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68-39-3 molecular structure
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4-amino-1,2-oxazolidin-3-one

ChemBase ID: 145
Molecular Formular: C3H6N2O2
Molecular Mass: 102.09194
Monoisotopic Mass: 102.04292744
SMILES and InChIs

SMILES:
O1NC(=O)C(N)C1
Canonical SMILES:
NC1CONC1=O
InChI:
InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)
InChIKey:
DYDCUQKUCUHJBH-UHFFFAOYSA-N

Cite this record

CBID:145 http://www.chembase.cn/molecule-145.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-amino-1,2-oxazolidin-3-one
IUPAC Traditional name
(+-)-4-amino-3-isoxazolidinone
DL-cycloserine
Brand Name
Closerin
Closina
Cyclomycin
Cyclorin
Cycloserin
Farmiserina
Farmiserine
Micoserina
Miroserina
Miroseryn
Novoserin
Orientomycin
Oxamicina
Oxamycin
Oxymycin
Seromycin
Tebemicina
Tisomycin
Wasserina
Synonyms
alpha-Cycloserine
Cicloserina
D-CS
D-Cycloserine
D-Cycloserine synth. BP 88
D-Cycloserine, synthetic
D-Oxamicina
D-Oxamycin
DL-Cycloserine
L-Cycloserine
Cycloserine
4-Amino-3-isoxazolidone
DL-Cycloserine
4-Amino-3-isoxazolidinone
(+/-)-3-Oxoisooxazolidin-4-amine
rac Cycloserine
D-Cycloserine
4-Aminoisoxazolidin-3-one
(R)-(+)-4-Amino-3-isoxazolidinone
4-amino-1,2-oxazolidin-3-one
D-Cycloserine
4-氨基-3-异噁唑烷酮
DL-环丝氨酸
D-环丝氨酸
CAS Number
68-39-3
68-41-7
EC Number
200-687-9
200-688-4
MDL Number
MFCD00005353
MFCD00064323
Beilstein Number
80798
Merck Index
142751
PubChem SID
24278332
160963608
PubChem CID
401

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.210087  H Acceptors
H Donor LogD (pH = 5.5) -2.4357781 
LogD (pH = 7.4) -2.4206417  Log P -2.4213324 
Molar Refractivity 21.8488 cm3 Polarizability 9.062646 Å3
Polar Surface Area 64.35 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -2.31  LOG S 0.93 
Solubility (Water) 8.77e+02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Soluble expand Show data source
Soluble in water. Slightly soluble in methanol, propylene glycol. expand Show data source
Water expand Show data source
Apperance
crystalline expand Show data source
Off-White Solid expand Show data source
Melting Point
>183°C (dec.) expand Show data source
137°C dec. expand Show data source
Optical Rotation
+115 (c=2 in water) expand Show data source
Hydrophobicity(logP)
-0.9 expand Show data source
-1.192 expand Show data source
Storage Condition
Refrigerator expand Show data source
Storage Warning
Air Sensitive expand Show data source
RTECS
NY2974900 expand Show data source
NY2975000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... GPT(2875), GPT2(84706) expand Show data source
Purity
95% expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
98+% expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C3H6N2O2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC Sigma Aldrich Sigma Aldrich
DrugBank - DB00260 external link
Item Information
Drug Groups approved
Description Antibiotic substance produced by Streptomyces garyphalus. [PubChem]
Indication 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).
Pharmacology Cycloserine, a broad-spectrum antibiotic, may be bactericidal or bacteriostatic, depending on its concentration at the site of infection and the susceptibility of the organism. Cycloserine works by blocking the formation of these peptidoglycans. By doing this the walls of the bacteria become weak and it results in the death of the bacteria
Toxicity Oral LD50 in mouse is 5290 mg/kg, and in rat is over 5000 mg/kg. Symptoms of a cycloserine overdose include drowsiness, confusion, headache, dizziness, irritability, numbness and tingling, difficulty speaking, paralysis, abnormal behavior, seizures, and unconsciousness.
Affected Organisms
Enteric bacteria and other eubacteria
Absorption Rapidly and almost completely absorbed (70 to 90%) from the gastrointestinal tract following oral administration.
Half Life Half-life in patients with normal renal function is 10 hours, and is prolonged in patients with impaired renal function.
External Links
Wikipedia
Drugs.com
Toronto Research Chemicals - C988800 external link
Antibacterial (tuberculostatic).
Sigma Aldrich - C7005 external link
Biochem/physiol Actions
Inhibitor of alanine aminotransferase and other pyridoxal-phosphate-requiring transaminases1; blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase.
Sigma Aldrich - 862002 external link
Biochem/physiol Actions
Inhibitor of alanine aminotransferase and other pyridoxal-phosphate-requiring transaminases1; blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Lamb., J.W., et al.: Anal. Profiles Drug Subs., 1, 53 (1972)
  • • Gentry-Weeks, C., et al.: J. Biol. Chem., 268, 7298 (1972)
  • • Alexander, F., et al.: Eur. J. Biochem., 219, 953 (1972)
  • • Auger, S., et al.: Biochimie, 87, 231 (1972)
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PATENTS

PATENTS

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INTERNET

INTERNET

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