Thioguanine

Details

• Internal ID: a6b42893-93ee-4525-9075-9d3b83bf267e
• Taxonomy: Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > Purinethiones
• IUPAC Name: 2-amino-3,7-dihydropurine-6-thione
• SMILES (Canonical): C1=NC2=C(N1)C(=S)N=C(N2)N
• SMILES (Isomeric): 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)
• InChI Key: WYWHKKSPHMUBEB-UHFFFAOYSA-N
• Popularity: 7,944 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅H₅N₅S
• Molecular Weight: 167.19 g/mol
• Exact Mass: 167.02656635 g/mol
• Topological Polar Surface Area (TPSA): 111.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): 0.60
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 6-Thioguanine
• 154-42-7
• Tioguanine
• 2-Amino-6-mercaptopurine
• 6-Mercaptoguanine
• Tabloid
• 2-Amino-6-purinethiol
• Tioguanin
• 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-
• 2-amino-1H-purine-6(7H)-thione
• Tioguanina
• 6H-Purine-6-thione, 2-amino-1,7-dihydro-
• 2-Thioguanine
• 2-Amino-1,7-dihydro-6H-purine-6-thione
• Thioguanine Anhydrous
• NSC-752
• BW 5071
• Purine-6-thiol, 2-amino-
• Purine-6(1H)-thione, 2-amino-
• 2-amino-3,7-dihydropurine-6-thione
• 2-Amino-6-MP
• 2-Amino-1,9-Dihydro-6h-Purine-6-Thione
• Tioguaninum [INN-Latin]
• TG
• Thioguanine Hemihydrate
• C5H5N5S
• Thioguanine, anhydrous
• 2-Aminopurin-6-thiol [Czech]
• THG
• Guanine, thio- (VAN)
• NSC 752
• 2-Amino-1,7-dihydro-6H-purin-6-thion
• 2-Amino-6-merkaptopurin [Czech]
• X 27
• 6-Thioguanine (6-TG)
• 6-Tioguanine
• Thioguanine [USAN:BAN]
• Tioguanina [INN-Spanish]
• 6-TG/Thioguanine
• Tioguanine (INN)
• Tioguanine [INN]
• Lanvis (TN)
• CCRIS 8997
• 2-amino-6,7-dihydro-3H-purine-6-thione
• HSDB 2504
• EINECS 205-827-2
• 2-amino-1,9-dihydropurine-6-thione
• Thioguanine [USAN:USP]
• 2-Amino-1,7-dihydro-6H-purin-6-thion [Czech]
• CHEMBL727
• UNII-WIX31ZPX66
• WIX31ZPX66
• 2-amino-3,7-dihydro-6H-purine-6-thione
• AI3-26078
• CHEBI:9555
• NSC752
• DTXSID6023652
• Thioguanine2-Amino-6-purinethiol
• 2-amino-1H-purine-6(9H)-thione
• 2-amino-1,7-dihydropurine-6-thione
• NSC-76504
• NCGC00094792-01
• Thioguanine hydrate
• purine antimetabolite: antimetabolite: inhibits nucleic acid replication
• Tioguanine hemihydrate
• DTXCID803652
• ThioguaninGSK
• 6 Thioguanine
• Thioguanin GSK
• Thioguanin-GSK
• Thioguanine Tabloid
• Tioguanina Wellcome
• CAS-154-42-7
• DX4
• SMR000857244
• 2 Amino 6 Purinethiol
• Purine-6-thiol, 2-amino-, hemihydrate
• SR-05000002077
• Thioguanine Monosodium Salt
• Thioquanine
• 6-thioguano-sine
• 6H-Purine-6-thione, 2-amino-1,7-dihydro-, hemihydrate
• MFCD00233553
• 1330266-29-9
• Spectrum_000235
• Guanine, thio-(VAN)
• Tioguanina[INN-Spanish]
• THIOGUANINE [MI]
• 5580-03-0
• Spectrum2_000695
• Spectrum3_000577
• Spectrum4_000926
• Spectrum5_001455
• THIOGUANINE [HSDB]
• 2-Amino-6-mercapto-purin
• D02ZXM
• 6-Thioguanine, Thioguanine
• 6-Thioguanine, >=98%
• SCHEMBL3701
• SCHEMBL5898
• NCIOpen2_004153
• TIOGUANINE [WHO-DD]
• BSPBio_001994
• C5H7N5S
• KBioGR_001452
• KBioGR_002476
• KBioSS_000715
• KBioSS_002483
• MLS001333131
• MLS001333132
• MLS006010896
• Wellcome Brand of Thioguanine
• DivK1c_000428
• SPECTRUM1500573
• SPBio_000849
• 154-42-7|6-Thioguanine
• 2-amino-6-mercapto-9H-purine
• GTPL6845
• Thioguanine (TN) (GlaxoSmith)
• Tioguanine GlaxoSmithKline Brand
• 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
• Glaxo Wellcome Brand of Tioguanine
• BCP27718
• Glaxo Wellcome Brand of Thioguanine
• GlaxoSmithKline Brand of Tioguanine
• GlaxoSmithKline Brand of Thioguanine
• Tox21_111035
• Tox21_113184
• Tox21_202401
• Tox21_300275
• BDBM50200099
• CCG-39890
• HB1379
• LS-888
• 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
• AC-23020
• BT166463
• HY-13765
• NCI60_041643
• SMR004701808
• SBI-0051533.P003
• FT-0611217
• LT00455187
• T0212
• 2-Amino-1,7-dihydro-6H-purine-6-thione #
• C07648
• D08603
• EN300-119530
• T71841
• AB00174074_06
• AB00918694_06
• AB01273926-01
• AB01273926-02
• AB01273926_03
• A809532
• Q385347
• SR-05000002077-1
• SR-05000002077-5
• W-108030
• W-205813
• Z2299468139
• 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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9826	98.26%
Caco-2	-	0.7974	79.74%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Lysosomes	0.6749	67.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9660	96.60%
OATP1B3 inhibitior	+	0.9476	94.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8684	86.84%
P-glycoprotein inhibitior	-	0.9871	98.71%
P-glycoprotein substrate	-	0.8216	82.16%
CYP3A4 substrate	-	0.6848	68.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8875	88.75%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.6575	65.75%
CYP2C19 inhibition	+	0.5517	55.17%
CYP2D6 inhibition	-	0.8881	88.81%
CYP1A2 inhibition	+	0.7904	79.04%
CYP2C8 inhibition	-	0.8766	87.66%
CYP inhibitory promiscuity	-	0.8537	85.37%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4468	44.68%
Eye corrosion	-	0.9882	98.82%
Eye irritation	+	0.5284	52.84%
Skin irritation	+	0.6150	61.50%
Skin corrosion	-	0.9487	94.87%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5699	56.99%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.9750	97.50%
skin sensitisation	-	0.9111	91.11%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7385	73.85%
Acute Oral Toxicity (c)	III	0.7417	74.17%
Estrogen receptor binding	-	0.7206	72.06%
Androgen receptor binding	-	0.6708	67.08%
Thyroid receptor binding	-	0.4877	48.77%
Glucocorticoid receptor binding	-	0.7826	78.26%
Aromatase binding	+	0.5634	56.34%
PPAR gamma	-	0.6774	67.74%
Honey bee toxicity	-	0.8791	87.91%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.5348	53.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	35481.3 nM	Potency	via CMAUP
CHEMBL256	P0DMS8	Adenosine A3 receptor	21687 nM	IC50	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	3981.1 nM; 3981.1 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL221	P23219	Cyclooxygenase-1	601 nM	IC50	via CMAUP
CHEMBL4331	P68871	Hemoglobin beta chain	5011.9 nM; 1122.02 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3385	P27361	MAP kinase ERK1	5516 nM	IC50	via CMAUP
CHEMBL2362980	Q06710	Paired box protein Pax-8	< 260 nM; < 260 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	7079.5 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	91.90%	85.30%
CHEMBL1952	P04818	Thymidylate synthase	88.66%	93.53%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	87.25%	93.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.72%	96.09%
CHEMBL213	P08588	Beta-1 adrenergic receptor	82.53%	95.56%
CHEMBL4070	P19784	Casein kinase II alpha (prime)	81.87%	91.67%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.03%	91.11%
CHEMBL255	P29275	Adenosine A2b receptor	80.57%	98.59%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	80.15%	95.48%

Plants that contains it

• Paris polyphylla

Cross-Links

• PubChem: 2723601
• NPASS: NPC51000
• ChEMBL: CHEMBL727
• LOTUS: LTS0219478
• wikiData: Q385347