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(R)-N-(1-Methyl-2-phenylethyl)adenosine

PubChem CID
93205
Structure
(R)-N-(1-Methyl-2-phenylethyl)adenosine_small.png
(R)-N-(1-Methyl-2-phenylethyl)adenosine_3D_Structure.png
Molecular Formula
Synonyms
  • 38594-96-6
  • (R)-PIA
  • (-)-N6-(2-Phenylisopropyl)adenosine
  • (-)-(Phenylisopropyl)adenosine
  • (-)-N6-(2-PHENYLISOPROPYL)-ADENOSINE
Molecular Weight
385.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18
Description
(-)-n6-(2-phenylisopropyl)adenosine is a purine nucleoside.
N-Isopropyl-N-phenyl-adenosine. Antilipemic agent. Synonym: TH 162.
See also: Phenylisopropyladenosine (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(R)-N-(1-Methyl-2-phenylethyl)adenosine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[[(2R)-1-phenylpropan-2-yl]amino]purin-9-yl]oxolane-3,4-diol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C19H23N5O4/c1-11(7-12-5-3-2-4-6-12)23-17-14-18(21-9-20-17)24(10-22-14)19-16(27)15(26)13(8-25)28-19/h2-6,9-11,13,15-16,19,25-27H,7-8H2,1H3,(H,20,21,23)/t11-,13-,15-,16-,19-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RIRGCFBBHQEQQH-SSFGXONLSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C[C@H](CC1=CC=CC=C1)NC2=C3C(=NC=N2)N(C=N3)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C19H23N5O4
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 Deprecated CAS

129601-64-5, 31747-27-0

2.3.3 European Community (EC) Number

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 Nikkaji Number

2.3.8 Pharos Ligand ID

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Isopropylphenyladenosine
  • L Phenylisopropyladenosine
  • L-Phenylisopropyladenosine
  • N(6)-Phenylisopropyl-Adenosine
  • Phenylisopropyladenosine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
385.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
385.17500423 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
385.17500423 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
126 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
28
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
509
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
5
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Solubility

>57.8 [ug/mL] (The mean of the results at pH 7.4)

5 Chemical Vendors

6 Literature

6.1 Consolidated References

6.2 NLM Curated PubMed Citations

6.3 Springer Nature References

6.4 Chemical Co-Occurrences in Literature

6.5 Chemical-Gene Co-Occurrences in Literature

6.6 Chemical-Disease Co-Occurrences in Literature

7 Patents

7.1 Depositor-Supplied Patent Identifiers

7.2 WIPO PATENTSCOPE

7.3 Chemical Co-Occurrences in Patents

7.4 Chemical-Disease Co-Occurrences in Patents

7.5 Chemical-Gene Co-Occurrences in Patents

8 Interactions and Pathways

8.1 Chemical-Target Interactions

9 Biological Test Results

9.1 BioAssay Results

10 Classification

10.1 MeSH Tree

10.2 ChEBI Ontology

10.3 ChemIDplus

10.4 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

10.5 ChEMBL Target Tree

10.6 EPA DSSTox Classification

10.7 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. Burnham Center for Chemical Genomics
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. ChEBI
  7. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  8. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  9. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  10. Therapeutic Target Database (TTD)
  11. Japan Chemical Substance Dictionary (Nikkaji)
  12. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
    2-Hydroxymethyl-5-[6-(1-methyl-2-phenyl-ethylamino)-purin-9-yl]-tetrahydro-furan-3,4-diol
    https://pharos.nih.gov/ligands/41PRC3TZL693
  13. Springer Nature
  14. Wikidata
  15. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  16. PubChem
  17. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  18. PATENTSCOPE (WIPO)
CONTENTS