D-Chicoric acid

Details

• Internal ID: 1e823404-bce2-4ff7-9b94-3884d935699a
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: (2S,3S)-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-/m0/s1
• InChI Key: YDDGKXBLOXEEMN-QFZCZCNSSA-N
• Popularity: 5 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

• D-DCTA
• Dicaffeoyl-D-tartaric acid
• 52248-48-3
• NSC 699176
• CHEMBL29660
• NSC699176
• NSC-699176
• (1S,2S)-1,2-Bis(3-(3,4-dihydroxyphenyl)prop-2-enoyloxy)ethane-1,2-dicarboxylic acid
• (2S,3S)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
• Butanedioic acid, 2,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (2S,3S)-
• (1S,2S)-1,2-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]ethane-1,2-dicarboxylic acid
• Butanedioic acid, 2,3-bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2S,3S)-
• ( -)-Chicoric acid
• Chicoric acid; Cichoric acid
• Cichoric acid, Cichoriens?ure
• SCHEMBL13772650
• BDBM50076267
• A14733
• Q-100787
• 2-O,3-O-Bis[3-(3,4-dihydroxyphenyl)acryloyl]-D-tartaric acid
• (2S,3S)-2,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid
• (2S,3S)-2,3-Bis-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-succinic 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
CHEMBL4096	P04637	Cellular tumor antigen p53	6.3 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	794.3 nM	Potency	via Super-PRED

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

• Cichorium intybus
• Cichorium pumilum
• Isodon rubescens
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum

Cross-Links

• PubChem: 5470299
• NPASS: NPC237506
• ChEMBL: CHEMBL29660