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Record Information
Version2.0
Created at2022-09-06 00:45:40 UTC
Updated at2022-09-06 00:45:40 UTC
NP-MRD IDNP0222827
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3r)-5-[(1r,2s,3s,4as,8ar)-3-(acetyloxy)-6-hydroxy-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpentanoic acid
Description(3R)-5-[(1R,2S,3S,4aS,8aR)-3-(acetyloxy)-6-hydroxy-1,2,4a,5-tetramethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoic acid 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. (3r)-5-[(1r,2s,3s,4as,8ar)-3-(acetyloxy)-6-hydroxy-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2h-naphthalen-1-yl]-3-methylpentanoic acid is found in Oedera genistifolia. Based on a literature review very few articles have been published on (3R)-5-[(1R,2S,3S,4aS,8aR)-3-(acetyloxy)-6-hydroxy-1,2,4a,5-tetramethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoic acid.
Structure
Thumb
Synonyms
ValueSource
(3R)-5-[(1R,2S,3S,4AS,8ar)-3-(acetyloxy)-6-hydroxy-1,2,4a,5-tetramethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoateGenerator
Chemical FormulaC22H34O6
Average Mass394.5080 Da
Monoisotopic Mass394.23554 Da
IUPAC Name(3R)-5-[(1R,2S,3S,4aS,8aR)-3-(acetyloxy)-6-hydroxy-1,2,4a,5-tetramethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoic acid
Traditional Name(3R)-5-[(1R,2S,3S,4aS,8aR)-3-(acetyloxy)-6-hydroxy-1,2,4a,5-tetramethyl-7-oxo-3,4,8,8a-tetrahydro-2H-naphthalen-1-yl]-3-methylpentanoic acid
CAS Registry NumberNot Available
SMILES
C[C@H](CC[C@@]1(C)[C@H](C)[C@H](C[C@@]2(C)[C@@H]1CC(=O)C(O)=C2C)OC(C)=O)CC(O)=O
InChI Identifier
InChI=1S/C22H34O6/c1-12(9-19(25)26)7-8-21(5)13(2)17(28-15(4)23)11-22(6)14(3)20(27)16(24)10-18(21)22/h12-13,17-18,27H,7-11H2,1-6H3,(H,25,26)/t12-,13-,17+,18-,21+,22-/m1/s1
InChI KeyLJQHKOKKBQLTOA-GJJPQWRWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Oedera genistifoliaLOTUS 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
  • Carbocyclic fatty acid
  • Medium-chain fatty acid
  • Branched fatty acid
  • Cyclohexenone
  • Methyl-branched fatty acid
  • Hydroxy fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Carboxylic acid ester
  • Cyclic ketone
  • Ketone
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.26ChemAxon
pKa (Strongest Acidic)4.53ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.5 m³·mol⁻¹ChemAxon
Polarizability42.78 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 Compound162953810
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]