Identification
Name5'-Deoxy-5'-Methylthioadenosine
Accession NumberDB02282  (EXPT02241)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs NSC-335422
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII634Z2VK3UQ
CAS numberNot Available
WeightAverage: 297.334
Monoisotopic: 297.089560061
Chemical FormulaC11H15N5O3S
InChI KeyWUUGFSXJNOTRMR-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
CSC[[email protected]]1O[[email protected]]([[email protected]](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Modification methylase RsrIProteinunknownNot AvailableRhodobacter sphaeroidesP14751 details
S-methyl-5'-thioadenosine phosphorylaseProteinunknownNot AvailableHumanQ13126 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot 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
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
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.Investigational
MoricizineThe serum concentration of Moricizine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Approved, 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
ThiethylperazineThe serum concentration of Thiethylperazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.Withdrawn
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with 5'-Deoxy-5'-Methylthioadenosine.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
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-000i-0940000000-16b1106966ac98c7a107View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000i-0940000000-30fc68e7b5ff7576069bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-000i-0940000000-30fc68e7b5ff7576069bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-01ti-0900000000-312bd8eec3c461e919f9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-01ti-0900000000-312bd8eec3c461e919f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000j-0940000000-55655e7a0a6c8acba0f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-f37865ca2029a623ace7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2900000000-ae0e3df9bf25c100940dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0090000000-72139812c5b2ede077edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-0910000000-0c3d173f36272e3271ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-0900000000-f3443ca133811f52c5d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-1900000000-49cc299525d7fca27818View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000i-3900000000-39bebdcaa7ce2695465bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-76b935f4f0a78c15ca0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0002-4900000000-d8c0df43305b934d71dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0900000000-d3bfbeb6fb95e3768ef6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0910000000-56784be58ef9065f21f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-6ec86a11bf8ad7331bd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-b9006ef8eecdaefc89a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-949c013f4e9edec10cb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub Class5'-deoxyribonucleosides
Direct Parent5'-deoxy-5'-thionucleosides
Alternative ParentsGlycosylamines / 6-aminopurines / Pentoses / Aminopyrimidines and derivatives / Primary aromatic amines / Imidolactams / N-substituted imidazoles / Oxolanes / Heteroaromatic compounds / 1,2-diols
Substituents5'-deoxy-5'-thionucleoside / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / 6-aminopurine / Purine / Imidazopyrimidine / Aminopyrimidine / Primary aromatic amine / Pyrimidine
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsthioadenosine (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
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 biosynthesis. Responsible for the first step in the methionine salvage pathway after MTA has been generated from S-adenosylmethionine. Has broad substrate specificity with 6-aminopurine nucleosides as preferr...
Gene Name:
MTAP
Uniprot ID:
Q13126
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 July 18, 2017 17:07