Methyl farnesoate

Details

• Internal ID: 1c5d89fb-63b4-48c3-8c4f-55992c694a93
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: methyl (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate
• SMILES (Canonical): CC(=CCCC(=CCCC(=CC(=O)OC)C)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC/C(=C/C(=O)OC)/C)/C)C
• InChI: InChI=1S/C16H26O2/c1-13(2)8-6-9-14(3)10-7-11-15(4)12-16(17)18-5/h8,10,12H,6-7,9,11H2,1-5H3/b14-10+,15-12+
• InChI Key: NWKXNIPBVLQYAB-VDQVFBMKSA-N
• Popularity: 134 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₆O₂
• Molecular Weight: 250.38 g/mol
• Exact Mass: 250.193280068 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.58
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 3675-00-1
• 10485-70-8
• Methyl (2E,6E)-farnesoate
• (2E,6E)-Methyl 3,7,11-trimethyldodeca-2,6,10-trienoate
• methyl (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoate
• (E,E)-METHYL FARNESOATE
• (2E,6E)-farnesyl methyl ester
• CHEBI:80535
• 2,6,10-Dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester
• 2,6,10-Dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester, (E,E)-
• 2,6,10-Dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester, (2E,6E)-
• a methyl farnesoate
• (2E,6E)-3,7,11-Trimethyl-dodeca-2,6,10-trienoic acid methyl ester
• Methyl trans,cis-farnesate
• Methyl farnesate
• Farnesic acid methyl
• Farnesyl methyl ester
• methyl (E,E)-farnesate
• Methyl (E,E)-farnesoate
• Methyl trans,trans-farnesate
• Methyl (2E,6E)-farnesate
• Methyl trans,trans-farnesoate
• Methyl trans,trans-farnesenate
• CHEMBL171329
• SCHEMBL2023438
• methyl (trans,trans)-farnesoate
• 2,6,10-Dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester, (E,Z)-
• (2E,6E)-Methyl3,7,11-trimethyldodeca-2,6,10-trienoate
• DTXSID80893654
• NWKXNIPBVLQYAB-VDQVFBMKSA-N
• C12H26N2O7
• 2-trans-Farnesic acid methyl ester
• methyl (2-trans,6-trans)-farnesoate
• methyl (2-trans-6-trans)-farnesoate
• Methyl 3,7,11-trimethyl-2,6,10-dodecatrienoate
• Methyl 3,7,11-trimethyl-2E,6E,10-dodecatrienoate
• Q27149580
• Methyl (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienoate
• Methyl (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrienoate #
• (trans,trans)-2,6,10-dodecatrienoic acid, 3,7,11-trimethyl-, methyl ester
• 4176-79-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9934	99.34%
Caco-2	+	0.9216	92.16%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5056	50.56%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9416	94.16%
OATP1B3 inhibitior	+	0.8590	85.90%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5330	53.30%
P-glycoprotein inhibitior	-	0.8218	82.18%
P-glycoprotein substrate	-	0.9348	93.48%
CYP3A4 substrate	-	0.5398	53.98%
CYP2C9 substrate	+	0.6219	62.19%
CYP2D6 substrate	-	0.9080	90.80%
CYP3A4 inhibition	-	0.9761	97.61%
CYP2C9 inhibition	-	0.8814	88.14%
CYP2C19 inhibition	-	0.8803	88.03%
CYP2D6 inhibition	-	0.9584	95.84%
CYP1A2 inhibition	-	0.8105	81.05%
CYP2C8 inhibition	-	0.9609	96.09%
CYP inhibitory promiscuity	-	0.7996	79.96%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5500	55.00%
Carcinogenicity (trinary)	Non-required	0.6324	63.24%
Eye corrosion	+	0.5857	58.57%
Eye irritation	-	0.5603	56.03%
Skin irritation	+	0.7415	74.15%
Skin corrosion	-	0.9951	99.51%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7810	78.10%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.6974	69.74%
skin sensitisation	+	0.6494	64.94%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	-	1.0000	100.00%
Mitochondrial toxicity	-	0.9375	93.75%
Nephrotoxicity	+	0.7041	70.41%
Acute Oral Toxicity (c)	III	0.6413	64.13%
Estrogen receptor binding	-	0.7988	79.88%
Androgen receptor binding	-	0.6565	65.65%
Thyroid receptor binding	-	0.6591	65.91%
Glucocorticoid receptor binding	-	0.6413	64.13%
Aromatase binding	-	0.5926	59.26%
PPAR gamma	-	0.5474	54.74%
Honey bee toxicity	-	0.8122	81.22%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9845	98.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.20%	96.09%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	92.27%	92.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.09%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.15%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.10%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	88.70%	83.82%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.61%	94.33%
CHEMBL2581	P07339	Cathepsin D	84.49%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	84.00%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.80%	89.34%
CHEMBL340	P08684	Cytochrome P450 3A4	81.41%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	80.46%	90.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.14%	91.24%

Plants that contains it

• Aloe vera
• Dendrobium chrysanthum
• Mentha arvensis
• Mentha canadensis

Cross-Links

• PubChem: 5275508
• NPASS: NPC128280
• LOTUS: LTS0189662
• wikiData: Q27149580