Butyrolactone 3 - ≥95% , CAS No.778649-18-6

CAS: 778649-18-6 Cat. No.: B344763 Molecular Weight: 184.19 EC Number: 663-946-9

GRADE & PURITY ≥95%

Synonyms

(2S,3R)-4-Methylidene-5-oxo-2-propyloxolane-3- | CHEBI:125615 | DTXSID60435253 | BRD-K68584490-001-01-2 | Butyrolactone 3 | (2S,3R)-4-methylene-5-oxo-2-propyl-3-oxolanecarboxylic acid | AKOS006290263 | BDBM50371233 | Q27216229 | SCHEMBL23682959 | (2S,3R)-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Butyrolactone 3, also called MB-3 is an inhibitor of Histone acetyltransferase GCN5 (general control of amino-acid synthesis 5). Gcn5 HAT activity is required to acetylate histone H3 lysine 9 (K9) and K14, which allows transcription elongation by relaxing nucleosomes. Butyrolactone 3 specifically inhibits Gcn5's HAT activity. It has been shown to display anti-inflammatory and anti-carcinogenic effects.

Specifications

Synonyms

(2S, 3R)-4-Methylidene-5-oxo-2-propyloxolane-3- | CHEBI:125615 | DTXSID60435253 | BRD-K68584490-001-01-2 | Butyrolactone 3 | (2S, 3R)-4-methylene-5-oxo-2-propyl-3-oxolanecarboxylic acid | AKOS006290263 | BDBM50371233 | Q27216229 | SCHEMBL23682959 | (2S, 3R)-

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

MB-3 can modify gene expression in mouse embryonic stem cells and yeast. It inhibits the acetyltransferase activity of Universal Control Protein 5 (GCN5) by binding to the acetyl CoA pocket in GCN5. MB-3 is a Gcn5 HAT (histone acetyltransferase) inhibitor

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

≥95%

Names and Identifiers

• Canonical Smiles: CCCC1C(C(=C)C(=O)O1)C(=O)O
• IUPAC Name: (2S,3R)-4-methylidene-5-oxo-2-propyloxolane-3-carboxylic acid
• InChIKey: SRQUTZJZABSZRQ-NKWVEPMBSA-N
• INCHI: 1S/C9H12O4/c1-3-4-6-7(8(10)11)5(2)9(12)13-6/h6-7H,2-4H2,1H3,(H,10,11)/t6-,7+/m0/s1
• Isomeric SMILES: CCC[C@H]1[C@@H](C(=C)C(=O)O1)C(=O)O
• Molecular Weight: 184.19
• Reaxy-Rn: 35447591
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=35447591&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Lactones
      • Subclass Gamma butyrolactones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Lactones
• Subclass: Gamma butyrolactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Gamma butyrolactones
• Alternative Parents: Dicarboxylic acids and derivatives Tetrahydrofurans Enoate esters Oxacyclic compounds Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Gamma butyrolactone - Dicarboxylic acid or derivatives - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Tetrahydrofuran - Carboxylic acid ester - Oxacycle - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
• 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(non-human)

GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

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.
• Refractive Index: n20D1.50 (Predicted)
• Boil Point(°C): 386.21° C at 760 mmHg (Predicted)
• Melt Point(°C): 60° C
• Molecular Weight: 184.190 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 184.074 Da
• Monoisotopic Mass: 184.074 Da
• Topological Polar Surface Area: 63.600 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 256.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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