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Basic Description
| Synonyms | L7995C4D7F | 4-Amino-7-.beta.-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine-5-carbonitrile | NSC-99843 | Antibiotic E212 | 4-Amino-7-beta-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile | BDBM50049823 | Toyocamycin, >=98% (HPLC), from Streptomyce |
|---|---|
| Specifications & Purity | ≥98% |
| Biochemical and Physiological Mechanisms | Selective IRE1α inhibitor. Adenosine analog. PI3-kinase inhibitor. Inhibits RNA self-cleavage. Induces apoptosis in cancer cell lines. Suppresses thapsigargin-, tunicamycin- and 2-deoxyglucose-induced XBP1 mRNA splicing. |
| Storage Temp | Store at -20°C,Desiccated |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
| Product Description |
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Taxonomic Classification
Taxonomy Tree
- Kingdom Organic compounds
| Kingdom | Organic compounds |
|---|---|
| Superclass | Nucleosides, nucleotides, and analogues |
| Class | Pyrrolopyrimidine nucleosides and nucleotides |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyrrolopyrimidine nucleosides and nucleotides |
| Alternative Parents | Glycosylamines Pentoses Pyrrolo[2,3-d]pyrimidines Aminopyrimidines and derivatives Substituted pyrroles Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Azacyclic compounds Oxacyclic compounds Nitriles Primary amines Hydrocarbon derivatives Organopnictogen compounds Primary alcohols |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Pyrrolopyrimidine ribonucleoside - Glycosyl compound - N-glycosyl compound - Pentose monosaccharide - Pyrrolo[2,3-d]pyrimidine - Pyrrolopyrimidine - Aminopyrimidine - Monosaccharide - Pyrimidine - Imidolactam - Substituted pyrrole - Heteroaromatic compound - Pyrrole - Tetrahydrofuran - Secondary alcohol - Carbonitrile - Nitrile - Oxacycle - Azacycle - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Amine - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Organic nitrogen compound - Primary alcohol - Primary amine - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7. |
| External Descriptors | Not available |
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Associated Targets(Human)
MAOA
Tclin
Monoamine oxidase A (11911 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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MAOB
Tclin
Monoamine oxidase B (8835 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ADK
Tchem
Adenosine kinase (1481 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HFF (3142 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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KB (17409 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HeLa (62764 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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DOT1L
Tchem
Histone-lysine N-methyltransferase, H3 lysine-79 specific (648 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
Associated Targets(non-human)
Hdac6
Histone deacetylase 6 (222 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Candida albicans (78123 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Human alphaherpesvirus 2 (4932 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Human respirovirus 3 (1674 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Human betaherpesvirus 5 (5122 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Oryctolagus cuniculus (11301 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Vaccinia virus (4609 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Human alphaherpesvirus 1 (11089 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Poliovirus 1 (1274 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Sindbis virus (1599 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Vesicular stomatitis virus (4460 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Coxsackievirus B4 (2249 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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B16 (5829 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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L1210 (27553 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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P388 (20296 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Vero (26788 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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rep
Replicase polyprotein 1ab (378 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mammalian orthoreovirus 1 (1523 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Simplexvirus (54 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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HSPA8
Heat shock cognate 71 kDa protein (1 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| Pubchem Sid | 504752203 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504752203 |
| IUPAC Name | 4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile |
| INCHI | InChI=1S/C12H13N5O4/c13-1-5-2-17(11-7(5)10(14)15-4-16-11)12-9(20)8(19)6(3-18)21-12/h2,4,6,8-9,12,18-20H,3H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1 |
| InChIKey | XOKJUSAYZUAMGJ-WOUKDFQISA-N |
| Smiles | C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)C#N |
| Isomeric SMILES | C1=C(C2=C(N=CN=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)C#N |
| PubChem CID | 11824 |
| Molecular Weight | 291.26 |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 C2303055 |
Certificate of Analysis | Dec 22, 2023 | T275971 |
| C2303060 |
Certificate of Analysis | Dec 22, 2023 | T275971 |
| C2303061 |
Certificate of Analysis | Dec 22, 2023 | T275971 |
Chemical and Physical Properties
| Molecular Weight | 291.260 g/mol |
|---|---|
| XLogP3 | -1.600 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 2 |
| Exact Mass | 291.097 Da |
| Monoisotopic Mass | 291.097 Da |
| Topological Polar Surface Area | 150.000 Ų |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Complexity | 443.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
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