Showing Compound Card for Zeaxanthin (CDB004942)

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Record Information
Version1.0
Created at2020-04-17 18:52:54 UTC
Updated at2020-12-07 19:11:20 UTC
CannabisDB IDCDB004942
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameZeaxanthin
DescriptionZeaxanthin, also known as anchovyxanthin or 3R,3'r-zeaxanthin, 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. Thus, zeaxanthin is considered to be an isoprenoid lipid molecule. Zeaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Zeaxanthin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight568.89
Monoisotopic Molecular Weight568.428
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSZeaxanthin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-2000190000-2cc8481518a353268253Spectrum
Predicted GC-MSZeaxanthin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-3000049000-45b1b78e4b208f89e457Spectrum
Predicted GC-MSZeaxanthin, "Zeaxanthin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSZeaxanthin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSZeaxanthin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSZeaxanthin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QIT 20V, positivesplash10-0xsi-0000490000-61514ff28dff7d7222e12020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QIT 1V, positivesplash10-0udi-0000290000-09f7ca5714961ff8f77e2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-00or-0930100000-c29159f503dad4260c042020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00or-0960430000-8996d3474c2f84178dd02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-0aba-0930000000-8b9aa98251b44f2236fa2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-014i-0930030000-987a65a5fdcee38163382020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-b50e7afd480c604277302021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-82e2fd12101c0f8a5aa32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-376dfbe507c212fad75c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-7a03386b81c0af2daaae2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-63535133943f458f56192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-0930030000-18da3552a389eec494702021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950420000-97b603fc0db5c5d1268c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-a5be07cc9aa560c7ad052021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0aba-0930000000-247f26afe81a420dd3292021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00or-0950320000-a6da820e1ac88487b3542021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0111190000-a3e4a4d0d67ea298da492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0frt-0649330000-191e0ac14dcad154b4b32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-0449130000-5644e7cc2bbfa6ef09f02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-8f8c6909e2b7e1022ce92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0000090000-421f46802deab60d756d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-0553390000-883720ed84543eb475e22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001090000-762864ffd0f72009c6882021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0104290000-79f130816293d1629a5c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003b-0229210000-8aa487c6a883739666a22021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002789
DrugBank IDDB11176
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available