Chartreusin - ≥98% , CAS No.6377-18-0

CAS: 6377-18-0 Cat. No.: C329562 Molecular Weight: 640.59 EC Number: 636-314-5

GRADE & PURITY ≥98%

Synonyms

M01618 | BRN 0075649 | C09181 | Benzo(h)(1)benzopyrano(5,4,3-cde)(1)benzopyran-5,12-dione, 10-((6-deoxy-2-O-(6-deoxy-3-O-methyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl)oxy)-6-hydroxy-1-methyl- (9CI) | CHEBI:3580 | Lambdamycin | X 465A | [(2S,3R,

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Product Describtion:

Chartreusin is a potent anti-proliferative agent originally derived from Streptomyces chartreusis. This compound has been shown to be a potent inhibitor of the catalytic activity of Topo II (topoisomerase II). Experiments have reported that Chartreusin binds to GC-rich tracts in DNA, inhibits RNA synthesis, and causes single-strand scission of DNA via formation of free radicals. Additionally, this agent has been shown to inhibit formation of several DNA-protein complexes.

Specifications

Synonyms

M01618 | BRN 0075649 | C09181 | Benzo(h)(1)benzopyrano(5, 4, 3-cde)(1)benzopyran-5, 12-dione, 10-((6-deoxy-2-O-(6-deoxy-3-O-methyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl)oxy)-6-hydroxy-1-methyl- (9CI) | CHEBI:3580 | Lambdamycin | X 465A | [(2S, 3R,

Specifications & Purity

≥98%

Source

Streptomyces chartreusis

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%

Product Properties

• pKa: pKa: 6.64 (Predicted)

Names and Identifiers

• Canonical Smiles: CC1C(C(C(C(O1)OC2=CC=CC3=C2C4=C5C6=C(C=CC(=C6C(=O)O4)C)OC(=O)C5=C3O)OC7C(C(C(C(O7)C)O)OC)O)O)O
• IUPAC Name: 3-[(2S,3R,4S,5R,6R)-3-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-8-hydroxy-15-methyl-11,18-dioxapentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(19),2(7),3,5,8,12(20),13,15-octaene-10,17-dione
• InChIKey: PONPPNYZKHNPKZ-RYBWXQSLSA-N
• INCHI: 1S/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/t11-,12-,21+,22+,24+,25-,27+,28-,31-,32+/m1/s1
• Isomeric SMILES: C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=CC3=C2C4=C5C6=C(C=CC(=C6C(=O)O4)C)OC(=O)C5=C3O)O[C@@H]7[C@@H]([C@H]([C@H]([C@H](O7)C)O)OC)O)O)O
• RTECS: FL7350000
• Molecular Weight: 640.59
• Reaxy-Rn: 24724997
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24724997&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Naphthopyrans
      • Subclass Naphthopyranones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Naphthopyrans
• Subclass: Naphthopyranones
• Intermediate Tree Nodes: Not available
• Direct Parent: Naphthopyranone glycosides
• Alternative Parents: Phenolic glycosides O-glycosyl compounds Naphthols and derivatives Isocoumarins and derivatives Coumarins and derivatives Disaccharides 1-benzopyrans 2-benzopyrans Pyranones and derivatives Oxanes Vinylogous acids Heteroaromatic compounds Secondary alcohols Lactones Oxacyclic compounds Acetals Dialkyl ethers Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Naphthopyranone glycoside - Phenolic glycoside - 1-naphthol - Coumarin - Disaccharide - Glycosyl compound - O-glycosyl compound - Isocoumarin - Naphthalene - Benzopyran - 1-benzopyran - 2-benzopyran - Pyranone - Oxane - Benzenoid - Pyran - Vinylogous acid - Heteroaromatic compound - Secondary alcohol - Lactone - Acetal - Dialkyl ether - Ether - Oxacycle - Alcohol - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as naphthopyranone glycosides. These are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety.
• External Descriptors: glycoside - benzochromenone

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)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

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

FEN1 Tchem Flap endonuclease 1 (12055 Activities)

Discover Target: FEN1

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

HL (112 Activities)

Explore this target

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

POLK Tbio DNA polymerase kappa (8653 Activities)

Discover Target: POLK

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

POLI Tchem DNA polymerase iota (116820 Activities)

Discover Target: POLI

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

CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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Associated Targets(non-human)

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

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

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

Discover Target: fba

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

FTL Ferritin light chain (43324 Activities)

Discover Target: FTL

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (partly miscible), and acetone.
• Sensitivity: Moisture sensitive.
• Refractive Index: n20D1.72 (Predicted)
• Melt Point(°C): 241-244°C
• Molecular Weight: 640.600 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 5
• Exact Mass: 640.179 Da
• Monoisotopic Mass: 640.179 Da
• Topological Polar Surface Area: 200.000 Ų
• Heavy Atom Count: 46
• Formal Charge: 0
• Complexity: 1150.000
• 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