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Record Information
Version2.0
Created at2022-09-12 09:59:20 UTC
Updated at2022-09-12 09:59:21 UTC
NP-MRD IDNP0327424
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r)-3-[(2r,6s)-6-hydroxy-5-[(3e)-4-methyl-6-[(1s,2s)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl]-5-oxo-2h-furan-2-yl acetate
Description(2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1S,2S)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (2r)-3-[(2r,6s)-6-hydroxy-5-[(3e)-4-methyl-6-[(1s,2s)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2h-pyran-2-yl]-5-oxo-2h-furan-2-yl acetate is found in Luffariella variabilis. Based on a literature review very few articles have been published on (2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1S,2S)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(2R)-3-[(2R,6S)-6-Hydroxy-5-[(3E)-4-methyl-6-[(1S,2S)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetic acidGenerator
Chemical FormulaC27H38O6
Average Mass458.5950 Da
Monoisotopic Mass458.26684 Da
IUPAC Name(2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1S,2S)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate
Traditional Name(2R)-3-[(2R,6S)-6-hydroxy-5-[(3E)-4-methyl-6-[(1S,2S)-2-methyl-1-(prop-1-en-2-yl)cyclopentyl]hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2H-furan-2-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@H]1CCC[C@@]1(CC\C(C)=C\CCC1=CC[C@@H](O[C@@H]1O)C1=CC(=O)O[C@H]1OC(C)=O)C(C)=C
InChI Identifier
InChI=1S/C27H38O6/c1-17(2)27(14-7-9-19(27)4)15-13-18(3)8-6-10-21-11-12-23(32-25(21)30)22-16-24(29)33-26(22)31-20(5)28/h8,11,16,19,23,25-26,30H,1,6-7,9-10,12-15H2,2-5H3/b18-8+/t19-,23+,25-,26+,27+/m0/s1
InChI KeyXHZRTBPTEWIFSK-PHYBXUPTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Luffariella variabilisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • 11-noriridane monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Acylal
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Pyran
  • Dihydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Hemiacetal
  • Carboxylic acid ester
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP5.48ChemAxon
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity127.83 m³·mol⁻¹ChemAxon
Polarizability51.23 ųChemAxon
Number of Rings3ChemAxon
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 Compound163188444
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]