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(-)-beta-Selinene

PubChem CID
28237
Structure
(-)-beta-Selinene_small.png
(-)-beta-Selinene_3D_Structure.png
Molecular Formula
Synonyms
  • (-)-beta-selinene
  • (3S,4aR,8aS)-8a-methyl-5-methylidene-3-prop-1-en-2-yl-1,2,3,4,4a,6,7,8-octahydronaphthalene
  • CHEBI:49274
  • (4aS,7S,8aR)-7-isopropenyl-4a-methyl-1-methylenedecahydronaphthalene
  • 17066-67-0
Molecular Weight
204.35 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-04
Description
(-)-beta-selinene is the (4aS,7S,8aR)-stereoisomer of beta-selinene. It is an enantiomer of a (+)-beta-selinene.
(-)-beta-Selinene has been reported in Cyperus rotundus, Hyalosperma glutinosum, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(-)-beta-Selinene.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S,4aR,8aS)-8a-methyl-5-methylidene-3-prop-1-en-2-yl-1,2,3,4,4a,6,7,8-octahydronaphthalene
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3/t13-,14+,15-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

YOVSPTNQHMDJAG-ZNMIVQPWSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(=C)[C@H]1CC[C@@]2(CCCC(=C)[C@H]2C1)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H24
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

17066-67-0

2.3.2 ChEBI ID

2.3.3 Lipid Maps ID (LM_ID)

2.3.4 Metabolomics Workbench ID

2.3.5 Nikkaji Number

2.3.6 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • beta-selinene
  • beta-selinene, ((4aalpha,7alpha,8abeta)-(+-))-isomer
  • beta-selinene, (4aR-(4aalpha,7beta,8aalpha))-isomer
  • beta-selinene, (4aS-(4aalpha,7beta,8abeta))-isomer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
204.35 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
5.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
204.187800766 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
204.187800766 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
0 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
286
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
3
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 Kovats Retention Index

Standard polar
1733

3.3 Chemical Classes

3.3.1 Lipids

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Chemical Co-Occurrences in Literature

7.4 Chemical-Gene Co-Occurrences in Literature

7.5 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

9 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

10 Classification

10.1 MeSH Tree

10.2 ChEBI Ontology

10.3 LIPID MAPS Classification

10.4 ChemIDplus

10.5 LOTUS Tree

10.6 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. ChEBI
  2. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. Japan Chemical Substance Dictionary (Nikkaji)
  5. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  6. Metabolomics Workbench
  7. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    5bH,7b,10a-selina-4(14),11-diene
    http://www.nist.gov/srd/nist1a.cfm
  8. SpectraBase
  9. Wikidata
  10. PubChem
  11. 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
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS