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Record Information
Version1.0
Creation date2010-04-08 22:15:02 UTC
Update date2019-11-26 03:18:56 UTC
Primary IDFDB020443
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-trans-Caffeoyltormentic acid
Description3-trans-Caffeoyltormentic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-trans-Caffeoyltormentic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number144604-16-0
Structure
Thumb
Synonyms
SynonymSource
3-trans-CaffeoyltormentateGenerator
10-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,11-dihydroxy-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-carboxylateGenerator
3-trans-Caffeoyltormentic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0019 g/LALOGPS
logP5.95ALOGPS
logP6.7ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.64ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity180.19 m³·mol⁻¹ChemAxon
Polarizability72.95 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC39H54O8
IUPAC name10-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,11-dihydroxy-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/C39H54O8/c1-22-14-17-39(33(44)45)19-18-36(5)24(31(39)38(22,7)46)10-12-29-35(4)21-27(42)32(34(2,3)28(35)15-16-37(29,36)6)47-30(43)13-9-23-8-11-25(40)26(41)20-23/h8-11,13,20,22,27-29,31-32,40-42,46H,12,14-19,21H2,1-7H3,(H,44,45)/b13-9+
InChI KeyMFPIVTNHMCQSEM-UKTHLTGXSA-N
Isomeric SMILESCC1CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(OC(=O)\C=C\C6=CC=C(O)C(O)=C6)C(C)(C)C5CCC34C)C2C1(C)O)C(O)=O
Average Molecular Weight650.8413
Monoisotopic Molecular Weight650.381868704
Classification
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Benzenoid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Tertiary alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic 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 - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.97%; H 8.36%; O 19.67%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +1.2 (c, 1 in MeOH)DFC
Spectroscopic UV Data333 (e ) (EtOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-2203907000-4e4cf95eb47df0db9c1aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ff0-0300419000-8ee5dddb52b780d11160JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900836000-793988fa2ca6b51495b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00g3-1401911000-0d06d690b110050167c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0200219000-11383b227e5a15c61f9aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0700936000-edeb5978adee2bc08264JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02g6-1600900000-a7e9388cbea1b5f90d6bJSpectraViewer
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 IDHMDB40650
CRC / DFC (Dictionary of Food Compounds) IDJST83-G:MSM22-L
EAFUS IDNot Available
Dr. Duke ID3-O-TRANS-CAFFEOYLTORMENTIC-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 / Bioactivities
DescriptorIDDefinitionReference
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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).