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Record Information
Version2.0
Created at2022-09-06 22:27:17 UTC
Updated at2022-09-06 22:27:18 UTC
NP-MRD IDNP0238962
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-[1-methyl-6-(3-methylbut-2-en-1-yl)-7-methylidene-12-(prop-1-en-2-yl)bicyclo[8.2.0]dodecan-4-yl]prop-2-enoic acid
DescriptionRaoulic acid, also known as raoulate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 2-[1-methyl-6-(3-methylbut-2-en-1-yl)-7-methylidene-12-(prop-1-en-2-yl)bicyclo[8.2.0]dodecan-4-yl]prop-2-enoic acid is found in Raoulia australis. Raoulic acid is a very weakly acidic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
RaoulateGenerator
Chemical FormulaC25H38O2
Average Mass370.5770 Da
Monoisotopic Mass370.28718 Da
IUPAC Name2-[1-methyl-6-(3-methylbut-2-en-1-yl)-7-methylidene-12-(prop-1-en-2-yl)bicyclo[8.2.0]dodecan-4-yl]prop-2-enoic acid
Traditional Name2-[1-methyl-6-(3-methylbut-2-en-1-yl)-7-methylidene-12-(prop-1-en-2-yl)bicyclo[8.2.0]dodecan-4-yl]prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1CC(CCC2(C)C(CC2C(C)=C)CCC1=C)C(=C)C(O)=O
InChI Identifier
InChI=1S/C25H38O2/c1-16(2)8-10-20-14-21(19(6)24(26)27)12-13-25(7)22(11-9-18(20)5)15-23(25)17(3)4/h8,20-23H,3,5-6,9-15H2,1-2,4,7H3,(H,26,27)
InChI KeyAGTGBEMIMBKQTR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Raoulia australisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
logP6.57ALOGPS
logP6.83ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)5.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity114.52 m³·mol⁻¹ChemAxon
Polarizability44.58 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
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 Compound49771359
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]