Record Information
Version1.0
Creation date2010-04-08 22:11:56 UTC
Update date2019-11-26 03:11:53 UTC
Primary IDFDB015577
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTormentic acid
DescriptionTormentic acid, also known as tormentate, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Tormentic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Tormentic acid can be found in loquat and olive, which makes tormentic acid a potential biomarker for the consumption of these food products. Tormentic acid is a bio-active isolate of Luehea divaricata and Agrimonia eupatoria. Tormentic acid derivatives have been synthesized and researched .
CAS Number13850-16-3
Structure
Thumb
Synonyms
SynonymSource
TormentateGenerator
2,3,19-Trihydroxyurs-12-en-28-oic acid (2alpha,3beta)-biospider
Tomentic acidbiospider
Tormentic aciddb_source
Urs-12-en-28-oic acid, 2,3,19-trihydroxy-, (2alpha,3beta)-biospider
Predicted Properties
PropertyValueSource
logP4.27ChemAxon
pKa (Strongest Acidic)4.64ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity136.66 m³·mol⁻¹ChemAxon
Polarizability56.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC30H48O5
IUPAC name(1R,2R,4aS,6aS,6bR,10R,11R,12aR,12bR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
InChI IdentifierInChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)
InChI KeyOXVUXGFZHDKYLS-UHFFFAOYSA-N
Isomeric SMILESCC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(O)C(C)(C)C5CCC34C)C2C1(C)O)C(O)=O
Average Molecular Weight488.6991
Monoisotopic Molecular Weight488.350174646
Classification
Description Belongs to the class of organic compounds known as taraxastane, ursane, and bauerane triterpenoids. These are triterpenoids with a structure based on either the taraxastane, ursane, or bauerane skeleton. These are obtained by methyl migration in ring E of the oleanane backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTaraxastane, ursane, and bauerane triterpenoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 73.73%; H 9.90%; O 16.37%DFC
Melting PointMp 273°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -20 (Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID73193
Pubchem Substance IDNot Available
ChEBI ID505804
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJST83-G:KDM07-N
EAFUS IDNot Available
Dr. Duke IDTORMENTIC-ACID
BIGG IDNot Available
KNApSAcK IDC00019490
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 / Bioactivities
DescriptorIDDefinitionReference
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.