Compounds > millepachine
Page last updated: 2024-11-13

millepachine

Description

millepachine: isolated from Millettia pachycarpa Benth (Leguminosae); structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
MillettiagenusA plant genus of the family FABACEAE. Members contain ISOFLAVONES, some of which show molluscicidal and schistosomicidal activity. Some species of Pongamia have been reclassified to this genus and some to DERRIS.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]
Millettia pachycarpaspecies[no description available]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID66573474
CHEMBL ID2041121
SCHEMBL ID16697964
SCHEMBL ID16697961
MeSH IDM0587529

Synonyms (14)

Synonym
CHEMBL2041121
millepachine
SCHEMBL16697964
SCHEMBL16697961
HY-N7591
CS-0134506
E75119
1-(5-methoxy-2,2-dimethyl-2h-chromen-8-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
1579976-20-7
(e)-1-(5-methoxy-2,2-dimethyl-2h-chromen-8-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
(e)-1-(5-methoxy-2,2-dimethylchromen-8-yl)-3-(4-methoxyphenyl)prop-2-en-1-one
MS-25411
1393922-01-4
AKOS040756722

Research Excerpts

Overview

Millepachine (MIL) is a bioactive natural product that shows great potential for cancer treatment.

ExcerptReferenceRelevance
"Millepachine (MIL) is a bioactive natural product that shows great potential for cancer treatment. "( The effect and mechanism of millepachine-disrupted spindle assembly in tumor cells.
Gong, Y; Liu, F; Liu, Y; Su, A; Wu, W; Ye, H; Zhao, W; Zhu, J, 2018)		2.22

Bioavailability

ExcerptReferenceRelevance
" Furthermore, the hydrochloride salt of 8 (8·HCl) significantly improved the bioavailability up to 47% while retaining the antiproliferative activity."( Synthesis and biological evaluation of novel millepachine derivatives as a new class of tubulin polymerization inhibitors.
Cao, D; Chen, L; Li, L; Liu, L; Ma, L; Tang, M; Wang, F; Wang, G; Wang, J; Wen, J; Wu, W; Xiang, M; Xiang, W; Yang, J; Yang, Z; You, J; Zhang, R; Zhu, J, 2014)		0.66
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID733797Cytotoxicity against human LO2 cells by MTT assay2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis and biological evaluation of novel pyranochalcone derivatives as a new class of microtubule stabilizing agents.
AID1905035Antiproliferative activity against human A2780 cells assessed as cell viability incubated for 48 hrs by MTT assay2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
Discovery of a Novel Stilbene Derivative as a Microtubule Targeting Agent Capable of Inducing Cell Ferroptosis.
AID667443Antiproliferative activity against human SKOV3 cells after 24 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID733798Cytotoxicity against human A375 cells by MTT assay2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis and biological evaluation of novel pyranochalcone derivatives as a new class of microtubule stabilizing agents.
AID667446Antiproliferative activity against human SW620 cells after 24 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID1474394Cytotoxicity against human T24 cells after 48 hrs by MTT assay2017European journal of medicinal chemistry, May-26, Volume: 132Synthesis and biological evaluation of novel chalcone derivatives as a new class of microtubule destabilizing agents.
AID667452Cell cycle arrest in human HepG2 cells assessed as accumulation at G1 phase at 2.5 uM after 8 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 49.86%)2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID667456Cell cycle arrest in human HepG2 cells assessed as accumulation at S phase at 5 uM after 8 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 32.43%)2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID733800Cytotoxicity against human HepG2 cells by MTT assay2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis and biological evaluation of novel pyranochalcone derivatives as a new class of microtubule stabilizing agents.
AID1130047Antiproliferative activity against human HepG2 cells after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry, Apr-01, Volume: 22, Issue:7
Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents.
AID1604238Cytotoxicity against human HepG2 cells assessed as reduction in cell viability2019European journal of medicinal chemistry, Dec-01, Volume: 183Recent advances in α,β-unsaturated carbonyl compounds as mitochondrial toxins.
AID667457Cell cycle arrest in human HepG2 cells assessed as accumulation at G2/M phase at 5 uM after 8 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 17.72%)2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID1474391Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay2017European journal of medicinal chemistry, May-26, Volume: 132Synthesis and biological evaluation of novel chalcone derivatives as a new class of microtubule destabilizing agents.
AID667445Antiproliferative activity against human HT-29 cells after 24 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID1905036Antiproliferative activity against human HCT-8 cells assessed as cell viability incubated for 48 hrs by MTT assay2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
Discovery of a Novel Stilbene Derivative as a Microtubule Targeting Agent Capable of Inducing Cell Ferroptosis.
AID1905034Antiproliferative activity against human HeLa cells assessed as cell viability incubated for 48 hrs by MTT assay2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
Discovery of a Novel Stilbene Derivative as a Microtubule Targeting Agent Capable of Inducing Cell Ferroptosis.
AID1905033Antiproliferative activity against human A549 cells assessed as cell viability incubated for 48 hrs by MTT assay2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
Discovery of a Novel Stilbene Derivative as a Microtubule Targeting Agent Capable of Inducing Cell Ferroptosis.
AID733799Cytotoxicity against human K562 cells by MTT assay2013European journal of medicinal chemistry, Apr, Volume: 62Synthesis and biological evaluation of novel pyranochalcone derivatives as a new class of microtubule stabilizing agents.
AID667458Antitumor activity against human A549 cells xenografted in BALB/c mouse assessed as tumor growth inhibition at 20 mg/kg, iv administered at intervals of 2 days for 18 days relative to control2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID1474392Cytotoxicity against human MGC803 cells after 48 hrs by MTT assay2017European journal of medicinal chemistry, May-26, Volume: 132Synthesis and biological evaluation of novel chalcone derivatives as a new class of microtubule destabilizing agents.
AID1474393Cytotoxicity against human SKOV3 cells after 48 hrs by MTT assay2017European journal of medicinal chemistry, May-26, Volume: 132Synthesis and biological evaluation of novel chalcone derivatives as a new class of microtubule destabilizing agents.
AID1905037Antiproliferative activity against human MCF7 cells assessed as cell viability incubated for 48 hrs by MTT assay2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
Discovery of a Novel Stilbene Derivative as a Microtubule Targeting Agent Capable of Inducing Cell Ferroptosis.
AID667442Antiproliferative activity against human K562 cells after 24 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID667447Inhibition of alpha-tubulin in human HepG2 cells assessed as decrease in microtubule formation at 1 uM after 24 hrs by DAPI staining-based immunofluorescence analysis2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID1474390Cytotoxicity against human NCI-H460 cells after 48 hrs by MTT assay2017European journal of medicinal chemistry, May-26, Volume: 132Synthesis and biological evaluation of novel chalcone derivatives as a new class of microtubule destabilizing agents.
AID667448Inhibition of alpha-tubulin in human HepG2 cells assessed as decrease in spindle formation at 1 uM after 24 hrs by DAPI staining-based immunofluorescence analysis2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID667441Antiproliferative activity against human HepG2 cells after 24 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID1163570Antiproliferative activity against human A375 cells assessed as inhibition of cell proliferation after 48 hrs by MTT assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Synthesis and biological evaluation of novel millepachine derivatives as a new class of tubulin polymerization inhibitors.
AID667449Cell cycle arrest in human HepG2 cells assessed as accumulation at G1 phase at 1.25 uM after 8 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 49.86%)2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID1163571Antiproliferative activity against human K562 cells assessed as inhibition of cell proliferation after 48 hrs by MTT assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Synthesis and biological evaluation of novel millepachine derivatives as a new class of tubulin polymerization inhibitors.
AID667444Antiproliferative activity against human HCT116 cells after 24 hrs by MTT assay2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID1474395Cytotoxicity against human HL7702 cells after 48 hrs by MTT assay2017European journal of medicinal chemistry, May-26, Volume: 132Synthesis and biological evaluation of novel chalcone derivatives as a new class of microtubule destabilizing agents.
AID667455Cell cycle arrest in human HepG2 cells assessed as accumulation at G1 phase at 5 uM after 8 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 49.86%)2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID667451Cell cycle arrest in human HepG2 cells assessed as accumulation at G2/M phase at 1.25 uM after 8 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 17.72%)2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID667454Cell cycle arrest in human HepG2 cells assessed as accumulation at G2/M phase at 2.5 uM after 8 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 17.72%)2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID1163569Antiproliferative activity against human HepG2 cells assessed as inhibition of cell proliferation after 48 hrs by MTT assay2014Journal of medicinal chemistry, Oct-09, Volume: 57, Issue:19
Synthesis and biological evaluation of novel millepachine derivatives as a new class of tubulin polymerization inhibitors.
AID667459Toxicity in BALB/c mouse bearing human A549 cells assessed as decrease in body weight at 20 mg/kg, iv administered at intervals of 2 days for 18 days2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID667450Cell cycle arrest in human HepG2 cells assessed as accumulation at S phase at 1.25 uM after 8 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 32.43%)2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
AID667453Cell cycle arrest in human HepG2 cells assessed as accumulation at S phase at 2.5 uM after 8 hrs by propidium iodide staining-based flow cytometric analysis (Rvb = 32.43%)2012European journal of medicinal chemistry, Aug, Volume: 54Design, synthesis, and structure-activity relationship studies of novel millepachine derivatives as potent antiproliferative agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's14 (77.78)24.3611
2020's4 (22.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.63

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 Index11.63 (24.57)
Research Supply Index2.94 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other16 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.110nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
vincristine
[no description available]		2.4110acetate ester;
formamides;
methyl ester;
organic heteropentacyclic compound;
organic heterotetracyclic compound;
tertiary alcohol;
tertiary amino compound;
vinca alkaloid		antineoplastic agent;
drug;
microtubule-destabilising agent;
plant metabolite;
tubulin modulator
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.		3.0340alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
paclitaxel
Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).		3.0540taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		2.2510divalent inorganic anion;
phosphite ion
doxorubicin hydrochloride
[no description available]		2.5820anthracycline
chalcone
trans-chalcone : The trans-isomer of chalcone.		7.0810chalconeEC 3.2.1.1 (alpha-amylase) inhibitor
isoliquiritigenin
[no description available]		3.3110chalconesantineoplastic agent;
biological pigment;
EC 1.14.18.1 (tyrosinase) inhibitor;
GABA modulator;
geroprotector;
metabolite;
NMDA receptor antagonist
xanthohumol
xanthohumol: from hop plant, Humulus lupulus. xanthohumol : A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.		3.3110aromatic ether;
chalcones;
polyphenol		anti-HIV-1 agent;
antineoplastic agent;
antiviral agent;
apoptosis inducer;
EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor;
metabolite
shogaol
shogaol: from ginger, ZINGIBER OFFICINALE; less mutagenic than GINGEROL; structure given in first source		3.3110enone;
monomethoxybenzene;
phenols
licochalcone a
licochalcone A: has both anti-inflammatory and antineoplastic activities; structure given in first source; isolated from root of Glycyrrhiza inflata; RN given refers to (E)-isomer		3.3110chalcones
fosbretabulin
[no description available]		2.1510stilbenoid
2',4'-dihydroxychalcone
2',4'-dihydroxychalcone: RN given refers to (E)-isomer; RN for cpd without isomeric designation not available 6/89; structure given in first source		3.3110
erastin
erastin: an antineoplastic agent; structure in first source. erastin : A member of the class of quinazolines that is quinazolin-4(3H)-one in which the hydrogens at positions 2 and 3 are replaced by 1-{4-[(4-chlorophenoxy)acetyl]piperazin-1-yl}ethyl and 2-ethoxyphenyl groups, respectively. It is an inhibitor of voltage-dependent anion-selective channels (VDAC2 and VDAC3) and a potent ferroptosis inducer.		2.4110aromatic ether;
diether;
monochlorobenzenes;
N-acylpiperazine;
N-alkylpiperazine;
quinazolines;
tertiary carboxamide		antineoplastic agent;
ferroptosis inducer;
voltage-dependent anion channel inhibitor
longikaurin a
longikaurin A: from Isodon adenolomus; structure in first source		3.3110kaurane diterpenoidmetabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		04.1550
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		04.1550
Experimental Neoplasms
[description not available]		02.5220
Hepatocellular Carcinoma
[description not available]		08.8230
Cancer of Liver
[description not available]		03.8230
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		03.8230
Liver Neoplasms
Tumors or cancer of the LIVER.		03.8230
Epithelial Ovarian Cancer
[description not available]		02.1710
Cancer of Ovary
[description not available]		02.5520
Carcinoma, Ovarian Epithelial
A malignant neoplasm that originates in cells on the surface EPITHELIUM of the ovary and is the most common form of ovarian cancer. There are five histologic subtypes: papillary serous, endometrioid, mucinous, clear cell, and transitional cell. Mutations in BRCA1, OPCML, PRKN, PIK3CA, AKT1, CTNNB1, RRAS2, and CDH1 genes are associated with this cancer.		02.1710
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.5520
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.1510
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