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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (1) Show 2 proteins XML

enzymes (1)transporters (1) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2023-02-21 17:18:11 UTC

HMDB ID

HMDB0014496

Secondary Accession Numbers

HMDB14496

Metabolite Identification

Common Name

Thioguanine

Description

Thioguanine is only found in individuals that have used or taken this drug. It is an antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia. [PubChem]Thioguanine competes with hypoxanthine and guanine for the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase) and is itself converted to 6-thioguanilyic acid (TGMP), which reaches high intracellular concentrations at therapeutic doses. TGMP interferes with the synthesis of guanine nucleotides by its inhibition of purine biosynthesis by pseudofeedback inhibition of glutamine-5-phosphoribosylpyrophosphate amidotransferase, the first enzyme unique to the de novo pathway of purine ribonucleotide synthesis. TGMP also inhibits the conversion of inosinic acid (IMP) to xanthylic acid (XMP) by competition for the enzyme IMP dehydrogenase. Thioguanine nucleotides are incorporated into both the DNA and the RNA by phosphodiester linkages, and some studies have shown that incorporation of such false bases contributes to the cytotoxicity of thioguanine. Its tumor inhibitory properties may be due to one or more of its effects on feedback inhibition of de novo purine synthesis; inhibition of purine nucleotide interconversions; or incorporation into the DNA and RNA. The overall result of its action is a sequential blockade of the utilization and synthesis of the purine nucleotides.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Amino 6MP	ChEBI
2-Amino-1,7-dihydro-6H-purine-6-thione	ChEBI
2-Amino-1,9-dihydropurine-6-thione	ChEBI
2-Amino-6-mercaptopurine	ChEBI
2-Amino-6-merkaptopurin	ChEBI
2-Amino-6-purinethiol	ChEBI
2-Aminopurin-6-thiol	ChEBI
2-Aminopurine-6(1H)-thione	ChEBI
2-Aminopurine-6-thiol	ChEBI
6-Mercapto-2-aminopurine	ChEBI
6-Mercaptoguanine	ChEBI
6-TG	ChEBI
6-Thioguanine	ChEBI
TG	ChEBI
ThG	ChEBI
Tioguanin	ChEBI
Tioguanina	ChEBI
Tioguaninum	ChEBI
Lanvis	Kegg
6 Thioguanine	HMDB
Glaxo wellcome brand OF thioguanine	HMDB
GlaxoSmithKline brand OF thioguanine	HMDB
ThioguaninGSK	HMDB
Thioguanine hemihydrate	HMDB
Tioguanina wellcome	HMDB
Wellcome brand OF thioguanine	HMDB
2 Amino 6 purinethiol	HMDB
GlaxoSmithKline brand OF tioguanine	HMDB
Thioguanine tabloid	HMDB
Glaxo wellcome brand OF tioguanine	HMDB
Tabloid	HMDB
Thioguanine anhydrous	HMDB
Anhydrous, thioguanine	HMDB
Thioguanin GSK	HMDB
Thioguanin-GSK	HMDB
Thioguanine monosodium salt	HMDB
Tioguanine glaxosmithkline brand	HMDB
Thioguanine	ChEBI

Chemical Formula

C₅H₅N₅S

Average Molecular Weight

167.192

Monoisotopic Molecular Weight

167.026565875

IUPAC Name

2-amino-6,7-dihydro-3H-purine-6-thione

Traditional Name

thioguanine

CAS Registry Number

154-42-7

SMILES

NC1=NC(=S)C2=C(N1)N=CN2

InChI Identifier

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purinethiones. These are purines in which the purine moiety bears a thioketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purinethiones

Alternative Parents

Substituents

Purinethione
Aminopyrimidine
Pyrimidinethione
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organopnictogen compound
Primary amine
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

2-aminopurines (CHEBI:9555 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0014496)
Kidney (HMDB: HMDB0014496)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014496)

Endogenous

Endogenous (HMDB: HMDB0014496)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Thioguanine Pathway (HMDB: HMDB0014496)
Thioguanine Action Pathway (PathBank: SMP0000430)

Metabolic pathway

Thioguanine Metabolism Pathway (PathBank: SMP0000647)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	> 360 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.83 g/L	Not Available
LogP	-0.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.83 g/L	ALOGPS
logP	-0.36	ALOGPS
logP	-0.35	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.53	ChemAxon
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.09 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.89 m³·mol⁻¹	ChemAxon
Polarizability	15.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.617	31661259
DarkChem	[M-H]-	133.148	31661259
DeepCCS	[M+H]+	133.453	30932474
DeepCCS	[M-H]-	130.167	30932474
DeepCCS	[M-2H]-	167.298	30932474
DeepCCS	[M+Na]+	142.601	30932474
AllCCS	[M+H]+	135.3	32859911
AllCCS	[M+H-H2O]+	130.8	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.8	32859911
AllCCS	[M-H]-	129.2	32859911
AllCCS	[M+Na-2H]-	130.2	32859911
AllCCS	[M+HCOO]-	131.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.25 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9595 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.73 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	90.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	661.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	375.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	46.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	248.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	305.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	261.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	806.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	645.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	40.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	743.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	205.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	680.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	288.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	307.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thioguanine	NC1=NC(=S)C2=C(N1)N=CN2	2943.2	Standard polar	33892256
Thioguanine	NC1=NC(=S)C2=C(N1)N=CN2	1976.8	Standard non polar	33892256
Thioguanine	NC1=NC(=S)C2=C(N1)N=CN2	2482.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thioguanine,1TMS,isomer #1	C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]1	2218.4	Semi standard non polar	33892256
Thioguanine,1TMS,isomer #1	C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]1	2345.0	Standard non polar	33892256
Thioguanine,1TMS,isomer #1	C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]1	3298.3	Standard polar	33892256
Thioguanine,1TMS,isomer #2	C[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]2	2146.7	Semi standard non polar	33892256
Thioguanine,1TMS,isomer #2	C[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]2	2313.1	Standard non polar	33892256
Thioguanine,1TMS,isomer #2	C[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]2	3261.3	Standard polar	33892256
Thioguanine,1TMS,isomer #3	C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]2	2159.2	Semi standard non polar	33892256
Thioguanine,1TMS,isomer #3	C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]2	2186.2	Standard non polar	33892256
Thioguanine,1TMS,isomer #3	C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]2	3149.5	Standard polar	33892256
Thioguanine,2TMS,isomer #1	C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C	2103.2	Semi standard non polar	33892256
Thioguanine,2TMS,isomer #1	C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C	2370.9	Standard non polar	33892256
Thioguanine,2TMS,isomer #1	C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C	3054.9	Standard polar	33892256
Thioguanine,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]1	2250.3	Semi standard non polar	33892256
Thioguanine,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]1	2226.2	Standard non polar	33892256
Thioguanine,2TMS,isomer #2	C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]1	2938.7	Standard polar	33892256
Thioguanine,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C	2183.3	Semi standard non polar	33892256
Thioguanine,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C	2437.5	Standard non polar	33892256
Thioguanine,2TMS,isomer #3	C[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C	2962.2	Standard polar	33892256
Thioguanine,2TMS,isomer #4	C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C	2217.2	Semi standard non polar	33892256
Thioguanine,2TMS,isomer #4	C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C	2246.7	Standard non polar	33892256
Thioguanine,2TMS,isomer #4	C[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C	2965.2	Standard polar	33892256
Thioguanine,3TMS,isomer #1	C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C	2186.6	Semi standard non polar	33892256
Thioguanine,3TMS,isomer #1	C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C	2242.2	Standard non polar	33892256
Thioguanine,3TMS,isomer #1	C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C	2652.2	Standard polar	33892256
Thioguanine,3TMS,isomer #2	C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C	2169.1	Semi standard non polar	33892256
Thioguanine,3TMS,isomer #2	C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C	2504.2	Standard non polar	33892256
Thioguanine,3TMS,isomer #2	C[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C	2679.5	Standard polar	33892256
Thioguanine,3TMS,isomer #3	C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C	2240.6	Semi standard non polar	33892256
Thioguanine,3TMS,isomer #3	C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C	2238.9	Standard non polar	33892256
Thioguanine,3TMS,isomer #3	C[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C	2718.4	Standard polar	33892256
Thioguanine,4TMS,isomer #1	C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C	2264.2	Semi standard non polar	33892256
Thioguanine,4TMS,isomer #1	C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C	2320.6	Standard non polar	33892256
Thioguanine,4TMS,isomer #1	C[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C	2468.0	Standard polar	33892256
Thioguanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]1	2431.4	Semi standard non polar	33892256
Thioguanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]1	2566.3	Standard non polar	33892256
Thioguanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)[NH]1	3338.2	Standard polar	33892256
Thioguanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]2	2385.6	Semi standard non polar	33892256
Thioguanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]2	2548.2	Standard non polar	33892256
Thioguanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(N)=NC(=S)C2=C1N=C[NH]2	3267.0	Standard polar	33892256
Thioguanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]2	2402.7	Semi standard non polar	33892256
Thioguanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]2	2400.8	Standard non polar	33892256
Thioguanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)[NH]2	3229.6	Standard polar	33892256
Thioguanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C	2506.3	Semi standard non polar	33892256
Thioguanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C	2847.5	Standard non polar	33892256
Thioguanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C	3061.9	Standard polar	33892256
Thioguanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1	2588.8	Semi standard non polar	33892256
Thioguanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1	2593.0	Standard non polar	33892256
Thioguanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1	3018.6	Standard polar	33892256
Thioguanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C	2567.7	Semi standard non polar	33892256
Thioguanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C	2913.8	Standard non polar	33892256
Thioguanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C	2975.7	Standard polar	33892256
Thioguanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C(C)(C)C	2602.1	Semi standard non polar	33892256
Thioguanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C(C)(C)C	2644.8	Standard non polar	33892256
Thioguanine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C=NC2=C1C(=S)N=C(N)N2[Si](C)(C)C(C)(C)C	3020.6	Standard polar	33892256
Thioguanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C	2718.6	Semi standard non polar	33892256
Thioguanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C	2860.7	Standard non polar	33892256
Thioguanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C	2835.0	Standard polar	33892256
Thioguanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2729.8	Semi standard non polar	33892256
Thioguanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3160.6	Standard non polar	33892256
Thioguanine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2819.6	Standard polar	33892256
Thioguanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2797.9	Semi standard non polar	33892256
Thioguanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2854.6	Standard non polar	33892256
Thioguanine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C	2879.3	Standard polar	33892256
Thioguanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2950.3	Semi standard non polar	33892256
Thioguanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3101.9	Standard non polar	33892256
Thioguanine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NC(=S)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2804.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thioguanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-4900000000-d9b2da47228aaa85556a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thioguanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thioguanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 90V, Negative-QTOF	splash10-014i-9300000000-cbba0d635918d03d8b2e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 45V, Negative-QTOF	splash10-001i-1900000000-ec9120f0aa3a2ea84060	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 60V, Negative-QTOF	splash10-001i-2900000000-4050d4a4a73935d7865c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 75V, Negative-QTOF	splash10-00lr-8900000000-d82747e1ca135bce8a18	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 75V, Positive-QTOF	splash10-0ue9-0900000000-98689cd23c829bc3ef98	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 90V, Positive-QTOF	splash10-0zgi-2900000000-df4f1659bf9a0fa9e4c2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 30V, Negative-QTOF	splash10-00lr-0900000000-811eb76446c5cb3d13bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 15V, Negative-QTOF	splash10-00lr-0900000000-4d8f4082707719cd5d04	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 45V, Positive-QTOF	splash10-014i-0900000000-9110b43ff3c8ed002843	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 60V, Positive-QTOF	splash10-0uxr-0900000000-3a1c799a60e88b9de127	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 30V, Positive-QTOF	splash10-014i-0900000000-c4db837d0a7e413fc9e7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thioguanine 15V, Positive-QTOF	splash10-014i-0900000000-195639211a5dd07a4cf1	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 10V, Positive-QTOF	splash10-014i-0900000000-c1b1c192793adf5933a9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 20V, Positive-QTOF	splash10-014i-0900000000-379c32e68ff490bc5f5c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 40V, Positive-QTOF	splash10-0a59-9700000000-757c534cc2a9d57cf055	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 10V, Negative-QTOF	splash10-014i-0900000000-f711c8fa62d6eed053b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 20V, Negative-QTOF	splash10-0159-2900000000-afd9900ecc0fd78faf88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 40V, Negative-QTOF	splash10-014i-9300000000-2ef0a5c247f78f7847a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 10V, Positive-QTOF	splash10-014i-0900000000-c0ee1b32f4e590209c56	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 20V, Positive-QTOF	splash10-014i-0900000000-800eeaab9deb1a1ba9ae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 40V, Positive-QTOF	splash10-066r-7900000000-43adeb7fa61eea70589c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 10V, Negative-QTOF	splash10-014i-0900000000-4e59f276b6876f830b90	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 20V, Negative-QTOF	splash10-0a4i-9800000000-76282c4c7f26457ec3f9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thioguanine 40V, Negative-QTOF	splash10-066r-9100000000-310b12df78498951fb54	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Thioguanine Action Pathway		Not Available
Thioguanine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00352	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00352	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00352

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Thioguanine

METLIN ID

Not Available

PubChem Compound

2723601

PDB ID

DX4

ChEBI ID

9555

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). FDA label . .

Enzymes

Enzyme Details

1. Hypoxanthine-guanine phosphoribosyltransferase

General function:: Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:: Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:: HPRT1
Uniprot ID:: P00492
Molecular weight:: 24579.155

Reactions

Thioguanine + Phosphoribosyl pyrophosphate → 6-Thioguanosine monophosphate + Pyrophosphate	details

References

Shivashankar K, Subbayya IN, Balaram H: Development of a bacterial screen for novel hypoxanthine-guanine phosphoribosyltransferase substrates. J Mol Microbiol Biotechnol. 2001 Oct;3(4):557-62. [PubMed:11545274 ]
Horikawa K, Kawaguchi T, Ishihara S, Nagakura S, Hidaka M, Kagimoto T, Mitsuya H, Nakakuma H: Frequent detection of T cells with mutations of the hypoxanthine-guanine phosphoribosyl transferase gene in patients with paroxysmal nocturnal hemoglobinuria. Blood. 2002 Jan 1;99(1):24-9. [PubMed:11756148 ]
Fuscoe JC, Zimmerman LJ, Fekete A, Setzer RW, Rossiter BJ: Analysis of X-ray-induced HPRT mutations in CHO cells: insertion and deletions. Mutat Res. 1992 Oct;269(2):171-83. [PubMed:1383700 ]
Elgemeie GH: Thioguanine, mercaptopurine: their analogs and nucleosides as antimetabolites. Curr Pharm Des. 2003;9(31):2627-42. [PubMed:14529546 ]
Suzuki M, Tsuruoka C, Kanai T, Kato T, Yatagai F, Watanabe M: Qualitative and quantitative difference in mutation induction between carbon- and neon-ion beams in normal human cells. Biol Sci Space. 2003 Dec;17(4):302-6. [PubMed:15136753 ]

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Bai J, Lai L, Yeo HC, Goh BC, Tan TM: Multidrug resistance protein 4 (MRP4/ABCC4) mediates efflux of bimane-glutathione. Int J Biochem Cell Biol. 2004 Feb;36(2):247-57. [PubMed:14643890 ]

Showing metabocard for Thioguanine (HMDB0014496)

MOL for HMDB0014496 (Thioguanine)

3D MOL for HMDB0014496 (Thioguanine)

3D SDF for HMDB0014496 (Thioguanine)

3D-SDF for HMDB0014496 (Thioguanine)

PDB for HMDB0014496 (Thioguanine)

3D PDB for HMDB0014496 (Thioguanine)

SMILES for HMDB0014496 (Thioguanine)

INCHI for HMDB0014496 (Thioguanine)

Structure for HMDB0014496 (Thioguanine)

3D Structure for HMDB0014496 (Thioguanine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

References

Transporters

References