Coumermycin A₁ - Moligand™, ≥97% , CAS No.4434-05-3

CAS: 4434-05-3 Cat. No.: C332269 Molecular Weight: 1110.08 Beilstein Registry Number: 470805 EC Number: 636-952-4

GRADE & PURITY Moligand™, ≥97%

Synonyms

Coumermycin [USAN] | Cumamicina | HY-N7452 | [(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[5-[[4-hydroxy-7-[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]carbamoyl]-4-methyl-1H-pyr

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Coumermycin A|1|, a cell permeable antibiotic, has been found to be a dimerizing agent that can activate a modified Raf-1 protein and stimulate the mitogen-activated protein kinase cascade. This compound has also been reported to induce autophosphorylation of GyrB-Janus Kinase (JAK) 2 fusion proteins, thus bypassing receptor activation. JAKs are cytoplasmic protein kinases that interact with intracellular domains of cytokine receptors which plays an important role in signal transduction. The activation of JAK is thought to induce cell proliferation. Studies suggest that Coumermycin A|1|can inhibit the supercoiling activity of gyrase by binding to the gyrase B subunit.

Specifications

Synonyms

Coumermycin [USAN] | Cumamicina | HY-N7452 | [(3R, 4S, 5R, 6R)-5-hydroxy-6-[4-hydroxy-3-[[5-[[4-hydroxy-7-[(2R, 3R, 4S, 5R)-3-hydroxy-5-methoxy-6, 6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]carbamoyl]-4-methyl-1H-pyr

Specifications & Purity

Moligand™, ≥97%

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.

Grade

Moligand™

Action Type

INHIBITOR

Purity

≥97%

Names and Identifiers

• Canonical Smiles: CC1=CC=C(N1)C(=O)OC2C(C(OC(C2OC)(C)C)OC3=C(C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CNC(=C5C)C(=O)NC6=C(C7=C(C(=C(C=C7)OC8C(C(C(C(O8)(C)C)OC)OC(=O)C9=CC=C(N9)C)O)C)OC6=O)O)O)C)O
• IUPAC Name: [(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[5-[[4-hydroxy-7-[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]carbamoyl]-4-methyl-1H-pyrrole-3-carbonyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
• InChIKey: WTIJXIZOODAMJT-DHFGXMAYSA-N
• INCHI: 1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1
• Isomeric SMILES: CC1=CC=C(N1)C(=O)O[C@H]2[C@H]([C@@H](OC([C@@H]2OC)(C)C)OC3=C(C4=C(C=C3)C(=C(C(=O)O4)NC(=O)C5=CNC(=C5C)C(=O)NC6=C(C7=C(C(=C(C=C7)O[C@H]8[C@@H]([C@@H]([C@H](C(O8)(C)C)OC)OC(=O)C9=CC=C(N9)C)O)C)OC6=O)O)O)C)O
• WGK Germany: 3
• RTECS: UX9375000
• Molecular Weight: 1110.08
• Beilstein: 470805
• Reaxy-Rn: 470805
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=470805&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Coumarin glycosides

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Coumarin glycosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Coumarin glycosides
• Alternative Parents: Phenolic glycosides 4-hydroxycoumarins O-glycosyl compounds 1-benzopyrans 2-heteroaryl carboxamides Pyrrole carboxamides Pyranones and derivatives Substituted pyrroles Benzenoids Dicarboxylic acids and derivatives Monosaccharides Oxanes Heteroaromatic compounds Vinylogous amides Vinylogous acids Secondary alcohols Lactones Carboxylic acid esters Secondary carboxylic acid amides Acetals Dialkyl ethers Oxacyclic compounds Azacyclic compounds Organic oxides Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Coumarin-7-o-glycoside - Coumarin o-glycoside - Phenolic glycoside - 4-hydroxycoumarin - Hydroxycoumarin - Glycosyl compound - O-glycosyl compound - Benzopyran - 1-benzopyran - 2-heteroaryl carboxamide - Pyrrole-3-carboxamide - Pyrrole-2-carboxamide - Pyrrole-3-carboxylic acid or derivatives - Pyrrole-2-carboxylic acid or derivatives - Pyranone - Dicarboxylic acid or derivatives - Monosaccharide - Oxane - Pyran - Benzenoid - Substituted pyrrole - Vinylogous amide - Pyrrole - Vinylogous acid - Heteroaromatic compound - Carboxamide group - Secondary carboxylic acid amide - Secondary alcohol - Carboxylic acid ester - Lactone - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Dialkyl ether - Ether - Oxacycle - Acetal - Organopnictogen compound - Organonitrogen compound - Organic oxide - Alcohol - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
• External Descriptors: glycoside - aromatic amide - pyrroles - coumarins - heteroarenecarboxylate ester

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)

MCF7 (126967 Activities)

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

SK-BR-3 (5175 Activities)

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Associated Targets(non-human)

Streptococcus pneumoniae (31063 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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gyrB DNA gyrase (2092 Activities)

Discover Target: gyrB

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 DMSO (50 mg/ml).
• Refractive Index: n20D1.68
• Molecular Weight: 1110.100 g/mol
• XLogP3: 4.600
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 16
• Exact Mass: 1109.38 Da
• Monoisotopic Mass: 1109.38 Da
• Topological Polar Surface Area: 347.000 Ų
• Heavy Atom Count: 80
• Formal Charge: 0
• Complexity: 2440.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• 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