Acetylshikonin - Moligand™, 2mM in DMSO , CAS No.24502-78-1

CAS: 24502-78-1 Cat. No.: A422831 Molecular Weight: 330.33

GRADE & PURITY Moligand™, 2mM in DMSO

Synonyms

Shikonin, acetyl | AC-20169 | Acetylshikonin | AC-35023 | acetyl shikonin | DTXSID901317360 | AKOS015965847 | Q-100314 | 1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-pentenyl acetate # | (R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronapht

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Acetylshikonin is a biologically active compound with anti-cancer and anti-inflammatory activity, which is isolated from the roots of Lithospermum erythrorhizoma. It is a novel generalP450inhibitor withIC50 valuesof 1.4-4.0 μM for all tested P450s.

Targets

P450

application：

Acetylshikonin is the main ingredient of Zicao, which has used in clinics as a traditional Chinese for thousands of years. It exerts anti-obesity and anti-NAFLD effects through the regulation of lipid metabolism and anti-inflammatory effects. Also, it is a 1,4-naphthoquinone pigment extracted from the roots of Lithospermum erythrorhizon with anti-tumor effects.

Specifications

Synonyms

Shikonin, acetyl | AC-20169 | Acetylshikonin | AC-35023 | acetyl shikonin | DTXSID901317360 | AKOS015965847 | Q-100314 | 1-(5, 8-Dihydroxy-1, 4-dioxo-1, 4-dihydro-2-naphthalenyl)-4-methyl-3-pentenyl acetate # | (R)-1-(5, 8-Dihydroxy-1, 4-dioxo-1, 4-dihydronapht

Specifications & Purity

Moligand™, 2mM in DMSO

Biochemical and Physiological Mechanisms

Acetylshikonin is a biologically active compound with anti-cancer and anti-inflammatory activity, which is isolated from the roots of Lithospermum erythrorhizoma. It is a novel general P450 inhibitor with IC50 values of 1.4-4.0 μM for all tested P450s.

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.

Grade

Moligand™

Product Properties

• ALogP: 2.824
• hba_count: 4
• HBD Count: 2
• Rotatable Bond: 5

Names and Identifiers

• Canonical Smiles: CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C)C
• IUPAC Name: [(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
• InChIKey: WNFXUXZJJKTDOZ-OAHLLOKOSA-N
• INCHI: 1S/C18H18O6/c1-9(2)4-7-15(24-10(3)19)11-8-14(22)16-12(20)5-6-13(21)17(16)18(11)23/h4-6,8,15,20-21H,7H2,1-3H3/t15-/m1/s1
• Isomeric SMILES: CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C)C
• Molecular Weight: 330.33
• Reaxy-Rn: 2062001
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2062001&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Naphthalenes
      • Subclass Naphthoquinones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Naphthalenes
• Subclass: Naphthoquinones
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthoquinones
• Alternative Parents: Bicyclic monoterpenoids Aromatic monoterpenoids Quinones Aryl ketones 1-hydroxy-2-unsubstituted benzenoids Vinylogous acids Carboxylic acid esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Naphthoquinone - Aromatic monoterpenoid - Bicyclic monoterpenoid - Monoterpenoid - Aryl ketone - Quinone - 1-hydroxy-2-unsubstituted benzenoid - Vinylogous acid - Ketone - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Organooxygen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthoquinones. These are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
• 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

Chemical and Physical Properties

• Sensitivity: Moisture sensitive；light sensitive
• DMSO(mg / mL) Max Solubility: 2
• DMSO(mM) Max Solubility: 6.05451631801129
• Molecular Weight: 330.300 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 330.11 Da
• Monoisotopic Mass: 330.11 Da
• Topological Polar Surface Area: 101.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 599.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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