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D-Cycloserine for biochemistry

CAT: 1288-2377GR100Size: 100 gDry Ice: NoHazardous: No
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CAS Number
68-41-7

Chemical Information

Cycloserine

D-cycloserine is a 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanineD-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis). It has a role as a metabolite, an antitubercular agent, an antimetabolite, an antiinfective agent and a NMDA receptor agonist. It is a 4-amino-1,2-oxazolidin-3-one, an organonitrogen heterocyclic antibiotic and an organooxygen heterocyclic antibiotic. It is a conjugate base of a D-cycloserine(1+). It is an enantiomer of a L-cycloserine. It is a tautomer of a D-cycloserine zwitterion.

CAS Number68-41-7
PubChem CID6234
IUPAC Name(4R)-4-amino-1,2-oxazolidin-3-one
Molecular FormulaC3H6N2O2
Molecular Weight102.09
XLogP-1.5
Topological Polar Surface Area64.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Heavy Atom Count7
Formal Charge0
Complexity92
SMILES
C1[C@H](C(=O)NO1)N
InChI
InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
InChIKey
DYDCUQKUCUHJBH-UWTATZPHSA-N
Chemical Structure
2D Structure
2D structure of Cycloserine
CAS: 68-41-7
CID: 6234
Formula: C3H6N2O2
MW: 102.09
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight102.09
XLogP3-1.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass102.042927438
Monoisotopic Mass102.042927438
Topological Polar Surface Area64.4 Ų
Heavy Atom Count7
Formal Charge0
Complexity92.9
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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