Showing Compound Card for Neoxanthin (CDB005177)

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Record Information
Version1.0
Created at2020-04-17 19:17:05 UTC
Updated at2020-11-18 16:39:28 UTC
CannabisDB IDCDB005177
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNeoxanthin
DescriptionNeoxanthin, also known as 9'-cis-neoxanthin or foliaxanthin, 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. Neoxanthin is an extremely weak basic (essentially neutral) compound (based on its pKa). Neoxanthin 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
all-trans-NeoxanthinKegg
6,7-Didehydro-5',6'-epoxy-5,5',6,6'-tetrahydro-b,b-carotene-3,3',5-triolHMDB
FoliaxanthinHMDB
TrolliflorHMDB
TrollixanthinHMDB
9'-cis-NeoxanthinHMDB
Neoxanthin, (trans)-isomerHMDB
Chemical FormulaC40H56O4
Average Molecular Weight600.88
Monoisotopic Molecular Weight600.4179
IUPAC Name(1R,3S)-6-[(3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,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-ylidene]-1,5,5-trimethylcyclohexane-1,3-diol
Traditional Nameneoxanthin
CAS Registry Number14660-91-4
SMILES
[H]C(=C=C1C(C)(C)C[C@]([H])(O)C[C@@]1(C)O)C(\C)=C(/[H])\C(\[H])=C(/[H])\C(\C)=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])\C(\[H])=C(/C)\C(\[H])=C(/[H])[C@@]12O[C@]1(C)C[C@@]([H])(O)CC2(C)C
InChI Identifier
InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35-36(5,6)25-33(41)27-38(35,9)43)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)26-34(42)28-39(40,10)44-40/h11-21,23-24,33-34,41-43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20+/t22?,33-,34-,38+,39+,40-/m0/s1
InChI KeyPGYAYSRVSAJXTE-CLONMANBSA-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
  • Tertiary alcohol
  • 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 Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.85ALOGPS
logP6.69ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)14.01ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.22 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity194.03 m³·mol⁻¹ChemAxon
Polarizability74.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNeoxanthin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053l-0000090000-eba564ea5bff8d75c3ceSpectrum
Predicted GC-MSNeoxanthin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-4100019000-8db432e3b230dd9950bcSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QIT 20V, positivesplash10-0162-0000090000-2be2bfdecc95ed083ef92020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0001291000-3182e203a68c515d6a552016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02cr-0221920000-38690bfbd04703cb9af02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1394310000-2cc8d5afd284c382306b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0300090000-443389e01a5be82283522016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0200190000-b6a19dc5634b7ed96e542016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052k-1600390000-452d15111fa201e6baee2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003020
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015886
KNApSAcK IDC00003780
Chemspider ID4444659
KEGG Compound IDC08606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeoxanthin
METLIN ID3673
PubChem Compound5281247
PDB IDNot Available
ChEBI ID25501
References
General ReferencesNot Available