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Record Information
Version3.6
Creation Date2012-09-06 15:16:48 UTC
Update Date2016-02-11 01:28:02 UTC
HMDB IDHMDB14284
Secondary Accession NumbersNone
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
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 KeyInChIKey=KBPHJBAIARWVSC-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
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
  • Food
Biofunction
  • Cell signaling
  • Dietary supplement
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Micronutrient
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00137
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00137
  • Not Applicable
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 LinkHMDB14284
Metagene LinkHMDB14284
METLIN IDNot Available
PubChem Compound5368396
PDB IDNot Available
ChEBI ID27325
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available