Citiolone

Details

• Internal ID: 2616bd13-7be2-46ab-9d5e-661c8e551174
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > N-acyl-alpha amino acids and derivatives
• IUPAC Name: N-(2-oxothiolan-3-yl)acetamide
• InChI: InChI=1S/C6H9NO2S/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)
• InChI Key: NRFJZTXWLKPZAV-UHFFFAOYSA-N
• Popularity: 97 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₉NO₂S
• Molecular Weight: 159.21 g/mol
• Exact Mass: 159.03539970 g/mol
• Topological Polar Surface Area (TPSA): 71.50 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.15
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 1195-16-0
• 17896-21-8
• Citiolase
• Thioxidrene
• Ahctl
• Achtl
• DL-N-Acetylhomocysteine thiolactone
• AHCT
• Acetamide, N-(tetrahydro-2-oxo-3-thienyl)-
• N-(2-Oxotetrahydrothiophen-3-yl)acetamide
• N-Acetyl-dl-homocysteine thiolactone
• N-Acetylhomocysteine thiolactone
• N-(2-oxothiolan-3-yl)acetamide
• N-(TETRAHYDRO-2-OXO-3-THIENYL)ACETAMIDE
• 2-Acetamido-4-mercaptobutyric acid gamma-thiolactone
• N-Acetylhmocysteinethiolactone
• BO 714
• N-Acetylhomocysteinthiolakton
• NSC 22878
• 2-Acetamido-4-mercaptobutyric acid thiolactone
• N-(TETRAHYDRO-2-OXO-3-THIENYL)-ACETAMIDE
• NSC-22878
• 70JKL15MUH
• DTXSID0045888
• Citiolone (INN)
• 3-Acetamidotetrahydro-2-thiophenone
• CITIOLONE [INN]
• .alpha.-Acetamido-.gamma.-thiobutyrolactone
• 2-Acetamido-4-mercaptobutyric acid $g-thiolactone
• Acetamide, N-(tetrahydro-2-oxo-3-thienyl)-, (A+/-)-
• DTXCID8025888
• Citiolonum
• Citiolona
• Mucorex
• Sitilon
• Citiolone [INN:DCF]
• Citiolonum [INN-Latin]
• Citiolona [INN-Spanish]
• alpha-Acetamido-gamma-thiobutyrolactone
• SR-01000872700
• EINECS 214-793-8
• EINECS 241-841-5
• N-(Tetrahydro-2-oxothienyl)acetamide
• N-Acetylhomocysteinthiolakton [German]
• UNII-70JKL15MUH
• BRN 0004338
• Prestwick_1
• N-Acetyl-DL-homocystein thiolacton
• NCGC00016568-01
• CAS-1195-16-0
• CITIOLONE [MI]
• Prestwick0_000644
• Prestwick1_000644
• Prestwick2_000644
• Prestwick3_000644
• CITIOLONE [MART.]
• (1)-N-(Tetrahydro-2-oxothien-3-yl)acetamide
• CITIOLONE [WHO-DD]
• 2-Thiolanone, 3-acetamido-
• BSPBio_000647
• 5-18-11-00320 (Beilstein Handbook Reference)
• SCHEMBL364495
• SPBio_002568
• BPBio1_000713
• CHEMBL2104457
• CHEBI:94403
• N-(2-oxo-3-thiolanyl)acetamide
• dl-N-Acetylhomocysteinethiolactone
• HMS1570A09
• HMS2097A09
• HMS3714A09
• Pharmakon1600-01503205
• BCP30727
• HY-B0931
• N-Acetyl-DL-homocystein Thiolactone
• NSC22878
• Tox21_111388
• Tox21_113346
• MFCD00005480
• NSC758402
• s4558
• AKOS002808092
• AKOS016162043
• Tox21_113346_1
• CCG-213865
• DB13442
• NSC-758402
• N-(2-Oxotetrahydro-3-thienyl)acetamide
• NCGC00179491-01
• NCGC00179491-04
• AS-11951
• DL-N-Acetylhomocysteine thiolactone, 98%
• SBI-0207034.P001
• DL-3-(Acetylamino)tetrahydro-2-thiophenone
• FT-0637623
• FT-0774860
• N,N-dimethyl-2,4-dinitro-benzenesulfonamide
• D07105
• EN300-100347
• F17228
• A804305
• 2-Acetamido-4-mercaptobutyric acid I(3)-thiolactone
• J-011416
• SR-01000872700-1
• SR-01000872700-2
• BRD-A57957888-001-01-5
• BRD-A57957888-001-06-4
• Q15408416
• 2-Acetamide-4-mercaptobutyric acid .gamma.-thiolactone
• 2-Acetamido-4-mercaptobutyric acid .gamma.-thiolactone
• Z995084668
• Citiolase;Citiolona; Citiolonum; NSC 22878; NSC22878; NSC-22878

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9729	97.29%
Caco-2	-	0.8371	83.71%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5171	51.71%
OATP2B1 inhibitior	-	0.8417	84.17%
OATP1B1 inhibitior	+	0.9622	96.22%
OATP1B3 inhibitior	+	0.9466	94.66%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7564	75.64%
BSEP inhibitior	-	0.9632	96.32%
P-glycoprotein inhibitior	-	0.9833	98.33%
P-glycoprotein substrate	-	0.8705	87.05%
CYP3A4 substrate	-	0.6144	61.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8478	84.78%
CYP3A4 inhibition	-	0.9644	96.44%
CYP2C9 inhibition	-	0.9564	95.64%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9606	96.06%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9904	99.04%
CYP inhibitory promiscuity	-	0.8303	83.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.6075	60.75%
Eye corrosion	-	0.9160	91.60%
Eye irritation	-	0.7064	70.64%
Skin irritation	-	0.7539	75.39%
Skin corrosion	-	0.8935	89.35%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7068	70.68%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.8824	88.24%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	+	0.5636	56.36%
Acute Oral Toxicity (c)	III	0.6833	68.33%
Estrogen receptor binding	-	0.8932	89.32%
Androgen receptor binding	-	0.9093	90.93%
Thyroid receptor binding	-	0.8326	83.26%
Glucocorticoid receptor binding	-	0.9289	92.89%
Aromatase binding	-	0.8832	88.32%
PPAR gamma	-	0.8339	83.39%
Honey bee toxicity	-	0.9639	96.39%
Biodegradation	+	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.7452	74.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.63%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.86%	96.09%
CHEMBL2581	P07339	Cathepsin D	88.40%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	84.46%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.15%	99.23%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.01%	93.03%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.53%	94.33%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.43%	95.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.35%	91.11%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 14520
• LOTUS: LTS0037009
• wikiData: Q15408416