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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:01:07 UTC
Update Date2019-07-23 07:14:17 UTC
HMDB IDHMDB0060416
Secondary Accession Numbers
  • HMDB60416
Metabolite Identification
Common Name6-Thioinosine-5'-monophosphate
Description6-Thioinosine-5'-monophosphate, also known as 6-TIMP or ion(-2) OF thioinosinic acid, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. 6-Thioinosine-5'-monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Mercaptopurine (also called 6-mercaptopurine, 6-MP or its brand name Purinethol) is an immunosuppressive drug. 6-Thioinosine-5'-monophosphate exists in all living organisms, ranging from bacteria to humans. Within humans, 6-thioinosine-5'-monophosphate participates in a number of enzymatic reactions. In particular, 6-thioinosine-5'-monophosphate can be biosynthesized from mercaptopurine and phosphoribosyl pyrophosphate; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In addition, 6-thioinosine-5'-monophosphate can be converted into thioxanthine monophosphate through its interaction with the enzyme inosine-5'-monophosphate dehydrogenase 1. 6-Thioinosine-5'-monophosphate is a metabolite of mercaptopurine. It is a thiopurine. In humans, 6-thioinosine-5'-monophosphate is involved in mercaptopurine metabolism pathway.
Structure
Data?1563866057
Synonyms
ValueSource
9-(5-Phospho-1-ribofuranosyl)-6-mercaptopurineKegg
6-Thioinosine-5'-monophosphoric acidGenerator
6-TIMPHMDB
6-Mercaptopurine ribonucleoside 5'-monophosphateHMDB
6-Thio-impHMDB
6-Thioinosine 5'-monophosphateHMDB
Ion(-2) OF thioinosinic acidHMDB
Chemical FormulaC10H13N4O7PS
Average Molecular Weight364.272
Monoisotopic Molecular Weight364.024255992
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanyl-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
Traditional NameThio-IMP
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2S
InChI Identifier
InChI=1S/C10H13N4O7PS/c15-6-4(1-20-22(17,18)19)21-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)23/h2-4,6-7,10,15-16H,1H2,(H,11,12,23)(H2,17,18,19)/t4-,6-,7-,10-/m1/s1
InChI KeyZKRFOXLVOKTUTA-KQYNXXCUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Purinethione
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Pyrimidinethione
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.12 g/LALOGPS
logP-0.94ALOGPS
logP-1.6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.3ChemAxon
pKa (Strongest Basic)0.45ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area160.05 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.38 m³·mol⁻¹ChemAxon
Polarizability31.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9612000000-a74111380007299b2135Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-9412200000-c26fea11eb214c387e75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0913000000-80ef082378137b80cdb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-841a3c66f7f8d3a5f565Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-3900000000-a2c9bd3787ad7fcb372bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imi-6709000000-c2114b8c00dbf084377dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9700000000-6bde5e07b26405551d25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-928327df5699c8b1cda5Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC04646
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3034391
PDB IDNot Available
ChEBI ID2332
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in thiopurine S-methyltransferase activity
Specific function:
Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
Gene Name:
TPMT
Uniprot ID:
P51580
Molecular weight:
28180.09
Reactions
6-Thioinosine-5'-monophosphate + S-Adenosylmethionine → 6-Methylthiopurine 5'-monophosphate ribonucleotide + S-Adenosylhomocysteinedetails
General function:
Involved in hydrolase activity
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Molecular weight:
16833.23
Reactions
6-Mercaptopurine ribonucleoside triphosphate + Water → 6-Thioinosine-5'-monophosphate + Pyrophosphatedetails
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
Mercaptopurine + Phosphoribosyl pyrophosphate → 6-Thioinosine-5'-monophosphate + Pyrophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
Gene Name:
IMPDH2
Uniprot ID:
P12268
Molecular weight:
55804.495
Reactions
6-Thioinosine-5'-monophosphate + NAD + Water → 6-Thioxanthine 5'-monophosphate + NADH + Hydrogen Iondetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
Gene Name:
IMPDH1
Uniprot ID:
P20839
Molecular weight:
63252.24
Reactions
6-Thioinosine-5'-monophosphate + NAD + Water → 6-Thioxanthine 5'-monophosphate + NADH + Hydrogen Iondetails