6377-18-0

Basic information

• Product Name: CHARTREUSIN
• Synonyms: LAMBDAMYCIN;CHARTREUSIN;antibioticx-465a;nsc5159;u-7257;chartreusin from streptomyces*chartreusis;10-[[6-Deoxy-2-O-(6-deoxy-3-O-methyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]oxy]-6-hydroxy-1-methylbenzo[h][1]benzopyrano[5,4,3-cde][1]benzopyran-5,12-dione;LaMbdaMycin, NSC 5159, 747, 1293, X465A, G 261A
• CAS NO: 6377-18-0
• Molecular Formula: C32H32O14
• Molecular Weight: 640.59
• Product Categories: Antibiotic
• Mol File: 6377-18-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 185℃
• Boiling Point: 592.39°C (rough estimate)
• Flash Point: 307.8°C
• Appearance: /
• Density: 1.3027 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6130 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly), Pyridine (Slightly)
• Water Solubility: 15mg/L(25 oC)
• Stability: Hygroscopic
• CAS DataBase Reference: CHARTREUSIN(CAS DataBase Reference)
• NIST Chemistry Reference: CHARTREUSIN(6377-18-0)
• EPA Substance Registry System: CHARTREUSIN(6377-18-0)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36/37/39-45
• Hazardous Substances Data: 6377-18-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 6377-18-0 differently. You can refer to the following data:
1. Chartreusin is an antitumour antibiotic that binds to GC-rich tracts in DNA, with a clear preference for B-DNA over Z-DNA. It inhibits RNA synthesis and causes single-strand scission of DNA via the formation of free radicals. Chartreusin is also a potent inhibitor of topoisomerase II.
2. Chartreusin is an antitumor antibiotic that binds to GC-rich tracts in DNA, with a clear preference for B-DNA over Z-DNA. It inhibits RNA synthesis and causes single-strand scission of DNA via the formation of free radicals. Chartreusin is also a potent inhibitor of topoisomerase II.
3. Chartreusin is an antiproliferative agent that inhibits topoisomerase II.

InChI:InChI=1/C32H32O14/c1-10-8-9-15-18-16(10)29(38)45-26-17-13(23(35)20(19(18)26)30(39)43-15)6-5-7-14(17)44-32-28(24(36)21(33)11(2)42-32)46-31-25(37)27(40-4)22(34)12(3)41-31/h5-9,11-12,21-22,24-25,27-28,31-37H,1-4H3

Upstream product

• 67-56-1 methanol 

Downstream Products

• 34170-23-5 chartarin 

Relevant articles and documents

Molecular Basis for the Final Oxidative Rearrangement Steps in Chartreusin Biosynthesis

Oxidative rearrangements play key roles in introducing structural complexity and biological activities of natural products biosynthesized by type II polyketide synthases (PKSs). Chartreusin (1) is a potent antitumor polyketide that contains a unique rearranged pentacyclic aromatic bilactone aglycone derived from a type II PKS. Herein, we report an unprecedented dioxygenase, ChaP, that catalyzes the final α-pyrone ring formation in 1 biosynthesis using flavin-activated oxygen as an oxidant. The X-ray crystal structures of ChaP and two homologues, docking studies, and site-directed mutagenesis provided insights into the molecular basis of the oxidative rearrangement that involves two successive C-C bond cleavage steps followed by lactonization. ChaP is the first example of a dioxygenase that requires a flavin-activated oxygen as a substrate despite lacking flavin binding sites, and represents a new class in the vicinal oxygen chelate enzyme superfamily.