8-O-acetyl shanzhiside methyl ester - ≥98% , CAS No.57420-46-9

CAS: 57420-46-9 Cat. No.: O414373 Molecular Weight: 448.42

GRADE & PURITY ≥98%

Synonyms

5beta-Dihydro Finasteride | Umbroside | HY-N0758 | MFCD15071141 | methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate | Barle

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

8-O-acetyl shanzhiside methyl ester 8-O-acetyl shanzhiside methyl ester (Barlerin, ND01), isolated from the leaves of Lamiophlomis rotata Kudo , promotes angiogenesis, which leads to the improvement of functional outcome after stroke.8-O-Acetyl shanzhiside methyl ester can inhibts NF-κB .

Targets

NF-κB

Specifications

Synonyms

5beta-Dihydro Finasteride | Umbroside | HY-N0758 | MFCD15071141 | methyl (1S, 4aS, 5R, 7S, 7aS)-7-acetyloxy-5-hydroxy-7-methyl-1-[(2S, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a, 5, 6, 7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate | Barle

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

8-O-acetyl shanzhiside methyl ester (Barlerin, ND01), isolated from the leaves of Lamiophlomis rotata Kudo, promotes angiogenesis, which leads to the improvement of functional outcome after stroke.8-O-Acetyl shanzhiside methyl ester can inhibts NF-κB.

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%

Names and Identifiers

• Pubchem Sid: 488188355
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488188355
• Canonical Smiles: CC(=O)OC1(CC(C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O)O)C
• IUPAC Name: methyl (1S,4aS,5R,7S,7aS)-7-acetyloxy-5-hydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• InChIKey: ARFRZOLTIRQFCI-NGQYDJQZSA-N
• INCHI: 1S/C19H28O12/c1-7(21)31-19(2)4-9(22)11-8(16(26)27-3)6-28-17(12(11)19)30-18-15(25)14(24)13(23)10(5-20)29-18/h6,9-15,17-18,20,22-25H,4-5H2,1-3H3/t9-,10-,11+,12-,13-,14+,15-,17+,18+,19+/m1/s1
• Isomeric SMILES: CC(=O)O[C@]1(C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)C
• Molecular Weight: 448.42
• Reaxy-Rn: 56660266
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=56660266&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Terpene glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Iridoid O-glycosides
• Alternative Parents: Hexoses O-glycosyl compounds Bicyclic monoterpenoids Iridoids and derivatives Dicarboxylic acids and derivatives Oxanes Methyl esters Enoate esters Vinylogous esters Secondary alcohols Cyclic alcohols and derivatives Polyols Acetals Oxacyclic compounds Organic oxides Primary alcohols Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Iridoid o-glycoside - Hexose monosaccharide - Glycosyl compound - Iridoid-skeleton - O-glycosyl compound - Bicyclic monoterpenoid - Monoterpenoid - Dicarboxylic acid or derivatives - Monosaccharide - Oxane - Cyclic alcohol - Vinylogous ester - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Carboxylic acid ester - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Acetal - Carboxylic acid derivative - Polyol - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Carbonyl group - Primary alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.
• 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)

Plasmodium falciparum (966862 Activities)

Explore this target

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

Respiratory syncytial virus (3434 Activities)

Explore this target

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: 90 mg/mL (200.7 mM)
• Molecular Weight: 448.400 g/mol
• XLogP3: -2.000
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 448.158 Da
• Monoisotopic Mass: 448.158 Da
• Topological Polar Surface Area: 181.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 725.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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