Basic information
- CAS
24386-93-4- Standard SMILES
Nc1ncnc2c1c(I)cn2C1OC(CO)C(O)C1O- InChIKey
WHSIXKUPQCKWBY-UHFFFAOYSA-N- Molecular formula
- C11H13IN4O4
- Average molar mass
- 392.15 g/mol
- Monoisotopic mass
- 391.99815
Overview
2-(4-amino-5-iodo-7-pyrrolo[2,3-d]pyrimidinyl)-5-(hydroxymethyl)oxolane-3,4-diol is a nucleobase-containing molecular entity.
Names & identifiers
- Preferred name
- 7-Iodo-7-deaza-D-guanosine
- IUPAC
- 2-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- English name
- 5-IODOTUBERCIDIN
- Molecular formula
- C11H13IN4O4
- Molecular weight
- 392.15
Names & synonyms
7-Iodo-7-deaza-D-guanosine(2S,3S,4R,5S)-2-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diolITUBiomolKI_000049BiomolKI2_000055BMK1-F1BSPBio_001227KBioGR_000567KBioSS_000567CHEMBL633884-Amino-5-iodo-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidineSCHEMBL2043545
Show more names
5-IODOTUBERICIDIN5-ITuCS-824NSC 113939IODOTUBERCIDIN7-I-7-Deaza-Ar5-IODOTUBERCIDINIodotubercidin,Itu5-Iodo-Tubercidine
CHEBI:93817KBio2_000567KBio2_003135KBio2_005703KBio3_001013KBio3_001014WHSIXKUPQCKWBY-UHFFFAOYSA-NBio2_000444
Database identifiers
- CAS
24386-93-4- PubChem CID
- 1830
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 127 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 365
Physicochemical properties
- Melting point
- 216 · 216-217°C dec.
- Boiling point
- 701.5 · 701.5±60.0 °C(Predicted)
- Density
- 2.49 · 2.49±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 0.1 M · 0.1 M HCl: 0.7 mg/mL
- form
- solid
- pka
- 12.33 · 12.33±0.70(Predicted)
- color
- tan
- Stability
- 4 °C; · Store tightly sealed at 4°C; Light Sensitive
- InChI
- InChI=1/C11H13IN4O4/c12-4-1-16(10-6(4)9(13)14-3-15-10)11-8(19)7(18)5(2-17)20-11/h1,3,5,7-8,11,17-19H,2H2,(H2,13,14,15)/t5-,7-,8-,11-/s3
- InChIKey
- WHSIXKUPQCKWBY-IOSLPCCCSA-N
- SMILES
- N1(C=C(I)C2C(N)=NC=NC1=2)[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 |&1:11,12,14,16,r|
- CAS DataBase Reference
- 24386 · 24386-93-4
- UNSPSC Code
- 12352202 · 12352202
- NACRES
- 77 · NA.77
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29349990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Applications
UsesAn analogue of the antibiotic tubercidin, a pyrrolo[2,3-d]pyrimidine nucleoside antibiotic. A potent inhibitor of adenosine kinase from rat or guinea pig brain. Inhibits uptake of 3H-adenosine into brain slices.
UsesA potent and competitive inhibitor of ERK2, PKA, and ADK.
Uses5-Iodotubercidin has been used for the inhibition of retinoblastoma cells, astroglial cultures and for the inhibition of adenosine kinase in human umbilical vein endothelial cells (HUVECs).
General Descriptionsolubility: 10 mg/mL in DMSO
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
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