Cardamonin - 10mM in DMSO , CAS No.19309-14-9

CAS: 19309-14-9 Cat. No.: C422358 Molecular Weight: 270.28 EC Number: 663-565-8

GRADE & PURITY 10mM in DMSO

Synonyms

(E)-Cardamomin; (E)-Alpinetin chalcone | 2',4'-dihydroxy-6'-methoxychalcone | Cardamonin | 2-Propen-1-one, 1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenyl-, (2E)- | MFCD00238554 | NCGC00180767-02!(E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one |

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Store at +4°C. Store under desiccating conditions. The product can be stored for up to 12 months.

Specifications

Synonyms

(E)-Cardamomin; (E)-Alpinetin chalcone | 2', 4'-dihydroxy-6'-methoxychalcone | Cardamonin | 2-Propen-1-one, 1-(2, 4-dihydroxy-6-methoxyphenyl)-3-phenyl-, (2E)- | MFCD00238554 | NCGC00180767-02!(E)-1-(2, 4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one |

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Anticancer, anti-inflammatory spice-derived chalcone analog. Shown to supress numerous signaling pathways including TNF-α, COX-2, Wnt/β-catenin and NF-κB.

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.

Names and Identifiers

• Canonical Smiles: COC1=CC(=CC(=C1C(=O)C=CC2=CC=CC=C2)O)O
• IUPAC Name: (E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one
• InChIKey: NYSZJNUIVUBQMM-BQYQJAHWSA-N
• INCHI: 1S/C16H14O4/c1-20-15-10-12(17)9-14(19)16(15)13(18)8-7-11-5-3-2-4-6-11/h2-10,17,19H,1H3/b8-7+
• Isomeric SMILES: COC1=CC(=CC(=C1C(=O)/C=C/C2=CC=CC=C2)O)O
• Molecular Weight: 270.28
• Reaxy-Rn: 1990785
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1990785&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Linear 1,3-diarylpropanoids
      • Subclass Chalcones and dihydrochalcones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Linear 1,3-diarylpropanoids
• Subclass: Chalcones and dihydrochalcones
• Intermediate Tree Nodes: Not available
• Direct Parent: 2'-Hydroxychalcones
• Alternative Parents: Cinnamylphenols Methoxyphenols Styrenes Resorcinols Phenoxy compounds Methoxybenzenes Anisoles Benzoyl derivatives Aryl ketones 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Vinylogous acids Acryloyl compounds Enones Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 2'-hydroxychalcone - Cinnamylphenol - Methoxyphenol - Anisole - Benzoyl - Phenoxy compound - Phenol ether - Resorcinol - Styrene - Aryl ketone - Methoxybenzene - 1-hydroxy-2-unsubstituted benzenoid - 1-hydroxy-4-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Alpha,beta-unsaturated ketone - Enone - Acryloyl-group - Ketone - Ether - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.
• External Descriptors: Chalcones and dihydrochalcones

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)

KCNA3 Tclin Potassium voltage-gated channel subfamily A member 3 (2 Activities)

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PTH1R Tclin Parathyroid hormone receptor (47172 Activities)

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KCNA3 Tclin Voltage-gated potassium channel subunit Kv1.3 (1067 Activities)

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MAPK9 Tchem c-Jun N-terminal kinase 2 (4655 Activities)

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MAPK8 Tchem c-Jun N-terminal kinase 1 (5038 Activities)

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AGS (1999 Activities)

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CCRF-CEM (65223 Activities)

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DLD-1 (17511 Activities)

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PANC-1 (6144 Activities)

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HCT-116 (91556 Activities)

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HepG2 (196354 Activities)

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 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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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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TNFRSF10B Tbio Tumor necrosis factor receptor superfamily member 10B (15 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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GMNN Tbio Geminin (128009 Activities)

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APOBEC3G Tchem DNA dC->dU-editing enzyme APOBEC-3G (12481 Activities)

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BAZ2B Tchem Bromodomain adjacent to zinc finger domain protein 2B (56204 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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RAPGEF3 Tchem Rap guanine nucleotide exchange factor 3 (15528 Activities)

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

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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Leishmania amazonensis (3813 Activities)

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Schistosoma mansoni (6170 Activities)

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RAW264.7 (28094 Activities)

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Dengue virus type 2 NS3 protein (2214 Activities)

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Npsr1 Neuropeptide S receptor (260 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Protease (18 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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vpr Aberrant vpr protein (14595 Activities)

Discover Target: vpr

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 270.280 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 270.089 Da
• Monoisotopic Mass: 270.089 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 346.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Kun Hu, Yuanxia Lv, Fanggui Ye, Tao Chen, Shulin Zhao.  (2019)  Boric-Acid-Functionalized Covalent Organic Framework for Specific Enrichment and Direct Detection of cis-Diol-Containing Compounds by Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry.  ANALYTICAL CHEMISTRY,      [PMID:30999744] [10.1021/acs.analchem.9b01376]

2. Miao Luo, Sheng Wang, Chengpeng Li, Wangen Miao, Xiang Ma.  (2019)  Aggregation-induced emission organogel formed by both sonication and thermal processing based on tetraphenylethylene and cholesterol derivative.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2019.02.041]

3. Miao Luo, Sheng Wang, Meiling Wang, Shaorong Huang, Chengpeng Li, Lin Chen, Xiang Ma.  (2016)  Novel organogel harnessing Excited-State Intramolecular Proton Transfer process with aggregation induced emission and photochromism.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2016.04.036]

4. Yuhong Xiao, Yizhe He, Da Zhong, Bo Liu, ZhiBo Tang, Xiaoyong Lan, YiYang Dong, Huixian Du, Yu Liu, Jun Luo.  (2025)  Effect of Engineered Cyanobacterial Capsules on a Neurogenic Bladder after Spinal Cord Injury.  ACS Nano,      [PMID:40116782] [10.1021/acsnano.4c14140]

5. Chen Jiejian, Li Yonghao, Gan Xiaoning, Weng Chengyin, Fang Xisheng, Liu Guolong.  (2024)  Unlocking the potential: phenylboronic acid as a nuclear-targeting boron agent for neutron capture therapy.  MEDICAL ONCOLOGY,  41  (5): (1-5).  [PMID:38573420] [10.1007/s12032-024-02351-3]

6. Ruiwen Li, Heng Fan, Hao Shen, Shaoning Yu.  (2024)  Versatile MOF@COF catalyzed and magnetically multivalent aptamer assisted biosensing platform for rapid and ultrasensitive dual-mode detection of multidrug-resistant bacteria.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2024.135719]