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Showing Compound (+)-Hardwickiic acid (FDB006871)

Record Information
Version1.0
Creation date2010-04-08 22:07:20 UTC
Update date2025-11-18 23:02:56 UTC
Primary IDFDB006871
Secondary Accession Numbers
  • FDB006884
Chemical Information
FooDB Name(+)-Hardwickiic acid
Description(+)-hardwickiic acid is a member of the class of compounds known as colensane and clerodane diterpenoids. Colensane and clerodane diterpenoids are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations (+)-hardwickiic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (+)-hardwickiic acid can be found in blackcurrant, which makes (+)-hardwickiic acid a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
5-[2-(Furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylateGenerator
(+)-HardwickiateGenerator
Hardwickic acid, (-)-isomerMeSH
Hardwickic acidMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.0071 g/LALOGPS
logP5.33ALOGPS
logP5.08ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.08 m³·mol⁻¹ChemAxon
Polarizability36.26 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H28O3
IUPAC name5-[2-(furan-3-yl)ethyl]-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid
InChI IdentifierInChI=1S/C20H28O3/c1-14-7-10-20(3)16(18(21)22)5-4-6-17(20)19(14,2)11-8-15-9-12-23-13-15/h5,9,12-14,17H,4,6-8,10-11H2,1-3H3,(H,21,22)
InChI KeyHHWOKJDCJVESIF-UHFFFAOYSA-N
Isomeric SMILESCC1CCC2(C)C(CCC=C2C(O)=O)C1(C)CCC1=COC=C1
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
Classification
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
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0097000000-fed39af9417d4a080f432016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rj-0391000000-5e076b8451e26c71ba142016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-2980000000-7f9587534f8731d225632016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0049000000-26269078d2d5b32a37da2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-0093000000-094c9e1bfbdeae11ab012016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ll-1090000000-edf67d81c1d3829d273c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0094000000-c8b34837a6610be3fcbb2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fz9-0490000000-914b8f387fe0cd72b0972021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fxt-5930000000-35dd4033a8477f12cd442021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-0098000000-5616871189dc97fa5f812021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0095000000-eba827a65da349366bb42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0600-3190000000-bf82fbc21d16e353611f2021-10-21View Spectrum
NMRNot Available
ChemSpider ID26503523
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID15559627
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHPP29-J:JGP73-D
EAFUS IDNot Available
Dr. Duke ID(+)-HARDWICKIIC ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).