Compounds > laulimalide
Page last updated: 2024-12-11

laulimalide

Description

laulimalide: isolated from Cacospongia mycofijiensis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

laulimalide : A macrolide with formula C30H42O7 that is isolated from the marine sponges, Cacospongia mycofijiensis and Hyattella sp. [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]

Cross-References

ID SourceID
PubMed CID6918457
CHEMBL ID155405
CHEBI ID69134
SCHEMBL ID13404885
MeSH IDM0301171

Synonyms (13)

Synonym
laulimalide
(-)-laulimalide
fijianolide b
CHEMBL155405
chebi:69134 ,
SCHEMBL13404885
115268-43-4
(1r,3s,7s,8s,10s,12s,15z,18r)-12-[(1s,2e)-3-[(2s)-3,6-dihydro-4-methyl-2h-pyran-2-yl]-1-hydroxy-2-propen-1-yl]-7-hydroxy-3-methyl-5-methylene-9,13,22-trioxatricyclo[16.3.1.08,10]docosa-15,19-dien-14-one
(1r,3s,7s,8s,10s,12s,15z,18r)-7-hydroxy-12-{(1s,2e)-1-hydroxy-3-[(2s)-4-methyl-3,6-dihydro-2h-pyran-2-yl]prop-2-en-1-yl}-3-methyl-5-methylidene-9,13,22-trioxatricyclo[16.3.1.0~8,10~]docosa-15,19-dien-14-one
DTXSID10893501
Q27137474
AKOS037435215
(1r,3s,7s,8s,10s,12s,18r,z)-7-hydroxy-12-((s,e)-1-hydroxy-3-((s)-4-methyl-3,6-dihydro-2h-pyran-2-yl)allyl)-3-methyl-5-methylene-9,13,22-trioxatricyclo[16.3.1.08,10]docosa-15,19-dien-14-one

Research Excerpts

Overview

Laulimalide (LA) is a microtubule-stabilizing agent, currently in preclinical studies. It has strong taxoid-like properties but binds to a distinct site on β-tubulin in theMicrotubule (MT) lattice. Laulimalides is a cytotoxic natural product isolated from marine sponges.

ExcerptReferenceRelevance
"Laulimalide is a microtubule-binding drug that was originally isolated from marine sponges. "( Laulimalide induces dose-dependent modulation of microtubule behaviour in the C. elegans embryo.
Bajaj, M; Srayko, M, 2013)		3.28
"Laulimalide (LA) is a microtubule-stabilizing agent, currently in preclinical studies. "( Analysis of the binding mode of laulimalide to microtubules: Establishing a laulimalide-tubulin pharmacophore.
Churchill, CD; Klobukowski, M; Tuszynski, JA, 2016)		2.16
"Laulimalide is a potent microtubule stabilizing agent and a promising anticancer therapeutic lead. "( Function-oriented synthesis: biological evaluation of laulimalide analogues derived from a last step cross metathesis diversification strategy.
Clark, EA; Hilinski, MK; Mooberry, SL; Wender, PA, )		1.82
"Laulimalide is a structurally unique 20-membered marine macrolide displaying microtubule stabilizing activity similar to that of paclitaxel and the epothilones. "( Evaluating transition-metal-catalyzed transformations for the synthesis of laulimalide.
Amans, D; Chung, CK; Seganish, WM; Trost, BM, 2009)		2.03
"Laulimalide is a natural product that has strong taxoid-like properties but binds to a distinct site on β-tubulin in the microtubule (MT) lattice. "( Low-dose laulimalide represents a novel molecular probe for investigating microtubule organization.
Bennett, MJ; Chan, GK; Rattner, JB; Schriemer, DC, 2012)		2.24
"Laulimalide is a cytotoxic natural product that stabilizes microtubules. "( The microtubule stabilizing agent laulimalide does not bind in the taxoid site, kills cells resistant to paclitaxel and epothilones, and may not require its epoxide moiety for activity.
Andreu, JM; Bilcer, G; Díaz, JF; Ghosh, AK; Giannakakou, P; Hamel, E; Jung, MK; Kabaki, M; O'Brate, A; Pryor, DE; Wang, Y, 2002)		2.04
"Laulimalide is a potent, structurally unique microtubule-stabilizing agent originally isolated from the marine sponge Cacospongia mycofijiensis. "( Microtubule-stabilizing agents based on designed laulimalide analogues.
Hegde, SG; Hubbard, RD; Leal, RM; Mooberry, SL; Randall-Hlubek, DA; Wender, PA; Zhang, L, 2004)		2.02
"Laulimalide is a potent microtubule stabilizer that binds to tubulin at a site that does not overlap the taxane-binding site."( Laulimalide and synthetic laulimalide analogues are synergistic with paclitaxel and 2-methoxyestradiol.
Clark, EA; Davidson, BS; Hills, PM; Mooberry, SL; Wender, PA, )		2.3
"Laulimalide is a cytotoxic natural product isolated from marine sponges. "( In vitro and in vivo anticancer activities of synthetic (-)-laulimalide, a marine natural product microtubule stabilizing agent.
Cheng, H; Fang, FG; Gallagher, BM; Johannes, CW; Kuznetsov, G; Littlefield, BA; Liu, J; Murphy, EA; Pesant, M; Reardon, C; Saxton, P; Towle, MJ; Tremblay, MR; Vermeulen, MW; Wu, J; Zhao, H, )		1.82
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (5)

RoleDescription
microtubule-stabilising agentAny substance that interacts with tubulin to promote polymerisation of microtubules.
antimitoticAny compound that inhibits cell division (mitosis).
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
marine metaboliteAny metabolite produced during a metabolic reaction in marine macro- and microorganisms.
animal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
[role 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]

Drug Classes (5)

ClassDescription
macrolideA macrocyclic lactone with a ring of twelve or more members derived from a polyketide.
epoxideAny cyclic ether in which the oxygen atom forms part of a 3-membered ring.
carboxylic esterAn ester of a carboxylic acid, R(1)C(=O)OR(2), where R(1) = H or organyl and R(2) = organyl.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
secondary allylic alcoholAn allylic alcohol in which the carbon atom that links the double bond to the hydroxy group is also attached to one other carbon and one hydrogen.
[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]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID296720Cytotoxicity against human HCT116 cells assessed as cell kill at 10 ng/mL after 24 hrs2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID1587834Potency index, ratio of paclitaxel IC50 to laulimalide IC50 for cytotoxicity against human SKVLB-1 cells2019European journal of medicinal chemistry, Jun-01, Volume: 171Anti-tubulin agents of natural origin: Targeting taxol, vinca, and colchicine binding domains.
AID296714Abnormal circular mitotic spindles formation in human HCT116 cells at 2 to 20 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID638665Induction of microfilament disruption in human HeLa cells at 20 ug/ml after 24 hrs by Hoechst staining-based fluorescence microscopic analysis2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Natural product libraries to accelerate the high-throughput discovery of therapeutic leads.
AID424797Cytotoxicity against human HCT116 xenografted in SCID mouse at 25 mg/kg/day, iv administered as bolus dose from 3 days after tumor implantation for 5 days measured on day 11 relative to control2009Journal of natural products, Mar-27, Volume: 72, Issue:3
A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.
AID638670Antiproliferative activity against human U937 cells assessed as cell viability after 96 hrs by CellTiter-Glo luminescence assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Natural product libraries to accelerate the high-throughput discovery of therapeutic leads.
AID253342Inhibitory concentration measured in term of cytotoxicity against human A2780/AD10 cells2005Bioorganic & medicinal chemistry letters, May-02, Volume: 15, Issue:9
Design, synthesis and biological evaluation of novel, simplified analogues of laulimalide: modification of the side chain.
AID296704Cytotoxicity against human H125 cells at 9 ug/disk by disk diffusion method2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID253353Inhibitory concentration of compound required for exhibiting cytotoxic effect on human A2780 cells2005Bioorganic & medicinal chemistry letters, May-02, Volume: 15, Issue:9
Design, synthesis and biological evaluation of novel, simplified analogues of laulimalide: modification of the side chain.
AID296687Cytotoxicity against human HCT116 cells after 72 hrs by SRB assay2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296694Cytotoxicity against mouse C38 cells at 36 ug/disk by disk diffusion method2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID424799Toxicity in human HCT116 xenografted SCID mouse assessed as increase in body weight at 25 mg/kg/day, iv administered as bolus dose from 3 days after tumor implantation for 5 days measured after 30 days2009Journal of natural products, Mar-27, Volume: 72, Issue:3
A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.
AID638667Antiproliferative activity against human MDA-MB-435 cells assessed as cell viability after 96 hrs by CellTiter-Glo luminescence assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Natural product libraries to accelerate the high-throughput discovery of therapeutic leads.
AID296721Cytotoxicity against human HCT116 cells assessed as cell kill at 1.2 ng/mL after 168 hrs2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296725Antitumor activity against HCT116 bearig SCID mouse assessed as tumor weight at 25 mg/kg, iv after 30 mins2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296686Cytotoxicity against human MDA-MB-435 cells after 72 hrs by SRB assay2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296723Drug level in HCT116 bearing SCID mice plasma at 25 mg/kg, iv after 2 hrs2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296689Cytotoxicity against mouse L1210 cells at 9 ug/disk by disk diffusion method2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID638668Antiproliferative activity against human HT-29 cells assessed as cell viability after 96 hrs by CellTiter-Glo luminescence assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Natural product libraries to accelerate the high-throughput discovery of therapeutic leads.
AID638666Antitrypanosomal activity against Trypanosoma brucei brucei clone 427-221a assessed as growth inhibition after 40 hrs by ATP-bioluminescence assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Natural product libraries to accelerate the high-throughput discovery of therapeutic leads.
AID424795Cytotoxicity against human KB cells2009Journal of natural products, Mar-27, Volume: 72, Issue:3
A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.
AID424786Cytotoxicity against human MDA-MB-435 cells2009Journal of natural products, Mar-27, Volume: 72, Issue:3
A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.
AID296726Antitumor activity against HCT116 bearig SCID mouse assessed as tumor weight at 25 mg/kg, iv after 24 hrs2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID638669Antiproliferative activity against human H522-T1 cells assessed as cell viability after 96 hrs by CellTiter-Glo luminescence assay2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Natural product libraries to accelerate the high-throughput discovery of therapeutic leads.
AID424796Cytotoxicity against human HCT116 xenografted in SCID mouse at 12.3 mg/kg/day, iv administered as bolus dose from 3 days after tumor implantation for 5 days measured on day 9 relative to control2009Journal of natural products, Mar-27, Volume: 72, Issue:3
A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.
AID296699Cytotoxicity against human H116 cells at 9 ug/disk by disk diffusion method2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296716Formation of thick bundles of microtubule stabilization in human HCT116 cells at 20 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296724Drug level in HCT116 bearing SCID mice plasma at 25 mg/kg, iv after 24 hrs2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296708Cytotoxicity against human CEM cells at 36 ug/disk by disk diffusion method2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID252387In vitro inhibitory concentration against alpha-1-B glycoprotein induced multi drug resistance in A2780 cells2005Bioorganic & medicinal chemistry letters, May-02, Volume: 15, Issue:9
Design, synthesis and biological evaluation of novel, simplified analogues of laulimalide: modification of the side chain.
AID296728Antitumor activity against HCT116 bearing SCID mice at 25 mg/kg bolus iv after 11 days relative to control2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296710Cytotoxicity against human CFU-GM cells at 9 ug/disk by disk diffusion method2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296722Drug level in HCT116 bearing SCID mice plasma at 25 mg/kg, iv after 1 min2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296729Survival of human HCT116 cells at 5 ng/mL after 168 hrs2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296713Formation of thick bundles of microtubule stabilization in human HCT116 cells at 2 to 20 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID296715Increase in microtubule density in human HCT116 cells at 20 uM2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID424798Toxicity in human HCT116 xenografted SCID mouse assessed as increase in body weight at 12.3 mg/kg/day, iv administered as bolus dose from 3 days after tumor implantation for 5 days measured after 30 days2009Journal of natural products, Mar-27, Volume: 72, Issue:3
A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.
AID105033In vitro growth inhibitory activity against MDA-MB-435 human breast cancer cell line2004Bioorganic & medicinal chemistry letters, Feb-09, Volume: 14, Issue:3
Synthesis and biological evaluation of (-)-laulimalide analogues.
AID296727Antitumor activity against HCT116 bearing SCID mice at 12.5 mg/kg bolus iv after 9 days relative to control2007Journal of medicinal chemistry, Aug-09, Volume: 50, Issue:16
Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.
AID83619In vitro growth inhibitory activity against HT-29 human colon cancer cell line2004Bioorganic & medicinal chemistry letters, Feb-09, Volume: 14, Issue:3
Synthesis and biological evaluation of (-)-laulimalide analogues.
AID638664Stabilization of microtubule in human HeLa cells at 20 ug/ml after 24 hrs by Hoechst staining-based fluorescence microscopic analysis2011Journal of natural products, Dec-27, Volume: 74, Issue:12
Natural product libraries to accelerate the high-throughput discovery of therapeutic leads.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (73)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (1.37)18.2507
2000's37 (50.68)29.6817
2010's33 (45.21)24.3611
2020's2 (2.74)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.84

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index26.84 (24.57)
Research Supply Index4.34 (2.92)
Research Growth Index6.51 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (26.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews11 (14.47%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other65 (85.53%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbamates
[no description available]		4.0320amino-acid anion
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		2.0210sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		2.110elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
4'-bromoflavone
4'-bromoflavone: structure in first source		210
nocodazole
[no description available]		2.0610aromatic ketone;
benzimidazoles;
carbamate ester;
thiophenes		antimitotic;
antineoplastic agent;
microtubule-destabilising agent;
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.		8.5320alkaloid;
colchicine		anti-inflammatory agent;
gout suppressant;
mutagen
acetonitrile
acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.		2.1310aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent
quinazolines
Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.		2.0210azaarene;
mancude organic heterobicyclic parent;
ortho-fused heteroarene;
quinazolines
oxetane
oxetane: structure. oxetane : A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.		7.0510oxetanes;
saturated organic heteromonocyclic parent
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		2.0210metal allergen;
nickel group element atom;
platinum group metal atom
rhodium
Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.		2.0710cobalt group element atom
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
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		2.110dihydrogen
alkenes
[no description available]		2.4820
glutamic acid
Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.		2.0310glutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
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).		6.68290taxane diterpenoid;
tetracyclic diterpenoid		antineoplastic agent;
human metabolite;
metabolite;
microtubule-stabilising agent
topotecan
Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.		2.0210pyranoindolizinoquinolineantineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor
irinotecan
[no description available]		2.0210carbamate ester;
delta-lactone;
N-acylpiperidine;
pyranoindolizinoquinoline;
ring assembly;
tertiary alcohol;
tertiary amino compound		antineoplastic agent;
apoptosis inducer;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
prodrug
paxilline
paxilline: structure given in first source; RN given refers to (2R-(2alpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-isomer. paxilline : An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2(+)- and voltage-activated K(+) (BK)-type channels.		2.0310diterpene alkaloid;
enone;
organic heterohexacyclic compound;
terpenoid indole alkaloid;
tertiary alcohol		anticonvulsant;
Aspergillus metabolite;
EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor;
genotoxin;
geroprotector;
mycotoxin;
Penicillium metabolite;
potassium channel blocker
imatinib mesylate
imatinib methanesulfonate : A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.		2.0210methanesulfonate saltanticoronaviral agent;
antineoplastic agent;
apoptosis inducer;
tyrosine kinase inhibitor
gefitinib
[no description available]		2.0210aromatic ether;
monochlorobenzenes;
monofluorobenzenes;
morpholines;
quinazolines;
secondary amino compound;
tertiary amino compound		antineoplastic agent;
epidermal growth factor receptor antagonist
docetaxel anhydrous
Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.		2.7330secondary alpha-hydroxy ketone;
tetracyclic diterpenoid		antimalarial;
antineoplastic agent;
photosensitizing agent
noscapine
Noscapine: A naturally occurring opium alkaloid that is a centrally acting antitussive agent.. (-)-noscapine : A benzylisoquinoline alkaloid that is 1,2,3,4-tetrahydroisoquinoline which is substituted by a 4,5-dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl group at position 1, a methylenedioxy group at positions 6-7 and a methoxy group at position 8. Obtained from plants of the Papaveraceae family, it lacks significant painkilling properties and is primarily used for its antitussive (cough-suppressing) effects.		8.1710aromatic ether;
benzylisoquinoline alkaloid;
cyclic acetal;
isobenzofuranone;
organic heterobicyclic compound;
organic heterotricyclic compound;
tertiary amino compound		antineoplastic agent;
antitussive;
apoptosis inducer;
plant metabolite
o-(chloroacetylcarbamoyl)fumagillol
O-(Chloroacetylcarbamoyl)fumagillol: Semisynthetic analog of fumagillin (a cyclohexane-sesquiterpene antibiotic isolated from ASPERGILLUS FUMIGATUS) that inhibits angiogenesis.. O-(chloroacetylcarbamoyl)fumagillol : A carbamate ester that is fumagillol in which the hydroxy group has been converted to the corresponding N-(chloroacetyl)carbamate derivative.		3.1410carbamate ester;
organochlorine compound;
semisynthetic derivative;
sesquiterpenoid;
spiro-epoxide		angiogenesis inhibitor;
antineoplastic agent;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
methionine aminopeptidase 2 inhibitor;
retinoic acid receptor alpha antagonist
taccalonolide a
taccalonolide A: has microtubule stabilizing activity; isolated from Tacca chantrieri; structure in first source		2.0610withanolide
latrunculin a
latrunculin A: 16-membered macrolide attached to 2-thiazolidinone moiety; from Red Sea sponge Latrunculia magnifica; see also latrunculin B; structure given in first source. latrunculin A : A bicyclic macrolide natural product consisting of a 16-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica and from the Fiji Islands sponge Cacospongia mycofijiensis. Latrunculin A inhibits actin polymerisation, microfilament organsation and microfilament-mediated processes.		2.0610cyclic hemiketal;
macrolide;
oxabicycloalkane;
thiazolidinone		actin polymerisation inhibitor;
metabolite;
toxin
epothilone b
[no description available]		9.2250epothilone;
epoxide		antineoplastic agent;
apoptosis inducer;
microtubule-stabilising agent
epothilone a
Epothilones: A group of 16-member MACROLIDES which stabilize MICROTUBULES in a manner similar to PACLITAXEL. They were originally found in the myxobacterium Sorangium cellulosum, now renamed to Polyangium (MYXOCOCCALES).		5.5990epothilone;
epoxide		antineoplastic agent;
metabolite;
microtubule-stabilising agent;
tubulin modulator
6-bromoflavone
6-bromoflavone: a high affinity ligand for the central benzodiazepine receptors; structure given in first source		210
discodermolide
[no description available]		2.0210diterpenoid
sesquiterpenes
[no description available]		3.2310
centaureidin
centaureidin: structure given in first source; isolated from Tanacetum microphyllum, Brickellia veronicaefolia. centaureidin : A trihydroxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6 and 4' have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii and Athroisma proteiforme.		3.3110trihydroxyflavone;
trimethoxyflavone		antineoplastic agent;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
plant metabolite
ixabepilone
[no description available]		7.77301,3-thiazoles;
beta-hydroxy ketone;
epoxide;
lactam;
macrocycle		antineoplastic agent;
microtubule-destabilising agent
fumagillin
[no description available]		3.1410antibiotic antifungal drug;
carboxylic ester;
dicarboxylic acid monoester;
meroterpenoid;
organooxygen heterocyclic antibiotic;
spiro-epoxide		angiogenesis inhibitor;
antibacterial drug;
antimicrobial agent;
antiprotozoal drug;
fungal metabolite;
methionine aminopeptidase 2 inhibitor
soblidotin
soblidotin: a dolastatin 10 derivative; RN refers to (2S-(1(1R*(R*),2S*),2R*(1S*,2S*)))-isomer; structure given in first source. soblidotin : A tetrapeptide derivative of dolastatin 10. It is an inhibitor of tubulin polymerization which exhibits potent antitumor activity.		2.0210tetrapeptideantineoplastic agent;
apoptosis inducer;
microtubule-destabilising agent
eleutherobin
eleutherobin: structure in first source		4.0320
phenylahistin
phenylahistin: antineoplastic from Aspergillus ustus; structure in first source		3.3110
tryprostatin b
tryprostatin B: isolated from Aspergillus fumigatus; a mammalian cell cycle inhibitor; structure given in first source. tryprostatin B : A cyclic dipeptide that is brevianamide F (cyclo-L-Trp-L-Pro) substituted at position 2 on the indole ring by a prenyl group.		3.3110dipeptide;
indole alkaloid;
indoles;
pyrrolopyrazine
tryprostatin a
tryprostatin A: isolated from Aspergillus fumigatus; a mammalian cell cycle inhibitor; structure given in first source. tryprostatin A : A cyclic dipeptide that is brevianamide F (cyclo-L-Trp-L-Pro) substituted at positions 2 and 6 on the indole ring by prenyl and methoxy groups respectively.		3.3110aromatic ether;
dipeptide;
indole alkaloid;
indoles;
pyrrolopyrazine		breast cancer resistance protein inhibitor
halichondrin b
halichondrin B: from marine sponge Halichondria okadai; binds in the Vinca domain of tubulin		3.1610furopyran
peloruside a
peloruside A: Antibiotics, Antineoplastic from the sponge Mycale; structure in first source. peloruside A : A macrolide that is a novel secondary metabolite isolated from a New Zealand marine sponge, Mycale hentscheli.		6.16230
zampanolide
zampanolide: structure in first source		3.9330
isolaulimalide
isolaulimalide: isolated from Cacospongia mycofijiensis; structure in first source		7.9440
discodermolide
discodermolide: a lactone-bearing polyhydroxylated alkatetraene from the marine sponge Discodermia dissoluta; microtubule-stabilizing agent like taxol		4.0320
neopeltolide
neopeltolide: a macrolide from a lithistid sponge of the family Neopeltidae; structure in first source		3.1610
spongia-13(16),14-dien-19-oic acid
spongia-13(16),14-dien-19-oic acid : A tetracyclic diterpenoid that is 3b,4,5,5a,6,7,8,9,9a,9b,10,11-dodecahydrophenanthro[1,2-c]furan substituted by methyl groups at positions 3b, 6 and 9 and a carboxy group at position 6. Isolated from Spongia, it exhibits inhibitory activity against androgen receptor.		2.0610cyclic ether;
monocarboxylic acid;
tetracyclic diterpenoid		androgen antagonist;
metabolite
dictyoceratin-c
dictyoceratin-C: from the marine species Spongia sp.; structure in first source		3.2310
tartrolon b
tartrolon B: isolated from myxobacterium Sorangium cellulosum; a macrocyclic compound containing a boron atom; structure given in first source		3.1210
latrunculol a
latrunculol A: has antineoplastic activity; structure in first source		2.0610macrolidemetabolite
bryostatin 1
bryostatin 1: a protein kinase C activator; macrocyclic lactone from marine Bryozoan Bugula neritina; RN given refers to (1S*-(1R*,3R*,5Z,7S*,8E,11R*,12R*(2E,4E),13E,15R*,17S*(S*),21S*,23S*,25R*))-isomer; structure given in first source; activates protein kinase c. bryostatin 1 : A member of the class of bryostatins that is (17E)-2-oxooxacyclohexacos-17-ene which is substituted by hydroxy groups at positions 4, 10, and 20; an acetoxy group at position 8; methyl groups at positions 9, 9, 18, and 19; 2-methoxy-2-oxoethylidene groups at positions 14 and 24; an (E,E)-octa-2,4-dienoyloxy group at position 21; and with oxygen bridges linking positions 6 to 10, 12 to 16, and 20 to 24. It is one of the most abundant member of the class of bryostatins.		3.1610
interleukin-8
Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.		3.1310
taccalonolide aj
taccalonolide AJ: isolated from plants of the genus Tacca; structure in first source		2.0810
guanosine triphosphate
Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.		2.4320guanosine 5'-phosphate;
purine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.4220
Cancer of Colon
[description not available]		02.0210
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.4220
Colonic Neoplasms
Tumors or cancer of the COLON.		02.0210
Cancer of Ovary
[description not available]		04.4780
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.		04.4780
Benign Neoplasms
[description not available]		03.8320
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.		03.8320
Carcinoma, Anaplastic
[description not available]		02.0710
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		07.0710
Chromosomal Breakage
[description not available]		02.0710
Tauopathies
Neurodegenerative disorders involving deposition of abnormal tau protein isoforms (TAU PROTEINS) in neurons and glial cells in the brain. Pathological aggregations of tau proteins are associated with mutation of the tau gene on chromosome 17 in patients with ALZHEIMER DISEASE; DEMENTIA; PARKINSONIAN DISORDERS; progressive supranuclear palsy (SUPRANUCLEAR PALSY, PROGRESSIVE); and corticobasal degeneration.		02.0710
Benign Neoplasms, Brain
[description not available]		02.0710
Brain Neoplasms
Neoplasms of the intracranial components of the central nervous system, including the cerebral hemispheres, basal ganglia, hypothalamus, thalamus, brain stem, and cerebellum. Brain neoplasms are subdivided into primary (originating from brain tissue) and secondary (i.e., metastatic) forms. Primary neoplasms are subdivided into benign and malignant forms. In general, brain tumors may also be classified by age of onset, histologic type, or presenting location in the brain.		02.0710
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		02.0710
Adenocarcinoma, Basal Cell
[description not available]		03.3320
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		03.3320
Chromosome-Defective Micronuclei
[description not available]		02.0210
Experimental Hepatoma
[description not available]		0210
Experimental Mammary Neoplasms
[description not available]		0210
Cancer of Lung
[description not available]		02.0110
Lung Neoplasms
Tumors or cancer of the LUNG.		02.0110
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