Fraxetin - analytical standard, ≥98% , CAS No.574-84-5

CAS: 574-84-5 Cat. No.: F115713 Molecular Weight: 208.17 EC Number: 209-376-2

GRADE & PURITY Analytical standard, ≥98%

Synonyms

C09265 | KBio2_001987 | MEGxp0_000506 | NCGC00017270-03 | Spectrum5_000332 | KBio2_007123 | SMR000112323 | TNP00177 | KBio1_001517 | Coumarin, 7,8-dihydroxy-6-methoxy | SR-05000002449-1 | MLS002207123 | 7,8-Dihydroxy-6-methoxycoumarin | HAVWRBANWNTOJX-UHF

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

C09265 | KBio2_001987 | MEGxp0_000506 | NCGC00017270-03 | Spectrum5_000332 | KBio2_007123 | SMR000112323 | TNP00177 | KBio1_001517 | Coumarin, 7, 8-dihydroxy-6-methoxy | SR-05000002449-1 | MLS002207123 | 7, 8-Dihydroxy-6-methoxycoumarin | HAVWRBANWNTOJX-UHF

Specifications & Purity

analytical standard, ≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Analytical standard

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: COC1=C(C(=C2C(=C1)C=CC(=O)O2)O)O
• IUPAC Name: 7,8-dihydroxy-6-methoxychromen-2-one
• InChIKey: HAVWRBANWNTOJX-UHFFFAOYSA-N
• INCHI: 1S/C10H8O5/c1-14-6-4-5-2-3-7(11)15-10(5)9(13)8(6)12/h2-4,12-13H,1H3
• Isomeric SMILES: COC1=C(C(=C2C(=C1)C=CC(=O)O2)O)O
• WGK Germany: 3
• Molecular Weight: 208.17
• Reaxy-Rn: 198796
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=198796&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Hydroxycoumarins

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Hydroxycoumarins
• Intermediate Tree Nodes: Not available
• Direct Parent: 7,8-dihydroxycoumarins
• Alternative Parents: 7-hydroxycoumarins 1-benzopyrans Anisoles Pyranones and derivatives Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids Heteroaromatic compounds Lactones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 7,8-dihydroxycoumarin - 7-hydroxycoumarin - Benzopyran - 1-benzopyran - Anisole - 1-hydroxy-4-unsubstituted benzenoid - Alkyl aryl ether - Pyranone - Pyran - Benzenoid - Heteroaromatic compound - Lactone - Organoheterocyclic compound - Ether - Oxacycle - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 7,8-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively.
• External Descriptors: coumarins

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)

CA9 Tclin Carbonic anhydrase 9 (1 Activities)

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

CA2 Tclin Carbonic anhydrase II (17698 Activities)

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ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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CA1 Tclin Carbonic anhydrase I (13240 Activities)

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AMY2A Tclin Pancreatic alpha-amylase (74 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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CASP1 Tchem Caspase-1 (6235 Activities)

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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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CASP7 Tchem Caspase-7 (3146 Activities)

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CA12 Tclin Carbonic anhydrase XII (6231 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CA9 Tclin Carbonic anhydrase IX (8255 Activities)

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U-937 (7138 Activities)

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HaCaT (4069 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

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MCL1 Tchem Induced myeloid leukemia cell differentiation protein Mcl-1 (3820 Activities)

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

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POLK Tbio DNA polymerase kappa (8653 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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GMNN Tbio Geminin (128009 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 Activities)

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RAN Tchem GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 (21853 Activities)

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Associated Targets(non-human)

Ca7 Carbonic anhydrase VII (3 Activities)

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Ca13 Carbonic anhydrase XIII (322 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Aspergillus flavus (8875 Activities)

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Aspergillus fumigatus (16427 Activities)

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Rattus norvegicus (775804 Activities)

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lef Anthrax lethal factor (7585 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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ddn Putative uncharacterized protein (49 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 230-231°C
• Molecular Weight: 208.170 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 208.037 Da
• Monoisotopic Mass: 208.037 Da
• Topological Polar Surface Area: 76.000 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 288.000
• 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. Qing Wang, Di Zhuang, Wenchang Feng, Bitao Ma, Liping Qin, Lilun Jin.  (2020)  Fraxetin inhibits interleukin-1β-induced apoptosis, inflammation, and matrix degradation in chondrocytes and protects rat cartilage in vivo.  SAUDI PHARMACEUTICAL JOURNAL,      [PMID:33424243] [10.1016/j.jsps.2020.09.016]

2. Dingli Ye, Junqiang Hao, Rongxu Zhang, Yangyang Zhou, Shurong Chen, Weijian Zhang, Lei Zhao, Jiahan Xie, Zhibing Wang.  (2024)  Optimization of ultrasonic-assisted supramolecular solvent microextraction of coumarins from Cortex fraxini using response surface methodology combined with artificial neural network-genetic algorithm.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:38320432] [10.1016/j.chroma.2024.464692]