Show more...
Record Information
Version2.0
Created at2022-09-06 22:55:46 UTC
Updated at2022-09-06 22:55:47 UTC
NP-MRD IDNP0239351
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s,5ar,5br,7ar,8s,11as,11br,13as)-8-ethyl-3,5b,8,11a,13a-pentamethyl-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h-chryseno[1,2-c]furan-1,13-dione
Description(1R,2R,6S,10S,13R,14S,18S,19R)-18-ethyl-1,6,10,14,18-pentamethyl-7-oxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-5(9)-ene-8,11-dione belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. (3s,5ar,5br,7ar,8s,11as,11br,13as)-8-ethyl-3,5b,8,11a,13a-pentamethyl-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h-chryseno[1,2-c]furan-1,13-dione is found in Carteriospongia foliascens. Based on a literature review very few articles have been published on (1R,2R,6S,10S,13R,14S,18S,19R)-18-ethyl-1,6,10,14,18-pentamethyl-7-oxapentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicos-5(9)-ene-8,11-dione.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H40O3
Average Mass412.6140 Da
Monoisotopic Mass412.29775 Da
IUPAC Name(1R,2R,6S,10S,13R,14S,18S,19R)-18-ethyl-1,6,10,14,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-ene-8,11-dione
Traditional Name(1R,2R,6S,10S,13R,14S,18S,19R)-18-ethyl-1,6,10,14,18-pentamethyl-7-oxapentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicos-5(9)-ene-8,11-dione
CAS Registry NumberNot Available
SMILES
CC[C@@]1(C)CCC[C@@]2(C)[C@@H]1CC[C@@]1(C)[C@H]3CCC4=C(C(=O)O[C@H]4C)[C@@]3(C)C(=O)C[C@H]21
InChI Identifier
InChI=1S/C27H40O3/c1-7-24(3)12-8-13-25(4)18(24)11-14-26(5)19-10-9-17-16(2)30-23(29)22(17)27(19,6)21(28)15-20(25)26/h16,18-20H,7-15H2,1-6H3/t16-,18+,19+,20+,24-,25-,26-,27+/m0/s1
InChI KeyOTZAFYKTECUBAV-CHELDCNLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Phyllospongia foliascensLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentScalarane sesterterpenoids
Alternative Parents
Substituents
  • Scalarane sesterterpenoid
  • Steroid lactone
  • Oxosteroid
  • 7-oxosteroid
  • 16-oxasteroid
  • Steroid
  • 2-furanone
  • Dihydrofuran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
logP6.28ChemAxon
pKa (Strongest Acidic)13.33ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity118.94 m³·mol⁻¹ChemAxon
Polarizability47.66 ųChemAxon
Number of Rings5ChemAxon
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 Compound162948438
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]