Page last updated: 2024-12-06

trimethylcolchicinic acid methyl ether

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

trimethylcolchicinic acid methyl ether: RN given refers to (S)-isomer; synonyms NSC-36354 & TMCA refers to tartrate [1:1] [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID18991
CHEMBL ID1063
CHEBI ID80676
SCHEMBL ID13259801
MeSH IDM0044779

Synonyms (35)

Synonym
CHEMBL1063 ,
chebi:80676 ,
colchinic acid trimethyl
trimethylcolchicinic acid methyl ether
n-deacetylcolchicine
tmca methyl ether
trimethylcolchicinsaeuremethyl ester
nsc-201400
deacetylcolchicine
3476-50-4
colchicine, n-deacetyl-
(s)-7-amino-6,7-dihydro-1,2,3,10-tetramethoxybenzo(a)heptalen-9(5h)-one
brn 2822162
trimethylcolchicinsaeuremethyl ester [german]
nsc 201400
benzo(a)heptalen-9(5h)-one, 7-amino-6,7-dihydro-1,2,3,10-tetramethoxy-, (s)-
desacetylcolchicine
n-desacetylcolchicine
(7s)-7-amino-1,2,3,10-tetramethoxy-6,7-dihydro-5h-benzo[a]heptalen-9-one
bdbm50014862
unii-2iap3wio1p
4-14-00-00938 (beilstein handbook reference)
2iap3wio1p ,
(s)-n-deacetyl colchicine
(-)-7-deacetylcolchicine
benzo(a)heptalen-9(5h)-one, 7-amino-6,7-dihydro-1,2,3,10-tetramethoxy-, (7s)-
HFPMXDMZJUJZBX-AWEZNQCLSA-N
SCHEMBL13259801
AKOS027256590
desacetylcolchicin
J-019744
(s)-7-amino-1,2,3,10-tetramethoxy-6,7-dihydrobenzo[a]heptalen-9(5h)-one
Q27149718
DTXSID601150161
(7s)-7-amino-6,7-dihydro-1,2,3,10-tetramethoxybenzo[a]heptalen-9(5h)-one

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"A method for extracting LD50 values from antitumor test data is described."( Toxicity quantitative structure--activity relationships of colchicines.
Beisler, JA; Neiman, Z; Quinn, FR, 1981
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
carbotricyclic compoundA carbopolyclic compound comprising of three carbocyclic rings.
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
acetamidesCompounds with the general formula RNHC(=O)CH3.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
colchicine biosynthesis018

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tubulin beta-2B chainBos taurus (cattle)IC50 (µMol)3.00000.25001.88388.7000AID214332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
microtubule-based processTubulin beta-2B chainBos taurus (cattle)
nervous system developmentTubulin beta-2B chainBos taurus (cattle)
positive regulation of axon guidanceTubulin beta-2B chainBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
GTPase activityTubulin beta-2B chainBos taurus (cattle)
metal ion bindingTubulin beta-2B chainBos taurus (cattle)
protein heterodimerization activityTubulin beta-2B chainBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
microtubule cytoskeletonTubulin beta-2B chainBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID23461Partition coefficient (logP)1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Quantitative structure-activity relationships of colchicines against P388 leukemia in mice.
AID154376Antitumor activity against murine lymphocytic leukemia P388 cells1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Quantitative structure-activity relationships of colchicines against P388 leukemia in mice.
AID645083Cytotoxicity against human HUVEC cells after 96 hrs using tetracolor one2011ACS medicinal chemistry letters, May-12, Volume: 2, Issue:5
Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B.
AID140029Acute toxicity after intramuscular injection in mice.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Antitubulin effects of derivatives of 3-demethylthiocolchicine, methylthio ethers of natural colchicinoids, and thioketones derived from thiocolchicine. Comparison with colchicinoids.
AID123245Toxicity found after a single im injection. The total number of deaths were counted after 7 days and LD50 was determined by probit analysis; 106.2-176.81981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Biological effects of modified colchicines. Improved preparation of 2-demethylcolchicine, 3-demethylcolchicine, and (+)-colchicine and reassignment of the position of the double bond in dehydro-7-deacetamidocolchicines.
AID397098Inhibition of bovine brain tubulin polymerization
AID337172Cytotoxicity against human H9 cells
AID671075Antiproliferative activity against human HBL100 after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
Synthesis and biological evaluation of novel anticancer bivalent colchicine-tubulizine hybrids.
AID152694The compound was tested for its potency against lymphocytic leukemia P388 screen in mice; Inactive1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Biological effects of modified colchicines. Improved preparation of 2-demethylcolchicine, 3-demethylcolchicine, and (+)-colchicine and reassignment of the position of the double bond in dehydro-7-deacetamidocolchicines.
AID645084Selectivity ratio of IC50 for human HUVEC cells to IC50 for human HT-29 cells2011ACS medicinal chemistry letters, May-12, Volume: 2, Issue:5
Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B.
AID337171Antiviral activity against HIV1 HTLV-3B in human H9 cells after 3 days by p24 antigen capture assay
AID645071Cytotoxicity against human A549 cells after 96 hrs using tetracolor one2011ACS medicinal chemistry letters, May-12, Volume: 2, Issue:5
Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B.
AID23448Partition coefficient (logP)1981Journal of medicinal chemistry, May, Volume: 24, Issue:5
Toxicity quantitative structure--activity relationships of colchicines.
AID120593Dose of compound which caused an average weight loss >3g in a set of mice or the death of one or more of the mice in the set in the P388 NCI screen.1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Biological effects of modified colchicines. Improved preparation of 2-demethylcolchicine, 3-demethylcolchicine, and (+)-colchicine and reassignment of the position of the double bond in dehydro-7-deacetamidocolchicines.
AID139239Logarithm of toxic activity (1/lethal dose) in mice bearing P388 leukemia on chronic regimen (Q 1-9)1981Journal of medicinal chemistry, May, Volume: 24, Issue:5
Toxicity quantitative structure--activity relationships of colchicines.
AID214375Inhibition of [3H]colchicine binding to microtubule protein tubulin1981Journal of medicinal chemistry, Mar, Volume: 24, Issue:3
Biological effects of modified colchicines. Improved preparation of 2-demethylcolchicine, 3-demethylcolchicine, and (+)-colchicine and reassignment of the position of the double bond in dehydro-7-deacetamidocolchicines.
AID645070Cytotoxicity against human HT-29 cells after 96 hrs using tetracolor one2011ACS medicinal chemistry letters, May-12, Volume: 2, Issue:5
Design, Synthesis, and Antitumor Activity of 4-Halocolchicines and Their Pro-drugs Activated by Cathepsin B.
AID671076Inhibition of sheep tubulin assembly assessed as half inhibitory molar ratio of compound to tubulin by DAPI fluorometric assay2012Bioorganic & medicinal chemistry, Jul-15, Volume: 20, Issue:14
Synthesis and biological evaluation of novel anticancer bivalent colchicine-tubulizine hybrids.
AID214332Inhibitory effect on the polymerization of purified bovine brain tubulin.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Antitubulin effects of derivatives of 3-demethylthiocolchicine, methylthio ethers of natural colchicinoids, and thioketones derived from thiocolchicine. Comparison with colchicinoids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-199018 (72.00)18.7374
1990's4 (16.00)18.2507
2000's0 (0.00)29.6817
2010's3 (12.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.82

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.82 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index4.15 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other27 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]