3BDO - Moligand™,≥95% , CAS No.890405-51-3

CAS: 890405-51-3 Cat. No.: B413969 Molecular Weight: 327.33

GRADE & PURITY Moligand™, ≥95%

Synonyms

3-benzyl-5-((2-nitrophenoxy) methyl)-dihydrofuran-2(3H)-onePentonic acid,2,​3-​dideoxy-​5-​O-​(2-​nitrophenyl)​-​2-​(phenylmethyl)​-​,γ-​lactone

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

3BDO 3BDO, a butyrolactone derivative, could target FKBP1A and activate the mTOR signaling pathway. It inhibits autophagy in HUVECs. 3BDO inhibits oxLDL-induced apoptosis .

Targets

FKBP1A (Cell-free assay)

In vitro

3BDO inhibits autophagy in human umbilical vein endothelial cells (HUVECs) and neuronal cells. It suppresses lipopolysaccharide-induced HUVEC autophagic injury by downregulating the protein levels of NUPR1 (nuclear protein, transcriptional regulator) and TP53 (tumor protein p53), TP53 nuclear translocation and reactive oxygen species overproduction. 3BDO activates MTOR by targeting FKBP1A (FK506-binding protein 1A, 12 kDa). 3BDO greatly decreases the level of a long noncoding RNA (lncRNA) derived from the 3′ untranslated region (3′UTR) of TGFB2, known as FLJ11812, but does not affect TGFB2 expression. ATG13 protein level is decreased along with 3BDO-decreased FLJ11812 level. 3BDO inhibits excessive Aβ (25 to 35) peptide-induced autophagy in PC12 neuronal cells and increased the phosphorylation of RPS6KB1. 3BDO could inhibit human umbilical vein EC (HUVEC) apoptosis and senescence induced by deprivation of serum and basic fibroblast growth factor 2. iT selectively protecteS vascular ECs (VECs) and inhibitS vascular smooth muscle cell (VSMC) proliferation and migration. 3BDO (20-60 μg/ml) could inhibit VEC apoptosis and suppress integrin β4 expression, but it could not depress the ROS level induced by deprivation of serum and FGF-2.

In vivo

In vivo experiments showed that 3BDO had a good safety profile. 3BDO treatment could significantly reduce the number of autophagosomes and improve neuronal function in App and Psen1 transgenic mice. 3BDO activated mTOR in vivo and decreased the protein level of ATG13 in the plaque endothelium of apoE-/- mice. It does not affect the activity of mTOR and autophagy in macrophage cell line RAW246.7 and vascular smooth muscle cells of apoE-/- mice, but suppressed plaque endothelial cell death and restricted atherosclerosis development in the mice. 3BDO protecteS VECs by activating mTOR and thus stabilized atherosclerotic lesions in apoE-/- mice.

Cell Research(from reference)

Cell lines：HUVECs 

Concentrations：60 μM 

Incubation Time：24 h 

Specifications

Synonyms

3-benzyl-5-((2-nitrophenoxy) methyl)-dihydrofuran-2(3H)-onePentonic acid, 2, ​3-​dideoxy-​5-​O-​(2-​nitrophenyl)​-​2-​(phenylmethyl)​-​, γ-​lactone

Specifications & Purity

Moligand™, ≥95%

Biochemical and Physiological Mechanisms

3BDO, a butyrolactone derivative, could target FKBP1A and activate the mTOR signaling pathway. It inhibits autophagy in HUVECs. 3BDO inhibits oxLDL-induced apoptosis.

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥95%

Names and Identifiers

• Canonical Smiles: C1C(C(=O)OC1COC2=CC=CC=C2[N+](=O)[O-])CC3=CC=CC=C3
• IUPAC Name: 3-benzyl-5-[(2-nitrophenoxy)methyl]oxolan-2-one
• InChIKey: AXPZIVKEZRHGAS-UHFFFAOYSA-N
• INCHI: 1S/C18H17NO5/c20-18-14(10-13-6-2-1-3-7-13)11-15(24-18)12-23-17-9-5-4-8-16(17)19(21)22/h1-9,14-15H,10-12H2
• Isomeric SMILES: C1C(C(=O)OC1COC2=CC=CC=C2[N+](=O)[O-])CC3=CC=CC=C3
• Molecular Weight: 327.33
• Reaxy-Rn: 10563145
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10563145&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Nitrobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Nitrobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrophenyl ethers
• Alternative Parents: Phenoxy compounds Phenol ethers Nitroaromatic compounds Alkyl aryl ethers Gamma butyrolactones Oxolanes Carboxylic acid esters Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Organic oxoazanium compounds Monocarboxylic acids and derivatives Organonitrogen compounds Hydrocarbon derivatives Organic oxides Organic salts Carbonyl compounds Organic cations
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Nitrophenyl ether - Phenoxy compound - Nitroaromatic compound - Phenol ether - Alkyl aryl ether - Gamma butyrolactone - Oxolane - Carboxylic acid ester - Lactone - C-nitro compound - Organic nitro compound - Carboxylic acid derivative - Ether - Monocarboxylic acid or derivatives - Oxacycle - Organic oxoazanium - Organoheterocyclic compound - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organic nitrogen compound - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Organic salt - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic cation - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring.
• 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility：DMSO ；Ethanol
• Molecular Weight: 327.300 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 327.111 Da
• Monoisotopic Mass: 327.111 Da
• Topological Polar Surface Area: 81.400 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 443.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 2
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1