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Record Information
Version2.0
Created at2022-09-07 12:52:00 UTC
Updated at2022-09-07 12:52:00 UTC
NP-MRD IDNP0250119
Secondary Accession NumbersNone
Natural Product Identification
Common Namediadinoxanthin
DescriptionDiadinoxanthin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, diadinoxanthin is considered to be an isoprenoid. diadinoxanthin is found in Corbicula japonica, Euglena gracilis, Euglena sanguinea, Euglena viridis, Eutreptiella gymnastica, Grammatophora oceanica, Gymnodinium catenatum, Heterosigma akashiwo, Meretrix petechialis, Pelagococcus subviridis, Rhinogobius brunneus and Thoracosphaera heimii. diadinoxanthin was first documented in 2021 (PMID: 34683379). Based on a literature review a significant number of articles have been published on Diadinoxanthin (PMID: 36005496) (PMID: 35951151) (PMID: 35557488) (PMID: 35092009) (PMID: 34822985) (PMID: 34651379).
Structure
Thumb
Synonyms
ValueSource
Diadinoxanthin aKegg
Chemical FormulaC40H54O3
Average Mass582.8690 Da
Monoisotopic Mass582.40730 Da
IUPAC Name(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15-octaen-17-yn-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
Traditional Name(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15-octaen-17-yn-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C=C(/C)\C=C\[C@@]12O[C@]1(C)C[C@@H](O)CC2(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)C#CC1=C(C)C[C@@H](O)CC1(C)C
InChI Identifier
InChI=1S/C40H54O3/c1-29(17-13-19-31(3)21-22-36-33(5)25-34(41)26-37(36,6)7)15-11-12-16-30(2)18-14-20-32(4)23-24-40-38(8,9)27-35(42)28-39(40,10)43-40/h11-20,23-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20+/t34-,35+,39-,40+/m1/s1
InChI KeyOGHZCSINIMWCSB-GHIQLMQGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Corbicula japonicaLOTUS Database
Euglena gracilisLOTUS Database
Euglena sanguineaLOTUS Database
Euglena viridisLOTUS Database
Eutreptiella gymnasticaLOTUS Database
Grammatophora oceanicaLOTUS Database
Gymnodinium catenatumLOTUS Database
Heterosigma akashiwoLOTUS Database
Meretrix petechialisLOTUS Database
Pelagococcus subviridisLOTUS Database
Rhinogobius brunneusLOTUS Database
Thoracosphaera heimiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • 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
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
logP7.75ChemAxon
pKa (Strongest Acidic)15.14ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.99 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity191.88 m³·mol⁻¹ChemAxon
Polarizability73.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00022941
Chemspider ID4952559
KEGG Compound IDC19921
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiadinoxanthin
METLIN IDNot Available
PubChem Compound6449888
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Guerin S, Raguenes L, Croteau D, Babin M, Lavaud J: Potential for the Production of Carotenoids of Interest in the Polar Diatom Fragilariopsis cylindrus. Mar Drugs. 2022 Jul 29;20(8):491. doi: 10.3390/md20080491. [PubMed:36005496 ]
  2. Kagatani K, Nagao R, Shen JR, Yamano Y, Takaichi S, Akimoto S: Excitation relaxation dynamics of carotenoids constituting the diadinoxanthin cycle. Photosynth Res. 2022 Oct;154(1):13-19. doi: 10.1007/s11120-022-00944-5. Epub 2022 Aug 11. [PubMed:35951151 ]
  3. Goss R, Volke D, Werner LE, Kunz R, Kansy M, Hoffmann R, Wilhelm C: Isolation of fucoxanthin chlorophyll protein complexes of the centric diatom Thalassiosira pseudonana associated with the xanthophyll cycle enzyme diadinoxanthin de-epoxidase. IUBMB Life. 2023 Jan;75(1):66-76. doi: 10.1002/iub.2650. Epub 2022 May 26. [PubMed:35557488 ]
  4. Seydoux C, Storti M, Giovagnetti V, Matuszynska A, Guglielmino E, Zhao X, Giustini C, Pan Y, Blommaert L, Angulo J, Ruban AV, Hu H, Bailleul B, Courtois F, Allorent G, Finazzi G: Impaired photoprotection in Phaeodactylum tricornutum KEA3 mutants reveals the proton regulatory circuit of diatoms light acclimation. New Phytol. 2022 Apr;234(2):578-591. doi: 10.1111/nph.18003. Epub 2022 Feb 21. [PubMed:35092009 ]
  5. Li Y, Sun H, Wang Y, Yang S, Wang J, Wu T, Lu X, Chu Y, Chen F: Integrated metabolic tools reveal carbon alternative in Isochrysis zhangjiangensis for fucoxanthin improvement. Bioresour Technol. 2022 Mar;347:126401. doi: 10.1016/j.biortech.2021.126401. Epub 2021 Nov 23. [PubMed:34822985 ]
  6. Brun P, Piovan A, Caniato R, Dalla Costa V, Pauletto A, Filippini R: Anti-Inflammatory Activities of Euglena gracilis Extracts. Microorganisms. 2021 Sep 29;9(10):2058. doi: 10.3390/microorganisms9102058. [PubMed:34683379 ]
  7. Buck JM, Kroth PG, Lepetit B: Identification of sequence motifs in Lhcx proteins that confer qE-based photoprotection in the diatom Phaeodactylum tricornutum. Plant J. 2021 Dec;108(6):1721-1734. doi: 10.1111/tpj.15539. Epub 2021 Nov 3. [PubMed:34651379 ]
  8. Tamaki S, Mochida K, Suzuki K: Diverse Biosynthetic Pathways and Protective Functions against Environmental Stress of Antioxidants in Microalgae. Plants (Basel). 2021 Jun 19;10(6):1250. doi: 10.3390/plants10061250. [PubMed:34205386 ]
  9. Blommaert L, Chafai L, Bailleul B: The fine-tuning of NPQ in diatoms relies on the regulation of both xanthophyll cycle enzymes. Sci Rep. 2021 Jun 17;11(1):12750. doi: 10.1038/s41598-021-91483-x. [PubMed:34140542 ]
  10. Nagao R, Yokono M, Kato KH, Ueno Y, Shen JR, Akimoto S: High-light modification of excitation-energy-relaxation processes in the green flagellate Euglena gracilis. Photosynth Res. 2021 Sep;149(3):303-311. doi: 10.1007/s11120-021-00849-9. Epub 2021 May 26. [PubMed:34037905 ]
  11. LOTUS database [Link]