Geranyl tiglate

Details

• Internal ID: 1379b097-34c3-47b4-bb73-44856914c51b
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty alcohol esters
• IUPAC Name: [(2E)-3,7-dimethylocta-2,6-dienyl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OCC=C(C)CCC=C(C)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)OC/C=C(\C)/CCC=C(C)C
• InChI: InChI=1S/C15H24O2/c1-6-14(5)15(16)17-11-10-13(4)9-7-8-12(2)3/h6,8,10H,7,9,11H2,1-5H3/b13-10+,14-6+
• InChI Key: OGHBUHJLMHQMHS-KRDNBFTESA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.35 g/mol
• Exact Mass: 236.177630004 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.19
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 7785-33-3
• Tiglic acid, geraniol ester
• Geranium extract
• [(2E)-3,7-dimethylocta-2,6-dienyl] (E)-2-methylbut-2-enoate
• 8000-46-2
• 2-Butenoic acid, 2-methyl-, 3,7-dimethyl-2,6-octadienyl ester, (E,E)-
• tiglic acid geranyl ester
• EINECS 232-078-9
• UNII-CUP7SL28J8
• cis-alpha,beta-Dimethyl acrylic acid, geraniol ester
• CUP7SL28J8
• (E)-3,7-Dimethyl-2,6-octadienyl 2-methylcrotonate
• AI3-36201
• DTXSID9047413
• (E)-(E)-3,7-Dimethylocta-2,6-dien-1-yl 2-methylbut-2-enoate
• trans-3,7-Dimethyl-2,6-octadien-1-yl cis-alpha,beta-dimethyl acrylate
• 2-Butenoic acid, 2(or 3)-methyl-, (2E)-3,7-dimethyl-2,6-octadienyl ester
• 2-Butenoic acid, 2-methyl-, (2E)-3,7-dimethyl-2,6-octadienyl ester, (2E)-
• 2-Butenoic acid, 2-methyl-, 3,7-dimethyl-2,6-octadienyl ester, (E,E,E)-
• 2-Butenoic acid, 2-methyl-, (2E)-3,7-dimethyl-2,6-octadien-1-yl ester, (2E)-
• 61827-81-4
• (2E)-3,7-Dimethyl-2,6-octadienyl (2E)-2-methyl-2-butenoate
• (2E)-3,7-dimethylocta-2,6-dien-1-yl (2E)-2-methylbut-2-enoate
• 2,6-OCTADIEN-1-OL, 3,7-DIMETHYL-, 2-METHYL-2-BUTENOATE, (E,E,E)-
• 2-Butenoic acid, 2-methyl-, (2E)-3,7-dimethyl-2,6-octadienyl ester,(2E)-
• 2-Butenoic acid, 2(or 3)-methyl-, (2E)-3,7-dimethyl-2,6-octadien-1-yl ester
• Gernyl tiglate
• Geranyl?Tiglate
• (E)-GERANYL TIGLATE
• SCHEMBL874195
• SCHEMBL874196
• GERANYL TIGLATE [FHFI]
• CHEMBL3186926
• DTXCID7027413
• DTXSID8069511
• FEMA NO. 4044
• 2-Butenoic acid, 2(or 3)-methyl-, 3,7-dimethyl-2,6-octadienyl ester, (?,E)-
• CHEBI:169735
• OGHBUHJLMHQMHS-KRDNBFTESA-N
• TIGLIC ACID, GERANYL ESTER
• Tox21_302492
• LMFA07010898
• MFCD00016622
• AKOS015836332
• NCGC00256644-01
• BS-49190
• LS-97801
• PD087226
• CAS-7785-33-3
• GERANYL (E)-2-METHYL-2-BUTENOATE
• CS-0206129
• G0430
• Q27275815
• cis-.alpha.,.beta.-Dimethyl acrylic acid, geraniol ester
• (E)-((E)-3,7-dimethylocta-2,6-dienyl) 2-methylbut-2-enoate
• TIGLIC ACID, TRANS-3,7-DIMETHYL-2,6-OCTADIENYL ESTER
• (E) - 3,7 - dimethyl - 2,6 - octadienyl 2 - methylcrotonate
• 2,6-Octadien-1-ol, 3,7-dimethyl-, 2-methyl-2-butenoate, (E,E)--
• trans-3,7-Dimethyl-2,6-octadien-1-yl cis-.alpha.,.beta.-dimethyl acrylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9953	99.53%
Caco-2	+	0.9301	93.01%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6095	60.95%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9172	91.72%
OATP1B3 inhibitior	+	0.8637	86.37%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5811	58.11%
P-glycoprotein inhibitior	-	0.9510	95.10%
P-glycoprotein substrate	-	0.9643	96.43%
CYP3A4 substrate	-	0.5395	53.95%
CYP2C9 substrate	+	0.6120	61.20%
CYP2D6 substrate	-	0.8828	88.28%
CYP3A4 inhibition	-	0.9647	96.47%
CYP2C9 inhibition	-	0.8935	89.35%
CYP2C19 inhibition	-	0.8874	88.74%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.7663	76.63%
CYP2C8 inhibition	-	0.9441	94.41%
CYP inhibitory promiscuity	-	0.7180	71.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6200	62.00%
Carcinogenicity (trinary)	Non-required	0.5291	52.91%
Eye corrosion	+	0.7105	71.05%
Eye irritation	+	0.7719	77.19%
Skin irritation	+	0.8399	83.99%
Skin corrosion	-	0.9912	99.12%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7006	70.06%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	+	0.5505	55.05%
Respiratory toxicity	-	0.8444	84.44%
Reproductive toxicity	-	1.0000	100.00%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	+	0.7578	75.78%
Acute Oral Toxicity (c)	III	0.5909	59.09%
Estrogen receptor binding	-	0.8529	85.29%
Androgen receptor binding	-	0.7998	79.98%
Thyroid receptor binding	-	0.6961	69.61%
Glucocorticoid receptor binding	-	0.6362	63.62%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.6672	66.72%
Honey bee toxicity	-	0.8345	83.45%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.5755	57.55%
Fish aquatic toxicity	+	0.9912	99.12%

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	92.80%	96.09%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	90.70%	92.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.25%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.25%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	84.15%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	83.82%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.78%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.69%	89.34%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.55%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.69%	96.95%
CHEMBL2581	P07339	Cathepsin D	80.04%	98.95%

Plants that contains it

• Citrus maxima
• Cryptomeria japonica
• Pittosporum balfourii

Cross-Links

• PubChem: 5367785
• NPASS: NPC236338
• LOTUS: LTS0056306
• wikiData: Q27275815