Orobol - ≥99% , CAS No.480-23-9

CAS: 480-23-9 Cat. No.: O650798 Peso molecular: 286.24 PubChem CID: 5281801

GRADE & PURITY ≥99%

Synonyms

Q7103718 | 3'-hydroxygenistein | 3'-hydroxy-genistein | 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one | 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(3,4-dihydroxyphenyl)- | UNII-LU8UZM1T51 | LMPK12050251 | BRN 0292790 | Isoluteolin | NSC 678114 | SCHEMBL

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Orobol is one of the major soy isoflavones and has various pharmacological activities, including anti-skin-aging and anti-obesity effects. Orobol inhibits CK1ε , VEGFR2, MAP4K5, MNK1 , MUSK, TOPK , and TNIK (IC 50 =1.24-4.45 μM). Orobol also inhibits PI3K isoforms (IC 50 =3.46-5.27 μM for PI3K α/β/γ/K/δ).

In Vitro

Orobol binds to CK1ε in an ATP-competitive manner and exerts anti-obesity effects by targeting casein kinase 1 epsilon. Orobol (5-20 μM) effectively suppresses MDI (isobutylmethylxanthine, dexamethasone and insulin (MDI))-induced phosphorylation of 4E-BP1. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Orobol attenuates high fat diet-induced weight gain and lipid accumulation without affecting food intake in C57BL/6J mice. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: HFD-induced obesity in C57BL/6J miceDosage: 10 mg/kg Administration: Intragastrically; daily for 23 weeks Result: Significantly reduced body weight by 17.3% compared to the HFD group.

Form:Solid

Specifications

Sinónimos

Q7103718 | 3'-hydroxygenistein | 3'-hydroxy-genistein | 3-(3, 4-dihydroxyphenyl)-5, 7-dihydroxy-chromen-4-one | 4H-1-Benzopyran-4-one, 5, 7-dihydroxy-3-(3, 4-dihydroxyphenyl)- | UNII-LU8UZM1T51 | LMPK12050251 | BRN 0292790 | Isoluteolin | NSC 678114 | SCHEMBL

Especificaciones y pureza

≥99%

Mecanismos bioquímicos y fisiológicos

Orobol is one of the major soy isoflavones and has various pharmacological activities, including anti-skin-aging and anti-obesity effects. Orobol inhibits CK1ε , VEGFR2 , MAP4K5, MNK1 , MUSK, TOPK , and TNIK (IC 50 =1.24-4.45 μM). Orobol also inhibits PI3

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Tipo de acción

INHIBITOR

Pureza

≥99%

Nombres e identificadores

• Sonrisas canónicas: C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O)O
• IUPAC Name: 3-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• InChIKey: IOYHCQBYQJQBSK-UHFFFAOYSA-N
• INCHI: 1S/C15H10O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-6,16-19H
• Isómeros SMILES: C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O)O
• CAS alternativo: 480-23-9
• PubChem CID: 5281801
• Número NSC: 678114
• Términos de entrada MeSH: 3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one;isoluteolin;orobol
• Peso molecular: 286.24

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Isoflavonoids
      • Subclass Isoflav-2-enes

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Isoflavonoids
• Subclass: Isoflav-2-enes
• Intermediate Tree Nodes: Not available
• Direct Parent: Isoflavones
• Alternative Parents: Hydroxyisoflavonoids Chromones Catechols Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Hydroxyisoflavonoid - Isoflavone - Chromone - Benzopyran - 1-benzopyran - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Pyranone - Monocyclic benzene moiety - Pyran - Benzenoid - Heteroaromatic compound - Vinylogous acid - Organoheterocyclic compound - Oxacycle - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
• External Descriptors: Isoflavonoids

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

Objetivos asociados (humanos)

EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)

Discover Target: EGFR

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U-937 (7138 Activities)

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Objetivos asociados (no humanos)

Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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NRK (373 Activities)

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RAW264.7 (28094 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Peso molecular: 286.240 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 286.048 Da
• Monoisotopic Mass: 286.048 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 447.000
• 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

Referencias

1. Ruyue Dong, Jiaying Wang, Jian Tian, Guoshun Xu, Ziqi Liang, Xing Qin, Xiaolu Wang, Xiaoqing Liu, Huiying Luo, Bin Yao, Yaru Wang, Tao Tu.  (2025)  ESTEEM Strategy: Revolutionizing Enzymatic Catalysis through the Evolutionary Gateway of Enzyme Tunnels.  ACS Catalysis,      [PMID:] [10.1021/acscatal.5c03170]