Compound: D-cycloserine
SMILES: O=C1NOC[C@H]1N
InChIKey: DYDCUQKUCUHJBH-UWTATZPHSA-N
Synonyms: D-cycloserine, cycloserine, 68-41-7, Seromycin, orientomycin, Oxamycin, Cyclo-D-serine, Cicloserina, Cyclorin, Farmiserina, Tisomycin, Wasserina, Miroseryn, Closina, D-4-amino-3-isoxazolidinone, Cycloserinum, Novoserin, (4R)-4-amino-1,2-oxazolidin-3-one, (+)-4-Amino-3-isoxazolidinone, alpha-Cycloserine, D-4-amino-3-isoxazolidone, (+)-Cycloserine, (4R)-4-aminoisoxazolidin-3-one, PA 94, PA-94, D-(+)-Cycloserine, RO-1-9213, 3-Isoxazolidinone, 4-amino-, (R)-, 3-Isoxazolidinone, 4-amino-, d-, 3-Isoxazolidinone, 4-amino-, (+)-, 95IK5KI84Z, DTXSID8022870, CHEBI:40009, NSC-76029, NSC-154851, DTXCID902870, NSC154851, R-4-Amino-3-isoxazolidinone, RefChem:56415, J04AB01, (4R)-4-azaniumyl-4,5-dihydro-1,2-oxazol-3-olate, 200-688-4, (R)-4-AMINOISOXAZOLIDIN-3-ONE, Miroserina, Tebemicina, Oxamicina, 3-Isoxazolidinone, 4-amino-, (4R)-, Cycloserin, Micoserina, E-733-A, (R)-4-AMINO-ISOXAZOLIDIN-3-ONE, D-Oxamycin, D-CS, D-4-Amino-3-isossazolidone, MFCD00005353, K-300, I-1431, HSDB 3218, D-Oxamicina, NSC 154851, (R)-4-Amino-3-isoxazolidone, AI3-50153, C3H6N2O2, D-Cycloserine, synthetic, D-Cycloserine (Standard), DCS, CHEMBL771, SC-49088, CAS-68-41-7, NCGC00016306-01, Oxamicina [Italian], Cicloserina [Italian], M01471, Cycloserinum [INN-Latin], Cicloserina [INN-Spanish], Cycloserine, D-, Orientmycin, Closerin, (R)-(+)-Cycloserine, .alpha.-Cycloserine, (R)-Cycloserine, Seromycin (TN), SMR000058313, D-4-Amino-3-isossazolidone [Italian], R-(+)-Cycloserine, (R)-4-Amino-3-isoxazolidinone, (4R)-4-Amino-3-isoxazolidinone, CYCLOSERINE (D), SR-01000075432, DRG-0195, EINECS 200-688-4, D-amino-3-isoxazolidinone, BRN 0080798, UNII-95IK5KI84Z, Orientomycin;, Cyclomycin;, Farmiserina;, Micoserina;, Seromycin;, Cycloserine RS, Oxamycin;, Oxymycin;, Closina;, cycloserine-(d), Serine, cyclo-, 3-Isoxazolidinone, 4-amino-, D, R(+)-4-Amino-3-isoxazolidinone, Cycloserine [USP:INN:BAN:JAN], NJ-21, 4AX, 3-Isoxazolidinone, 4-amino-, (R), (R)-(+)-4-Amino-3-isoxazolidinone, Antibiotic 5915;, Antibiotic 8217;, Cycloserine, D(+), Antibiotic NJ 21;, Antibiotic PA 94;, D-Cycloserine, powder, Antibiotic K 300;, Spectrum_000860, 1pb9, Antibiotic 106-7;, Antibiotic 17452;, Antibiotic E 733A;, Antibiotic I 1431;, CYCLOSERINE [MI], Prestwick0_001089, Prestwick1_001089, Prestwick2_001089, Prestwick3_001089, Spectrum2_000084, Spectrum3_000371, Spectrum4_000305, Spectrum5_000797, CYCLOSERINE [INN], CYCLOSERINE [JAN], Lopac-C-1159, Lopac-C-3909, Lopac-C-7005, CYCLOSERINE [HSDB], 3-Isoxazolidinone, 4-amino-, (4R)- (9CI), C 3909, CYCLOSERINE [VANDF], Antibiotic Ro 1-9213;, CYCLOSERINE [MART.], Lopac0_000252, SCHEMBL34322, BSPBio_001138, BSPBio_002121, CYCLOSERINE [WHO-DD], CYCLOSERINE [WHO-IP], KBioGR_000890, KBioSS_001340, 4-27-00-05549 (Beilstein Handbook Reference), MLS000758215, MLS001423962, MLS002548887, BIDD:GT0707, D-Cycloserine synth. BP 88, DivK1c_000098, SPECTRUM1500215, SPBio_000008, SPBio_003029, BPBio1_001252, FA6C7F8B-D080-4EA3-978F-1ECFB5A29D09, GTPL9489, orb1308085, orb3141370, Cycloserine (JP18/USP/INN), 4-Amino-3-isoxazolidinone, D-, HMS500E20, HY-B0030R, KBio1_000098, KBio2_001340, KBio2_003908, KBio2_006476, KBio3_001341, CYCLOSERINE [ORANGE BOOK], NINDS_000098, CYCLOSERINE [USP IMPURITY], HMS1571I20, HMS1920C06, HMS2051C15, HMS2091I14, HMS2098I20, HMS2232F03, HMS3259L19, HMS3260D06, HMS3715I14, Pharmakon1600-01500215, CYCLOSERINE [USP MONOGRAPH], (R)-3-Isoxazolidinone, 4-amino-, 4-Amino-3-isoxazolidinone, (R)-, CYCLOSERINUM [WHO-IP LATIN], HY-B0030, Tox21_110361, Tox21_500252, BDBM50038178, BDBM50103516, CCG-39705, D-Cycloserine, >=96.0% (NT), EBC-03937, LMPK14000007, NSC756712, s1998, 4-Isoxazolidinamine, 3-oxo-, (D)-, AKOS015994626, Tox21_110361_1, AC-4721, D-Cycloserine, Streptomyces orchidaceus, DB00260, FC15208, HS-0079, LP00252, NC00050, NC00676, NSC-756712, SDCCGSBI-0050240.P005, IDI1_000098, SMP1_000167, NCGC00015213-01, NCGC00015213-02, NCGC00015213-03, NCGC00016306-02, NCGC00016306-03, NCGC00016306-04, NCGC00016306-05, NCGC00016306-07, NCGC00016306-08, NCGC00016306-17, NCGC00093713-01, NCGC00093713-02, NCGC00260937-01, CAS-339-72-0, ST075697, SY005636, SBI-0050240.P004, AB00443920, CS-0695020, EU-0100252, NS00009120, 3-Isoxazolidinone, 4-amino-, (+)- (8CI), EN300-97131, (4R)-4-amino-2,4,5-trihydroisoxazol-3-one, C08057, D00877, AB00443920_09, AB00443920_10, Q418508, SR-01000759389, SR-01000075432-1, SR-01000075432-2, SR-01000075432-5, SR-01000075432-9, SR-01000759389-4, BRD-K87226815-001-17-1, BRD-K87226815-001-18-9, BRD-K87226815-001-19-7, BRD-K87226815-001-20-5, SR-01000075432-10, F2173-1228, Z1198154206, Cycloserine, United States Pharmacopeia (USP) Reference Standard, Cycloserine, Pharmaceutical Secondary Standard; Certified Reference Material
Theoretical properties:
molecular_formula: C3H6N2O2
molecular_weight: 102.09 g/mol
exact_mass: 102.042927438 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 7
topological_polar_surface_area: 64.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: CRYSTALS
color: CRYSTALS
odor: ODORLESS OR HAS FAINT ODOR
solubility: Soluble
Descriptions:
{"pubchem": "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.", "chebi": "A 4-amino-1,2-oxazolidin-3-one that has <i>R</i> configuration. It is an antibiotic produced by <em>Streptomyces garyphalus</em> or <em>S. orchidaceus</em> 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 <small>D</small>-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of <small>L</small>-alanine racemase (which forms <small>D</small>-alanine from <small>L</small>-alanine) and  <small>D</small>-alanine\u2014<small>D</small>-alanine ligase (which incorporates <small>D</small>-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).", "chembl": "CYCLOSERINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Cycloserine, sold under the brand name Seromycin, is an antibiotic, used to treat tuberculosis. Specifically it is used, along with other antituberculosis medications, for active drug resistant tuberculosis. It is given by mouth.\nCommon side effects include allergic reactions, seizures, sleepiness, unsteadiness, and numbness. It is not recommended in people who have kidney failure, epilepsy, depression, or are alcoholics. It is unclear if use during pregnancy is safe for the baby. Cycloserine is similar in structure to the amino acid D-alanine and works by interfering with the formation of the bacteria's cell wall.\nCycloserine was discovered in 1954 from a type of Streptomyces. It is on the World Health Organization's List of Essential Medicines."}