Phaseic Acid
PubChem CID
5281527
Structure
Molecular Formula
Synonyms
- Phaseic acid
- 24394-14-7
- (-)-Phaseic acid
- (-)-Neophasic acid
- YL2MMW26MJ
Molecular Weight
280.32 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-06-24
- Modify:2025-01-11
Description
Phaseic acid is an apo carotenoid sesquiterpenoid and an alpha,beta-unsaturated monocarboxylic acid. It has a role as a metabolite. It is a conjugate acid of a phaseic acid anion.
Phaseic acid has been reported in Nigrospora, Illicium dunnianum, and other organisms with data available.
Chemical Structure Depiction
(2Z,4E)-5-[(1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C15H20O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6-/t13-,14-,15+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
IZGYIFFQBZWOLJ-UUZREKTLSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C/C(=C/C(=O)O)/C=C/[C@@]1([C@@]2(CC(=O)C[C@]1(OC2)C)C)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C15H20O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)
phaseic acid
- Phaseic acid
- 24394-14-7
- (-)-Phaseic acid
- (-)-Neophasic acid
- YL2MMW26MJ
- (2Z,4E)-5-[(1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid
- CHEBI:28205
- (2Z,4E)-3-Methyl-5-[(1S)-1beta-hydroxy-2,6-dimethyl-6beta,2beta-(epoxymethano)-4-oxocyclohexane-1-yl]-2,4-pentadienoic acid
- (7E,9Z)-(1R,5R,6S)-5,16-epoxy-6-hydroxy-3-oxo-5,6-dihydro-11-apo-beta-caroten-11-oic acid
- (2Z,4E)-5-((1R,5R,8S)-8-Hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo(3.2.1)oct-8-yl)-3-methyl-2,4-pentadienoic acid
- (2Z,4E)-5-[(1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]oct-8-yl]-3-methylpenta-2,4-dienoic acid
- 2,4-Pentadienoic acid, 5-((1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo(3.2.1)oct-8-yl)-3-methyl-, (2Z,4E)-
- 2,4-Pentadienoic acid, 5-(8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo(3.2.1)oct-8-yl)-3-methyl-
- 2,4-PENTADIENOIC ACID, 5-(8-HYDROXY-1,5-DIMETHYL-3-OXO-6-OXABICYCLO(3.2.1)OCT-8-YL)-3-METHYL-, (1R-(1.ALPHA.,5.ALPHA.,8S*(2Z,4E)))-
- 2,4-Pentadienoic acid, 5-(8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo(3.2.1)oct-8-yl)-3-methyl-, (1R-(1alpha,5alpha,8S*(2Z,4E)))-
- 2,4-Pentadienoic acid, 5-(8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]oct-8-yl)-3-methyl-
- 2,4-Pentadienoic acid, 5-(8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]oct-8-yl)-3-methyl-, [1R-[1.alpha.,5.alpha.,8S*(2Z,4E)]]-
- (2Z,4E)-5-((1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo(3.2.1)oct-8-yl)-3-methylpenta-2,4-dienoic acid
- (2Z,4E)-5-((1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo(3.2.1)oct-8-yl)-3-methylpenta-2,4-dienoic acid;(7E,9Z)-(1R,5R,6S)-5,16-epoxy-6-hydroxy-3-oxo-5,6-dihydro-11-apo-beta-caroten-11-oic acid
- (2Z,4E)-5-((1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo(3.2.1)octan-8-yl)-3-methylpenta-2,4-dienoic acid
- (2Z,4E)-5-((5R,8S)-8-Hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo(3.2.1)octan-8-yl)-3-methylpenta-2,4-dienoate
- (2Z,4E)-5-[(1R,5R,8S)-8-Hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]oct-8-yl]-3-methyl-2,4-pentadienoic acid
- (2Z,4E)-5-[(1R,5R,8S)-8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]oct-8-yl]-3-methylpenta-2,4-dienoic acid;(7E,9Z)-(1R,5R,6S)-5,16-epoxy-6-hydroxy-3-oxo-5,6-dihydro-11-apo-beta-caroten-11-oic acid
- (2Z,4E)-5-[(5R,8S)-8-Hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoate
- UNII-YL2MMW26MJ
- 6-Oxabicyclo(3.2.1)octane, 2,4-pentadienoic acid deriv.
- 6-Oxabicyclo[3.2.1]octane, 2,4-pentadienoic acid deriv.
- CHEMBL3594247
- DTXSID801028483
- 2,4-Pentadienoic acid, 5-(8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]oct-8-yl)-3-methyl-, [1R-[1.alpha.,5.alpha.,8S*(Z,E)]]-
- DA-59501
- MS-23977
- HY-111973
- CS-0094770
- C09707
- G88935
- Q7180977
- 2,4-Pentadienoic acid, 5-(8-hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo(3.2.1)oct-8-yl)-3-methyl-, (1R-(1alpha,5alpha,8S*(Z,E)))-
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
280.32 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
280.13107373 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
280.13107373 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
83.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
520
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
2
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)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
- CAS Common ChemistryLICENSEThe 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/(-)-Phaseic acidhttps://commonchemistry.cas.org/detail?cas_rn=24394-14-7
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSTox(2Z,4E)-5-[(1R,5R,8S)-8-Hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]oct-8-yl]-3-methyl-2,4-pentadienoic acidhttps://comptox.epa.gov/dashboard/DTXSID801028483CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- FDA Global Substance Registration System (GSRS)LICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
- ChEBI
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/Phaseic acidhttps://www.wikidata.org/wiki/Q7180977LOTUS Treehttps://lotus.naturalproducts.net/
- ChEMBLLICENSEAccess 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
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlPhytochemical compoundshttp://www.genome.jp/kegg-bin/get_htext?br08003.keg
- Natural Product Activity and Species Source (NPASS)
- Metabolomics Workbench
- Springer Nature
- Wikidataphaseic acidhttps://www.wikidata.org/wiki/Q7180977
- WikipediaPimagedinehttps://en.wikipedia.org/wiki/PimagedinePhaseic acidhttps://en.wikipedia.org/wiki/Phaseic_acid
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.htmlphaseic acidhttps://www.ncbi.nlm.nih.gov/mesh/2017426
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
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