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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:26 UTC
Update Date2019-07-23 05:45:40 UTC
HMDB IDHMDB0003020
Secondary Accession Numbers
  • HMDB0036920
  • HMDB03020
  • HMDB36920
Metabolite Identification
Common NameNeoxanthin
DescriptionNeoxanthin is a carotenoid, an intermediate in the synthesis of abscisic acid from violaxanthin. Neoxanthin is found in apple. Neoxanthin is a constituent of paprika, lucerne, Valencia orange and other species. Neoxanthin has been shown to exhibit apoptotic and anti-proliferative functions (PMID 15333710 , 15333710 ).
Structure
Data?1563860740
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 Weight600.884
Monoisotopic Molecular Weight600.417860283
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]O[C@]1([H])C([H])([H])[C@]2(O[C@@]2(\C([H])=C(/[H])\C(=C(/[H])\C(\[H])=C(/[H])\C(=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(\C(\[H])=C(/[H])\C(\[H])=C(\C([H])=C=C2[C@@](O[H])(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])/C([H])([H])[H])\C([H])([H])[H])\C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])C1([H])[H])C([H])([H])[H]
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point200 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00088 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053l-0000090000-eba564ea5bff8d75c3ceJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-4100019000-8db432e3b230dd9950bcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0001291000-3182e203a68c515d6a55JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02cr-0221920000-38690bfbd04703cb9af0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1394310000-2cc8d5afd284c382306bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0300090000-443389e01a5be8228352JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0200190000-b6a19dc5634b7ed96e54JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052k-1600390000-452d15111fa201e6baeeJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Czeczuga-Semeniuk E, Wolczynski S: Identification of carotenoids in ovarian tissue in women. Oncol Rep. 2005 Nov;14(5):1385-92. [PubMed:16211314 ]
  2. Asai A, Terasaki M, Nagao A: An epoxide-furanoid rearrangement of spinach neoxanthin occurs in the gastrointestinal tract of mice and in vitro: formation and cytostatic activity of neochrome stereoisomers. J Nutr. 2004 Sep;134(9):2237-43. [PubMed:15333710 ]