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Identification
Name5'-Deoxy-5'-(Methylthio)-Tubercidin
Accession NumberDB02933  (EXPT02244)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers 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
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 296.345
Monoisotopic: 296.094311088
Chemical FormulaC12H16N4O3S
InChI KeyInChIKey=WBPLMFVTQMIPLW-MFYTUXHUSA-N
InChI
InChI=1S/C12H16N4O3S/c1-20-4-7-8(17)9(18)12(19-7)16-3-2-6-10(13)14-5-15-11(6)16/h2-3,5,7-9,12,17-18H,4H2,1H3,(H2,13,14,15)/t7-,8-,9-,12-/m1/s1
IUPAC Name
(2R,3R,4S,5S)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
SMILES
[H][C@]1(CSC)O[C@@]([H])(N2C=CC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • Pyrrolopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Substituted pyrrole
  • Pyrimidine
  • Primary aromatic amine
  • Monosaccharide
  • Heteroaromatic compound
  • Pyrrole
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8637
Caco-2 permeable-0.7003
P-glycoprotein substrateNon-substrate0.6412
P-glycoprotein inhibitor INon-inhibitor0.9308
P-glycoprotein inhibitor IINon-inhibitor0.9451
Renal organic cation transporterNon-inhibitor0.939
CYP450 2C9 substrateNon-substrate0.8191
CYP450 2D6 substrateNon-substrate0.8248
CYP450 3A4 substrateSubstrate0.521
CYP450 1A2 substrateNon-inhibitor0.8809
CYP450 2C9 inhibitorNon-inhibitor0.8696
CYP450 2D6 inhibitorNon-inhibitor0.9366
CYP450 2C19 inhibitorNon-inhibitor0.8407
CYP450 3A4 inhibitorNon-inhibitor0.9246
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9375
Ames testNon AMES toxic0.5887
CarcinogenicityNon-carcinogens0.9367
BiodegradationNot ready biodegradable0.9959
Rat acute toxicity2.5582 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9849
hERG inhibition (predictor II)Non-inhibitor0.8708
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.64 mg/mLALOGPS
logP0.04ALOGPS
logP0.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)7.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.42 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity76.21 m3·mol-1ChemAxon
Polarizability29.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Methylthioadenosine nucleosidase activity
Specific Function:
Catalyzes the irreversible cleavage of the glycosidic bond in both 5'-methylthioadenosine (MTA) and S-adenosylhomocysteine (SAH/AdoHcy) to adenine and the corresponding thioribose, 5'-methylthioribose and S-ribosylhomocysteine, respectively. Can also use 5'-isobutylthioadenosine, 5'-n-butylthioadenosine, S-adenosyl-D-homocysteine, decarboxylated adenosylhomocysteine, deaminated adenosylhomocyst...
Gene Name:
mtnN
Uniprot ID:
P0AF12
Molecular Weight:
24353.725 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 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23