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Record Information
Version2.0
Created at2022-09-02 00:44:27 UTC
Updated at2022-09-02 00:44:27 UTC
NP-MRD IDNP0145521
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2r,4r,5r,6s,8r,10s,11s,12r,14r,15r,16r,19s,21r)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-4-yl acetate
Description(1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-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. (1s,2r,4r,5r,6s,8r,10s,11s,12r,14r,15r,16r,19s,21r)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-4-yl acetate is found in Melia azedarach. Based on a literature review very few articles have been published on (1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-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,10S,11S,12R,14R,15R,16R,19S,21R)-21-(Acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-3-oxo-9,17-dioxahexacyclo[13.3.3.0,.0,.0,.0,]henicosan-4-yl acetic acidGenerator
Chemical FormulaC34H44O11
Average Mass628.7150 Da
Monoisotopic Mass628.28836 Da
IUPAC Name(1S,2R,4R,5R,6R,8R,10S,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-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,10S,11S,12R,14R,15R,16R,19S,21R)-21-(acetyloxy)-6-(furan-3-yl)-12,19-dihydroxy-5,11,15-trimethyl-16-(2-methylpropanoyl)-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(C)C(=O)[C@@H]1OC[C@]23[C@@H](O)C[C@@H](OC(C)=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/C34H44O11/c1-15(2)25(39)28-30(5)20-11-21(37)32(7)27(33(20,14-42-28)22(38)12-23(30)43-16(3)35)26(40)29(44-17(4)36)31(6)19(18-8-9-41-13-18)10-24-34(31,32)45-24/h8-9,13,15,19-24,27-29,37-38H,10-12,14H2,1-7H3/t19-,20-,21+,22-,23+,24+,27-,28-,29-,30+,31+,32+,33+,34+/m0/s1
InChI KeyXZVSQEQUTVXEMX-PDMXXUAHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Melia azedarachLOTUS Database
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
  • Dicarboxylic acid or derivatives
  • Pyran
  • Oxane
  • Cyclic alcohol
  • Furan
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Ether
  • Oxirane
  • Oxacycle
  • Dialkyl ether
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP2.59ALOGPS
logP1.69ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)12.02ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area162.1 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity154.76 m³·mol⁻¹ChemAxon
Polarizability65.51 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162968915
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]