Cycloserine

Details

• Internal ID: b7ec2f9a-094e-4f71-a843-1beaede4a18c
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives
• IUPAC Name: (4R)-4-amino-1,2-oxazolidin-3-one
• InChI: InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
• InChI Key: DYDCUQKUCUHJBH-UWTATZPHSA-N
• Popularity: 6,386 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃H₆N₂O₂
• Molecular Weight: 102.09 g/mol
• Exact Mass: 102.042927438 g/mol
• Topological Polar Surface Area (TPSA): 64.40 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.62
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• cycloserine
• 68-41-7
• Seromycin
• orientomycin
• Oxamycin
• Cyclo-D-serine
• Cicloserina
• Cyclorin
• Farmiserina
• Tisomycin
• Wasserina
• Miroseryn
• Closina
• D-4-amino-3-isoxazolidinone
• (4R)-4-amino-1,2-oxazolidin-3-one
• Cycloserinum
• Novoserin
• (+)-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
• MFCD00005353
• D-CS
• D-4-Amino-3-isossazolidone
• 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
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9761	97.61%
Caco-2	-	0.8419	84.19%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Lysosomes	0.4220	42.20%
OATP2B1 inhibitior	-	0.8637	86.37%
OATP1B1 inhibitior	+	0.9798	97.98%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9227	92.27%
P-glycoprotein inhibitior	-	0.9861	98.61%
P-glycoprotein substrate	-	0.9344	93.44%
CYP3A4 substrate	-	0.7354	73.54%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.7720	77.20%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9860	98.60%
CYP inhibitory promiscuity	-	0.9608	96.08%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5436	54.36%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.5886	58.86%
Skin irritation	-	0.7397	73.97%
Skin corrosion	-	0.9255	92.55%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7429	74.29%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8429	84.29%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5064	50.64%
Acute Oral Toxicity (c)	III	0.7710	77.10%
Estrogen receptor binding	-	0.8836	88.36%
Androgen receptor binding	-	0.7896	78.96%
Thyroid receptor binding	-	0.8825	88.25%
Glucocorticoid receptor binding	-	0.9325	93.25%
Aromatase binding	-	0.7936	79.36%
PPAR gamma	-	0.8646	86.46%
Honey bee toxicity	-	0.8192	81.92%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	-	0.9510	95.10%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	2.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137262	O60341	LSD1/CoREST complex	95.51%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.24%	91.11%
CHEMBL3384	Q16512	Protein kinase N1	88.17%	80.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.37%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	82.75%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.86%	96.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6234
• LOTUS: LTS0157189
• wikiData: Q418508