Record Information
Version1.0
Creation date2011-03-17 23:26:14 UTC
Update date2019-11-26 03:20:42 UTC
Primary IDFDB021672
Secondary Accession Numbers
  • FDB015790
Chemical Information
FooDB NameMethyl 15beta-hydroxy-19-trachylobanoate
Description15beta-hydroxy-19-trachylobanoic acid is a member of the class of compounds known as kaurane diterpenoids. Kaurane diterpenoids are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. 15beta-hydroxy-19-trachylobanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 15beta-hydroxy-19-trachylobanoic acid can be found in fats and oils, which makes 15beta-hydroxy-19-trachylobanoic acid a potential biomarker for the consumption of this food product.
CAS Number83508-81-0
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP2.33ALOGPS
logP3.31ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.64ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.97 m³·mol⁻¹ChemAxon
Polarizability36.16 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H30O3
IUPAC name16-hydroxy-5,9,13-trimethylpentacyclo[11.2.1.0¹,¹⁰.0⁴,⁹.0¹²,¹⁴]hexadecane-5-carboxylic acid
InChI IdentifierInChI=1S/C20H30O3/c1-17-6-4-7-18(2,16(22)23)13(17)5-8-20-10-12-11(9-14(17)20)19(12,3)15(20)21/h11-15,21H,4-10H2,1-3H3,(H,22,23)
InChI KeyMHVNHDYWKUKRRJ-UHFFFAOYSA-N
Isomeric SMILESCC12C3CC4(CCC5C(C)(CCCC5(C)C(O)=O)C4CC13)C2O
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
Classification
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentKaurane diterpenoids
Alternative Parents
Substituents
  • Atisane diterpenoid
  • Kaurane diterpenoid
  • Villanovane, atisane, trachylobane or helvifulvane diterpenoid
  • Alkaloid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS15beta-Hydroxy-19-trachylobanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-5394000000-337b088c7f7925f09afcSpectrum
Predicted GC-MS15beta-Hydroxy-19-trachylobanoic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006t-9036600000-cf300ccc616e3c8efc26Spectrum
Predicted GC-MS15beta-Hydroxy-19-trachylobanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS15beta-Hydroxy-19-trachylobanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0049000000-61f9f606707e152dff0e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-0295000000-c3f9644e7a9625bc33962015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-5970000000-092246a2ed6e70b95e1d2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0069000000-99df82d2accafd9a25bc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06dj-0093000000-347444462e602f772ad52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1091000000-783cd1b640f4e40d17652015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-062ad2a35e11d303cf232021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-062ad2a35e11d303cf232021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1009000000-ccc99b100decfcf422772021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-0098000000-acc22a07ab5e6edf097e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01di-0093000000-8efb5bd4f03a205c78352021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7960000000-c6b172908bef2f473a182021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJGT16-I:JGT14-G
EAFUS IDNot Available
Dr. Duke ID15-BETA-HYDROXY-TRACHYLOBAN-19-OIC-ACID-METHYL-ESTER
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
SunflowerExpected but not quantifiedNot AvailableDUKE
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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).