Record Information
Version2.0
Created at2022-04-28 22:25:56 UTC
Updated at2022-04-28 22:25:56 UTC
NP-MRD IDNP0077267
Secondary Accession NumbersNone
Natural Product Identification
Common NameToosendanin
Description(1S,2R,4R,5R,6R,8R,10R,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-4-yl acetate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Toosendanin is found in Melia azedarach , Melia toosendan Sieb.et Zuce. , Toona sinensis and Turnera ulmifolia . Based on a literature review very few articles have been published on (1S,2R,4R,5R,6R,8R,10R,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-4-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1S,2R,4R,5R,6R,8R,10R,11S,12R,14R,15R,16R,19S,21R)-21-(Acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0,.0,.0,.0,]henicosan-4-yl acetic acidGenerator
Chemical FormulaC30H38O11
Average Mass574.6230 Da
Monoisotopic Mass574.24141 Da
IUPAC Name(1S,2R,4R,5R,6R,8R,10R,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-4-yl acetate
Traditional Name(1S,2R,4R,5R,6R,8R,10R,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-4-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@@H]1C[C@H](O)[C@@]23CO[C@@H](O)[C@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@@H]3C(=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](C[C@H]3O[C@]123)C1=COC=C1
InChI Identifier
InChI=1S/C30H38O11/c1-13(31)39-20-10-19(34)29-12-38-25(36)26(20,3)17(29)9-18(33)28(5)23(29)22(35)24(40-14(2)32)27(4)16(15-6-7-37-11-15)8-21-30(27,28)41-21/h6-7,11,16-21,23-25,33-34,36H,8-10,12H2,1-5H3/t16-,17-,18+,19-,20+,21+,23-,24-,25+,26+,27+,28+,29+,30-/m0/s1
InChI KeyNAHTXVIXCMUDLF-DUJPAFNYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Melia azedarachPlant
Melia toosendan Sieb.et Zuce.Plant
Toona sinensisPlant
Turnera ulmifoliaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid skeleton
  • 17-furanylsteroid skeleton
  • Steroid ester
  • Naphthopyran
  • Naphthalene
  • Alpha-acyloxy ketone
  • Pyran
  • Oxane
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Furan
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP1.28ALOGPS
logP0.067ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)11.35ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area165.26 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity137.21 m³·mol⁻¹ChemAxon
Polarizability101.48 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound154497598
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available