D-Cycloserine

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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 Number	68-41-7
PubChem CID	6234
IUPAC Name	(4R)-4-amino-1,2-oxazolidin-3-one
Molecular Formula	C3H6N2O2
Molecular Weight	102.09
XLogP	-1.5
Topological Polar Surface Area	64.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Heavy Atom Count	7
Formal Charge	0
Complexity	92

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

CAS: 68-41-7

CID: 6234

Formula: C3H6N2O2

MW: 102.09

Interactive 3D Structure

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Computed Properties

Property	Value
Molecular Weight	102.09
XLogP3	-1.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Exact Mass	102.042927438
Monoisotopic Mass	102.042927438
Topological Polar Surface Area	64.4 Å²
Heavy Atom Count	7
Formal Charge	0
Complexity	92.9
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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Alternative Products

Catalog	Name
F-1480.0025	D-Cycloserine
abx282593-01	D (+) -Cycloserine

D-Cycloserine

Chemical Information

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