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Record Information
Version2.0
Created at2022-04-29 04:10:40 UTC
Updated at2022-04-29 04:10:40 UTC
NP-MRD IDNP0083139
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Luffasterol A
Description(1BS,4S,5aR,5bS)-1b-methyl--[(1R,2S,3R)-2-methyl-3-[(2R)-6-methylheptan-2-yl]-2-(2-oxoethyl)cyclopentyl]--oxo-H,1bH,2H,3H,4H,5H,5bH-naphtho[1,8a-b]oxiren-4-yl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (-)-Luffasterol A is found in Luffariella sp. Based on a literature review very few articles have been published on (1bS,4S,5aR,5bS)-1b-methyl--[(1R,2S,3R)-2-methyl-3-[(2R)-6-methylheptan-2-yl]-2-(2-oxoethyl)cyclopentyl]--oxo-H,1bH,2H,3H,4H,5H,5bH-naphtho[1,8a-b]oxiren-4-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1BS,4S,5AR,5BS)-1b-methyl--[(1R,2S,3R)-2-methyl-3-[(2R)-6-methylheptan-2-yl]-2-(2-oxoethyl)cyclopentyl]--oxo-H,1BH,2H,3H,4H,5H,5BH-naphtho[1,8a-b]oxiren-4-yl acetic acidGenerator
Chemical FormulaC29H44O5
Average Mass472.6660 Da
Monoisotopic Mass472.31887 Da
IUPAC Name(1bS,4S,5aR,5bS)-1b-methyl--[(1R,2S,3R)-2-methyl-3-[(2R)-6-methylheptan-2-yl]-2-(2-oxoethyl)cyclopentyl]--oxo-H,1bH,2H,3H,4H,5H,5bH-naphtho[1,8a-b]oxiren-4-yl acetate
Traditional Name(1bS,4S,5aR,5bS)-1b-methyl--[(1R,2S,3R)-2-methyl-3-[(2R)-6-methylheptan-2-yl]-2-(2-oxoethyl)cyclopentyl]--oxo-2H,3H,4H,5H,5bH-naphtho[1,8a-b]oxiren-4-yl acetate
CAS Registry NumberNot Available
SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@@H](C2=C[C@@H]3O[C@@]33C[C@H](CC[C@]3(C)C2=O)OC(C)=O)[C@@]1(C)CC=O
InChI Identifier
InChI=1S/C29H44O5/c1-18(2)8-7-9-19(3)23-10-11-24(27(23,5)14-15-30)22-16-25-29(34-25)17-21(33-20(4)31)12-13-28(29,6)26(22)32/h15-16,18-19,21,23-25H,7-14,17H2,1-6H3/t19-,21+,23-,24+,25+,27+,28-,29+/m1/s1
InChI KeyLULBFAIQTMKTGW-SPZRSCIOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Luffariella sp.-
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cyclopentane sesquiterpenoid
  • Sesquiterpenoid
  • Cyclohexenone
  • Alpha-hydrogen aldehyde
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP5.32ALOGPS
logP5.55ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)17.87ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area72.97 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity132.29 m³·mol⁻¹ChemAxon
Polarizability55.5 ųChemAxon
Number of Rings4ChemAxon
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 Compound163018956
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available