15,15'-cis-Phytoene
PubChem CID
9963391
Structure
Molecular Formula
Synonyms
- 15-cis-Phytoene
- 13920-14-4
- cis-Phytoene
- (6E,10E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaene
- 15,15'-cis-Phytoene
Molecular Weight
544.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2006-10-25
- Modify:2024-12-28
Description
15-cis-phytoene is a phytoene.
15-cis-Phytoene has been reported in Rhodotorula toruloides, Rhodotorula glutinis, and other organisms with data available.
Phytoene is a 40 carbon dietary fatty acid produced by the conversion of two molecules of geranylgeranyl pyrophosphate by the enzyme phytoene synthase that is an intermediate in carotenoid biosynthesis in plants with potential to absorb ultraviolet radiation (UV), and potential antioxidant, chemopreventive, and anti-inflammatory activities in skin. Following ingestion and digestion, phytoene may accumulate in the epidermis where it may prevent UV-mediated sun damage and carcinogenesis. In addition, phytofluene may prevent carcinogenesis by protecting cells against DNA damage through its free radical scavenger effects.
Chemical Structure Depiction
Conformer generation is disallowed since too flexible
(6E,10E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaene
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
InChI=1S/C40H64/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,19-22,27-30H,13-18,23-26,31-32H2,1-10H3/b12-11-,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
YVLPJIGOMTXXLP-BHLJUDRVSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CC(=CCC/C(=C/CC/C(=C/CC/C(=C/C=C\C=C(\CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)/C)/C)/C)/C)C
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)
C40H64
Computed by PubChem 2.2 (PubChem release 2021.10.14)
- (all-E) phytoene
- 15-cis-phytoene
- 7,7',8,8',11,11',12,12'-octahydro-psi,psi-carotene
- all-trans-phytoene
- phytoene
- phytoene, (15-cis)-isomer
- phytoene, (all-E)-
- phytoene, (cis)-isomer
- trans-phytoene
- 15-cis-Phytoene
- 13920-14-4
- cis-Phytoene
- (6E,10E,14E,16Z,18E,22E,26E)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,16,18,22,26,30-nonaene
- 15,15'-cis-Phytoene
- 15-cis-Phytoene (>80%)
- 876K2ZK1OF
- (all-E) phytoene
- 15-cis-7,7',8,8',11,11',12,12'-octahydro-psi.psi-Carotene
- 15-cis-Pytoene
- 15-cis-7,7',8,8',11,11',12,12'-Octahydro-?,?-carotene; PhytoflORAL; 15-cis-7,7',8,8',11,11',12,12'-Octahydro-lycopene;
- (15Z)-Phytoene
- 15Z-Phytoene isomer
- starbld0003373
- phytoene, (cis)-isomer
- UNII-876K2ZK1OF
- CHEBI:27787
- DTXSID10433340
- LMPR01070255
- C05421
- Q302247
- 15-cis-7,7',8,8',11,11',12,12'-Octahydro-psi,psi-carotene
- 15-cis-7,8,11,12,7',8',11',12'-octahydro-psi,psi-carotene
- 7,7',8,8',11,11',12,12'-OCTAHYDRO-.PSI.,.PSI.-CAROTENE
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
544.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
15.3
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
20
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
544.500802041 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
544.500802041 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
0Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
40
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
887
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
0
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
7
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)
Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C40 isoprenoids (tetraterpenes) [PR0107]
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor m/z
545
Instrument
Esquire 4000
Instrument Type
QIT
Ionization
ESI
Ionization Mode
positive
Collision Energy
20->10V
Top 5 Peaks
339 100
450 100
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
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
PubMed Count
- Extracellular
- Membrane
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=YVLPJIGOMTXXLP-BHLJUDRVSA-N
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/
- ChemIDplusChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- EPA DSSTox15-cis-Phytoenehttps://comptox.epa.gov/dashboard/DTXSID10433340CompTox 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
- Human Metabolome Database (HMDB)LICENSEHMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.http://www.hmdb.ca/citing15-cis-Phytoenehttp://www.hmdb.ca/metabolites/HMDB0039093
- ChEBI15-cis-phytoenehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27787
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/15-cis-Phytoenehttps://www.wikidata.org/wiki/Q302247LOTUS Treehttps://lotus.naturalproducts.net/
- NCI Thesaurus (NCIt)LICENSEUnless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.https://www.cancer.gov/policies/copyright-reuseNCI Thesaurushttps://ncit.nci.nih.gov
- Japan Chemical Substance Dictionary (Nikkaji)
- 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
- KNApSAcK Species-Metabolite Database
- Natural Product Activity and Species Source (NPASS)
- LIPID MAPSLipid Classificationhttps://www.lipidmaps.org/
- MassBank of North America (MoNA)LICENSEThe content of the MoNA database is licensed under CC BY 4.0.https://mona.fiehnlab.ucdavis.edu/documentation/license
- Metabolomics Workbench
- Rhea - Annotated Reactions DatabaseLICENSERhea has chosen to apply the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/). This means that you are free to copy, distribute, display and make commercial use of the database in all legislations, provided you credit (cite) Rhea.https://www.rhea-db.org/help/license-disclaimer
- SpectraBase15-CIS-PHYTOENEhttps://spectrabase.com/spectrum/7H8D3JWBk8o
- Wikidata15-cis-phytoenehttps://www.wikidata.org/wiki/Q302247
- 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.html(all-E) phytoenehttps://www.ncbi.nlm.nih.gov/mesh/67100185
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 496459347https://pubchem.ncbi.nlm.nih.gov/substance/496459347
- NCBI
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