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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:19:10 UTC
Update Date2022-03-07 02:56:43 UTC
HMDB IDHMDB0040743
Secondary Accession Numbers
  • HMDB40743
Metabolite Identification
Common Name2'-Dehydroplectaniaxanthin
Description2'-Dehydroplectaniaxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Based on a literature review a small amount of articles have been published on 2'-Dehydroplectaniaxanthin.
Structure
Data?1563863583
Synonyms
ValueSource
1'-Hydroxy-3',4'-didehydro-1',2'-dihydro-b,y-caroten-2'-oneHMDB
Chemical FormulaC40H54O2
Average Molecular Weight566.8556
Monoisotopic Molecular Weight566.412380972
IUPAC Name(4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E)-2-hydroxy-2,6,10,14,19,23-hexamethyl-25-(2,6,6-trimethylcyclohex-1-en-1-yl)pentacosa-4,6,8,10,12,14,16,18,20,22,24-undecaen-3-one
Traditional Name(4E,6E,8E,10E,12E,14E,16E,18E,20E,22E,24E)-2-hydroxy-2,6,10,14,19,23-hexamethyl-25-(2,6,6-trimethylcyclohex-1-en-1-yl)pentacosa-4,6,8,10,12,14,16,18,20,22,24-undecaen-3-one
CAS Registry Number16796-12-6
SMILES
C\C(\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C(=O)C(C)(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C40H54O2/c1-31(19-13-21-33(3)22-15-24-35(5)27-29-38(41)40(9,10)42)17-11-12-18-32(2)20-14-23-34(4)26-28-37-36(6)25-16-30-39(37,7)8/h11-15,17-24,26-29,42H,16,25,30H2,1-10H3/b12-11+,19-13+,20-14+,22-15+,28-26+,29-27+,31-17+,32-18+,33-21+,34-23+,35-24+
InChI KeyXSEQEJQPEDASKY-RCMIEKQSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentXanthophylls
Alternative Parents
Substituents
  • Xanthophyll
  • Acyloin
  • Alpha,beta-unsaturated ketone
  • Tertiary alcohol
  • Enone
  • Alpha-hydroxy ketone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point169 - 170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.8e-11 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00045 g/LALOGPS
logP8.88ALOGPS
logP9.95ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)13.54ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity197.33 m³·mol⁻¹ChemAxon
Polarizability74.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+260.11930932474
DeepCCS[M-H]-258.29430932474
DeepCCS[M-2H]-291.53730932474
DeepCCS[M+Na]+265.72530932474
AllCCS[M+H]+253.832859911
AllCCS[M+H-H2O]+252.232859911
AllCCS[M+NH4]+255.432859911
AllCCS[M+Na]+255.832859911
AllCCS[M-H]-224.932859911
AllCCS[M+Na-2H]-228.732859911
AllCCS[M+HCOO]-233.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2'-DehydroplectaniaxanthinC\C(\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C(=O)C(C)(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C5547.6Standard polar33892256
2'-DehydroplectaniaxanthinC\C(\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C(=O)C(C)(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C4754.1Standard non polar33892256
2'-DehydroplectaniaxanthinC\C(\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C(=O)C(C)(C)O)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C4287.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2'-Dehydroplectaniaxanthin,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(C)/C=C/C(=O)C(C)(C)O[Si](C)(C)C)C(C)(C)CCC14763.9Semi standard non polar33892256
2'-Dehydroplectaniaxanthin,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C=C(C)/C=C/C(=O)C(C)(C)O[Si](C)(C)C(C)(C)C)C(C)(C)CCC14956.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Dehydroplectaniaxanthin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-2000190000-7b1b204e74eab17703982017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Dehydroplectaniaxanthin GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5200049000-513fd5f57032e14b65522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Dehydroplectaniaxanthin GC-MS ("2'-Dehydroplectaniaxanthin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Dehydroplectaniaxanthin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 10V, Positive-QTOFsplash10-014j-0311390000-c48b4a8f1c68392970622017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 20V, Positive-QTOFsplash10-02d1-0636900000-840ca6c3e392e528207f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 40V, Positive-QTOFsplash10-00pr-3336900000-d76e03b9d48e31e3be382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 10V, Negative-QTOFsplash10-014i-0000190000-33635427edbc7ad5bf082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 20V, Negative-QTOFsplash10-0aor-0000290000-08735fbd5ffaea659f752017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 40V, Negative-QTOFsplash10-05u5-8201790000-93b0ad66853b96c0b3722017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 10V, Negative-QTOFsplash10-014i-0001090000-8aaf56bffc1db05a6ba22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 20V, Negative-QTOFsplash10-0aos-8239280000-ea6e33a6a791fcbf545e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 40V, Negative-QTOFsplash10-056r-2116910000-57badb3ba972ba6221822021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 10V, Positive-QTOFsplash10-014j-0103950000-e2e62c7b127a34f9092f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 20V, Positive-QTOFsplash10-00fr-0123920000-30912ffeb78626aac9bb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Dehydroplectaniaxanthin 40V, Positive-QTOFsplash10-00fs-3213900000-f2941fc3f317e805d4382021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020553
KNApSAcK IDC00022995
Chemspider ID30777504
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound87443362
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1885931
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.