Geranyl butyrate

Details

• Internal ID: 53f85a31-0d55-4a2e-8bf7-9d62bb9ce09f
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty alcohol esters
• IUPAC Name: [(2E)-3,7-dimethylocta-2,6-dienyl] butanoate
• SMILES (Canonical): CCCC(=O)OCC=C(C)CCC=C(C)C
• SMILES (Isomeric): CCCC(=O)OC/C=C(\C)/CCC=C(C)C
• InChI: InChI=1S/C14H24O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,10H,5-7,9,11H2,1-4H3/b13-10+
• InChI Key: ZSBOMYJPSRFZAL-JLHYYAGUSA-N
• Popularity: 88 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₄O₂
• Molecular Weight: 224.34 g/mol
• Exact Mass: 224.177630004 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.02
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 7

Synonyms

• 106-29-6
• 3,7-Dimethylocta-2,6-dien-1-yl butyrate
• Geraniol butyrate
• Geranyl butanoate
• Geranyl n-butyrate
• Butanoic acid, (2E)-3,7-dimethyl-2,6-octadienyl ester
• FEMA No. 2512
• Butyric acid geranyl ester
• Geranyl butyrate (natural)
• Butanoic acid, 3,7-dimethyl-2,6-octadienyl ester, (E)-
• 3,7-Dimethyl-2,6-octadienyl Butyrate
• BUTYRIC ACID, 3,7-DIMETHYL-2,6-OCTADIENYL ESTER, (E)-
• AG 76
• EINECS 203-381-3
• NSC 46146
• 2173-82-2
• UNII-69AVH8L7KL
• 69AVH8L7KL
• 2,6-Octadien-1-ol, 3,7-dimethyl-, butyrate, (E)-
• AI3-15359
• (E)-3,7-Dimethyl-2,6-octadienyl butyrate
• DTXSID1047152
• 3,7-Dimethyl-2,6-octadienyl butyrate, (E)-
• 3,7-Dimethyl-2,6-octadienyl butanoate, (E)-
• trans-3,7-Dimethyl-2,6-octadien-1-yl butyrate
• 3,7-Dimethyl-2,6-octadien-1-yl butanoate, trans-
• NSC-46146
• NSC-70177
• WE(8:2(2E,6E)(3Me,7Me)/4:0)
• Butanoic acid, (2E)-3,7-dimethyl-2,6-octadien-1-yl ester
• Butanoic acid,7-dimethyl-2,6-octadienyl ester, (E)-
• Butyric acid,7-dimethyl-2,6-octadienyl ester, (E)-
• geranylbutyrate
• geranylbutyrat-
• [(2E)-3,7-dimethylocta-2,6-dienyl] butanoate
• n-Butyric acid, geranyl ester
• SCHEMBL118465
• SCHEMBL118466
• GERANYL BUTYRATE [FCC]
• GERANYL BUTYRATE [FHFI]
• CHEMBL3187344
• DTXCID9027152
• Geranyl butyrate, >=95%, FCC
• ZSBOMYJPSRFZAL-JLHYYAGUSA-N
• NSC46146
• NSC70177
• Tox21_301108
• LMFA07010616
• MFCD00036538
• 3,7-Dimethyl-2,6-octadienylButyrate
• AKOS015913959
• LS-2767
• Geranyl butyrate, natural, >=95%, FG
• NCGC00248290-01
• NCGC00255008-01
• AS-64315
• CAS-106-29-6
• 3,7-dimethyl-2,6-octadien-1-yl butyrate
• (2E)-3,7-Dimethyl-2,6-octadienyl butyrate #
• (2E)-3,7-dimethylocta-2,6-dien-1-yl butanoate
• (2Z)-3,7-dimethyl-2,6-octadien-1-yl butyrate
• A801412
• J-001564
• Q10864413

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.9549	95.49%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5488	54.88%
OATP2B1 inhibitior	-	0.8496	84.96%
OATP1B1 inhibitior	+	0.9208	92.08%
OATP1B3 inhibitior	+	0.9094	90.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5470	54.70%
P-glycoprotein inhibitior	-	0.9481	94.81%
P-glycoprotein substrate	-	0.9395	93.95%
CYP3A4 substrate	-	0.5421	54.21%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.9267	92.67%
CYP2C9 inhibition	-	0.9105	91.05%
CYP2C19 inhibition	-	0.8736	87.36%
CYP2D6 inhibition	-	0.9284	92.84%
CYP1A2 inhibition	-	0.6823	68.23%
CYP2C8 inhibition	-	0.9240	92.40%
CYP inhibitory promiscuity	-	0.6530	65.30%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6200	62.00%
Carcinogenicity (trinary)	Non-required	0.5336	53.36%
Eye corrosion	+	0.7056	70.56%
Eye irritation	+	0.9311	93.11%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9912	99.12%
Ames mutagenesis	-	0.8478	84.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.4600	46.00%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.6074	60.74%
Respiratory toxicity	-	0.9111	91.11%
Reproductive toxicity	-	1.0000	100.00%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	+	0.5405	54.05%
Acute Oral Toxicity (c)	IV	0.4928	49.28%
Estrogen receptor binding	-	0.9012	90.12%
Androgen receptor binding	-	0.9134	91.34%
Thyroid receptor binding	-	0.7287	72.87%
Glucocorticoid receptor binding	-	0.5445	54.45%
Aromatase binding	-	0.8176	81.76%
PPAR gamma	-	0.7311	73.11%
Honey bee toxicity	-	0.8997	89.97%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	+	0.5045	50.45%
Fish aquatic toxicity	+	0.9876	98.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	96.22%	92.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.20%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.84%	99.17%
CHEMBL221	P23219	Cyclooxygenase-1	89.23%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.46%	94.45%
CHEMBL2581	P07339	Cathepsin D	85.16%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	83.75%	91.19%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.97%	94.33%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.76%	82.50%

Plants that contains it

• Bothriochloa bladhii
• Cryptomeria japonica
• Cymbopogon khasianus
• Foeniculum vulgare
• Origanum syriacum
• Pelargonium quercifolium
• Schinus molle
• Thymus × citriodorus
• Thymus camphoratus
• Thymus funkii
• Thymus willkommii

Cross-Links

• PubChem: 5355856
• NPASS: NPC135698
• LOTUS: LTS0022511
• wikiData: Q10864413