Isopentenyladenosine
Basic information
- CAS
7724-76-7- Standard SMILES
CC(C)=CCNc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O- InChIKey
USVMJSALORZVDV-SDBHATRESA-N- Molecular formula
- C15H21N5O4
- Average molar mass
- 335.36 g/mol
- Monoisotopic mass
- 335.15935417
Overview
N(6)-(Delta(2)-isopentenyl)adenosine is a nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a 2-isopentenyl group. It has a role as a plant growth regulator, an antineoplastic agent and a plant metabolite. It is a N-ribosyl-N(6)-isopentenyladenine and a nucleoside analogue. It is functionally related to an adenosine.
Names & identifiers
- Preferred name
- Isopentenyladenosine
- IUPAC
- (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
- English name
- N6-Isopentenyladenosine-d6
- Molecular formula
- C15H21N5O4
- Molecular weight
- 335.36
Names & synonyms
7724-76-7RiboprineN6-IsopentenyladenosineIsopentenyladenosine2iPARiboprinaIsopentenyladenosine ribosideADENOSINE, N-(3-METHYL-2-BUTENYL)-Riboprinum2-IPA6-(3-Methyl-2-butenylamino)purine ribosideN-(3-methylbut-2-en-1-yl)adenosine
Show more names
sq22558Aids126321Aids-1263212-IP RIBOSIDEN6-(Δ2-Isopent
DTXSID1057828N-IsopentenyladenosineNSC-1055468EU82FAZ5JN(6)-(Delta(2)-isopentenyl)adenosineN6-(2-isopentenyl)-adenosine(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diolDTXCID2031617
Database identifiers
- CAS
7724-76-7- PubChem CID
- 24405
- DTXSID
DTXSID1057828- ChEMBL
CHEMBL452867- ChEBI
CHEBI:62881- UNII
- 8EU82FAZ5J
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 126 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 5
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 461
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 142 · 142-143 °C(Solv: ethanol (64-17-5))
- Boiling point
- 647.2 · 647.2±65.0 °C(Predicted)
- Density
- 1.56 · 1.56±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
- form
- Solid
- pka
- 13.12 · 13.12±0.70(Predicted)
- color
- White to Light Beige
- FDA UNII
- 8 EU82FAZ5J · 8EU82FAZ5J
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
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
- wgk
- 3
- rtecs
- AU7404910
- hs_code
- 29400090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.
Applications
DescriptionN6-(Δ2-Isopentenyl)adenosine is a precursor in the biosynthesis of the plant hormone N6-(Δ2-isopentenyl)adenine . N6-(Δ2-isopentenyl)adenine may be converted to the cytokinin trans-zeatin by cytochrome P450 mono-oxygenases. Cytokinins, including N6-(Δ2-isopentenyl)adenine and trans-zeatin, regulate diverse events in plant growth and development. N6-(Δ2-Isopentenyl)adenosine can also alter post-transcriptional processes in mammalian cells, altering proliferation and apoptosis.
Uses[2H6] N6-Isopentenyladenosine-D6 can be used as analyte in analytical study for acetylation of cytokinins and modified adenine compounds for gas chromatography-mass spectrometric analysis.
UsesN6-Isopentenyladenosine has antiproliferative activity on MCF-7 breast cancer cells.
Additional notes
DefinitionChEBI: A nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a Delta2-isopentenyl group.
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