Methylthiouracil - ≥98% , CAS No.91795-77-6

CAS: 91795-77-6 Cat. No.: M304970 Molecular Weight: 142

GRADE & PURITY ≥98%

Synonyms

methylthiouracil|6-Methyl-2-thiouracil|56-04-2|4-hydroxy-2-mercapto-6-methylpyrimidine|Thimecil|2-Mercapto-6-methylpyrimidin-4-ol|Methiocil|Alkiron|2-Thio-6-methyluracil|Thiomecil|Thiothymin|Metacil|Basethyrin|Prostrumyl|Thyreonorm|Thyreostat|Tiomeracil|A

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

methylthiouracil | 6-Methyl-2-thiouracil | 56-04-2 | 4-hydroxy-2-mercapto-6-methylpyrimidine | Thimecil | 2-Mercapto-6-methylpyrimidin-4-ol | Methiocil | Alkiron | 2-Thio-6-methyluracil | Thiomecil | Thiothymin | Metacil | Basethyrin | Prostrumyl | Thyreonorm | Thyreostat | Tiomeracil | A

Specifications & Purity

≥98%

Storage

Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1=CC(=O)NC(=S)N1
• IUPAC Name: 6-methyl-2-sulfanylidene-1H-pyrimidin-4-one
• InChIKey: HWGBHCRJGXAGEU-UHFFFAOYSA-N
• INCHI: 1S/C5H6N2OS/c1-3-2-4(8)7-5(9)6-3/h2H,1H3,(H2,6,7,8,9)
• Isomeric SMILES: CC1=CC(=O)NC(=S)N1
• Molecular Weight: 142
• Reaxy-Rn: 115648
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=115648&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidones
• Alternative Parents: Pyrimidinethiones 2-Thiopyrimidines Hydropyrimidines Vinylogous amides Heteroaromatic compounds Thioureas Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 2-thiopyrimidine - Pyrimidinethione - Thiopyrimidine - Pyrimidone - Hydropyrimidine - Heteroaromatic compound - Vinylogous amide - Lactam - Thiourea - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
• External Descriptors: 9,11,15-octadecatrienoic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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TYR Tclin Tyrosinase (717 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)

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MMP8 Tchem Matrix metalloproteinase 8 (1942 Activities)

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MMP1 Tchem Matrix metalloproteinase-1 (7046 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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Associated Targets(non-human)

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Mmp2 Matrix metalloproteinase-2 (12 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Mmp9 Matrix metalloproteinase 9 (38 Activities)

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lef Anthrax lethal factor (7585 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 142.180 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.02 Da
• Monoisotopic Mass: 142.02 Da
• Topological Polar Surface Area: 73.200 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 197.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xuan Liang, Yi-Heng Gui, Qing-Xian Yue, Rui Ding, Jie Liu, Hai-Bin Yu.  (2023)  Comparison of inhibition performance of thiadiazole derivatives containing sulfhydryl groups: Experimental and theoretical calculations.  INTERNATIONAL JOURNAL OF CHEMICAL KINETICS,  55  (9): (503-524).  [PMID:] [10.1002/kin.21652]

2. Haishuang Zhu, Jing Li, Jin Wang, Erkang Wang.  (2019)  Lighting Up the Gold Nanoclusters via Host–Guest Recognition for High-Efficiency Antibacterial Performance and Imaging.  ACS Applied Materials & Interfaces,      [PMID:31512853] [10.1021/acsami.9b11026]

3. Zhong‑Lu Ye, Xiao‑Xiao Hou, Re‑Ling Chen, Jie Ding, Guo‑Hua Zheng, Ming‑Zhen Chen, Chuan Tian.  (2014)  Effects of methylthiouracil on the proliferation and apoptosis of rat bone marrow stromal cells.  Experimental and Therapeutic Medicine,  7  (6): (1738-1744).  [PMID:24926377] [10.3892/etm.2014.1612]

4. Youlong Chen, Yihua Hu, Yushuang Zhang, Hao Huang, Xing Yang, Youlin Gu, Fanhao Meng, Yuhao Xia, Ziwei Fu, Xinyuan Zhang, Junhao Chu.  (2025)  Synergistic Enhancement of Fluorescence Through Plasmon Resonance and Interfacial Charge Transfer by AgNC@AgAux Core–Shell Quantum Dots.  ADVANCED MATERIALS,      [PMID:39901465] [10.1002/adma.202415388]