Record Information
Version1.0
Creation date2010-04-08 22:07:01 UTC
Update date2019-11-26 03:00:59 UTC
Primary IDFDB006174
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLithospermic acid
DescriptionLithospermic acid, also known as lithospermate, is a member of the class of compounds known as 2-arylbenzofuran flavonoids. 2-arylbenzofuran flavonoids are phenylpropanoids containing the 2-phenylbenzofuran moiety. Lithospermic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Lithospermic acid can be found in common thyme and peppermint, which makes lithospermic acid a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
LithospermateGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP3.58ALOGPS
logP3.75ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area211.28 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity133.07 m³·mol⁻¹ChemAxon
Polarizability50.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H22O12
IUPAC name4-[(1Z)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
InChI IdentifierInChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/b8-4-
InChI KeyUJZQBMQZMKFSRV-YWEYNIOJSA-N
Isomeric SMILESOC(=O)C(CC1=CC(O)=C(O)C=C1)OC(=O)\C=C/C1=C2C(C(OC2=C(O)C=C1)C1=CC=C(O)C(O)=C1)C(O)=O
Average Molecular Weight538.4564
Monoisotopic Molecular Weight538.111126168
Classification
Description Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Class2-arylbenzofuran flavonoids
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
  • Coumaric acid or derivatives
  • 3-phenylpropanoic-acid
  • Tricarboxylic acid or derivatives
  • Coumaran
  • Catechol
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Fatty acid ester
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Ether
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
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, Positivesplash10-0084-0937280000-227f74b662fa6b9152ebSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0942220000-b425c0918c73bd2853a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ds-0910000000-ea957fe6a8b59d72e06fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002u-0906660000-58c798988c876dd381f8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ia-0829400000-755e412807d83fd1a3a7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0619000000-1ca614a869972de195acSpectrum
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) IDCNV70-C:CNV70-C
EAFUS IDNot Available
Dr. Duke IDLITHOSPERMIC-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 ID1041
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti gonadotrophicDUKE
anti thyroidDUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.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).