-3-phosphate dehydrogenase, cytosolicQ01558Leishmania mexicanaPredicted (SEA)770.474
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)7661.45
Click to view 3D structureGlutamate receptor 1P19490Rattus norvegicusPredicted (SEA)1994.96
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)7768.18
Concentrations
Not Available
External Links
DrugBank IDDB00260
HMDB IDHMDB0014405
FooDB IDFDB098104
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-2482
METLIN IDNot Available
PDB ID4AX
Wikipedia LinkCycloserine
Chemspider ID5998
ChEBI ID40009
PubChem Compound ID6234
Kegg Compound IDC08057
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12076471
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17707326
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18316423
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18486041
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18930757
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22234379
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22368237
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22632472
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22892161
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23174090
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23416058
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23438729
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23523746
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23542909
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23656850
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23685206
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=4555420
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=5006234
19. 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.