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Record Information
Version2.0
Created at2022-09-02 14:31:47 UTC
Updated at2022-09-02 14:31:47 UTC
NP-MRD IDNP0157201
Secondary Accession NumbersNone
Natural Product Identification
Common Name(6-{[6-(3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-6,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-14-yl]oxy}-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methyl acetate
Description(6-{[6-(3,3-Dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-6,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icos-18-en-14-yl]oxy}-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methyl acetate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. (6-{[6-(3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-6,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-14-yl]oxy}-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methyl acetate is found in Ceratolimon feei. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5 (6-{[6-(3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-6,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icos-18-en-14-yl]oxy}-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
(6-{[6-(3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-6,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0,.0,.0,]icos-18-en-14-yl]oxy}-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methyl acetic acidGenerator
(6-{[6-(3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-6,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-14-yl]oxy}-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methyl acetic acidGenerator
Chemical FormulaC48H78O20
Average Mass975.1320 Da
Monoisotopic Mass974.50864 Da
IUPAC Name(6-{[6-(3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-6,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-14-yl]oxy}-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methyl acetate
Traditional Name(6-{[6-(3,3-dimethyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-6,16-dihydroxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-14-yl]oxy}-3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)methyl acetate
CAS Registry NumberNot Available
SMILES
CC1C2C(CC3C4CC=C5CC(O)CC(OC6OC(COC(C)=O)C(O)C(O)C6OC6OC(C)C(O)C(O)C6O)C5(C)C4CCC23C)OC1(O)CCC(C)(C)COC1OC(CO)C(O)C(O)C1O
InChI Identifier
InChI=1S/C48H78O20/c1-20-32-28(68-48(20,60)13-12-45(4,5)19-62-42-39(58)37(56)34(53)29(17-49)64-42)16-27-25-9-8-23-14-24(51)15-31(47(23,7)26(25)10-11-46(27,32)6)66-44-41(38(57)35(54)30(65-44)18-61-22(3)50)67-43-40(59)36(55)33(52)21(2)63-43/h8,20-21,24-44,49,51-60H,9-19H2,1-7H3
InChI KeyMUEYLOBZDULJMS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ceratolimon feeiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Eremophilane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP-0.11ALOGPS
logP-0.98ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.56ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area313.44 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity234.49 m³·mol⁻¹ChemAxon
Polarizability102.94 ųChemAxon
Number of Rings8ChemAxon
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 IDNot Available
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. LOTUS database [Link]