(-)-Chicoric acid - Moligand™,10mM in DMSO , CAS No.70831-56-0

CAS: 70831-56-0 Cat. No.: C425621 Molecular Weight: 474.37 EC Number: 615-177-5

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

CAS-70831-56-0 | Chicoric acid | MFCD00189418 | Cichoric acid;Dicaffeoyltartaric acid | (2R,3R)-2,3-Bis-[(E)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-succinic acid | D78144 | NCGC00258608-01 | (2R,3R)-2,3-bis((E)-3-(3,4-dihydroxyphenyl)acryloyloxy)succinic a

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyms

CAS-70831-56-0 | Chicoric acid | MFCD00189418 | Cichoric acid;Dicaffeoyltartaric acid | (2R, 3R)-2, 3-Bis-[(E)-3-(3, 4-dihydroxy-phenyl)-acryloyloxy]-succinic acid | D78144 | NCGC00258608-01 | (2R, 3R)-2, 3-bis((E)-3-(3, 4-dihydroxyphenyl)acryloyloxy)succinic a

Specifications & Purity

Moligand™, 10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: 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
• IUPAC Name: (2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
• InChIKey: YDDGKXBLOXEEMN-IABMMNSOSA-N
• 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
• Isomeric SMILES: 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
• Molecular Weight: 474.37
• Reaxy-Rn: 2927400
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2927400&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Tetracarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Tetracarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Tetracarboxylic acids and derivatives
• Alternative Parents: Coumaric acids and derivatives Cinnamic acid esters Styrenes Catechols Fatty acid esters 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Monosaccharides Enoate esters Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Tetracarboxylic acid or derivatives - 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 - Monosaccharide - Monocyclic benzene moiety - Fatty acyl - Benzenoid - Enoate ester - Alpha,beta-unsaturated carboxylic ester - Carboxylic acid ester - Carboxylic acid - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Carbonyl group - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
• External Descriptors: organooxygen compound

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CXCL8 Tchem Interleukin-8 (642 Activities)

Discover Target: CXCL8

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LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)

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SRC Tclin Tyrosine-protein kinase SRC (10310 Activities)

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STAT3 Tchem Signal transducer and activator of transcription 3 (3313 Activities)

Discover Target: STAT3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)

Discover Target: AKT1

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NFKBIA Tchem NF-kappaB inhibitor alpha (187 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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CEM-SS (2428 Activities)

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MT2 (2907 Activities)

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MT4 (17854 Activities)

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RELA Tchem Nuclear factor NF-kappa-B p65 subunit (627 Activities)

Discover Target: RELA

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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

Discover Target: HSD17B10

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STAT5B Tchem Signal transducer and activator of transcription 5B (90 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

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STAT1 Tchem Signal transducer and activator of transcription 1-alpha/beta (808 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

Discover Target: RUNX1

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MAPK13 Tchem MAP kinase p38 (1586 Activities)

Discover Target: MAPK13

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MAPK8 Tchem c-Jun N-terminal kinase, JNK (688 Activities)

Discover Target: MAPK8

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IKBKB Tchem Inhibitor of NF-kappa-B kinase alpha/beta (19 Activities)

Discover Target: IKBKB

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 integrase (9041 Activities)

Discover Target: pol

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Mus musculus (284745 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Human immunodeficiency virus (3636 Activities)

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lef Anthrax lethal factor (7585 Activities)

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yopH Tyrosine-protein phosphatase yopH (49 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 474.400 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 11
• Exact Mass: 474.08 Da
• Monoisotopic Mass: 474.08 Da
• Topological Polar Surface Area: 208.000 Ų
• Heavy Atom Count: 34
• Formal Charge: 0
• Complexity: 740.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1

References

1. Ji Ma, Maoru Li, Praveen Kumar Kalavagunta, Jiajing Li, Qiangqiang He, Yifan Zhang, Owais Ahmad, Hongli Yin, Tao Wang, Jing Shang.  (2018)  Protective effects of cichoric acid on H2O2-induced oxidative injury in hepatocytes and larval zebrafish models.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:29803928] [10.1016/j.biopha.2018.05.081]

2. Yi Hao, Ruixia Gao, Dechun Liu, Gaiyan He, Yuhai Tang, Zengjun Guo.  (2016)  Selective extraction and determination of chlorogenic acid in fruit juices using hydrophilic magnetic imprinted nanoparticles.  FOOD CHEMISTRY,      [PMID:26830581] [10.1016/j.foodchem.2016.01.004]

3. Binshuai Li, Xinran Liu, Mengai Yin, Lan Xue, Lina Lu, Fuju Dai, Wei Feng, Shengnan Yang, Jun Jiao, Qiang Chen.  (2022)  An Electrochemical Biosensor for Detection of Cichoric Acid as an Anti-Alzheimer’s Disease Agent in Chicory Samples Based on Setaria-Like Trimetallic Nanodendrites Decorated NH2-RGO Flakes.  JOURNAL OF THE ELECTROCHEMICAL SOCIETY,  169  (4): (046524).  [PMID:] [10.1149/1945-7111/ac68a4]