Compounds > methyl farnesoate
Page last updated: 2024-08-01 07:40:41

methyl farnesoate

Description

methyl farnesoate: RN given refers to cpd without isomeric designation [MeSH]

methyl farnesoate : A member of the juvenile hormone family of compounds that is the methyl ester of farnesoic acid. Found in several species of crustaceans. [CHeBI]

Cross-References

ID SourceID
PubMed CID5275508
CHEMBL ID171329
SCHEMBL ID2023438
CHEBI ID80535
MeSH IDM0101251

Synonyms (37)

Synonym
2,6,10-dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester, (2e,6e)-
methyl (2e,6e)-3,7,11-trimethyldodeca-2,6,10-trienoate
2,6,10-dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester
farnesyl methyl ester
methyl (2e,6e)-farnesoate
10485-70-8
methyl farnesoate
(2e,6e)-3,7,11-trimethyl-dodeca-2,6,10-trienoic acid methyl ester
methyl (trans,trans)-farnesoate
(trans,trans)-2,6,10-dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester
2,6,10-dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester, (e,e)-
methyl (2-trans-6-trans)-farnesoate
(2e,6e)-farnesyl methyl ester
methyl (2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrienoate
CHEMBL171329
chebi:80535 ,
3675-00-1
(2e,6e)-methyl 3,7,11-trimethyldodeca-2,6,10-trienoate
methyl 3,7,11-trimethyl-2,6,10-dodecatrienoate
methyl (2-trans,6-trans)-farnesoate
methyl (e,e)-farnesate
methyl farnesate
2-trans-farnesic acid methyl ester
methyl 3,7,11-trimethyl-2e,6e,10-dodecatrienoate
methyl (e,e)-farnesoate
methyl trans,trans-farnesate
methyl trans,trans-farnesoate
methyl (2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrienoate #
methyl trans,trans-farnesenate
NWKXNIPBVLQYAB-VDQVFBMKSA-N
methyl (2e,6e)-farnesate
SCHEMBL2023438
(e,e)-methyl farnesoate
(2e,6e)-methyl3,7,11-trimethyldodeca-2,6,10-trienoate
DTXSID80893654
Q27149580
a methyl farnesoate

Roles (1)

RoleDescription
crustacean metaboliteAn animal metabolite produced by arthropods such as crabs, lobsters, crayfish, shrimps and krill.

Drug Classes (3)

ClassDescription
juvenile hormoneA family of farnesane sesquiterpenoids that regulate many aspects of insect physiology.
enoate esterAn alpha,beta-unsaturated carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
fatty acid methyl esterA fatty acid ester that is the carboxylic ester obtained by the formal condensation of a fatty acid with methanol.

Pathways (1)

methyl farnesoate is involved in 1 pathway(s), involving a total of 4 unique proteins and 39 unique compounds

PathwayProteinsCompounds
juvenile hormone III biosynthesis I017
juvenile hormone III biosynthesis I422

Bioassays (2)

Assay IDTitleYearJournalArticle
AID47224In vitro inhibition of yeast cell growth of candida albicans; No inhibition2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
ISSN: 0960-894X		Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against Candida albicans dimorphism.
AID47226In vitro inhibition of yeast-to-hypha transition in candida albicans; No inhibition2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
ISSN: 0960-894X		Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against Candida albicans dimorphism.

Research

Studies (117)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (1.71)18.7374
1990's21 (17.95)18.2507
2000's41 (35.04)29.6817
2010's45 (38.46)24.3611
2020's8 (6.84)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews5 (4.10%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other117 (95.90%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
arecoline
0
enoate ester;
methyl ester;
pyridine alkaloid;
tetrahydropyridine		metabolite;
muscarinic agonist		00low000000
methylmethacrylate
0
enoate ester;
methyl ester		allergen;
polymerisation monomer		00low000000
methyl acrylate
0
enoate ester00low000000
butyl methacrylate
0
enoate ester00low000000
ethylene dimethacrylate
0
enoate esterallergen;
cross-linking reagent;
polymerisation monomer		00low000000
2-ethylhexyl acrylate
0
enoate ester00low000000
glycidyl methacrylate
0
enoate ester;
epoxide		00low000000
ethyl acrylate
0
enoate ester00low000000
hydroxyethyl methacrylate
0
enoate esterallergen;
polymerisation monomer		00low000000
2-hydroxypropyl methacrylate
0
enoate esterpolymerisation monomer00low000000
2-aminoethylmethacrylate
0
enoate ester00low000000
2,2-di(4-methacryloxyphenyl)propane
0
bisphenol;
enoate ester		metabolite00low000000
loganin
0
beta-D-glucoside;
cyclopentapyran;
enoate ester;
iridoid monoterpenoid;
methyl ester;
monosaccharide derivative;
secondary alcohol		anti-inflammatory agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
EC 3.4.23.46 (memapsin 2) inhibitor;
neuroprotective agent;
plant metabolite		00low000000
guvacoline
0
alpha,beta-unsaturated carboxylic ester;
beta-amino acid ester;
enoate ester;
methyl ester;
pyridine alkaloid;
secondary amino compound;
tetrahydropyridine		muscarinic agonist;
plant metabolite		00low000000
secologanin
0
aldehyde;
beta-D-glucoside;
enoate ester;
methyl ester;
pyrans;
secoiridoid glycoside		plant metabolite00low000000
secoxyloganin
0
beta-D-glucoside;
dicarboxylic acid monoester;
enoate ester;
methyl ester;
monosaccharide derivative;
pyrans;
secoiridoid glycoside		anti-allergic agent;
antioxidant;
plant metabolite		00low000000
dimethyl fumarate
0
diester;
enoate ester;
methyl ester		antipsoriatic;
immunomodulator		00low000000
monastrol
0
enoate ester;
ethyl ester;
phenols;
racemate;
thioureas		antileishmanial agent;
antimitotic;
antineoplastic agent;
EC 3.5.1.5 (urease) inhibitor		00low000000
azoxystrobin
0
aryloxypyrimidine;
enoate ester;
enol ether;
methoxyacrylate strobilurin antifungal agent;
methyl ester;
nitrile		antifungal agrochemical;
environmental contaminant;
mitochondrial cytochrome-bc1 complex inhibitor;
quinone outside inhibitor;
xenobiotic		00low000000
bryostatin 1
0
acetate ester;
bryostatins;
cyclic hemiketal;
enoate ester;
methyl ester;
organic heterotetracyclic compound;
secondary alcohol		alpha-secretase activator;
anti-HIV-1 agent;
antineoplastic agent;
marine metabolite;
protein kinase C agonist		00low000000
cassaine
0
enoate ester;
organic hydroxy compound;
tertiary amino compound;
tricyclic diterpenoid		antihypertensive agent;
cardiotonic drug;
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor;
local anaesthetic;
plant metabolite;
poison		00low000000
azadirachtin
0
acetate ester;
azadirachtin;
cyclic hemiketal;
enoate ester;
epoxide;
methyl ester;
organic heterotetracyclic compound;
secondary alcohol;
tertiary alcohol		hepatoprotective agent00low000000
petasin
0
alicyclic ketone;
enoate ester;
enone;
sesquiterpenoid		anti-allergic agent;
EC 2.7.11.31 {[hydroxymethylglutaryl-CoA reductase (NADPH)] kinase} activator;
plant metabolite;
vasodilator agent		00low000000
etretinate
0
enoate ester;
ethyl ester;
retinoid		keratolytic drug00low000000
meptyldinocap
0
C-nitro compound;
enoate ester		00low000000
monomethyl fumarate
0
dicarboxylic acid monoester;
enoate ester;
methyl ester		antioxidant;
drug metabolite;
immunomodulator		00low000000
cystothiazole a
0
1,3-thiazoles;
biaryl;
enoate ester;
enol ether;
methyl ester;
organonitrogen heterocyclic antibiotic		antifungal agent;
antineoplastic agent;
bacterial metabolite		00low000000
mucidin
0
enoate ester;
enol ether		antifungal agent;
fungal metabolite		00low000000
bryostatin 2
0
bryostatins;
cyclic hemiketal;
enoate ester;
methyl ester;
organic heterotetracyclic compound;
secondary alcohol		antineoplastic agent;
marine metabolite;
protein kinase C agonist		00low000000
n(3)-(4-methoxyfumaroyl)-2,3-diaminopropionic acid
0
enoate ester;
methyl ester;
monocarboxylic acid amide		metabolite00low000000
strobilurin b
0
enoate ester;
enol ether;
methoxyacrylate strobilurin antifungal agent;
monochlorobenzenes;
monomethoxybenzene		antifungal agent;
fungal metabolite;
mitochondrial cytochrome-bc1 complex inhibitor		00low000000
salvianolic acid B
0
1-benzofurans;
catechols;
dicarboxylic acid;
enoate ester;
polyphenol		anti-inflammatory agent;
antidepressant;
antineoplastic agent;
antioxidant;
apoptosis inducer;
autophagy inhibitor;
cardioprotective agent;
hepatoprotective agent;
hypoglycemic agent;
neuroprotective agent;
osteogenesis regulator;
plant metabolite		00low000000
3-O-feruloyl-D-quinic acid
0
enoate ester;
quinic acid		plant metabolite00low000000
fluacrypyrim
0
enoate ester;
enol ether;
methyl ester;
organofluorine acaricide;
pyrimidines		mitochondrial cytochrome-bc1 complex inhibitor00low000000
picoxystrobin
0
aromatic ether;
enoate ester;
enol ether;
methoxyacrylate strobilurin antifungal agent;
organofluorine compound;
pyridines		antifungal agrochemical;
mitochondrial cytochrome-bc1 complex inhibitor		00low000000
glyceryl ferulate
0
1-monoglyceride;
aromatic ether;
enoate ester;
phenols		antioxidant;
plant metabolite;
ultraviolet filter		00low000000
6-tuliposide b
0
6-O-acyl-D-glucose;
enoate ester		antibacterial agent;
antifungal agent;
plant metabolite		00low000000
gardenoside
0
beta-D-glucoside;
cyclopentapyran;
enoate ester;
methyl ester;
monosaccharide derivative;
tertiary alcohol		metabolite00low000000
dimethyl succinate
0
fatty acid methyl ester00low000000
methyl caproate
0
fatty acid methyl ester;
hexanoate ester		flavouring agent;
plant metabolite		00low000000
methyl octanoate
0
fatty acid methyl ester;
octanoate ester		metabolite00low000000
lauric acid methyl ester
0
dodecanoate ester;
fatty acid methyl ester		metabolite00low000000
methyl palmitate
0
fatty acid methyl estermetabolite00low000000
dimethyladipate
0
fatty acid methyl ester00low000000
methyl tetradecanoate
0
fatty acid methyl esterflavouring agent;
fragrance;
plant metabolite		00low000000
methyl palmitoleate
0
fatty acid methyl ester00low000000
5-[10-(5-methoxy-1,5-dioxopentyl)-1,7-dioxa-4,10-diazacyclododec-4-yl]-5-oxopentanoic acid methyl ester
0
fatty acid methyl ester00low000000
methyl linoleate
0
fatty acid methyl esterplant metabolite00low000000
methyl linolenate
0
fatty acid methyl esterinsect attractant;
plant metabolite		00low000000
methyl oleate
0
fatty acid methyl ester00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
carcinine
0
beta-alanine derivative;
imidazoles;
monocarboxylic acid amide;
organonitrogen compound;
organooxygen compound		antioxidant;
crustacean metabolite		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
farnesol
1
farnesolplant metabolite2002200222.0low000100
farnesoic acid
1
farnesoic acidanimal metabolite2002200222.0low000100
decaprenoic acid
1
alpha,beta-unsaturated monocarboxylic acid;
methyl-branched fatty acid;
monoterpenoid;
polyunsaturated fatty acid		antifungal agent;
EC 1.14.18.1 (tyrosinase) inhibitor;
melanin synthesis inhibitor;
pheromone;
plant metabolite		2002200222.0medium000100
geranylgeranic acid
1
alpha,beta-unsaturated monocarboxylic acid;
diterpenoid;
methyl-branched fatty acid;
trienoic fatty acid		2002200222.0low000100
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
carbon monoxide
1
carbon oxide;
gas molecular entity;
one-carbon compound		biomarker;
EC 1.9.3.1 (cytochrome c oxidase) inhibitor;
human metabolite;
ligand;
metabolite;
mitochondrial respiratory-chain inhibitor;
mouse metabolite;
neurotoxin;
neurotransmitter;
P450 inhibitor;
probe;
signalling molecule;
vasodilator agent		1981198143.0low010000
pentachlorophenol
1
aromatic fungicide;
chlorophenol;
organochlorine pesticide;
pentachlorobenzenes		human xenobiotic metabolite2008200816.0low000100
leucine
2
amino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite		2002200421.0low000200
methionine
1
aspartate family amino acid;
L-alpha-amino acid;
methionine zwitterion;
methionine;
proteinogenic amino acid		antidote to paracetamol poisoning;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical		202220222.0low000001
cycloheximide
1
antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor		2006200618.0low000100
17-alpha-hydroxyprogesterone
1
17alpha-hydroxy-C21-steroid;
17alpha-hydroxy steroid;
tertiary alpha-hydroxy ketone		human metabolite;
metabolite;
mouse metabolite;
progestin		2004200420.0low000100
pantothenic acid
1
pantothenic acid;
vitamin B5		antidote to curare poisoning;
geroprotector;
human blood serum metabolite		201620168.0low000010
bisphenol a
2
bisphenolendocrine disruptor;
environmental contaminant;
xenobiotic;
xenoestrogen		2005201812.5low000110
2-naphthol
1
naphtholantinematodal drug;
genotoxin;
human urinary metabolite;
human xenobiotic metabolite;
mouse metabolite;
radical scavenger		1998199826.0low001000
diazomethane
2
diazo compoundalkylating agent;
antineoplastic agent;
carcinogenic agent;
poison		1990199730.5low002000
naphthyl acetate
1
1998199826.0low001000
paraquat
1
organic cationgeroprotector;
herbicide		2008200816.0low000100
ecdysone
3
14alpha-hydroxy steroid;
22-hydroxy steroid;
25-hydroxy steroid;
2beta-hydroxy steroid;
3beta-sterol;
6-oxo steroid;
ecdysteroid		prohormone1993201916.3low001020
cadmium
1
cadmium molecular entity;
zinc group element atom		2004200420.0low000100
potassium dichromate
2
potassium saltallergen;
oxidising agent;
sensitiser		2008200816.0low000200
tetradecanoylphorbol acetate
1
acetate ester;
diester;
phorbol ester;
tertiary alpha-hydroxy ketone;
tetradecanoate ester		antineoplastic agent;
apoptosis inducer;
carcinogenic agent;
mitogen;
plant metabolite;
protein kinase C agonist;
reactive oxygen species generator		2000200024.0low001000
8-bromo cyclic adenosine monophosphate
1
3',5'-cyclic purine nucleotide;
adenyl ribonucleotide;
organobromine compound		antidepressant;
protein kinase agonist		1999199925.0low001000
fenarimol
1
monochlorobenzenes;
pyrimidines;
tertiary alcohol		2004200420.0low000100
colforsin
1
acetate ester;
cyclic ketone;
labdane diterpenoid;
organic heterotricyclic compound;
tertiary alpha-hydroxy ketone;
triol		adenylate cyclase agonist;
anti-HIV agent;
antihypertensive agent;
plant metabolite;
platelet aggregation inhibitor;
protein kinase A agonist		1999199925.0low001000
fenoxycarb
4
aromatic ether;
carbamate ester		environmental contaminant;
insecticide;
juvenile hormone mimic;
xenobiotic		2004201714.0low000220
pyriproxyfen
10
aromatic ether;
pyridines		juvenile hormone mimic2004201814.8medium000730
ponasterone a
1
14alpha-hydroxy steroid;
20-hydroxy steroid;
22-hydroxy steroid;
2beta-hydroxy steroid;
3beta-hydroxy steroid;
6-oxo steroid;
phytoecdysteroid		2008200816.0low000100
phytol
1
2005200519.0low000100
tretinoin
2
retinoic acid;
vitamin A		anti-inflammatory agent;
antineoplastic agent;
antioxidant;
AP-1 antagonist;
human metabolite;
keratolytic drug;
retinoic acid receptor agonist;
retinoid X receptor agonist;
signalling molecule		2005200817.5low000200
arachidonic acid
1
icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite		202020204.0low000010
farnesol
4
farnesolplant metabolite1990201821.2low002110
alitretinoin
1
retinoic acidantineoplastic agent;
keratolytic drug;
metabolite;
retinoid X receptor agonist		2008200816.0low000100
sesquiterpenes
16
1991202119.8medium006541
nadp
1
1981198143.0low010000
allatostatin 1
3
2002200819.0low000300
farnesoic acid
10
farnesoic acidanimal metabolite1998201516.9high001630
farnesal
2
farnesal;
polyprenal		2006201812.0medium000110
methoprene
2
isopropyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate;
isopropyl ester		juvenile hormone mimic1991200526.0low001100
ecdysterone
9
14alpha-hydroxy steroid;
20-hydroxy steroid;
22-hydroxy steroid;
25-hydroxy steroid;
2beta-hydroxy steroid;
3beta-sterol;
ecdysteroid;
phytoecdysteroid		animal metabolite;
plant metabolite		2002202013.7low000540
zr 777
1
farnesane sesquiterpenoid;
terminal acetylenic compound		juvenile hormone mimic2005200519.0medium000100
methyl 6,7-10,11-bis(epoxy)-3,7,11-trimethyl-2-dodecenoate
3
1991201519.3high001110
phenylalanyl-glycyl-leucyl-methioninamide
1
tetrapeptide2005200519.0low000100
nad
1
organophosphate oxoanioncofactor;
human metabolite;
hydrogen acceptor;
Saccharomyces cerevisiae metabolite		1981198143.0low010000
alamethicin
1
2011201113.0low000010
allatotropin
2
2003200321.0low000200
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
46,XX Gonadal Dysgenesis, Complete, Sry-Positive0
1
2006200618.0high000100
Ambiguous Genitalia0
1
2006200618.0medium000100
Disorders of Sex Development0
1
2006200618.0medium000100
Polyploid0
1
2011201113.0medium000010
Sensitivity and Specificity0
1
201720177.0medium000010

Safety/Toxicity (1)

ArticleYear
Comparative ovarian microarray analysis of juvenile hormone-responsive genes in water flea Daphnia magna: potential targets for toxicity.
Journal of applied toxicology : JAT, , Volume: 37, Issue:3		2017

Interactions (1)

ArticleYear
Effect of methyl farnesoate, alone and in combination with other hormones, on ovarian growth of the red swamp crayfish, Procambarus clarkii, during vitellogenesis.
General and comparative endocrinology, , Volume: 125, Issue:1		2002