5'-Deoxy-5'-(Methylthio)-Tubercidin

Identification

Name
5'-Deoxy-5'-(Methylthio)-Tubercidin
Accession Number
DB02933  (EXPT02244)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 296.345
Monoisotopic: 296.094311088
Chemical Formula
C12H16N4O3S
InChI Key
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][[email protected]]1(CSC)O[[email protected]@]([H])(N2C=CC3=C(N)N=CN=C23)[[email protected]]([H])(O)[[email protected]]1([H])O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
US-methyl-5'-thioadenosine phosphorylaseNot AvailableHuman
U5'-methylthioadenosine/S-adenosylhomocysteine nucleosidaseNot AvailableEscherichia coli (strain K12)
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
188350
PubChem Substance
46507618
ChemSpider
163705
ChEMBL
CHEMBL551561
HET
MTH
PDB Entries
1nc1 / 1sd2 / 2qtg / 5tc7

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 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This 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).
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Glycosylamines
Alternative Parents
Pentoses / Pyrrolo[2,3-d]pyrimidines / Aminopyrimidines and derivatives / Substituted pyrroles / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / 1,2-diols / Secondary alcohols / Sulfenyl compounds
show 6 more
Substituents
N-glycosyl compound / Pentose monosaccharide / Pyrrolo[2,3-d]pyrimidine / Pyrrolopyrimidine / Aminopyrimidine / Monosaccharide / Pyrimidine / Imidolactam / Substituted pyrrole / Heteroaromatic compound
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
N-glycosylpyrrolopyrimidine (CHEBI:44164)

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 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]
  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'-methylthiorib...
Gene Name
mtnN
Uniprot ID
P0AF12
Uniprot Name
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:05