Methyl indole-3-carboxylate - ≥99% , CAS No.942-24-5

CAS: 942-24-5 Cat. No.: M103561 Molecular Weight: 175.18 Beilstein Registry Number: 22,65 EC Number: 629-395-3

GRADE & PURITY ≥99%

Synonyms

DTXSID10343334 | Indole-3-carboxylic Acid Methyl Ester | Methyl 1H-indole-3-carboxylate # | methylindole-3-carboxylate | Indole-3-carboxylic acid methyl ester, 99% | METHYL INDOLE-3- CARBOXYLATE | HY-79635 | SY020043 | Z57164966 | InChI=1/C10H9NO2/c1-13-1

Storage

Room temperature

Shipped In

Normal

Overview

Usually uesed as reactant for preparation of Nitric oxide synthase (nNOS) inhibitorS,Protein kinase c alpha (PKCα) inhibitors,Organocatalysts for the anti-Mannich reaction,Inhibitors of Human 5-Lipoxygenase,Hyaluronidase inhibitors.

product description：

Methyl indole-3-carboxylate (3-Methoxycarbonylindole, 3-Carbomethoxyindole, Methyl indolyl-3-carboxylate) has been extracted from the marine Streptomyces sp. 060524. Its crystal structure indicates the presence of inter¬molecular N-H…O hydrogen bond. It is also obtained during the isolation of sorazinones A and B from Sorangium cellulosum strain Soce895. It undergoes regioselective dibromination with bromine in acetic acid to afford methyl 5,6-dibromoindole-3-carboxylate.

Specifications

Synonyms

DTXSID10343334 | Indole-3-carboxylic Acid Methyl Ester | Methyl 1H-indole-3-carboxylate # | methylindole-3-carboxylate | Indole-3-carboxylic acid methyl ester, 99% | METHYL INDOLE-3- CARBOXYLATE | HY-79635 | SY020043 | Z57164966 | InChI=1/C10H9NO2/c1-13-1

Specifications & Purity

≥99%

Storage

Room temperature

Shipped In

Normal

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488190497
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488190497
• Canonical Smiles: COC(=O)C1=CNC2=CC=CC=C21
• IUPAC Name: methyl 1H-indole-3-carboxylate
• InChIKey: QXAUTQFAWKKNLM-UHFFFAOYSA-N
• INCHI: 1S/C10H9NO2/c1-13-10(12)8-6-11-9-5-3-2-4-7(8)9/h2-6,11H,1H3
• Isomeric SMILES: COC(=O)C1=CNC2=CC=CC=C21
• WGK Germany: 3
• Molecular Weight: 175.18
• Beilstein: 22,65
• Reaxy-Rn: 142023
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=142023&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass Indolecarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: Indolecarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Indolecarboxylic acids and derivatives
• Alternative Parents: Indoles Pyrrole carboxylic acids and derivatives Substituted pyrroles Benzenoids Vinylogous amides Methyl esters Heteroaromatic compounds Monocarboxylic acids and derivatives Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Indolecarboxylic acid derivative - Indole - Pyrrole-3-carboxylic acid or derivatives - Substituted pyrrole - Benzenoid - Pyrrole - Methyl ester - Vinylogous amide - Heteroaromatic compound - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Azacycle - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. These are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
• External Descriptors: an indole-phytolexin

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)

TYR Tclin Tyrosinase (717 Activities)

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MCF7 (126967 Activities)

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A549 (127892 Activities)

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NR4A2 Tchem Nuclear receptor subfamily 4 group A member 2 (460 Activities)

Discover Target: NR4A2

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CREBBP Tchem CREB-binding protein (1602 Activities)

Discover Target: CREBBP

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BRD4 Tchem Bromodomain-containing protein 4 (13122 Activities)

Discover Target: BRD4

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Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Saccharomyces cerevisiae (19171 Activities)

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Candida albicans (78123 Activities)

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L929 (3802 Activities)

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Chromobacterium violaceum (349 Activities)

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Mucor hiemalis (184 Activities)

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Mycolicibacterium diernhoferi (48 Activities)

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Nocardia sp. (39 Activities)

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Wickerhamomyces anomalus (305 Activities)

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Cryphonectria parasitica (24 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Slightly soluble methanol and dimethyl sulfoxide. Insoluble in water.
• Melt Point(°C): 149-152°C
• Molecular Weight: 175.180 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063 Da
• Monoisotopic Mass: 175.063 Da
• Topological Polar Surface Area: 42.100 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 205.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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

References

1. Xiang Xu, Yi Shen, Yue Shu, Yong Guan, Dafu Wei.  (2022)  Synthesis and application of poly methyl indole-4-carboxylate with blue light blocking properties.  EUROPEAN POLYMER JOURNAL,      [PMID:] [10.1016/j.eurpolymj.2022.111198]