Thioguanine

Category	SARS-CoV
CAS	154-42-7
Description	Thioguanine incorporation alters the DNA cleavage induced by topoisomerase II in the presence and absence of etoposide

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Synonyms	thioguanine\|6-Thioguanine\|154-42-7\|Tioguanine\|2-Amino-6-mercaptopurine\|6-Mercaptoguanine\|Tioguanin\|Tabloid\|2-Amino-6-purinethiol\|Lanvis\|2-Amino 6MP\|2-Aminopurin-6-thiol\|2-Aminopurine-6-thiol\|2-Aminopurine-6(1H)-thione\|Wellcome U3B\|6-Mercapto-2-aminopurine\|2-Amino-9H-purine-6-thiol\|6-TG\|2-Amino-6-merkaptopurin\|Tioguaninum\|Guanine, thio-\|Tioguanina\|6H-Purine-6-thione, 2-amino-1,7-dihydro-\|2-Amino-1,7-dihydro-6H-purine-6-thione\|BW 5071\|Purine-6-thiol, 2-amino-\|Purine-6(1H)-thione, 2-amino-\|2-Amino-1,9-Dihydro-6h-Purine-6-Thione\|NSC-752\|Thioguanine Anhydrous\|TG\|Thioguanine Hemihydrate\|THG\|NSC 752\|2-Amino-1,7-dihydro-6H-purin-6-thion\|X 27\|UNII-WIX31ZPX66\|Tioguanine (INN)\|Thioguanine, anhydrous\|9H-Purine-6-thiol, 2-amino-\|2-amino-1,9-dihydropurine-6-thione\|CHEMBL727\|WIX31ZPX66\|2-amino-3,7-dihydro-6H-purine-6-thione\|2-amino-6,7-dihydro-3H-purine-6-thione\|CHEBI:9555\|NSC752\|Thioguanine2-Amino-6-purinethiol\|2-Thioguanine\|2-amino-1H-purine-6(9H)-thione\|Tioguanine [INN]\|2-amino-1,7-dihydropurine-6-thione\|NCGC00094792-01\|DSSTox_CID_3652\|2-Amino-6-MP\|DSSTox_RID_77129\|DSSTox_GSID_23652\|Tioguaninum [INN-Latin]\|C5H5N5S\|2-Aminopurin-6-thiol [Czech]\|Guanine, thio- (VAN)\|2-Amino-6-merkaptopurin [Czech]\|6-Tioguanine\|Tioguanina [INN-Spanish]\|CAS-154-42-7\|DX4\|SMR000857244\|Lanvis (TN)\|CCRIS 8997\|NSC-76504\|HSDB 2504\|SR-05000002077\|EINECS 205-827-2\|Thioguanine [USAN:USP]\|2-Amino-1,7-dihydro-6H-purin-6-thion [Czech]\|Thioquanine\|AI3-26078\|7H-Purine-6-thiol, 2-amino-\|6-thioguano-sine\|6-TG/Thioguanine\|MFCD00233553\|Tioguanine hemihydrate\|1H-Purine-6-thiol, 2-amino- (9CI)\|Spectrum_000235\|Spectrum2_000695\|Spectrum3_000577\|Spectrum4_000926\|Spectrum5_001455\|purine antimetabolite: antimetabolite: inhibits nucleic acid replication\|2-Amino-6-mercapto-purin\|6-Thioguanine, >=98%\|SCHEMBL3701\|SCHEMBL5898\|NCIOpen2_004153\|BSPBio_001994\|KBioGR_001452\|KBioGR_002476\|KBioSS_000715\|KBioSS_002483\|MLS001333131\|MLS001333132\|MLS006010896\|DivK1c_000428\|SPECTRUM1500573\|6H-Purine-6-thione, 2-amino-3,7-dihydro- (9CI)\|SPBio_000849\|154-42-7\|6-Thioguanine\|2-amino-6-mercapto-9H-purine\|GTPL6845\|Thioguanine (TN) (GlaxoSmith)\|DTXSID6023652\|HMS501F10\|KBio1_000428\|KBio2_000715\|KBio2_002476\|KBio2_003283\|KBio2_005044\|KBio2_005851\|KBio2_007612\|KBio3_001494\|KBio3_002954\|cMAP_000061\|NINDS_000428\|BCPE000001\|HMS1921E09\|HMS2092M11\|HMS2235F05\|HMS3865G13\|Pharmakon1600-01500573\|ALBB-023493\|BCP27718\|ZINC6382803\|Tox21_111035\|Tox21_113184\|Tox21_202401\|Tox21_300275\|BDBM50200099\|CCG-39890\|NSC757348\|s1774\|AKOS003389499\|AKOS015901298\|Tox21_111035_1\|2-Amino-1,7-dihydro-purine-6-thione\|2-Amino-1,9-dihydro-purine-6-thione\|AC-8421\|BCP9000197\|CCG-213953\|CCG-266338\|CS-1497\|DB00352\|NSC-757348\|PS-5007\|WLN: T56 BNM FYM INJ FUS HZ\|IDI1_000428\|SMP2_000326\|NCGC00094792-02\|NCGC00094792-03\|NCGC00094792-05\|NCGC00094792-06\|NCGC00094792-17\|NCGC00188976-01\|NCGC00188976-02\|NCGC00254082-01\|NCGC00259950-01\|NCGC00263442-01\|NCGC00263442-02\|NCGC00263442-05\|153981-51-2\|153981-52-3\|154034-61-4\|154034-62-5\|AC-23020\|BT166463\|HY-13765\|NCI60_041643\|SMR004701808\|SBI-0051533.P003\|FT-0611217\|T0212\|2-Amino-1,7-dihydro-6H-purine-6-thione #\|C07648\|D08603\|T71841\|AB00174074_06\|AB00918694_06\|AB01273926-01\|AB01273926-02\|AB01273926_03\|154T427\|A809532\|Q385347\|SR-05000002077-1\|SR-05000002077-5\|W-108030\|W-205813\|Z2768769146\|6-Thioguanine;6-TG;2-Amino-6-mercaptopurine;2-Amino-6-purinethiol\|Thioguanine, United States Pharmacopeia (USP) Reference Standard\|Thioguanine;6-TG; 2-Amino-6-mercaptopurine; 2-Amino-6-purinethiol\|6-Thioguanine, Hybri-Max(TM), 50 x, gamma-irradiated, lyophilized powder, BioXtra, suitable for hybridoma
IUPAC Name	2-amino-3,7-dihydropurine-6-thione
Molecular Weight	167.19
Molecular Formula	C5H5N5S
Canonical SMILES	C1=NC2=C(N1)C(=S)N=C(N2)N
InChI	InChI=1S/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChIKey	WYWHKKSPHMUBEB-UHFFFAOYSA-N
Boiling Point	460.7±37.0 °C at 760 mmHg
Melting Point	≥300 °C(lit.)
Flash Point	232.4±26.5 °C
Purity	>98%
Density	2.1±0.1 g/cm3
Solubility	In Vitro: DMSO : 10 mg/mL(59.81 mM;Need ultrasonic and warming) In Vivo: 1.Add each solvent one by one:10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline Solubility: ≥ 1.67 mg/mL (9.99 mM); Clear solution
Appearance	White to yellow (Solid)
Application	Antimetabolites, Antineoplastic
Storage	Powder: -20°C: 3 years 4°C: 2 years In solvent: -80°C: 6 months -20°C: 1 month
Complexity	225
Exact Mass	167.026566
Index Of Refraction	2.071
In Vitro	6-Thioguanine is an anti-leukemia and immunosuppressant agent, acts as an inhibitor of SARS and MERS coronavirus papain-like proteases (PLpros) and also potently inhibits USP2 activity, with IC50s of 25 μM and 40 μM for Plpros and recombinant human USP2, respectively.
PSA	119.28000
Target	SARS-CoV; Deubiquitinase; DNA Methyltransferase; Autophagy; Apoptosis;
Vapor Pressure	0.0±1.1 mmHg at 25°C
XLogP3-AA	-0.1