5'-Deoxy-5'-Methylthioadenosine

Identification

Name
5'-Deoxy-5'-Methylthioadenosine
Accession Number
DB02282  (EXPT02241)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-335422
Categories
UNII
634Z2VK3UQ
CAS number
Not Available
Weight
Average: 297.334
Monoisotopic: 297.089560061
Chemical Formula
C11H15N5O3S
InChI Key
WUUGFSXJNOTRMR-IOSLPCCCSA-N
InChI
InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
IUPAC Name
(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
SMILES

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UModification methylase RsrINot AvailableRhodobacter sphaeroides
US-methyl-5'-thioadenosine phosphorylaseNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcepromazineThe serum concentration of Acepromazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Vet Approved
AceprometazineThe serum concentration of Aceprometazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
AlimemazineThe serum concentration of Alimemazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Vet Approved
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
BL-1020The serum concentration of BL-1020 can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Investigational
ChlorproethazineThe serum concentration of Chlorproethazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Experimental
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Vet Approved
DapsoneThe risk or severity of adverse effects can be increased when 5'-Deoxy-5'-Methylthioadenosine is combined with Dapsone.Approved, Investigational
FluphenazineThe serum concentration of Fluphenazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
LumefantrineThe risk or severity of adverse effects can be increased when 5'-Deoxy-5'-Methylthioadenosine is combined with Lumefantrine.Approved
MesoridazineThe serum concentration of Mesoridazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Investigational
MethotrimeprazineThe serum concentration of Methotrimeprazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
Methylene blueThe serum concentration of Methylene blue can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Investigational
MoricizineThe serum concentration of Moricizine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Investigational, Withdrawn
PerazineThe serum concentration of Perazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Investigational
PerphenazineThe serum concentration of Perphenazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
ProchlorperazineThe serum concentration of Prochlorperazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Vet Approved
PromazineThe serum concentration of Promazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Vet Approved
PromethazineThe serum concentration of Promethazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
PropericiazineThe serum concentration of Propericiazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
PropiopromazineThe serum concentration of Propiopromazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Vet Approved
ThiazinamThe serum concentration of Thiazinam can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Experimental
ThiethylperazineThe serum concentration of Thiethylperazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Withdrawn
ThioproperazineThe serum concentration of Thioproperazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Withdrawn
TrifluoperazineThe serum concentration of Trifluoperazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
TriflupromazineThe serum concentration of Triflupromazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, Vet Approved
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01173
KEGG Compound
C00170
PubChem Compound
439176
PubChem Substance
46508330
ChemSpider
388321
BindingDB
22111
ChEBI
17509
ChEMBL
CHEMBL277041
HET
MTA
PDB Entries
1cg6 / 1eg2 / 1jdt / 1z5o / 2a8y / 2e5w / 2hte / 2ipx / 2o05 / 2o06
show 35 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.5 mg/mLALOGPS
logP-0.14ALOGPS
logP-0.61ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.31 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.03 m3·mol-1ChemAxon
Polarizability29.26 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7984
Caco-2 permeable-0.7152
P-glycoprotein substrateNon-substrate0.5431
P-glycoprotein inhibitor INon-inhibitor0.9292
P-glycoprotein inhibitor IINon-inhibitor0.9741
Renal organic cation transporterNon-inhibitor0.9405
CYP450 2C9 substrateNon-substrate0.8436
CYP450 2D6 substrateNon-substrate0.8225
CYP450 3A4 substrateSubstrate0.5148
CYP450 1A2 substrateNon-inhibitor0.895
CYP450 2C9 inhibitorNon-inhibitor0.8866
CYP450 2D6 inhibitorNon-inhibitor0.9371
CYP450 2C19 inhibitorNon-inhibitor0.8575
CYP450 3A4 inhibitorNon-inhibitor0.9365
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9444
Ames testNon AMES toxic0.5859
CarcinogenicityNon-carcinogens0.9304
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3307 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9821
hERG inhibition (predictor II)Non-inhibitor0.874
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-000i-0940000000-16b1106966ac98c7a107
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-0940000000-16b1106966ac98c7a107
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-000i-0940000000-30fc68e7b5ff7576069b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-01ti-0900000000-312bd8eec3c461e919f9
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000j-0940000000-55655e7a0a6c8acba0f0
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-000i-1900000000-f37865ca2029a623ace7
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-000i-2900000000-ae0e3df9bf25c100940d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0002-0090000000-72139812c5b2ede077ed
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-000i-0910000000-0c3d173f36272e3271eb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-000i-0900000000-f3443ca133811f52c5d7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-000i-1900000000-49cc299525d7fca27818
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-000i-3900000000-39bebdcaa7ce2695465b
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-000i-0900000000-76b935f4f0a78c15ca0e
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0002-4900000000-d8c0df43305b934d71dc
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-000i-0900000000-d3bfbeb6fb95e3768ef6
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0910000000-56784be58ef9065f21f6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0910000000-56784be58ef9065f21f6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-0090000000-72139812c5b2ede077ed
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0910000000-0c3d173f36272e3271eb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0900000000-f3443ca133811f52c5d7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-1900000000-6ec86a11bf8ad7331bd2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-3900000000-39bebdcaa7ce2695465b
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-b9006ef8eecdaefc89a6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-949c013f4e9edec10cb9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-d3bfbeb6fb95e3768ef6
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
5'-deoxyribonucleosides
Sub Class
5'-deoxy-5'-thionucleosides
Direct Parent
5'-deoxy-5'-thionucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Pentoses / Aminopyrimidines and derivatives / Imidolactams / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / 1,2-diols / Secondary alcohols
show 7 more
Substituents
5'-deoxy-5'-thionucleoside / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Pentose monosaccharide / Imidazopyrimidine / Purine / Aminopyrimidine / Monosaccharide / N-substituted imidazole
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
thioadenosine (CHEBI:17509)

Targets

Kind
Protein
Organism
Rhodobacter sphaeroides
Pharmacological action
Unknown
General Function
Site-specific dna-methyltransferase (adenine-specific) activity
Specific Function
This methylase recognizes the double-stranded sequence GAATTC, causes specific methylation on A-? on both strands, and protects the DNA from cleavage by the RsrI endonuclease.
Gene Name
rsrIM
Uniprot ID
P14751
Uniprot Name
Modification methylase RsrI
Molecular Weight
35654.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
S-methyl-5-thioadenosine phosphorylase activity
Specific Function
Catalyzes the reversible phosphorylation of S-methyl-5'-thioadenosine (MTA) to adenine and 5-methylthioribose-1-phosphate. Involved in the breakdown of MTA, a major by-product of polyamine biosynth...
Gene Name
MTAP
Uniprot ID
Q13126
Uniprot Name
S-methyl-5'-thioadenosine phosphorylase
Molecular Weight
31235.76 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:12