Showing metabocard for Zeaxanthin (BMDB0002789)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:38 UTC
Update Date2020-06-04 20:38:44 UTC
BMDB IDBMDB0002789
Secondary Accession Numbers
  • BMDB02789
Metabolite Identification
Common NameZeaxanthin
DescriptionZeaxanthin 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. Zeaxanthin is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Zeaxanthin exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3R,3'r)-Dihydroxy-beta,beta-caroteneChEBI
all-trans-beta-Carotene-3,3'-diolChEBI
all-trans-ZeaxanthinChEBI
AnchovyxanthinChEBI
beta,beta-Carotene-3,3'-diolChEBI
(3R,3'r)-beta,beta-Carotene-3,3'-diolKegg
(3R,3'r)-Dihydroxy-b,b-caroteneGenerator
(3R,3'r)-Dihydroxy-β,β-caroteneGenerator
all-trans-b-Carotene-3,3'-diolGenerator
all-trans-Β-carotene-3,3'-diolGenerator
b,b-Carotene-3,3'-diolGenerator
Β,β-carotene-3,3'-diolGenerator
(3R,3'r)-b,b-Carotene-3,3'-diolGenerator
(3R,3'r)-Β,β-carotene-3,3'-diolGenerator
3R,3'r ZeaxanthinMeSH
3R,3'r-ZeaxanthinMeSH
Beta Carotene 3,3' diolMeSH
ZeaxanthinsMeSH
beta-Carotene-3,3'-diolMeSH
(3R,3'r)-ZeaxanthinHMDB
all-trans-AnchovyxanthinHMDB
Xanthophyll 3HMDB
ZeaxantholHMDB
(3R,3'R)-Dihydroxy-beta-caroteneHMDB
(3R,3'R)-Dihydroxy-β-caroteneHMDB
(3R,3'R)-ZeaxanthinHMDB
(3R,3’R)-Dihydroxy-β-caroteneHMDB
(3R,3’R)-ZeaxanthinHMDB
(3R,3’R)-β,β-Carotene-3,3’-diolHMDB
all-E-ZeaxanthinHMDB
all-trans-3R,3'R-ZeaxanthinHMDB
all-trans-3R,3’R-ZeaxanthinHMDB
Chemical FormulaC40H56O2
Average Molecular Weight568.886
Monoisotopic Molecular Weight568.428031043
IUPAC Name(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-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-3-en-1-ol
Traditional Namezeaxanthin
CAS Registry Number144-68-3
SMILES
C\C(\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)C[C@@H](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/h11-24,35-36,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36-/m1/s1
InChI KeyJKQXZKUSFCKOGQ-QAYBQHTQSA-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
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point215.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.3ALOGPS
logP8.35ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-0.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity194.95 m³·mol⁻¹ChemAxon
Polarizability73.47 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-2000190000-2cc8481518a353268253View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-3000049000-45b1b78e4b208f89e457View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Zeaxanthin,1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - QIT 20V, positivesplash10-0xsi-0000490000-61514ff28dff7d7222e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QIT 1V, positivesplash10-0udi-0000290000-09f7ca5714961ff8f77eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00or-0930100000-c29159f503dad4260c04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00or-0960430000-8996d3474c2f84178dd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-0aba-0930000000-8b9aa98251b44f2236faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-014i-0930030000-987a65a5fdcee3816338View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-b50e7afd480c60427730View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-82e2fd12101c0f8a5aa3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-376dfbe507c212fad75cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-7a03386b81c0af2daaaeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-63535133943f458f5619View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-18da3552a389eec49470View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-97b603fc0db5c5d1268cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-a5be07cc9aa560c7ad05View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-247f26afe81a420dd329View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-a6da820e1ac88487b354View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0111190000-a3e4a4d0d67ea298da49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-0649330000-191e0ac14dcad154b4b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-0449130000-5644e7cc2bbfa6ef09f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-8f8c6909e2b7e1022ce9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-421f46802deab60d756dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0553390000-883720ed84543eb475e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001090000-762864ffd0f72009c688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0104290000-79f130816293d1629a5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003b-0229210000-8aa487c6a883739666a2View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Eye Lens
  • Milk
  • Retina
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Eye LensExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected and Quantified0.00176 uMNot SpecifiedNot Specified
Normal
    • International Dai...
 details
MilkDetected and Quantified0.00703 +/- 0.00176 uMNot SpecifiedNot Specified
Normal
    • International Dai...
 details
RetinaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002789
DrugBank IDDB11176
Phenol Explorer Compound IDNot Available
FooDB IDFDB023113
KNApSAcK IDC00000931
Chemspider ID4444421
KEGG Compound IDC06098
BioCyc IDCPD1F-130
BiGG IDNot Available
Wikipedia LinkZeaxanthin
METLIN IDNot Available
PubChem Compound5280899
PDB IDNot Available
ChEBI ID27547
References
Synthesis ReferencePaus, Joachim; Kriegl, Wolfgang. Process for the preparation of zeaxanthin and its intermediates. Eur. Pat. Appl. (1998), 19 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. M.S Havemose, Martin Riis Weisbjerg, Wender L.P Bredie, J.H Nielsen (2004). International Dairy Journal; Volume 14, Issue 7, July 2004, Pages 563-570. International Dairy Journal.