Citronellyl butyrate

Details

• Internal ID: 7dbc3b51-fdac-4a69-ac64-801f711edade
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty alcohol esters
• IUPAC Name: 3,7-dimethyloct-6-enyl butanoate
• SMILES (Canonical): CCCC(=O)OCCC(C)CCC=C(C)C
• SMILES (Isomeric): CCCC(=O)OCCC(C)CCC=C(C)C
• InChI: InChI=1S/C14H26O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,13H,5-7,9-11H2,1-4H3
• InChI Key: XQPZQXTWYZAXAK-UHFFFAOYSA-N
• Popularity: 48 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₆O₂
• Molecular Weight: 226.35 g/mol
• Exact Mass: 226.193280068 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.10
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

• 141-16-2
• Citronellyl n-butyrate
• 3,7-dimethyloct-6-enyl butanoate
• Citronellyl butanoate
• Butanoic acid, 3,7-dimethyl-6-octenyl ester
• 3,7-Dimethyl-6-octenyl butanoate
• Butanoic acid, 3,7-dimethyl-6-octen-1-yl ester
• Butyric acid, ester with citronellol
• Butyric acid, 3,7-dimethyl-6-octenyl ester
• 2,6-Dimethyl-2-octen-8-yl butyrate
• 3,7-Dimethyl-6-octen-1-yl butyrate
• 3,7-dimethyloct-6-en-1-yl butyrate
• FEMA No. 2312
• 3,7-dimethyloct-6-en-1-yl butanoate
• 2,6-Dimethyl-2-octen-8-ol, butyrate
• 3,7-Dimethyl-6-octenyl butyrate
• NSC 46147
• (1)-3,7-Dimethyloct-6-enyl butyrate
• Citronellyl butyrate (natural)
• 6-OCTEN-1-OL, 3,7-DIMETHYL-, BUTYRATE
• EINECS 205-463-4
• EINECS 278-467-7
• UNII-IY68QPD54V
• BRN 1707201
• IY68QPD54V
• AI3-24200
• DTXSID5047405
• NSC-46147
• 2-02-00-00248 (Beilstein Handbook Reference)
• 2, butyrate
• SCHEMBL310496
• CHEMBL3185221
• DTXCID3027405
• FEMA 2312
• 3,7-dimethyloct-6-enyl butyrate
• CHEBI:171871
• XQPZQXTWYZAXAK-UHFFFAOYSA-N
• CITRONELLYL BUTYRATE [FCC]
• CITRONELLYL BUTYRATE [FHFI]
• NSC46147
• WLN: 3VO2Y1&3UY1&1
• (+/-)-CITRONELLYL BUTYRATE
• Tox21_302488
• Citronellyl butyrate, FCC, >=90%
• LMFA07010814
• MFCD00036581
• 6-Octen-1-ol,7-dimethyl-, butyrate
• LS-2637
• CITRONELLYL BUTYRATE, (+/-)-
• (+-)-3,7-dimethyloct-6-enyl butyrate
• Butyric acid,7-dimethyl-6-octenyl ester
• NCGC00256871-01
• Butanoic acid,7-dimethyl-6-octenyl ester
• CAS-141-16-2
• E275
• CS-0223859
• FT-0623968
• Citronellyl butyrate, natural (US), >=85%, FG
• EN300-11686336
• Butyric acid, 3,7-dimethyl-6-octenyl ester (8CI)
• Q27280949
• Z2044751985

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.9717	97.17%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5488	54.88%
OATP2B1 inhibitior	-	0.8470	84.70%
OATP1B1 inhibitior	+	0.9157	91.57%
OATP1B3 inhibitior	+	0.9094	90.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5694	56.94%
P-glycoprotein inhibitior	-	0.9478	94.78%
P-glycoprotein substrate	-	0.8685	86.85%
CYP3A4 substrate	-	0.5248	52.48%
CYP2C9 substrate	+	0.5955	59.55%
CYP2D6 substrate	-	0.8761	87.61%
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	-	0.9631	96.31%
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	+	0.8913	89.13%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9912	99.12%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3860	38.60%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.6074	60.74%
Respiratory toxicity	-	0.8889	88.89%
Reproductive toxicity	-	1.0000	100.00%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	-	0.5741	57.41%
Acute Oral Toxicity (c)	IV	0.4928	49.28%
Estrogen receptor binding	-	0.9397	93.97%
Androgen receptor binding	-	0.9069	90.69%
Thyroid receptor binding	-	0.5554	55.54%
Glucocorticoid receptor binding	-	0.6365	63.65%
Aromatase binding	-	0.9053	90.53%
PPAR gamma	-	0.7660	76.60%
Honey bee toxicity	-	0.8962	89.62%
Biodegradation	+	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
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
CHEMBL221	P23219	Cyclooxygenase-1	95.99%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.86%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.78%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.08%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.77%	99.17%
CHEMBL202	P00374	Dihydrofolate reductase	91.59%	89.92%
CHEMBL340	P08684	Cytochrome P450 3A4	85.84%	91.19%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.62%	89.34%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.47%	92.08%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.85%	97.29%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.68%	82.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.41%	93.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.50%	89.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.25%	94.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.10%	96.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	80.35%	96.47%

Plants that contains it

• Citrus × aurantium
• Citrus deliciosa
• Cryptomeria japonica
• Nepeta ciliaris
• Origanum syriacum
• Pelargonium quercifolium
• Zingiber officinale

Cross-Links

• PubChem: 8835
• NPASS: NPC170167
• LOTUS: LTS0048348
• wikiData: Q27280949