Showing Compound Card for Violaxanthin (CDB005176)

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Record Information
Version1.0
Created at2020-04-17 19:16:59 UTC
Updated at2020-11-18 16:39:28 UTC
CannabisDB IDCDB005176
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameViolaxanthin
DescriptionViolaxanthin 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. Violaxanthin is an extremely weak basic (essentially neutral) compound (based on its pKa). Violaxanthin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
9-cis-ViolaxanthinHMDB
all-trans-ViolaxanthinHMDB
Chemical FormulaC40H56O4
Average Molecular Weight600.87
Monoisotopic Molecular Weight600.4179
IUPAC Name(1R,6R)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
Traditional Name(1R,6R)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
CAS Registry Number126-29-4
SMILES
C\C(\C=C\C=C(/C)\C=C\[C@]12O[C@]1(C)CC(O)CC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@@]12O[C@]1(C)CC(O)CC2(C)C
InChI Identifier
InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33?,34?,37-,38-,39-,40+/m1/s1
InChI KeySZCBXWMUOPQSOX-LOIAFDEVSA-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
  • Cyclic alcohol
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point200 °CWikipedia
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.33ALOGPS
logP7.26ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)14.84ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.52 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity192.33 m³·mol⁻¹ChemAxon
Polarizability74.47 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSViolaxanthin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053i-4000190000-c017f0fe87f0b7135dbbSpectrum
Predicted GC-MSViolaxanthin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9200018000-5d1afcc320f515006e8eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0232597000-bb8e4d32f6036049ff182017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u0-1496641000-ce91b3158fb7fbc389b42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-5694200000-45d5a59c724dd80910a02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-024ab7a6d31dea22bf5f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000090000-848deea0806eeeed87cb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3600490000-23e259080e3a665848722017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0011092000-e0d8754827bbad0fb75f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0012090000-21b243d8ae4fd22288b52021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1259320000-31706a73dcec9fb477d22021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000090000-ba6a2d7c7dd422ee3fac2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0101290000-0a64d5ce5ee7ec9d7fa02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052s-0917060000-8099c000bfa6a9628b902021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0304252
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030640
KNApSAcK IDC00003787
Chemspider ID35013050
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477762
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available