Compounds > 3-desmethylcolchicine
Page last updated: 2024-12-08

3-desmethylcolchicine

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

Description

3-desmethylcolchicine: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID299664
CHEMBL ID1081
SCHEMBL ID12246871
MeSH IDM0050372

Synonyms (50)

Synonym
o3-demethylcolchicine
o3-demethyl colchicine
3-demethylcolchicine
CHEMBL1081 ,
3-desmethylcolchicin
3-desmethylcolchicine
colchicine, o(3)-demethyl-
mls002703022 ,
nsc-172946
NSC172946 ,
7336-33-6
acetamide,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl)-, (s)-
colchicine,3-desmethyl
colchicine, 3-o-demethyl-
benzoheptalen-9(5h)-one, 7-acetamido-6,7-dihydro-, l-
nsc 50164
n-(5,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo(a)heptalen-7-yl)acetamide (s)-
acetamide, n-(5,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo(a)heptalen-7-yl)-, (s)-
acetamide, n-(5,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo(a)heptalen-7-yl)-, (s)
colchicine, o(sup 3)-demethyl-
colchiciine, 3-desmethyl-
nsc 172946
3-o-demethylcolchicine
desmethylcolchicine
NCI60_001400
n-[(7s)-3-hydroxy-1,2,10-trimethoxy-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide
n-(3-hydroxy-1,2,10-trimethoxy-9-oxo-5,6,7,9-tetrahydro-benzo[a]heptalen-7-yl)-acetamide
bdbm50014866
cid_494161
(-)-3-demethylcolchicine
SCHEMBL12246871
c939ks8qel ,
unii-c939ks8qel
n-[(7s,12am)-3-hydroxy-1,2,10-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
160338-75-0
colchicine impurity e [ep impurity]
acetamide, n-((7s)-5,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo(a)heptalen-7-yl)-
n-[(7s)-5,6,7,9-tetrahydro-3-hydroxy-1,2,10-trimethoxy-9-oxobenzo[a]heptalen-7-yl]acetamide
colchicine, o3-demethyl-
3-demethyl colchicine
3-demethyl-(-)-colchicine
DTXSID30223604
JRRUSQGIRBEMRN-HNNXBMFYSA-N
n-[(7s,12ara)-3-hydroxy-1,2,10-trimethoxy-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide (3-o-demethylcolchicine)
3-o-demethyl colchicine
Q27275337
AS-83238
HY-W021267
PD011312
AKOS040763648
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tubulin beta-2B chainBos taurus (cattle)IC50 (µMol)2.90000.25001.88388.7000AID214332
[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 (20)

Assay IDTitleYearJournalArticle
AID377075Toxicity in brine shrimp2005Journal of natural products, Feb, Volume: 68, Issue:2
New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.
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.
AID1668781Effect on autophagosome in Parkinson's disease patient derived human ONS cells assessed as LC3b parameters at 10 uM after 24 hrs by anti-LC3b 1/335 staining based fluorescence assay2020Journal of natural products, 05-22, Volume: 83, Issue:5
A Grand Challenge. 3. Unbiased Phenotypic Function of Metabolites from Australia Plants
AID377079Antimicrobial activity against Aspergillus niger after 3 days2005Journal of natural products, Feb, Volume: 68, Issue:2
New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.
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.
AID152693The compound was tested for its potency against lymphocytic leukemia P388 screen in mice.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.
AID377074Cytotoxicity against human SF-268 after 3 days by SRB assay2005Journal of natural products, Feb, Volume: 68, Issue:2
New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.
AID123248Toxicity found after a single im injection. The total number of deaths were counted after 7 days and LD50 was determined by probit analysis; 22.6-44.41981Journal 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.
AID1668779Effect on alpha-tublin parameters in Parkinson's disease patient derived human ONS cells at 10 uM after 24 hrs by anti-alphatubulin staining based fluorescence assay2020Journal of natural products, 05-22, Volume: 83, Issue:5
A Grand Challenge. 3. Unbiased Phenotypic Function of Metabolites from Australia Plants
AID1668778Cytotoxicity against Parkinson's disease patient derived human ONS cells assessed as effect on cell morphology parameters at 10 uM after 24 hrs by DAPI staining based fluorescence assay2020Journal of natural products, 05-22, Volume: 83, Issue:5
A Grand Challenge. 3. Unbiased Phenotypic Function of Metabolites from Australia Plants
AID377077Antimicrobial activity against Mycobacterium smegmatis after 3 days2005Journal of natural products, Feb, Volume: 68, Issue:2
New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.
AID1668777Cytotoxicity against Parkinson's disease patient derived human ONS cells assessed as effect on nucleus morphology parameters at 10 uM after 24 hrs by DAPI staining based fluorescence assay2020Journal of natural products, 05-22, Volume: 83, Issue:5
A Grand Challenge. 3. Unbiased Phenotypic Function of Metabolites from Australia Plants
AID377076Antimicrobial activity against Micrococcus luteus after 3 days2005Journal of natural products, Feb, Volume: 68, Issue:2
New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.
AID377073Cytotoxicity against human H460 after 3 days by SRB assay2005Journal of natural products, Feb, Volume: 68, Issue:2
New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.
AID1668780Effect on mitochondria parameters in Parkinson's disease patient derived human ONS cells at 10 uM after 24 hrs by MitoTracker Orange CMTMRos staining based fluorescence assay2020Journal of natural products, 05-22, Volume: 83, Issue:5
A Grand Challenge. 3. Unbiased Phenotypic Function of Metabolites from Australia Plants
AID377078Antimicrobial activity against Saccharomyces cerevisiae after 3 days2005Journal of natural products, Feb, Volume: 68, Issue:2
New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.
AID213858Percentage by which the binding of [3H]colchicine (2.5 uM) to tubulin from calf brain is reduced by 25 uM concentration of compound1987Journal of medicinal chemistry, Apr, Volume: 30, Issue:4
A novel synthesis of colchicide and analogues from thiocolchicine and congeners: reevaluation of colchicide as a potential antitumor agent.
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.
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.
AID377072Cytotoxicity against human MCF7 after 3 days by SRB assay2005Journal of natural products, Feb, Volume: 68, Issue:2
New colchicinoids from a native Jordanian meadow saffron, colchicum brachyphyllum: isolation of the first naturally occurring dextrorotatory colchicinoid.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (40.00)18.7374
1990's1 (20.00)18.2507
2000's1 (20.00)29.6817
2010's0 (0.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.63

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 Index12.63 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.63)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
colchicine
(S)-colchicine : A colchicine that has (S)-configuration. It is a secondary metabolite, has anti-inflammatory properties and is used to treat gout, crystal-induced joint inflammation, familial Mediterranean fever, and many other conditions.		3.0950alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
thiocholchicine
thiocholchicine: RN refers to (S)-isomer		2.6630
n-methylcolchiceinamide, (s)-isomer
[no description available]		1.9710
trimethylcolchicinic acid methyl ether
trimethylcolchicinic acid methyl ether: RN given refers to (S)-isomer; synonyms NSC-36354 & TMCA refers to tartrate [1:1]		2.3720acetamides;
alkaloid;
carbotricyclic compound
n-deacetyl-n-formylcolchicine
N-deacetyl-N-formylcolchicine: structure given in first source		2.2510cyclic ketone
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		2.0210delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
2-demethylthiocolchicine
2-demethylthiocolchicine: RN & structure given in first source; RN not in Chemline 10/85		1.9710
3-demethylthiocolchicine
3-demethylthiocolchicine: RN & structure given in first source; RN not in Chemline 10/85		2.3720
brexanolone
brexanolone: a mixture of allopregnanolone and sulfobutylether‐beta‐cyclodextrin for treatment of postpartum depression. brexanolone : A 3-hydroxy-5alpha-pregnan-20-one in which the hydroxy group at position 3 has alpha-configuration. It is a metabolite of the sex hormone progesterone and used for the treatment of postpartum depression in women.		2.02103-hydroxy-5alpha-pregnan-20-oneantidepressant;
GABA modulator;
human metabolite;
intravenous anaesthetic;
sedative
demecolcine
Demecolcine: An alkaloid isolated from Colchicum autumnale L. and used as an antineoplastic.. (-)-demecolcine : A secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than colchicine and is used as an antineoplastic.		2.6730alkaloid;
secondary amino compound		antineoplastic agent;
microtubule-destabilising agent
gamma-lumicolchicine
[no description available]		2.4820acetamides;
alkaloid;
carbotricyclic compound
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		01.9710
Experimental Neoplasms
[description not available]		01.9710
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		01.9610