Ezetimibe β-D-Glucuronide - ≥98% , CAS No.190448-57-8

CAS: 190448-57-8 Cat. No.: E351407 Formula: C₃₀H₂₉F₂NO₉ Molecular Weight: 585.55 PubChem CID: 9894653

GRADE & PURITY ≥98%

Synonyms

.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 4-((2S,3R)-1-(4-FLUOROPHENYL)-3-((3S)-3-(4-FLUOROPHENYL)-3-HYDROXYPROPYL)-4-OXO-2-AZETIDINYL)PHENYL | beta-D-Glucopyranosiduronic acid, 4-((2S,3R)-1-(4-fluorophenyl)-3-((3S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxo-2-a

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Ezetimibe β-D-Glucuronide is phase-II metabolite of Ezetimibe, an antihyperlipoproteinemic. A Cholesterol absorption inhibitor.

Specifications

Synonyms

.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 4-((2S,3R)-1-(4-FLUOROPHENYL)-3-((3S)-3-(4-FLUOROPHENYL)-3-HYDROXYPROPYL)-4-OXO-2-AZETIDINYL)PHENYL | beta-D-Glucopyranosiduronic acid, 4-((2S,3R)-1-(4-fluorophenyl)-3-((3S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxo-2-a

Specifications & Purity

≥98%

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.

Purity

≥98%

Product Properties

• pKa: pKa: 2.78 (Predicted)
• Ki Data: Niemann-Pick C1-like protein 1: Ki= 180 nM (rat)

Names and Identifiers

• Pubchem Sid: 504765053
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765053
• Canonical Smiles: C1=CC(=CC=C1C2C(C(=O)N2C3=CC=C(C=C3)F)CCC(C4=CC=C(C=C4)F)O)OC5C(C(C(C(O5)C(=O)O)O)O)O
• IUPAC Name: (2S,3S,4S,5R,6S)-6-[4-[(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• InChIKey: UOFYCFMTERCNEW-ADEYADIWSA-N
• INCHI: 1S/C30H29F2NO9/c31-17-5-1-15(2-6-17)22(34)14-13-21-23(33(28(21)38)19-9-7-18(32)8-10-19)16-3-11-20(12-4-16)41-30-26(37)24(35)25(36)27(42-30)29(39)40/h1-12,21-27,30,34-37H,13-14H2,(H,39,40)/t21-,22+,23-,24+,25+,26-,27+,30-/m1/s1
• Isomeric SMILES: C1=CC(=CC=C1[C@@H]2[C@H](C(=O)N2C3=CC=C(C=C3)F)CC[C@@H](C4=CC=C(C=C4)F)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O
• PubChem CID: 9894653
• Molecular Weight: 585.55

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: Fatty acyl glycosides of mono- and disaccharides Monobactams O-glucuronides Alkyl glycosides Hexoses O-glycosyl compounds Phenylazetidines Phenoxy compounds Phenol ethers Beta hydroxy acids and derivatives Fluorobenzenes Aryl fluorides Pyrans Oxanes Tertiary carboxylic acid amides Secondary alcohols Monocarboxylic acids and derivatives Oxacyclic compounds Polyols Carboxylic acids Azacyclic compounds Acetals Organopnictogen compounds Hydrocarbon derivatives Aromatic alcohols Carbonyl compounds Organonitrogen compounds Organic oxides Organofluorides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - Fatty acyl glycoside - Fatty acyl glycoside of mono- or disaccharide - Monobactam - 1-o-glucuronide - O-glucuronide - Glucuronic acid or derivatives - Alkyl glycoside - Hexose monosaccharide - O-glycosyl compound - 1-phenylazetidine - 2-phenylazetidine - Phenoxy compound - Phenol ether - Beta-hydroxy acid - Halobenzene - Fluorobenzene - Benzenoid - Fatty acyl - Oxane - Monosaccharide - Hydroxy acid - Aryl fluoride - Monocyclic benzene moiety - Aryl halide - Pyran - Beta-lactam - Tertiary carboxylic acid amide - Azetidine - Carboxamide group - Secondary alcohol - Lactam - Monocarboxylic acid or derivatives - Acetal - Oxacycle - Azacycle - Carboxylic acid derivative - Carboxylic acid - Organoheterocyclic compound - Polyol - Carbonyl group - Organofluoride - Organohalogen compound - Alcohol - Organopnictogen compound - Organic oxide - Aromatic alcohol - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• 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)

NPC1L1 Tclin NPC1-like intracellular cholesterol transporter 1 (2 Activities)

Discover Target: NPC1L1

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

NPC1L1 Tclin Niemann-Pick C1-like protein 1 (346 Activities)

Discover Target: NPC1L1

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

Liver microsomes (16955 Activities)

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

Associated Targets(non-human)

Rattus norvegicus (775804 Activities)

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

Cricetinae gen. sp. (3197 Activities)

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

NPC1L1 Niemann-Pick C1-like 1 protein (4 Activities)

Discover Target: NPC1L1

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in DMSO, and methanol.
• x_refractive_index: n20D1.65 (Predicted)
• x_boil_point_char: ~877.5° C at 760 mmHg (Predicted)
• x_melt_point_char: 130-140° C (dec.)
• Molecular Weight: 585.500 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 585.181 Da
• Monoisotopic Mass: 585.181 Da
• Topological Polar Surface Area: 157.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 920.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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. Xing Wang, Feiyang Deng, Tianyi Ji, Chengning Zhang, Yang Tian, Hui Zhang, Aiping Zheng, Ying Chen, Bing He, Wenbing Dai, Hua Zhang, Qiang Zhang, Xueqing Wang.  (2024)  Impact of Physiological Characteristics on Chylomicron Pathway-Mediated Absorption of Nanocrystals in the Pediatric Population.  ACS Nano,      [PMID:39153194] [10.1021/acsnano.4c05391]