Coumestrol - Moligand™,≥98% , Agonist of TAS2R14, CAS No.479-13-0, Agonist of TAS2R14

CAS: 479-13-0 Cat. No.: C609557 Molecular Weight: 268.22 Beilstein Registry Number: 266702 EC Number: 207-525-6

GRADE & PURITY Moligand™, ≥98%

Synonyms

3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one | Cumoesterol | Cumoestrol | Cumostrol | 3,9-Dihydroxycoumestan | Cumestrol

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Coumestrol, a phytoestrogen present in soybean products, exhibits activities against cancers, neurological disorders, and autoimmune diseases. It suppresses proliferation of ES2 cells with an IC50 of 50 μM.

Specifications

Synonyms

3, 9-Dihydroxy-6H-[1]benzofuro[3, 2-c]chromen-6-one | Cumoesterol | Cumoestrol | Cumostrol | 3, 9-Dihydroxycoumestan | Cumestrol

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of TAS2R14

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O
• IUPAC Name: 3,9-dihydroxy-[1]benzofuro[3,2-c]chromen-6-one
• InChIKey: ZZIALNLLNHEQPJ-UHFFFAOYSA-N
• INCHI: 1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H
• Isomeric SMILES: C1=CC2=C(C=C1O)OC3=C2C(=O)OC4=C3C=CC(=C4)O
• WGK Germany: 3
• RTECS: DF8077000
• Alternate CAS: 479-13-0
• NSC Number: 22842
• MeSH Entry Terms: Coumestrol
• Molecular Weight: 268.22
• Beilstein: 266702

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Isoflavonoids
      • Subclass Coumestans

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Isoflavonoids
• Subclass: Coumestans
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumestans
• Alternative Parents: Angular furanocoumarins 1-benzopyrans Furopyrans Benzofurans Pyranones and derivatives 1-hydroxy-2-unsubstituted benzenoids Heteroaromatic compounds Furans Lactones Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumestan - Angular furanocoumarin - Furanocoumarin - Coumarin - Benzopyran - 1-benzopyran - Benzofuran - Furopyran - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - Pyran - Benzenoid - Furan - Heteroaromatic compound - Lactone - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
• External Descriptors: an isoflavone

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)

ESR1 Tclin Estrogen receptor (4 Activities)

Discover Target: ESR1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ESR2 Tclin Estrogen receptor beta (4 Activities)

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TAS2R14 Tchem Taste receptor type 2 member 14 (0 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MGAM Tclin Maltase-glucoamylase (654 Activities)

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

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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

AR Tclin Androgen Receptor (11781 Activities)

Discover Target: AR

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

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

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

ACHE Tclin Acetylcholinesterase (18204 Activities)

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

ESR2 Tclin Estrogen receptor beta (9272 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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RXRA Tclin Retinoid X receptor alpha (3637 Activities)

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CSNK2A1 Tchem Casein kinase II alpha (3512 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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GLA Tclin Alpha-galactosidase A (5444 Activities)

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AHR Tclin Aryl hydrocarbon receptor (1071 Activities)

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PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

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GAA Tclin Lysosomal alpha-glucosidase (35701 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

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SMPD1 Tchem Sphingomyelin phosphodiesterase (13561 Activities)

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NR1I2 Tchem Pregnane X receptor (6667 Activities)

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PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)

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A498 (42825 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DLD-1 (17511 Activities)

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DMS-273 (14108 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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MCF7 (126967 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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SNB-78 (14240 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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XF498 (12972 Activities)

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Associated Targets(non-human)

NA Neuraminidase (1107 Activities)

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ampC Beta-lactamase AmpC (62480 Activities)

Discover Target: ampC

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

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Chlamydia pneumoniae (241 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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P388 (20296 Activities)

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P388/ADR (1216 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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BCHE Cholinesterase (8742 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

Discover Target: Mapt

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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FTL Ferritin light chain (43324 Activities)

Discover Target: FTL

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

ESR1 Estrogen receptor (4 Activities)

Discover Target: ESR1

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): ≥350 °C (lit.)
• Molecular Weight: 268.220 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 268.037 Da
• Monoisotopic Mass: 268.037 Da
• Topological Polar Surface Area: 79.900 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 411.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Tianzhu Guan, Yonghai Sun, Tiezhu Li, Ligang Hou, Jie Zhang, Yongjun Wang.  (2018)  Estrogen receptor-based multi-residue screening of bisphenol compounds in urine.  BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY,  66  (1): (68-73).  [PMID:30307064] [10.1002/bab.1697]