(3R,4S)-1-[(4-AMINO-5H-PYRROLO[3,2-D]PYRIMIDIN-7-YL)METHYL]-4-[(METHYLSULFANYL)METHYL]PYRROLIDIN-3-OL

Identification

Name
(3R,4S)-1-[(4-AMINO-5H-PYRROLO[3,2-D]PYRIMIDIN-7-YL)METHYL]-4-[(METHYLSULFANYL)METHYL]PYRROLIDIN-3-OL
Accession Number
DB08606
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: 293.388
Monoisotopic: 293.131030945
Chemical Formula
C13H19N5OS
InChI Key
NTHMDFGHOCNNOE-ZJUUUORDSA-N
InChI
InChI=1S/C13H19N5OS/c1-20-6-9-4-18(5-10(9)19)3-8-2-15-12-11(8)16-7-17-13(12)14/h2,7,9-10,15,19H,3-6H2,1H3,(H2,14,16,17)/t9-,10+/m1/s1
IUPAC Name
(3R,4S)-1-({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)-4-[(methylsulfanyl)methyl]pyrrolidin-3-ol
SMILES
[H][C@]1(O)CN(CC2=CNC3=C(N)N=CN=C23)C[C@]1([H])CSC

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
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
656970
PubChem Substance
99445077
ChemSpider
571206
BindingDB
22113
ChEMBL
CHEMBL405346
HET
TDI
PDB Entries
1y6q / 4f2w / 4wkb / 4wkn / 4x24 / 5tc8

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 Solubility0.996 mg/mLALOGPS
logP-0.07ALOGPS
logP0.44ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)13.47ChemAxon
pKa (Strongest Basic)8.71ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area91.06 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.52 m3·mol-1ChemAxon
Polarizability31.34 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9858
Blood Brain Barrier+0.7893
Caco-2 permeable-0.5476
P-glycoprotein substrateSubstrate0.7414
P-glycoprotein inhibitor INon-inhibitor0.9209
P-glycoprotein inhibitor IINon-inhibitor0.8482
Renal organic cation transporterNon-inhibitor0.7986
CYP450 2C9 substrateNon-substrate0.8595
CYP450 2D6 substrateNon-substrate0.7339
CYP450 3A4 substrateNon-substrate0.5362
CYP450 1A2 substrateNon-inhibitor0.7749
CYP450 2C9 inhibitorNon-inhibitor0.8801
CYP450 2D6 inhibitorNon-inhibitor0.8196
CYP450 2C19 inhibitorNon-inhibitor0.8524
CYP450 3A4 inhibitorNon-inhibitor0.9747
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9445
Ames testNon AMES toxic0.5377
CarcinogenicityNon-carcinogens0.9254
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5747 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5727
hERG inhibition (predictor II)Non-inhibitor0.5605
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 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolopyrimidines
Sub Class
Not Available
Direct Parent
Pyrrolopyrimidines
Alternative Parents
Aralkylamines / Aminopyrimidines and derivatives / Substituted pyrroles / N-alkylpyrrolidines / Imidolactams / Heteroaromatic compounds / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Sulfenyl compounds
show 5 more
Substituents
Pyrrolopyrimidine / Aminopyrimidine / Aralkylamine / Pyrimidine / Substituted pyrrole / N-alkylpyrrolidine / Imidolactam / Heteroaromatic compound / Pyrrole / Pyrrolidine
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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. 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 September 15, 2010 15:33 / Updated on June 02, 2018 08:09