Gemfibrozil 1-O-β-glucuronide - ≥99% , CAS No.91683-38-4

CAS: 91683-38-4 Cat. No.: G647264 Molecular Weight: 426.46 EC Number: 823-205-4

GRADE & PURITY ≥99%

Synonyms

AKOS027324600 | beta-D-Glucopyranuronic acid, 1-(5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoate) | 1-[5-(2,5-Dimethylphenoxy)-2,2-dimethylpentanoate] beta-D-Glucopyranuroic Acid | BDBM50397663 | Gemfibrozil 1-O- beta -Glucuronide | UNII-954F30WZ3Y | Gemfi

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Gemfibrozil 1-O-β-Glucuronide, a metabolite of Gemfibrozil (CI-719; HY-B0258), is a potent and competitive P450 (CYP) isoform CYP2C8 inhibitor with an IC 50 of 4.07 μM

In Vitro

Gemfibrozil 1-O-β-Glucuronide significantly inhibits the OATP2 (OATP1B1)-mediated uptake of Cerivastatin (CER; HY-129458) with an IC 50 of 24.3 μM. Gemfibrozil 1-O-β-Glucuronide inhibits CYP2C8-mediated M1, M23 formation with IC 50 s of 5.38 μM, 4.30 μM, and has no effects for CYP2C8-mediated M3 formation. Gemfibrozil 1-O-β-Glucuronide has an IC 50 of 243 μM for the CYP3A4- mediated metabolism. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:CYP3 CYP2C8 4.07 μM (IC 50 )

Specifications

Synonyms

AKOS027324600 | beta-D-Glucopyranuronic acid, 1-(5-(2, 5-dimethylphenoxy)-2, 2-dimethylpentanoate) | 1-[5-(2, 5-Dimethylphenoxy)-2, 2-dimethylpentanoate] beta-D-Glucopyranuroic Acid | BDBM50397663 | Gemfibrozil 1-O- beta -Glucuronide | UNII-954F30WZ3Y | Gemfi

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Gemfibrozil 1-O-β-Glucuronide, a metabolite of Gemfibrozil (CI-719; HY-B0258), is a potent and competitive P450 (CYP) isoform CYP2C8 inhibitor with an IC 50 of 4.07 μM.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Purity

≥99%

Product Properties

• pKa: pKa: 2.68 (Predicted)
• Ki Data: CYP2C8: Ki= 20 μM (human)

Names and Identifiers

• Canonical Smiles: CC1=CC(=C(C=C1)C)OCCCC(C)(C)C(=O)OC2C(C(C(C(O2)C(=O)O)O)O)O
• IUPAC Name: (2S,3S,4S,5R,6S)-6-[5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• InChIKey: CJMNXSKEVNPQOK-LVEJAMMSSA-N
• INCHI: 1S/C21H30O9/c1-11-6-7-12(2)13(10-11)28-9-5-8-21(3,4)20(27)30-19-16(24)14(22)15(23)17(29-19)18(25)26/h6-7,10,14-17,19,22-24H,5,8-9H2,1-4H3,(H,25,26)/t14-,15-,16+,17-,19-/m0/s1
• Isomeric SMILES: CC1=CC(=C(C=C1)C)OCCCC(C)(C)C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
• Molecular Weight: 426.46
• Reaxy-Rn: 22822346
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=22822346&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Sugar acids and derivatives
          • Level6 Glucuronic acid derivatives
            • Level7 Glucuronides
              • Level8 O-glucuronides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Sugar acids and derivatives - Glucuronic acid derivatives - Glucuronides
• Direct Parent: O-glucuronides
• Alternative Parents: Hexoses p-Xylenes Phenoxy compounds Phenol ethers Alkyl aryl ethers Beta hydroxy acids and derivatives Fatty acid esters Pyrans Oxanes Dicarboxylic acids and derivatives Secondary alcohols Carboxylic acid esters Oxacyclic compounds Carboxylic acids Acetals Polyols Carbonyl compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 1-o-glucuronide - O-glucuronide - Hexose monosaccharide - Phenoxy compound - P-xylene - Xylene - Phenol ether - Alkyl aryl ether - Beta-hydroxy acid - Fatty acid ester - Pyran - Benzenoid - Dicarboxylic acid or derivatives - Oxane - Fatty acyl - Monocyclic benzene moiety - Monosaccharide - Hydroxy acid - Carboxylic acid ester - Secondary alcohol - Ether - Organoheterocyclic compound - Carboxylic acid - Acetal - Carboxylic acid derivative - Oxacycle - Polyol - Carbonyl group - Hydrocarbon derivative - Organic oxide - Alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
• External Descriptors: Not available

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)

CYP2C8 Tchem Cytochrome P450 2C8 (1492 Activities)

Discover Target: CYP2C8

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

U2OS (164939 Activities)

Explore this target

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

Associated Targets(non-human)

Plasma (328 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (234.49 mM; Need ultrasonic)
• Refractive Index: n20D1.57 (Predicted)
• Boil Point(°C): ~611.2° C at 760 mmHg (Predicted)
• Melt Point(°C): 123-130° C
• Molecular Weight: 426.500 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 426.189 Da
• Monoisotopic Mass: 426.189 Da
• Topological Polar Surface Area: 143.000 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 593.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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