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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:26 UTC
Update Date2020-06-16 16:20:42 UTC
HMDB IDHMDB0003020
Secondary Accession Numbers
  • HMDB0036920
  • HMDB03020
  • HMDB36920
Metabolite Identification
Common NameNeoxanthin
DescriptionNeoxanthin 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. Xanthophylls arise by oxygenation of the carotene backbone. Neoxanthin is an intermediate in the synthesis of abscisic acid from violaxanthin. Neoxanthin has been detected, but not quantified in, several different foods, such as apples, paprikas, Valencia oranges, kiwis, globe artichokes, sparkleberries, hard wheat, and cinnamon. This could make neoxanthin a potential biomarker for the consumption of these foods. Neoxanthin has been shown to exhibit apoptotic and anti-proliferative functions (PMID: 15333710 , 15333710 ).
Structure
Data?1592324442
Synonyms
ValueSource
(3S,5R,6R,3's,5'r,6's)-9'-cis-6,7-didehydro-5,6,5',6'-tetrahydro-5',6'-Epoxy-beta,beta-carotene-3,5,3'-triolChEBI
(3S,5R,6R,3's,5'r,6's)-9'-cis-6,7-didehydro-5,6,5',6'-tetrahydro-5',6'-Epoxy-b,b-carotene-3,5,3'-triolGenerator
(3S,5R,6R,3's,5'r,6's)-9'-cis-6,7-didehydro-5,6,5',6'-tetrahydro-5',6'-Epoxy-β,β-carotene-3,5,3'-triolGenerator
(3S,3'S,5R,5'R,6R,6'S,9'-cis)-6,7-Didehydro-5',6'-epoxy-5',6'-dihydro-beta,beta-carotene-3,3',5(6H)-triolHMDB
(3S,3'S,5R,5'R,6R,6'S,9'-cis)-6,7-Didehydro-5',6'-epoxy-5',6'-dihydro-β,β-carotene-3,3',5(6H)-triolHMDB
(3S,3’S,5R,5’R,6R,6’S,9’-cis)-6,7-Didehydro-5’,6’-epoxy-5’,6’-dihydro-β,β-carotene-3,3’,5(6H)-triolHMDB
(9'Z)-NeoxanthinHMDB
(9’Z)-NeoxanthinHMDB
9'-cis-NeoxanthinHMDB
9'Z-(6R)-neoxanthinHMDB
9-cis-NeoxanthinHMDB
9’-cis-NeoxanthinHMDB
9’Z-(6R)-neoxanthinHMDB
FoliaxanthinHMDB
NeoxanthinHMDB
NeoxanthineHMDB
cis-NeoxanthinHMDB
Chemical FormulaC40H56O4
Average Molecular Weight600.8702
Monoisotopic Molecular Weight600.41786028
IUPAC Name(1R,3S)-6-[(1M,3E,5E,7E,9E,11E,13E,15Z,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 Name9'-cis-neoxanthin
CAS Registry Number14660-91-4
SMILES
[H]C(=[C@@]=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(\C)/C=C/[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-OQASCVKESA-N
Chemical Taxonomy
DescriptionThis compound 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
Polarizability72.71 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0111291000-3593ffdd4578d86f3cadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02cr-0332920000-c1a5b615a86a4744f95bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-2397510000-8482387fd9b359d38e81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0532-0300090000-2764649ced42edee6809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0200190000-d23886287e51c352530aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053b-1500390000-bfded22fbe2fa5d14b05Spectrum
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
FooDB IDFDB015886
KNApSAcK IDC00003780
Chemspider ID10392237
KEGG Compound IDC08606
BioCyc IDCPD-7424
BiGG IDNot Available
Wikipedia LinkNeoxanthin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID35306
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]