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Record Information
Version4.0
Creation Date2012-09-06 15:16:48 UTC
Update Date2017-09-25 12:09:53 UTC
HMDB IDHMDB0014284
Secondary Accession Numbers
  • HMDB14284
StatusExpected but not Quantified
Metabolite Identification
Common NameXanthophyll
DescriptionXanthophylls are yellow pigments from the carotenoid group that are widespread in nature. They are present in egg yolk, algae, and petals of yellow flowers, among other sources. The xanthophylls include lutein, zeaxanthin, neoxanthin, violaxanthin, and cryptoxanthin, of which lutein is the primary ingested one.
Structure
Thumb
Synonyms
ValueSource
(3R,3'r)-beta,beta-Carotene-3,3'-diol, luteinHMDB
(3R,3'r,6'r)-LuteinHMDB
(3R,3'r,6S)-4,5-didehydro-5,6-dihydro-beta,beta-Carotene-3,3'-diolHMDB
4,5-didehydro-5,6-dihydro-beta,beta-Carotene-3,3'-diolHMDB
all-trans-(+)-XanthophyllHMDB
all-trans-LuteinHMDB
all-trans-XanthophyllHMDB
beta,epsilon-Carotene-3,3'-diolHMDB
LuteinHMDB
Lutein esterHMDB
LuteineHMDB
PhylloxanthinHMDB
trans-LuteinHMDB
Vegetable luteinHMDB
Vegetable luteolHMDB
Lutein FMeSH
Lutein gMeSH
Lutein, gammaMeSH
gamma LuteinMeSH
Chemical FormulaC40H56O2
Average Molecular Weight568.8714
Monoisotopic Molecular Weight568.428031036
IUPAC Name4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-2-en-1-ol
Traditional Namexanthophyll
CAS Registry Number127-40-2
SMILES
C\C(\C=C\C=C(/C)\C=C\C1C(C)=CC(O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CC(O)CC1(C)C
InChI Identifier
InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+
InChI KeyKBPHJBAIARWVSC-DKLMTRRASA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition
Biological Location:
Source:
Route of exposure:
Subcellular:
Enteral:
Biofluid and excreta:
Role
Industrial application:
Biological role:
Process
Naturally occurring process:
Biological process:
Cellular process:
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.32e-04 g/LNot Available
LogP7.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000732 mg/mLALOGPS
logP8.29ALOGPS
logP8.55ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.22ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity195.06 m3·mol-1ChemAxon
Polarizability72.79 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00137 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00137 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00137
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4519703
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkXanthophyll
NuGOwiki LinkHMDB0014284
METLIN IDNot Available
PubChem Compound5368396
PDB IDNot Available
ChEBI ID27325
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available