You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
Name(1s)-1-(9-Deazaadenin-9-Yl)-1,4,5-Trideoxy-1,4-Imino-5-Methylthio-D-Ribitol
Accession NumberDB02158  (EXPT02247)
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: 297.377
Monoisotopic: 297.125945567
Chemical FormulaC12H19N5O2S
InChI KeyYLCQGEBEQIBOOJ-XKBJCNPTSA-N
InChI
InChI=1S/C12H19N5O2S/c1-20-3-6-10(18)11(19)8(17-6)5-2-14-9-7(5)15-4-16-12(9)13/h2,4,6,8,10-12,14,17-19H,3,13H2,1H3,(H,15,16)/t6-,8+,10-,11+,12-/m1/s1
IUPAC Name
(2S,3S,4R,5S)-2-[(4R)-4-amino-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-7-yl]-5-[(methylsulfanyl)methyl]pyrrolidine-3,4-diol
SMILES
CSC[[email protected]]1N[[email protected]]([[email protected]](O)[C@@H]1O)C1=CNC2=C1N=CN[[email protected]]2N
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
S-methyl-5'-thioadenosine phosphorylaseProteinunknownNot AvailableHumanQ13126 details
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidaseProteinunknownNot AvailableEscherichia coli (strain K12)P0AF12 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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
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
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9909
Blood Brain Barrier+0.6089
Caco-2 permeable-0.6451
P-glycoprotein substrateSubstrate0.7105
P-glycoprotein inhibitor INon-inhibitor0.9424
P-glycoprotein inhibitor IINon-inhibitor0.9199
Renal organic cation transporterNon-inhibitor0.8154
CYP450 2C9 substrateNon-substrate0.7087
CYP450 2D6 substrateNon-substrate0.7783
CYP450 3A4 substrateNon-substrate0.5355
CYP450 1A2 substrateNon-inhibitor0.6059
CYP450 2C9 inhibitorNon-inhibitor0.8653
CYP450 2D6 inhibitorNon-inhibitor0.7927
CYP450 2C19 inhibitorNon-inhibitor0.6957
CYP450 3A4 inhibitorNon-inhibitor0.8012
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.86
Ames testNon AMES toxic0.5457
CarcinogenicityNon-carcinogens0.9348
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5015 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.979
hERG inhibition (predictor II)Non-inhibitor0.7818
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 Solubility0.876 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.4ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.93ChemAxon
pKa (Strongest Basic)8.64ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area118.69 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.17 m3·mol-1ChemAxon
Polarizability31.06 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolopyrimidines
Sub ClassNot Available
Direct ParentPyrrolopyrimidines
Alternative Parents
Substituents
  • Pyrrolopyrimidine
  • Aralkylamine
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrolidine
  • Pyrrole
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Azacycle
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot 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 ]
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 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23