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Record Information
Version1.0
Created at2022-09-12 15:36:47 UTC
Updated at2022-09-12 15:36:47 UTC
NP-MRD IDNP0330352
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-[2-(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)ethylidene]-4,5-bis(acetyloxy)oxolan-2-yl acetate
Description3-[2-(1,2,4A-trimethyl-5-methylidene-decahydronaphthalen-1-yl)ethylidene]-4,5-bis(acetyloxy)oxolan-2-yl acetate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 3-[2-(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)ethylidene]-4,5-bis(acetyloxy)oxolan-2-yl acetate is found in Linaria saxatilis. 3-[2-(1,2,4A-trimethyl-5-methylidene-decahydronaphthalen-1-yl)ethylidene]-4,5-bis(acetyloxy)oxolan-2-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
3-[2-(1,2,4a-Trimethyl-5-methylidene-decahydronaphthalen-1-yl)ethylidene]-4,5-bis(acetyloxy)oxolan-2-yl acetic acidGenerator
Chemical FormulaC26H38O7
Average Mass462.5830 Da
Monoisotopic Mass462.26175 Da
IUPAC Name3-[2-(1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl)ethylidene]-4,5-bis(acetyloxy)oxolan-2-yl acetate
Traditional Name3-[2-(1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl)ethylidene]-4,5-bis(acetyloxy)oxolan-2-yl acetate
CAS Registry NumberNot Available
SMILES
CC1CCC2(C)C(CCCC2=C)C1(C)CC=C1C(OC(C)=O)OC(OC(C)=O)C1OC(C)=O
InChI Identifier
InChI=1S/C26H38O7/c1-15-9-8-10-21-25(15,6)13-11-16(2)26(21,7)14-12-20-22(30-17(3)27)24(32-19(5)29)33-23(20)31-18(4)28/h12,16,21-24H,1,8-11,13-14H2,2-7H3
InChI KeyQNCNCHBOPZBLDS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Linaria saxatilisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentColensane and clerodane diterpenoids
Alternative Parents
Substituents
  • Clerodane diterpenoid
  • Tricarboxylic acid or derivatives
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen 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
logP4.7ALOGPS
logP4.56ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area88.13 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity121.19 m³·mol⁻¹ChemAxon
Polarizability50.02 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
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 Compound73826394
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]