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Record Information
Version2.0
Created at2022-09-06 07:26:18 UTC
Updated at2022-09-06 07:26:18 UTC
NP-MRD IDNP0227945
Secondary Accession NumbersNone
Natural Product Identification
Common Namesiphonaxanthin
DescriptionSiphonaxanthin 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. Thus, siphonaxanthin is considered to be an isoprenoid. siphonaxanthin is found in Avrainvillea nigricans, Codium fragile and Euglena viridis. siphonaxanthin was first documented in 2022 (PMID: 35670598). Based on a literature review a small amount of articles have been published on Siphonaxanthin (PMID: 35589761) (PMID: 35460262) (PMID: 35251696).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC40H56O4
Average Mass600.8840 Da
Monoisotopic Mass600.41786 Da
IUPAC Name(3E,5E,7E,9E,11E,13E,15E,17E)-1-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3-(hydroxymethyl)-7,12,16-trimethyloctadeca-3,5,7,9,11,13,15,17-octaen-2-one
Traditional Namesiphonaxanthin
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\CO)C(=O)CC1=C(C)C[C@@H](O)CC1(C)C
InChI Identifier
InChI=1S/C40H56O4/c1-28(16-12-17-30(3)20-21-36-31(4)22-34(42)25-39(36,6)7)14-10-11-15-29(2)18-13-19-33(27-41)38(44)24-37-32(5)23-35(43)26-40(37,8)9/h10-22,34-36,41-43H,23-27H2,1-9H3/b11-10+,16-12+,18-13+,21-20+,28-14+,29-15+,30-17+,33-19+/t34-,35+,36-/m0/s1
InChI KeySUCKEYMKNGZJHK-ZARIWKGHSA-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
Avrainvillea nigricansLOTUS Database
Codium fragileLOTUS Database
Euglena viridisLOTUS Database
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
  • Long chain fatty alcohol
  • Fatty alcohol
  • Beta-hydroxy ketone
  • Fatty acyl
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
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
logP6.96ChemAxon
pKa (Strongest Acidic)14.73ChemAxon
pKa (Strongest Basic)-0.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity196.41 m³·mol⁻¹ChemAxon
Polarizability74.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00023022
Chemspider ID9379253
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11204185
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Brotosudarmo THP, Wittmann B, Seki S, Fujii R, Kohler J: Wavelength-Dependent Optical Response of Single Photosynthetic Antenna Complexes from Siphonous Green Alga Codium fragile. J Phys Chem Lett. 2022 Jun 7:5226-5231. doi: 10.1021/acs.jpclett.2c01160. [PubMed:35670598 ]
  2. Brotosudarmo THP, Wittmann B, Seki S, Fujii R, Kohler J: Preprocess dependence of optical properties of ensembles and single siphonaxanthin-containing major antenna from the marine green alga Codium fragile. Sci Rep. 2022 May 19;12(1):8461. doi: 10.1038/s41598-022-11572-3. [PubMed:35589761 ]
  3. Seki S, Yamano Y, Oka N, Kamei Y, Fujii R: Discovery of a novel siphonaxanthin biosynthetic precursor in Codium fragile that accumulates only by exposure to blue-green light. FEBS Lett. 2022 Jun;596(12):1544-1555. doi: 10.1002/1873-3468.14357. Epub 2022 May 4. [PubMed:35460262 ]
  4. Natarajan PM, Umapathy VR, Murali A, Swamikannu B: Computational simulations of identified marine-derived natural bioactive compounds as potential inhibitors of oral cancer. Future Sci OA. 2022 Jan 24;8(3):FSO782. doi: 10.2144/fsoa-2021-0148. eCollection 2022 Mar. [PubMed:35251696 ]
  5. LOTUS database [Link]