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

Identification

Generic Name
(3R,4S)-1-[(4-AMINO-5H-PYRROLO[3,2-D]PYRIMIDIN-7-YL)METHYL]-4-[(METHYLSULFANYL)METHYL]PYRROLIDIN-3-OL
DrugBank Accession Number
DB08606
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 293.388
Monoisotopic: 293.131030945
Chemical Formula
C13H19N5OS
Synonyms
Not Available

Pharmacology

Indication

Not Available

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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

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
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / Alcohol / Amine / Aminopyrimidine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Dialkylthioether / Heteroaromatic compound / Hydrocarbon derivative
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
656970
PubChem Substance
99445077
ChemSpider
571206
BindingDB
22113
ChEMBL
CHEMBL405346
ZINC
ZINC000011686540
PDBe Ligand
TDI
PDB Entries
1y6q / 4f2w / 4wkb / 4wkn / 4x24 / 5tc8 / 6ayq

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)8.42Chemaxon
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-MSsplash10-01ta-6890000000-f5293d73ee0a660faccd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-76873a0d616b090e5d3f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0290000000-b9ae60c93afae1a9b5d4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0390000000-834eca1aab6a0a6f3ee0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ba-0190000000-298af6dbd91e7333103e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0019-0960000000-157dbdc24f78dd73d404
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f7p-9460000000-e8d99a7ed14b221869a4
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]-161.69115
predicted
DeepCCS 1.0 (2019)
[M+H]+164.04915
predicted
DeepCCS 1.0 (2019)
[M+Na]+170.97198
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52