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Record Information
Version2.0
Created at2022-09-06 22:34:57 UTC
Updated at2022-09-06 22:34:57 UTC
NP-MRD IDNP0239075
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5s)-5-methyl-3-[(2r,13r)-2,8,10,13-tetrahydroxy-13-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-5h-furan-2-one
Description(5S)-5-methyl-3-[(2R,13R)-2,8,10,13-tetrahydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2,5-dihydrofuran-2-one 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. (5s)-5-methyl-3-[(2r,13r)-2,8,10,13-tetrahydroxy-13-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-5h-furan-2-one is found in Annona muricata. Based on a literature review very few articles have been published on (5S)-5-methyl-3-[(2R,13R)-2,8,10,13-tetrahydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2,5-dihydrofuran-2-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC35H64O8
Average Mass612.8890 Da
Monoisotopic Mass612.46012 Da
IUPAC Name(5S)-5-methyl-3-[(2R,13R)-2,8,10,13-tetrahydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2,5-dihydrofuran-2-one
Traditional Name(5S)-5-methyl-3-[(2R,13R)-2,8,10,13-tetrahydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-5H-furan-2-one
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@@H](O1)[C@H](O)CCC(O)CC(O)CCCCC[C@@H](O)CC1=C[C@H](C)OC1=O
InChI Identifier
InChI=1S/C35H64O8/c1-3-4-5-6-7-8-9-10-11-15-18-31(39)33-21-22-34(43-33)32(40)20-19-30(38)25-29(37)17-14-12-13-16-28(36)24-27-23-26(2)42-35(27)41/h23,26,28-34,36-40H,3-22,24-25H2,1-2H3/t26-,28+,29?,30?,31+,32+,33+,34+/m0/s1
InChI KeyQAIKIRDKCUWJQV-NFYXKZPZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Annona muricataLOTUS 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
  • Oxolane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • 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
logP6.25ChemAxon
pKa (Strongest Acidic)13.3ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity170.97 m³·mol⁻¹ChemAxon
Polarizability75.52 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 IDNot Available
Chemspider ID4478144
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319953
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]