Chicoric acid

Details

• Internal ID: c5c7e976-2083-45d6-8419-bea88544b8a7
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: (2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC(=C(C=C2)O)O)C(=O)O)O)O
• InChI: InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
• InChI Key: YDDGKXBLOXEEMN-IABMMNSOSA-N
• Popularity: 440 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₈O₁₂
• Molecular Weight: 474.40 g/mol
• Exact Mass: 474.07982601 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: 2.00

Synonyms

• Cichoric Acid
• L-Chicoric acid
• 70831-56-0
• 6537-80-0
• (-)-Chicoric acid
• dicaffeoyltartaric acid
• (2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
• (-)-L-Chicoric acid
• L-Cichoric acid
• NSC 699173
• L-DCTA
• Chicoric acid, (-)-
• UNII-S4YY3V8YHD
• NSC699173
• S4YY3V8YHD
• Dicaffeoyl-L-tartaric acid
• trans-Caffeoyltartaric acid
• CHEBI:3594
• CHEMBL282731
• DTXSID0033332
• 2,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid
• C22H18O12
• (R-(R*,R*-(E,E)))-2,3-Bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid
• NSC-699173
• (2R,3R)-2,3-bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic acid
• (2R,3R)-2,3-Bis[[(E)-3-(3,4-dihydroxyphenyl)acryloyl]oxy]succinic Acid
• ChicoricAcid
• (2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
• Butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (2R,3R)-
• Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2R,3R)-
• C22-H18-O12
• Butanedioic acid, 2,3-bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*-(E,E)))-
• L-Chicoricacid
• 1-chicoricacid
• Cichoric-Acid
• l-Chicoric-acid
• Cichoric acid;Dicaffeoyltartaric acid
• GKP
• (-)-Chicoric acid;trans-Caffeoyltartaric acid
• ECH PURPUREA PE
• Echinacea Purpurea powder
• L-CA
• ECH ANGUSTIFOLIA PE
• CHICORIC ACID [USP-RS]
• DTXCID8013332
• SCHEMBL15532218
• YDDGKXBLOXEEMN-IABMMNSOSA-N
• Chicoric Acid, >=95% (HPLC)
• HY-N0457
• Tox21_201055
• BDBM50076273
• MFCD00189418
• s9133
• AKOS000278435
• CCG-269487
• CS-4262
• ( -)-Chicoric acid, analytical standard
• NCGC00091914-01
• NCGC00091914-02
• NCGC00091914-04
• NCGC00258608-01
• AC-34315
• AC-36990
• AS-56447
• CAS-70831-56-0
• LS-176843
• C3450
• A914269
• Q5119402
• TARTARIC ACID, BIS(3,4-DIHYDROXYCINNAMATE)
• 2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid
• Chicoric Acid, United States Pharmacopeia (USP) Reference Standard
• (2R,3R)-2,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic acid
• (2R,3R)-2,3-bis((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)succinic acid
• (2R,3R)-2,3-Bis-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-succinic acid
• (2R,3R)-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid
• (2R,3R)-2,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}succinic acid
• (2R,3R)-2,3-bis{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
• [S-(R*,R*)]-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic acid
• butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (2R,3R)-
• Butanedioic acid, 2,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (R-(R*,R*))-
• Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2R,3R)- (9CI)
• Butanedioic acid, 2,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, [R-[R*,R*-(E,E)]]-
• NCGC00091914-04!(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	39810.7 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	6.3 nM; 6.3 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	31622.8 nM; 501.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	794.3 nM; 794.3 nM	Potency; Potency	via Super-PRED; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.08%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.20%	91.49%
CHEMBL3194	P02766	Transthyretin	95.03%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.33%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.78%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.37%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.90%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.94%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.11%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.84%	80.78%
CHEMBL2581	P07339	Cathepsin D	83.57%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.63%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.87%	89.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	80.80%	97.53%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.79%	96.09%

Plants that contains it

• Agathosma scaberula
• Balanophora harlandii
• Cichorium intybus
• Cichorium pumilum
• Echinacea angustifolia
• Echinacea atrorubens
• Echinacea pallida
• Echinacea purpurea
• Equisetum arvense
• Euphorbia nicaeensis
• Isodon rubescens
• Lapsana communis
• Lupinus cosentinii
• Polemonium caeruleum
• Rhodiola rosea
• Scorzonera humilis
• Strychnos ledermannii
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum
• Viburnum davidii

Cross-Links

• PubChem: 5281764
• NPASS: NPC217052
• ChEMBL: CHEMBL282731
• LOTUS: LTS0177566
• wikiData: Q5119402