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(5Z)-5-((2E,4E,6E,8E)-11-((4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2,9-dimethyl-2,4,6,8-undecatetraen-10-yn-1-ylidene)-3-((1E)-2-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo(4.1.0)hept-1-yl)ethenyl)-2(5H)-furanone

PubChem CID
134741793
Structure
(5Z)-5-((2E,4E,6E,8E)-11-((4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2,9-dimethyl-2,4,6,8-undecatetraen-10-yn-1-ylidene)-3-((1E)-2-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo(4.1.0)hept-1-yl)ethenyl)-2(5H)-furanone_small.png
(5Z)-5-((2E,4E,6E,8E)-11-((4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2,9-dimethyl-2,4,6,8-undecatetraen-10-yn-1-ylidene)-3-((1E)-2-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo(4.1.0)hept-1-yl)ethenyl)-2(5H)-furanone_3D_Structure.png
Molecular Formula
Synonyms
  • 54369-11-8
  • (5Z)-5-[(2E,4E,6E,8E)-11-[(4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl]-2,9-dimethyl-2,4,6,8-undecatetraen-10-yn-1-ylidene]-3-[(1E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl]-2(5H)-furanone
  • (5Z)-5-((2E,4E,6E,8E)-11-((4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2,9-dimethyl-2,4,6,8-undecatetraen-10-yn-1-ylidene)-3-((1E)-2-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo(4.1.0)hept-1-yl)ethenyl)-2(5H)-furanone
  • DTXSID001098105
  • Q63409127
Molecular Weight
570.8 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2018-09-05
  • Modify:
    2025-01-18
Description
(5Z)-5-[(2E,4E,6E,8E)-11-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-2,9-dimethylundeca-2,4,6,8-tetraen-10-ynylidene]-3-[(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]furan-2-one has been reported in Corbicula japonica, Mytilus coruscus, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(5Z)-5-((2E,4E,6E,8E)-11-((4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2,9-dimethyl-2,4,6,8-undecatetraen-10-yn-1-ylidene)-3-((1E)-2-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo(4.1.0)hept-1-yl)ethenyl)-2(5H)-furanone.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5Z)-5-[(2E,4E,6E,8E)-11-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-2,9-dimethylundeca-2,4,6,8-tetraen-10-ynylidene]-3-[(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]furan-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C37H46O5/c1-25(15-16-32-27(3)20-29(38)22-34(32,4)5)13-11-9-10-12-14-26(2)19-31-21-28(33(40)41-31)17-18-37-35(6,7)23-30(39)24-36(37,8)42-37/h9-14,17-19,21,29-30,38-39H,20,22-24H2,1-8H3/b11-9+,12-10+,18-17+,25-13+,26-14+,31-19-/t29-,30+,36-,37+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

JPHOIGCQEIPBBI-RHYXJIAFSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

CC1=C(C(C[C@@H](C1)O)(C)C)C#C/C(=C/C=C/C=C/C=C(\C)/C=C\2/C=C(C(=O)O2)/C=C/[C@]34[C@](O3)(C[C@H](CC4(C)C)O)C)/C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C37H46O5
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 DSSTox Substance ID

2.3.3 Lipid Maps ID (LM_ID)

2.3.4 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
570.8 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
7.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
570.33452456 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
570.33452456 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
79.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
42
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1440
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
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
6
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 2019.01.04)

3.2 Chemical Classes

3.2.1 Lipids

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C40 isoprenoids (tetraterpenes) [PR0107]

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
571.3418
Instrument
Xevo G2-S QtOF, Waters (USA) coupled to ACQUITY UPLC, Waters (USA).
Instrument Type
LC-ESI-QTOF
Ionization
ESI
Ionization Mode
positive
Collision Energy
20 V
Top 5 Peaks

571.342 100

553.329 54.99

572.344 38.37

554.340 11.28

554.321 10.91

Thumbnail
Thumbnail
License
CC BY

4.1.2 Other MS

MoNA ID
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M]+*
Precursor m/z
570.33
Instrument
JMS-HX/HX 110A, JEOL
Instrument Type
FAB-EBEB
Ionization
FAB
Ionization Mode
positive
Collision Energy
3 kV
Top 5 Peaks

570.3022 99.97

552.2960 53.37

555.3851 26.14

43.0226 16.98

91.0658 11.66

Thumbnail
Thumbnail
License
CC BY-SA

6 Literature

6.1 Consolidated References

6.2 Chemical Co-Occurrences in Literature

7 Taxonomy

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

8 Classification

8.1 LIPID MAPS Classification

8.2 EPA DSSTox Classification

8.3 LOTUS Tree

8.4 MolGenie Organic Chemistry Ontology

9 Information Sources

  1. 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/
    (5Z)-5-[(2E,4E,6E,8E)-11-[(4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl]-2,9-dimethyl-2,4,6,8-undecatetraen-10-yn-1-ylidene]-3-[(1E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl]-2(5H)-furanone
    https://commonchemistry.cas.org/detail?cas_rn=54369-11-8
  2. EPA DSSTox
    (5Z)-5-[(2E,4E,6E,8E)-11-[(4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl]-2,9-dimethyl-2,4,6,8-undecatetraen-10-yn-1-ylidene]-3-[(1E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl]-2(5H)-furanone
    https://comptox.epa.gov/dashboard/DTXSID001098105
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. LIPID MAPS
    Lipid Classification
    https://www.lipidmaps.org/
  4. 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/
    (5Z)-5-[(2E,4E,6E,8E)-11-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-2,9-dimethylundeca-2,4,6,8-tetraen-10-ynylidene]-3-[(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]furan-2-one
    https://www.wikidata.org/wiki/Q63409127
  5. Natural Product Activity and Species Source (NPASS)
  6. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  7. Wikidata
    (5Z)-5-[(2E,4E,6E,8E)-11-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-2,9-dimethylundeca-2,4,6,8-tetraen-10-ynylidene]-3-[(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]furan-2-one
    https://www.wikidata.org/wiki/Q63409127
  8. PubChem
  9. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS