Cleistanthin B - ≥99% , CAS No.30021-77-3

CAS: 30021-77-3 Cat. No.: C647578 Molecular Weight: 542.49 PubChem CID: 119458

GRADE & PURITY ≥99%

Synonyms

Naphtho(2,3-c)furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxy- | 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one | 9-(1,3-benzod

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Cleistanthin B (Diphyllin O-glucoside) is an orally active arylnaphthalene lignan lactone glycoside. Cleistanthin B exhibits anti-SARS-CoV-2 effects in Vero cells, with EC 50 of 6.51 µM. Cleistanthin B also exhibits antitumor, diuretic and antihypertensive effects in vivo

In Vitro

Cleistanthin B exhibits anti-SARS-CoV-2 effects in Vero cells, with EC 50 of 6.51 µM. Cleistanthin B shows no cytotoxic to Vero cells in concentrations up to 100 µM. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Cleistanthin B (25-100 mg/kg; p.o. for 10 dys) has antitumor activity against EAC and DAL tumor mice but it is not effective against solid tumor. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:IC50: 6.51 µM (SARS-CoV-2)

Specifications

Synonyms

Naphtho(2, 3-c)furan-1(3H)-one, 9-(1, 3-benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6, 7-dimethoxy- | 9-(1, 3-benzodioxol-5-yl)-6, 7-dimethoxy-4-[(2S, 3R, 4S, 5S, 6R)-3, 4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one | 9-(1, 3-benzod

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Cleistanthin B (Diphyllin O-glucoside) is an orally active arylnaphthalene lignan lactone glycoside. Cleistanthin B exhibits anti-SARS-CoV-2 effects in Vero cells, with EC 50 of 6.51 µM. Cleistanthin B also exhibits antitumor, diuretic and antihypertensiv

Storage

Protected from light, Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Canonical Smiles: COC1=C(C=C2C(=C1)C(=C3C(=C2OC4C(C(C(C(O4)CO)O)O)O)COC3=O)C5=CC6=C(C=C5)OCO6)OC
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one
• InChIKey: BJGIWVGXMRUMNA-WBYCZGBQSA-N
• INCHI: 1S/C27H26O12/c1-33-16-6-12-13(7-17(16)34-2)25(39-27-24(31)23(30)22(29)19(8-28)38-27)14-9-35-26(32)21(14)20(12)11-3-4-15-18(5-11)37-10-36-15/h3-7,19,22-24,27-31H,8-10H2,1-2H3/t19-,22-,23+,24-,27+/m1/s1
• Isomeric SMILES: COC1=C(C=C2C(=C1)C(=C3C(=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)COC3=O)C5=CC6=C(C=C5)OCO6)OC
• Alternate CAS: 30021-77-3
• PubChem CID: 119458
• MeSH Entry Terms: 9-(1,3-benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxynaphtho(2,3-c)furan-1(3H)-one;clei B;cleistanthin B
• Molecular Weight: 542.49

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lignans, neolignans and related compounds
    • Class Lignan glycosides

• Kingdom: Organic compounds
• Superclass: Lignans, neolignans and related compounds
• Class: Lignan glycosides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Lignan glycosides
• Alternative Parents: Arylnaphthalene lignans Lignan lactones Phenolic glycosides Naphthofurans Hexoses O-glycosyl compounds Phthalides Naphthalenes Benzodioxoles Anisoles Alkyl aryl ethers Oxanes Lactones Carboxylic acid esters Secondary alcohols Oxacyclic compounds Acetals Polyols Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Lignan glycoside - Arylnaphthalene lignan skeleton - Lignan lactone - Phenolic glycoside - Naphthofuran - Hexose monosaccharide - Glycosyl compound - O-glycosyl compound - Isobenzofuranone - Naphthalene - Phthalide - Isocoumaran - Benzodioxole - Anisole - Alkyl aryl ether - Monosaccharide - Oxane - Benzenoid - Carboxylic acid ester - Secondary alcohol - Lactone - Organoheterocyclic compound - Ether - Acetal - Carboxylic acid derivative - Oxacycle - Polyol - Monocarboxylic acid or derivatives - Primary alcohol - Organic oxygen compound - Alcohol - Hydrocarbon derivative - Organic oxide - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.
• External Descriptors: beta-D-glucoside - monosaccharide derivative - cleistanthins

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)

TOP2A Tclin DNA topoisomerase II alpha (6317 Activities)

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HT-29 (80576 Activities)

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Huh-7 (12904 Activities)

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MCF7 (126967 Activities)

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HCT-116 (91556 Activities)

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 542.500 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 542.142 Da
• Monoisotopic Mass: 542.142 Da
• Topological Polar Surface Area: 163.000 Ų
• Heavy Atom Count: 39
• Formal Charge: 0
• Complexity: 874.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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