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Record Information
Version1.0
Created at2022-09-11 15:26:21 UTC
Updated at2022-09-11 15:26:22 UTC
NP-MRD IDNP0316320
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-{13-[5'-(1,5-dihydroxyundecyl)-[2,2'-bioxolan]-5-yl]-13-hydroxytridecyl}-5-methyl-5h-furan-2-one
DescriptionAsitribin belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Asitribin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Asitribin has been detected, but not quantified in, fruits. 3-{13-[5'-(1,5-dihydroxyundecyl)-[2,2'-bioxolan]-5-yl]-13-hydroxytridecyl}-5-methyl-5h-furan-2-one is found in Annona atemoya, Annona glabra, Annona reticulata, Annona senegalensis, Annona squamosa, Asimina triloba, Annona mucosa, Annona papilionella and Uvaria chamae. It was first documented in 2000 (PMID: 11413487). This could make asitribin a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC37H66O7
Average Mass622.9157 Da
Monoisotopic Mass622.48085 Da
IUPAC Name3-(13-{5-[5-(1,5-dihydroxyundecyl)oxolan-2-yl]oxolan-2-yl}-13-hydroxytridecyl)-5-methyl-2,5-dihydrofuran-2-one
Traditional Name3-(13-{5-[5-(1,5-dihydroxyundecyl)oxolan-2-yl]oxolan-2-yl}-13-hydroxytridecyl)-5-methyl-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
CCCCCCC(O)CCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O
InChI Identifier
InChI=1S/C37H66O7/c1-3-4-5-15-19-30(38)20-17-22-32(40)34-24-26-36(44-34)35-25-23-33(43-35)31(39)21-16-13-11-9-7-6-8-10-12-14-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3
InChI KeyDAEFUOXKPZLQMM-UHFFFAOYSA-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
Annona atemoyaLOTUS Database
Annona glabraLOTUS Database
Annona reticulataLOTUS Database
Annona senegalensisLOTUS Database
Annona squamosaLOTUS Database
Asimina trilobaLOTUS Database
Rollinia mucosaLOTUS Database
Rollinia pittieriLOTUS Database
Uvaria chamaeLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentAnnonaceous acetogenins
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
  • Long chain fatty alcohol
  • 2-furanone
  • Dihydrofuran
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP6.87ALOGPS
logP8.68ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)13.87ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity176.4 m³·mol⁻¹ChemAxon
Polarizability78.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0029958
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001238
KNApSAcK IDNot Available
Chemspider ID323121
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound363980
PDB IDNot Available
ChEBI ID565074
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. LOTUS database [Link]