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Record Information
Version2.0
Created at2022-09-06 22:39:21 UTC
Updated at2022-09-06 22:39:21 UTC
NP-MRD IDNP0239133
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-hydroxy-18-[1-hydroxy-1-(4-methyl-5-oxo-2h-furan-2-yl)propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0³,⁷.0³,¹⁰.0¹⁴,¹⁶.0¹⁴,¹⁹]henicosan-5-one
Description1-Hydroxy-18-[1-hydroxy-1-(4-methyl-5-oxo-2,5-dihydrofuran-2-yl)propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0³,⁷.0³,¹⁰.0¹⁴,¹⁶.0¹⁴,¹⁹]Henicosan-5-one belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 1-hydroxy-18-[1-hydroxy-1-(4-methyl-5-oxo-2h-furan-2-yl)propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0³,⁷.0³,¹⁰.0¹⁴,¹⁶.0¹⁴,¹⁹]henicosan-5-one is found in Kadsura coccinea, Schisandra chinensis and Schisandra propinqua. 1-Hydroxy-18-[1-hydroxy-1-(4-methyl-5-oxo-2,5-dihydrofuran-2-yl)propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0³,⁷.0³,¹⁰.0¹⁴,¹⁶.0¹⁴,¹⁹]Henicosan-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H40O8
Average Mass516.6310 Da
Monoisotopic Mass516.27232 Da
IUPAC Name1-hydroxy-18-[1-hydroxy-1-(4-methyl-5-oxo-2,5-dihydrofuran-2-yl)propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0³,⁷.0³,¹⁰.0¹⁴,¹⁶.0¹⁴,¹⁹]henicosan-5-one
Traditional Name1-hydroxy-18-[1-hydroxy-1-(4-methyl-5-oxo-2H-furan-2-yl)propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0³,⁷.0³,¹⁰.0¹⁴,¹⁶.0¹⁴,¹⁹]henicosan-5-one
CAS Registry NumberNot Available
SMILES
CC(C(O)C1OC(=O)C(C)=C1)C1CC2OC22C3CCC4C(C)(C)OC5CC(=O)OC45CC3(O)CCC12C
InChI Identifier
InChI=1S/C29H40O8/c1-14-10-17(34-24(14)32)23(31)15(2)16-11-21-29(36-21)19-7-6-18-25(3,4)35-20-12-22(30)37-28(18,20)13-27(19,33)9-8-26(16,29)5/h10,15-21,23,31,33H,6-9,11-13H2,1-5H3
InChI KeyNOPJKUNZSJEAIR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Kadsura coccineaLOTUS Database
Schisandra chinensisLOTUS Database
Schisandra propinquaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassFurofurans
Sub ClassNot Available
Direct ParentFurofurans
Alternative Parents
Substituents
  • Furofuran
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Oxane
  • Cyclic alcohol
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Tertiary alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP3.14ALOGPS
logP2.28ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.38ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area114.82 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity131.1 m³·mol⁻¹ChemAxon
Polarizability56.19 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 Compound73307302
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]