MiMeDB: Showing metabocard for Thioguanine (MMDBc0016011)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:44:01 UTC

Update Date

2024-04-30 19:35:01 UTC

Metabolite ID

MMDBc0016011

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

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

Molecular Formula

C₅H₅N₅S

Average Mass

167.192

Monoisotopic Mass

167.026565875

IUPAC Name

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

Traditional Name

thioguanine

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-4900000000-d9b2da47228aaa85556a	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-014i-9300000000-cbba0d635918d03d8b2e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-001i-1900000000-ec9120f0aa3a2ea84060	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-001i-2900000000-4050d4a4a73935d7865c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-00lr-8900000000-d82747e1ca135bce8a18	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00lr-0900000000-811eb76446c5cb3d13bf	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-00lr-0900000000-4d8f4082707719cd5d04	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0ue9-0900000000-98689cd23c829bc3ef98	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0zgi-2900000000-df4f1659bf9a0fa9e4c2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-014i-0900000000-9110b43ff3c8ed002843	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0uxr-0900000000-3a1c799a60e88b9de127	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-c4db837d0a7e413fc9e7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-014i-0900000000-195639211a5dd07a4cf1	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-f711c8fa62d6eed053b2	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0159-2900000000-afd9900ecc0fd78faf88	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9300000000-2ef0a5c247f78f7847a3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-4e59f276b6876f830b90	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9800000000-76282c4c7f26457ec3f9	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-9100000000-310b12df78498951fb54	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-c1b1c192793adf5933a9	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-379c32e68ff490bc5f5c	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9700000000-757c534cc2a9d57cf055	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-c0ee1b32f4e590209c56	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-800eeaab9deb1a1ba9ae	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-7900000000-43adeb7fa61eea70589c	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Kidney
Liver

Tissue Locations

Kidney
Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192133	Hypoxanthine-guanine phosphoribosyltransferase	Unknown	P00492	Homo sapiens
MMDBp0193945	Multidrug resistance-associated protein 4	Transporter	O15439	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces; Human	Metabolic reconstruction
Bacteria	nah	1		Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0014496

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

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]
FDA Online Label Repository [Link]

Showing metabocard for Thioguanine (MMDBc0016011)

MOL for #<Metabolite:0x00007fece096e6f8>

3D MOL for #<Metabolite:0x00007fece096e6f8>

3D SDF for #<Metabolite:0x00007fece096e6f8>

3D-SDF for #<Metabolite:0x00007fece096e6f8>

PDB for #<Metabolite:0x00007fece096e6f8>

3D PDB for #<Metabolite:0x00007fece096e6f8>

SMILES for #<Metabolite:0x00007fece096e6f8>

INCHI for #<Metabolite:0x00007fece096e6f8>

Structure for #<Metabolite:0x00007fece096e6f8>

3D Structure for #<Metabolite:0x00007fece096e6f8>