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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:16:38 UTC
Update Date2022-03-07 02:54:27 UTC
HMDB IDHMDB0035316
Secondary Accession Numbers
  • HMDB35316
Metabolite Identification
Common Name(5R,5'R,6S,8'R)-Luteochrome
Description(5R,5'R,6S,8'R)-Luteochrome 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 (5R,5'R,6S,8'R)-Luteochrome.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC40H56O2
Average Molecular Weight568.8714
Monoisotopic Molecular Weight568.428031036
IUPAC Name4,4,7a-trimethyl-2-[(2Z,4E,6E,8Z,10E,12E,14Z,16Z)-6,11,15-trimethyl-17-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}heptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-2,4,5,6,7,7a-hexahydro-1-benzofuran
Traditional Name4,4,7a-trimethyl-2-[(2Z,4E,6E,8Z,10E,12E,14Z,16Z)-6,11,15-trimethyl-17-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}heptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-2,5,6,7-tetrahydro-1-benzofuran
CAS Registry NumberNot Available
SMILES
C/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C1
InChI Identifier
InChI=1S/C40H56O2/c1-30(19-13-20-32(3)23-28-40-37(7,8)25-16-27-39(40,10)42-40)17-11-12-18-31(2)21-14-22-33(4)34-29-35-36(5,6)24-15-26-38(35,9)41-34/h11-14,17-23,28-29,34H,15-16,24-27H2,1-10H3/b12-11-,19-13+,21-14+,28-23-,30-17+,31-18+,32-20-,33-22-
InChI KeyHSOIPJLINDKQOV-VCAYJPBHSA-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
  • Benzofuran
  • Oxepane
  • Dihydrofuran
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point170 - 171 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00018 g/LALOGPS
logP9.59ALOGPS
logP9.91ChemAxon
logS-6.5ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area21.76 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity188.95 m³·mol⁻¹ChemAxon
Polarizability72.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+241.61331661259
DarkChem[M-H]-234.70131661259
DeepCCS[M-2H]-283.55930932474
DeepCCS[M+Na]+257.97630932474
AllCCS[M+H]+258.932859911
AllCCS[M+H-H2O]+257.332859911
AllCCS[M+NH4]+260.432859911
AllCCS[M+Na]+260.932859911
AllCCS[M-H]-232.932859911
AllCCS[M+Na-2H]-236.932859911
AllCCS[M+HCOO]-241.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(5R,5'R,6S,8'R)-LuteochromeC/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C15537.3Standard polar33892256
(5R,5'R,6S,8'R)-LuteochromeC/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C14420.1Standard non polar33892256
(5R,5'R,6S,8'R)-LuteochromeC/C(/C=C/C=C(/C)\C=C/C12OC1(C)CCCC2(C)C)=C\C=C/C=C(\C)/C=C/C=C(/C)C1OC2(C)CCCC(C)(C)C2=C14395.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3600290000-0d89f3ab061f00837b0c2017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 10V, Positive-QTOFsplash10-014i-0595580000-da3de18d27b82cb1d09b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 20V, Positive-QTOFsplash10-066s-0296010000-524ab44bfc7e744fe09d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 40V, Positive-QTOFsplash10-06sr-8895100000-0b4914a0ec65ea13ef402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 10V, Negative-QTOFsplash10-014i-0100190000-2fa143c4500a2ba2b1192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 20V, Negative-QTOFsplash10-014i-0310190000-b1ae307cf33b96efccb42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 40V, Negative-QTOFsplash10-0f79-1910250000-f1afbd313656085a83652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 10V, Positive-QTOFsplash10-0uxr-0032090000-6706a10431c36ba6d7bd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 20V, Positive-QTOFsplash10-0udr-0165190000-324b7e0e884dcdfaa1b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 40V, Positive-QTOFsplash10-0019-0934200000-017fbb1202c93dade5a82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 10V, Negative-QTOFsplash10-014i-0200090000-44ba945db36b2df7c2e92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 20V, Negative-QTOFsplash10-014i-0124190000-52f3c445cf7537abb0442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (5R,5'R,6S,8'R)-Luteochrome 40V, Negative-QTOFsplash10-01c0-0298050000-53201085297316705a932021-09-24Wishart 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 IDFDB013985
KNApSAcK IDNot Available
Chemspider ID35013901
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751703
PDB IDNot Available
ChEBI ID176086
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.