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Record Information
Version2.0
Created at2021-06-20 20:23:52 UTC
Updated at2021-06-30 00:09:42 UTC
NP-MRD IDNP0037483
Secondary Accession NumbersNone
Natural Product Identification
Common Namexylocarpin L
Provided ByJEOL DatabaseJEOL Logo
DescriptionMethyl (2R)-2-(acetyloxy)-2-[(1R,2S,4S,5S,6R,10R,11R,12R,13R,14R,15R,17S,18S)-4,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,11,17-trihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadecan-18-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. xylocarpin L is found in Xylocarpus granatum. xylocarpin L was first documented in 2008 (Cui, J., et al.). Methyl (2R)-2-(acetyloxy)-2-[(1R,2S,4S,5S,6R,10R,11R,12R,13R,14R,15R,17S,18S)-4,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,11,17-trihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadecan-18-yl]acetate is a strongly basic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
Methyl (2R)-2-(acetyloxy)-2-[(1R,2S,4S,5S,6R,10R,11R,12R,13R,14R,15R,17S,18S)-4,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,11,17-trihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0,.0,.0,]octadecan-18-yl]acetic acidGenerator
Chemical FormulaC35H44O16
Average Mass720.7210 Da
Monoisotopic Mass720.26294 Da
IUPAC Namemethyl (2R)-2-(acetyloxy)-2-[(1R,2S,4S,5S,6R,10R,11R,12R,13R,14R,15R,17S,18S)-4,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,11,17-trihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadecan-18-yl]acetate
Traditional Name(R)-(methyl (acetyloxy)[(1R,2S,4S,5S,6R,10R,11R,12R,13R,14R,15R,17S,18S)-4,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,11,17-trihydroxy-1,5,15-trimethyl-8-oxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadecan-18-yl]acetate)
CAS Registry NumberNot Available
SMILES
[H]O[C@@]12C([H])([H])[C@@]3(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]1([H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]1(O[H])[C@]4([H])C([H])([H])C(=O)O[C@@]([H])(C5=C([H])OC([H])=C5[H])[C@]4(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])[C@]1(O[H])[C@]2(C([H])([H])[H])[C@@]3([H])[C@@]([H])(OC(=O)C([H])([H])[H])C(=O)OC([H])([H])[H]
InChI Identifier
InChI=1S/C35H44O16/c1-15(36)47-21-12-34(43)32(7)25(24(29(41)45-8)48-16(2)37)30(5)14-33(32,42)23(27(30)49-17(3)38)28(50-18(4)39)35(34,44)20-11-22(40)51-26(31(20,21)6)19-9-10-46-13-19/h9-10,13,20-21,23-28,42-44H,11-12,14H2,1-8H3/t20-,21+,23-,24-,25+,26+,27-,28-,30-,31+,32-,33+,34+,35-/m1/s1
InChI KeyWJAUNQLZJPTPBB-RIFVFNHGSA-N
Experimental Spectra
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Xylocarpus granatumJEOL database
    • Cui, J., et al, Magn. Reson. Chem. 46, 894 (2008)
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
  • Mexicanolide
  • Prostaglandin skeleton
  • Steroid lactone
  • Eicosanoid
  • Hexacarboxylic acid or derivatives
  • Oxosteroid
  • 2-oxosteroid
  • 3-oxasteroid
  • Steroid
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Delta_valerolactone
  • Fatty acyl
  • Oxane
  • Pyran
  • Tertiary alcohol
  • Methyl ester
  • Heteroaromatic compound
  • Furan
  • Cyclic alcohol
  • Lactone
  • Carboxylic acid ester
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • 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
logP1.45ALOGPS
logP-1.1ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.41ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area231.63 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity164.33 m³·mol⁻¹ChemAxon
Polarizability69.66 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
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 ID27023604
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Cui, J., et al. (2008). Cui, J., et al, Magn. Reson. Chem. 46, 894 (2008). Mag. Reson. Chem..