Daun02 - ≥95% , CAS No.290304-24-4

CAS: 290304-24-4 Cat. No.: D125914 Molecular Weight: 884.79 PubChem CID: 74891316

GRADE & PURITY ≥95%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Daun02 is a proagent of the topoisomerase inhibitor Daunorubicin. 

In vitro research

Daun02 is a prodrug, which is converted by β-galactosidase to Daunorubicin, which has been shown to reduce calcium ion (Ca2+)-dependent action potentials in neuroblastoma cells. Daunorubicin is a topoisomerase inhibitor. Daun02 is a good substrate for β-galactosidase (β-gal). The concentration of Daun02 producing 50% (EC50) decrease in cell viability is 0.5 μM, 1.5 μM, and 3.5 μM for T47-D, Panc02, and MCF-7, respectively 

In vivo research

Daun02 is a good substrate for β-gal with Km and Vmax values of 0.37 mM and 8.6 μmol/min/mg protein. At a concentration of 10-5 M, Daun02 is 79% bound to plasma protein compares to 94% for Daunomycin

Specifications

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Daun02 is a daunorubicin b-galactoside prodrug for use in conjunction.

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.

Action Type

INHIBITOR

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)NC(=O)OCC6=CC(=C(C=C6)OC7C(C(C(C(O7)CO)O)O)O)[N+](=O)[O-])O
• IUPAC Name: [3-nitro-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl N-[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamate
• InChIKey: BOIXMGNMIWJAEW-LCTCPDETSA-N
• INCHI: 1S/C41H44N2O20/c1-15-31(46)20(42-40(54)59-14-17-7-8-22(21(9-17)43(56)57)62-39-38(53)37(52)34(49)25(13-44)63-39)10-26(60-15)61-24-12-41(55,16(2)45)11-19-28(24)36(51)30-29(33(19)48)32(47)18-5-4-6-23(58-3)27(18)35(30)50/h4-9,15,20,24-26,31,34,37-39,44,46,48-49,51-53,55H,10-14H2,1-3H3,(H,42,54)/t15-,20-,24-,25+,26-,31+,34-,37-,38+,39+,41-/m0/s1
• Isomeric SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)NC(=O)OCC6=CC(=C(C=C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O)O)[N+](=O)[O-])O
• PubChem CID: 74891316
• Molecular Weight: 884.79

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Anthracyclines

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Anthracyclines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Anthracyclines
• Alternative Parents: Tetracenequinones Anthraquinones Phenolic glycosides O-glycosyl compounds Tetralins Benzyloxycarbonyls Nitrobenzenes Nitroaromatic compounds Aryl ketones Anisoles Phenoxy compounds Alkyl aryl ethers Monosaccharides Oxanes Alpha-hydroxy ketones Vinylogous acids Carbamate esters Tertiary alcohols Secondary alcohols Acetals Propargyl-type 1,3-dipolar organic compounds Polyols Oxacyclic compounds Organic oxoazanium compounds Organonitrogen compounds Organopnictogen compounds Primary alcohols Organic zwitterions Hydrocarbon derivatives Organic salts Aldehydes Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Anthracycline - Anthracyclinone-skeleton - Tetracenequinone - 9,10-anthraquinone - 1,4-anthraquinone - Phenolic glycoside - Anthracene - Glycosyl compound - O-glycosyl compound - Benzyloxycarbonyl - Tetralin - Nitrobenzene - Anisole - Phenoxy compound - Nitroaromatic compound - Phenol ether - Aryl ketone - Alkyl aryl ether - Benzenoid - Monocyclic benzene moiety - Monosaccharide - Oxane - Alpha-hydroxy ketone - Carbamic acid ester - Vinylogous acid - Tertiary alcohol - Secondary alcohol - Ketone - C-nitro compound - Organic nitro compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Acetal - Organoheterocyclic compound - Ether - Polyol - Oxacycle - Organic oxoazanium - Organic oxide - Organic salt - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organic zwitterion - Hydrocarbon derivative - Primary alcohol - Organic nitrogen compound - Organooxygen compound - Alcohol - Organonitrogen compound - Aldehyde - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
• 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

• Solubility: DMSO
• Molecular Weight: 884.800 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 11
• Exact Mass: 884.249 Da
• Monoisotopic Mass: 884.249 Da
• Topological Polar Surface Area: 343.000 Ų
• Heavy Atom Count: 63
• Formal Charge: 0
• Complexity: 1700.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 11
• 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