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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:26 UTC
Update Date2021-10-13 04:40:31 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
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point200 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.0e-08 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00088 g/LALOGPS
logP10(7.85) g/LALOGPS
logP10(6.69) g/LChemAxon
logS10(-5.8) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Neoxanthin[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)C6535.9Standard polar33892256
Neoxanthin[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)C4863.0Standard non polar33892256
Neoxanthin[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)C4711.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Neoxanthin,1TMS,isomer #1CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C4686.1Semi standard non polar33892256
Neoxanthin,1TMS,isomer #2CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O[Si](C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C4706.1Semi standard non polar33892256
Neoxanthin,1TMS,isomer #3CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C)CC2(C)C4669.6Semi standard non polar33892256
Neoxanthin,2TMS,isomer #1CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C)C[C@@]1(C)O[Si](C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C4612.4Semi standard non polar33892256
Neoxanthin,2TMS,isomer #2CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C)CC2(C)C4593.0Semi standard non polar33892256
Neoxanthin,2TMS,isomer #3CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O[Si](C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C)CC2(C)C4610.4Semi standard non polar33892256
Neoxanthin,3TMS,isomer #1CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C)C[C@@]1(C)O[Si](C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C)CC2(C)C4530.2Semi standard non polar33892256
Neoxanthin,1TBDMS,isomer #1CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C4909.9Semi standard non polar33892256
Neoxanthin,1TBDMS,isomer #2CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O[Si](C)(C)C(C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C4920.3Semi standard non polar33892256
Neoxanthin,1TBDMS,isomer #3CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC2(C)C4905.1Semi standard non polar33892256
Neoxanthin,2TBDMS,isomer #1CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]1(C)O[Si](C)(C)C(C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C5058.5Semi standard non polar33892256
Neoxanthin,2TBDMS,isomer #2CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]1(C)O)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC2(C)C5034.8Semi standard non polar33892256
Neoxanthin,2TBDMS,isomer #3CC(=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)C=C=C1C(C)(C)C[C@H](O)C[C@@]1(C)O[Si](C)(C)C(C)(C)C)/C=C/[C@@]12O[C@]1(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC2(C)C5059.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Neoxanthin GC-MS ("Neoxanthin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-20Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 10V, Positive-QTOFsplash10-00lr-0111291000-3593ffdd4578d86f3cad2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 20V, Positive-QTOFsplash10-02cr-0332920000-c1a5b615a86a4744f95b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 40V, Positive-QTOFsplash10-03dr-2397510000-8482387fd9b359d38e812019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 10V, Negative-QTOFsplash10-0532-0300090000-2764649ced42edee68092019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 20V, Negative-QTOFsplash10-001j-0200190000-d23886287e51c352530a2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 40V, Negative-QTOFsplash10-053b-1500390000-bfded22fbe2fa5d14b052019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 10V, Negative-QTOFsplash10-0002-0100090000-55a4e5043b9179353ba82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 20V, Negative-QTOFsplash10-0apj-1801190000-8d89966907ac5e0b03f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 40V, Negative-QTOFsplash10-05nr-0829330000-2990cef91d1578f4860f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 10V, Positive-QTOFsplash10-001j-0012390000-9ff807aadae250f50deb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 20V, Positive-QTOFsplash10-05o1-1142971000-4d9355283b3ed4e122032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Neoxanthin 40V, Positive-QTOFsplash10-00o3-2739410000-d6c02ec4b30318002b512021-09-22Wishart LabView Spectrum
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 IDFDB019089
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 IDNot Available
Good Scents IDrw1589021
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 ]