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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:48:53 UTC
Update Date2022-03-07 02:55:24 UTC
HMDB IDHMDB0037564
Secondary Accession Numbers
  • HMDB37564
Metabolite Identification
Common NameMutatoxanthin
DescriptionMutatoxanthin 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 Mutatoxanthin.
Structure
Data?1563863051
Synonyms
ValueSource
(3S,3'r,5R)-5,8-Epoxy-5,8-dihydro-beta,beta-carotene-3,3'-diolHMDB
5,8-Epoxy-5,8-dihydro-b,b-carotene-3,3'-diolHMDB
(8S)-MutatoxanthinHMDB
(8R)-MutatoxanthinHMDB
Chemical FormulaC40H56O3
Average Molecular Weight584.8708
Monoisotopic Molecular Weight584.422945658
IUPAC Name2-[(2E,4E,6E,8E,10E,12E,14E,16Z)-17-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-6-ol
Traditional Name2-[(2E,4E,6E,8E,10E,12E,14E,16Z)-17-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol
CAS Registry Number31661-06-0
SMILES
C\C(\C=C\C=C(/C)\C=C/C1=C(C)CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)C1OC2(C)CC(O)CC(C)(C)C2=C1
InChI Identifier
InChI=1S/C40H56O3/c1-28(17-13-18-30(3)21-22-35-32(5)23-33(41)25-38(35,6)7)15-11-12-16-29(2)19-14-20-31(4)36-24-37-39(8,9)26-34(42)27-40(37,10)43-36/h11-22,24,33-34,36,41-42H,23,25-27H2,1-10H3/b12-11+,17-13+,19-14+,22-21-,28-15+,29-16+,30-18+,31-20+
InChI KeyIFYMEZNJCAQUME-MTCCZOJNSA-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
  • Dihydrofuran
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point171 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00059 g/LALOGPS
logP8.14ALOGPS
logP7.53ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)15.13ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity193.51 m³·mol⁻¹ChemAxon
Polarizability72.57 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+250.47731661259
DarkChem[M-H]-245.5431661259
DeepCCS[M+H]+267.00630932474
DeepCCS[M-H]-265.11130932474
DeepCCS[M-2H]-298.35230932474
DeepCCS[M+Na]+272.68330932474
AllCCS[M+H]+261.832859911
AllCCS[M+H-H2O]+260.332859911
AllCCS[M+NH4]+263.332859911
AllCCS[M+Na]+263.732859911
AllCCS[M-H]-235.432859911
AllCCS[M+Na-2H]-239.532859911
AllCCS[M+HCOO]-244.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MutatoxanthinC\C(\C=C\C=C(/C)\C=C/C1=C(C)CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)C1OC2(C)CC(O)CC(C)(C)C2=C15733.7Standard polar33892256
MutatoxanthinC\C(\C=C\C=C(/C)\C=C/C1=C(C)CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)C1OC2(C)CC(O)CC(C)(C)C2=C14568.5Standard non polar33892256
MutatoxanthinC\C(\C=C\C=C(/C)\C=C/C1=C(C)CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)C1OC2(C)CC(O)CC(C)(C)C2=C14488.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mutatoxanthin,1TMS,isomer #1CC1=C(/C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C2C=C3C(C)(C)CC(O)CC3(C)O2)C(C)(C)CC(O[Si](C)(C)C)C14541.7Semi standard non polar33892256
Mutatoxanthin,1TMS,isomer #2CC1=C(/C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C2C=C3C(C)(C)CC(O[Si](C)(C)C)CC3(C)O2)C(C)(C)CC(O)C14564.2Semi standard non polar33892256
Mutatoxanthin,2TMS,isomer #1CC1=C(/C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C2C=C3C(C)(C)CC(O[Si](C)(C)C)CC3(C)O2)C(C)(C)CC(O[Si](C)(C)C)C14490.4Semi standard non polar33892256
Mutatoxanthin,1TBDMS,isomer #1CC1=C(/C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C2C=C3C(C)(C)CC(O)CC3(C)O2)C(C)(C)CC(O[Si](C)(C)C(C)(C)C)C14769.2Semi standard non polar33892256
Mutatoxanthin,1TBDMS,isomer #2CC1=C(/C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C2C=C3C(C)(C)CC(O[Si](C)(C)C(C)(C)C)CC3(C)O2)C(C)(C)CC(O)C14799.1Semi standard non polar33892256
Mutatoxanthin,2TBDMS,isomer #1CC1=C(/C=C\C(C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(/C)C2C=C3C(C)(C)CC(O[Si](C)(C)C(C)(C)C)CC3(C)O2)C(C)(C)CC(O[Si](C)(C)C(C)(C)C)C14956.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mutatoxanthin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-0200290000-4d6a40bb893975c7238a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mutatoxanthin GC-MS (1 TMS) - 70eV, Positivesplash10-0006-2400029000-35fbe6bece7aa55f05462017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mutatoxanthin GC-MS ("Mutatoxanthin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mutatoxanthin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mutatoxanthin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mutatoxanthin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mutatoxanthin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mutatoxanthin GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 10V, Positive-QTOFsplash10-014i-0111190000-84358dfd692bb609bc812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 20V, Positive-QTOFsplash10-02aj-0956840000-fc3c8803b4fb673bf67e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 40V, Positive-QTOFsplash10-08fr-0559510000-c7e6f45a56ea198e375c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 10V, Negative-QTOFsplash10-001i-0000090000-2d0701659ce708329fff2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 20V, Negative-QTOFsplash10-0159-0200090000-04552e74d9689bbe1e422016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 40V, Negative-QTOFsplash10-014i-0501490000-2fdaf55e3f5c779841112016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 10V, Negative-QTOFsplash10-001i-0000090000-bf6c6b47c5a7b499450e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 20V, Negative-QTOFsplash10-001i-0013190000-040d4d907ab60c8df2c02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 40V, Negative-QTOFsplash10-014m-0139540000-226c06c81326bd7ce50f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 10V, Positive-QTOFsplash10-000i-0132490000-40eff8703b3885e34d5d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 20V, Positive-QTOFsplash10-014r-0249380000-d07e67c9286e164a30e22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mutatoxanthin 40V, Positive-QTOFsplash10-03e9-0679100000-13092ab57685fe220c832021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB016647
KNApSAcK IDC00022950
Chemspider ID35014434
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752205
PDB IDNot Available
ChEBI IDNot Available
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.