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(2S,3S,4R,5S)-2-(4-Amino-4,5-dihydro-1H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[(methylsulfanyl)methyl]-3,4-pyrrolidinediol

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Overview

Structure
DrugBank ID
DB02158
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
(2S,3S,4R,5S)-2-(4-Amino-4,5-dihydro-1H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-[(methylsulfanyl)methyl]-3,4-pyrrolidinediol
DrugBank Accession Number
DB02158
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 297.377
Monoisotopic: 297.125945567
Chemical Formula
C12H19N5O2S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
US-methyl-5'-thioadenosine phosphorylaseNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
YLCQGEBEQIBOOJ-BOFBLULFSA-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-{4-amino-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-7-yl}-5-[(methylsulfanyl)methyl]pyrrolidine-3,4-diol
SMILES
CSC[C@H]1N[C@H]([C@H](O)[C@@H]1O)C1=CNC2=C1N=CNC2N

References

General References
Not Available
PubChem Compound
131704191
PubChem Substance
46508814
ChemSpider
26328084
PDBe Ligand
MTM
PDB Entries
1k27 / 1y6r / 1zos / 3eei

Clinical Trials

Clinical Trials
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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 Solubility0.876 mg/mLALOGPS
logP-1.6ALOGPS
logP-1.4Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.93Chemaxon
pKa (Strongest Basic)8.38Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area118.69 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity79.17 m3·mol-1Chemaxon
Polarizability31.03 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-a8979acf9bc1d33f8d10
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001j-0090000000-69c5464b23f5b56dcb42
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0089-0590000000-10750c205abc52ff83c8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kk-2960000000-4794b98d0ccffbde0488
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1940000000-b33b3e2700b0ec4bd070
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-4910000000-631bae42e338ed3d94ec
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.64627
predicted
DeepCCS 1.0 (2019)
[M+H]+167.04182
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.69283
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. S-methyl-5'-thioadenosine phosphorylase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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 preferred substrates
Specific Function
1,4-alpha-oligoglucan phosphorylase activity
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. [Article]
  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. [Article]
Details2. 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General 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 (PubMed:16101288, PubMed:3911944). Also cleaves 5'-deoxyadenosine, a toxic by-product of radical S-adenosylmethionine (SAM) enzymes, into 5-deoxyribose and adenine. Thus, is required for in vivo function of the radical SAM enzymes biotin synthase and lipoic acid synthase, that are inhibited by 5'-deoxyadenosine accumulation (PubMed:15911379). Can also use 5'-isobutylthioadenosine, 5'-n-butylthioadenosine, S-adenosyl-D-homocysteine, decarboxylated adenosylhomocysteine, deaminated adenosylhomocysteine and S-2-aza-adenosylhomocysteine as substrates in vitro (PubMed:3911944).
Specific Function
adenosylhomocysteine nucleosidase activity
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52