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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:07 UTC
Update Date2020-02-26 21:24:15 UTC
HMDB IDHMDB0002741
Secondary Accession Numbers
  • HMDB02741
Metabolite Identification
Common NameFucoxanthin
DescriptionFucoxanthin is a carotenoid, with formula C40H60O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510-525 nm by various estimates and absorbing significantly in the range of 450 to 540 nm. -- Wikipedia .
Structure
Data?1582752255
Synonyms
ValueSource
3'-Acetate-(7ci)-6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-a-caroteneHMDB
3'-Acetate-(7ci)-6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-alpha-caroteneHMDB
all-trans-FucoxanthinHMDB
3-Hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetic acidHMDB
Chemical FormulaC42H58O6
Average Molecular Weight658.9063
Monoisotopic Molecular Weight658.423339588
IUPAC Name3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetate
Traditional Name3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetate
CAS Registry Number3351-86-8
SMILES
CC(=O)OC1CC(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)CC23OC2(C)CC(O)CC3(C)C)C(C)(O)C1
InChI Identifier
InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+
InChI KeySJWWTRQNNRNTPU-BWRPRJLXSA-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
  • Oxepane
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Acryloyl-group
  • Cyclic alcohol
  • Enone
  • Tertiary alcohol
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point168 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00058 g/LALOGPS
logP7.54ALOGPS
logP6.83ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)14.03ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area96.36 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity202.76 m³·mol⁻¹ChemAxon
Polarizability78.29 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6100569000-dc17b7cf6b9e6d787d62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0077-0400729000-f2de10007b4a1af17be9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0230911000-4cfe3cce1a708eb557d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi1-1576900000-18a3b752aa3cd01f622eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4s-1400129000-6d000a9b56e4e4493571Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-4500549000-be7eb19143d533d9bf8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9800583000-69a5aa368c41cf1af3a6Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Intestine
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 IDFDB023058
KNApSAcK IDNot Available
Chemspider ID4516336
KEGG Compound IDC08596
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFucoxanthin
METLIN ID3685
PubChem Compound5364094
PDB IDNot Available
ChEBI ID5186
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Asai A, Sugawara T, Ono H, Nagao A: Biotransformation of fucoxanthinol into amarouciaxanthin A in mice and HepG2 cells: formation and cytotoxicity of fucoxanthin metabolites. Drug Metab Dispos. 2004 Feb;32(2):205-11. [PubMed:14744942 ]