GRADE & PURITY ≥98%

Synonyms

BAR 501 | BAR-501 | (3R,5S,6S,7S,8S,9S,10S,13R,14S,17R)-6-ethyl-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

BAR501 BAR501 is a potent and selective G protein-coupled bile acid receptor 1 (GPBAR1, GPCR19, TGR5) agonist that effectively transactivates GPBAR1 in HEK293 cells overexpressing a CRE along with GPBAR1 with EC50 of 1 μM.

Targets

GPCR19 (in HEK293 cells) 1 μM(EC50)

Specifications

Synonyms

BAR 501 | BAR-501 | (3R, 5S, 6S, 7S, 8S, 9S, 10S, 13R, 14S, 17R)-6-ethyl-17-[(2R)-5-hydroxypentan-2-yl]-10, 13-dimethyl-2, 3, 4, 5, 6, 7, 8, 9, 11, 12, 14, 15, 16, 17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3, 7-diol

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

BAR501 is a potent and selective G protein-coupled bile acid receptor 1 (GPBAR1, GPCR19, TGR5) agonist that effectively transactivates GPBAR1 in HEK293 cells overexpressing a CRE along with GPBAR1 with EC50 of 1 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.

Purity

≥98%

Product Properties

• ALogP: 4.842
• HBD Count: 3
• Rotatable Bond: 5

Names and Identifiers

• Pubchem Sid: 504772778
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504772778
• Canonical Smiles: CCC1C2CC(CCC2(C3CCC4(C(C3C1O)CCC4C(C)CCCO)C)C)O
• IUPAC Name: (3R,5S,6S,7S,8S,9S,10S,13R,14S,17R)-6-ethyl-17-[(2R)-5-hydroxypentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
• InChIKey: DQBAHTQWQZRMFH-CRPAWOMZSA-N
• INCHI: 1S/C26H46O3/c1-5-18-22-15-17(28)10-12-26(22,4)21-11-13-25(3)19(16(2)7-6-14-27)8-9-20(25)23(21)24(18)29/h16-24,27-29H,5-15H2,1-4H3/t16-,17-,18+,19-,20+,21+,22+,23+,24+,25-,26-/m1/s1
• Isomeric SMILES: CC[C@H]1[C@@H]2C[C@@H](CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3[C@H]1O)CC[C@@H]4[C@H](C)CCCO)C)C)O
• PubChem CID: 101886302
• Molecular Weight: 406.64

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Steroids and steroid derivatives
      • Subclass Bile acids, alcohols and derivatives
        • Level5 Hydroxy bile acids, alcohols and derivatives
          • Level6 Trihydroxy bile acids, alcohols and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Bile acids, alcohols and derivatives
• Intermediate Tree Nodes: Hydroxy bile acids, alcohols and derivatives
• Direct Parent: Trihydroxy bile acids, alcohols and derivatives
• Alternative Parents: 7-alpha-hydroxysteroids 3-alpha-hydroxysteroids Secondary alcohols Cyclic alcohols and derivatives Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Trihydroxy bile acid, alcohol, or derivatives - 24-hydroxysteroid - 7-hydroxysteroid - 7-alpha-hydroxysteroid - 3-alpha-hydroxysteroid - Hydroxysteroid - 3-hydroxysteroid - Cyclic alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
• 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)

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

Discover Target: NR3C1

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

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

Discover Target: PPARG

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

NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

Discover Target: NR1H4

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

NR1I2 Tchem Pregnane X receptor (6667 Activities)

Discover Target: NR1I2

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

GPBAR1 Tchem G-protein coupled bile acid receptor 1 (1723 Activities)

Discover Target: GPBAR1

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 81 mg/mL (199.19 mM); Water: Insoluble; Ethanol: 81 mg/mL
• DMSO(mg / mL) Max Solubility: 81
• DMSO(mM) Max Solubility: 199.193389730474
• Water(mg / mL) Max Solubility: ＜1
• Molecular Weight: 406.600 g/mol
• XLogP3: 5.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 406.345 Da
• Monoisotopic Mass: 406.345 Da
• Topological Polar Surface Area: 60.700 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 578.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• 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