Showing Compound Lithospermic acid (FDB006174)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:01 UTC

Update date

2019-11-26 03:00:59 UTC

Primary ID

FDB006174

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lithospermic acid

Description

Lithospermic 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 Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Lithospermate	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.58	ALOGPS
logP	3.75	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	211.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.07 m³·mol⁻¹	ChemAxon
Polarizability	50.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C27H22O12

IUPAC name

4-[(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 Identifier

InChI=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 Key

UJZQBMQZMKFSRV-YWEYNIOJSA-N

Isomeric SMILES

OC(=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 Weight

538.4564

Monoisotopic Molecular Weight

538.111126168

Classification

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0084-0937280000-227f74b662fa6b9152eb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0942220000-b425c0918c73bd2853a8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ds-0910000000-ea957fe6a8b59d72e06f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002u-0906660000-58c798988c876dd381f8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08ia-0829400000-755e412807d83fd1a3a7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0619000000-1ca614a869972de195ac	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CNV70-C:CNV70-C

EAFUS ID

Not Available

Dr. Duke ID

LITHOSPERMIC-ACID

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

1041

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti gonadotrophic		An agent that inhibits gonadotropin production or activity, regulating reproductive hormone secretion. It has therapeutic applications in managing conditions like precocious puberty, hormone-sensitive cancers, and infertility, with key medical uses including contraception and treatment of endometriosis.	DUKE
Anti-thyroid		An agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease.	DUKE
Cardiotonic	38070	An agent that strengthens heart muscle contractions, enhancing cardiac output. It plays a biological role in regulating heart function and is therapeutically used to treat heart failure, improving symptoms and exercise tolerance. Key medical uses include managing cardiomyopathy, atrial fibrillation, and congestive heart failure.	DUKE