(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(benzylsulfanyl)methyl]pyrrolidin-3-ol
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Identification
- Generic Name
- (3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(benzylsulfanyl)methyl]pyrrolidin-3-ol
- DrugBank Accession Number
- DB07649
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 369.484
Monoisotopic: 369.162331073 - Chemical Formula
- C19H23N5OS
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Not Available Escherichia coli O157:H7 - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Aminopyrimidines and derivatives / Aralkylamines / Benzene and substituted derivatives / Imidolactams / N-alkylpyrrolidines / Substituted pyrroles / Heteroaromatic compounds / Trialkylamines / 1,2-aminoalcohols / Secondary alcohols show 6 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Amine / Aminopyrimidine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Dialkylthioether / Heteroaromatic compound show 21 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
- DIGGNILBPCEZIV-CVEARBPZSA-N
- InChI
- InChI=1S/C19H23N5OS/c20-19-18-17(22-12-23-19)14(6-21-18)7-24-8-15(16(25)9-24)11-26-10-13-4-2-1-3-5-13/h1-6,12,15-16,21,25H,7-11H2,(H2,20,22,23)/t15-,16+/m1/s1
- IUPAC Name
- (3R,4S)-1-({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)-4-[(benzylsulfanyl)methyl]pyrrolidin-3-ol
- SMILES
- [H][C@]1(O)CN(CC2=CNC3=C2N=CN=C3N)C[C@]1([H])CSCC1=CC=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 10067695
- PubChem Substance
- 99444120
- ChemSpider
- 8243235
- ChEMBL
- CHEMBL1232180
- ZINC
- ZINC000013647999
- PDBe Ligand
- DF9
- PDB Entries
- 3df9
Clinical Trials
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
Property Value Source Water Solubility 0.0551 mg/mL ALOGPS logP 1.54 ALOGPS logP 2.06 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 13.47 Chemaxon pKa (Strongest Basic) 8.38 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 91.06 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 107.18 m3·mol-1 Chemaxon Polarizability 40.51 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9868 Blood Brain Barrier + 0.8625 Caco-2 permeable - 0.5294 P-glycoprotein substrate Substrate 0.7052 P-glycoprotein inhibitor I Non-inhibitor 0.8092 P-glycoprotein inhibitor II Non-inhibitor 0.735 Renal organic cation transporter Non-inhibitor 0.6906 CYP450 2C9 substrate Non-substrate 0.8581 CYP450 2D6 substrate Non-substrate 0.681 CYP450 3A4 substrate Non-substrate 0.5973 CYP450 1A2 substrate Non-inhibitor 0.7152 CYP450 2C9 inhibitor Non-inhibitor 0.8434 CYP450 2D6 inhibitor Non-inhibitor 0.7507 CYP450 2C19 inhibitor Non-inhibitor 0.7804 CYP450 3A4 inhibitor Non-inhibitor 0.9143 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8082 Ames test Non AMES toxic 0.5259 Carcinogenicity Non-carcinogens 0.9096 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4831 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.58 hERG inhibition (predictor II) Inhibitor 0.667
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0019000000-dee4bbb5f2c04174b04a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0fk9-1239000000-788f1260ce66d9581158 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0249000000-16c4df8e3de9cd21477f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-006x-6964000000-0377642441813548099f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0190000000-5542f113cbfcf4fe980e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-007o-9738000000-153aefbce201722ce284 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.5146 predictedDeepCCS 1.0 (2019) [M+H]+ 187.87263 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.38979 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli O157:H7
- 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.
- Specific Function
- Adenosylhomocysteine nucleosidase activity
- Gene Name
- mtnN
- Uniprot ID
- P0AF14
- Uniprot Name
- 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
- Molecular Weight
- 24353.725 Da
References
- 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 21:24 / Updated at June 12, 2020 16:52