Isoamyl salicylate

Details

• Internal ID: bbac163f-8996-4964-97a2-4f4e37d70116
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzoic acids and derivatives > Benzoic acid esters > o-Hydroxybenzoic acid esters
• IUPAC Name: 3-methylbutyl 2-hydroxybenzoate
• SMILES (Canonical): CC(C)CCOC(=O)C1=CC=CC=C1O
• SMILES (Isomeric): CC(C)CCOC(=O)C1=CC=CC=C1O
• InChI: InChI=1S/C12H16O3/c1-9(2)7-8-15-12(14)10-5-3-4-6-11(10)13/h3-6,9,13H,7-8H2,1-2H3
• InChI Key: PMGCQNGBLMMXEW-UHFFFAOYSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25 g/mol
• Exact Mass: 208.109944368 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 2.60
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 87-20-7
• Isopentyl 2-Hydroxybenzoate
• 3-Methylbutyl 2-hydroxybenzoate
• Isopentyl salicylate
• 3-Methylbutyl salicylate
• Isoamyl o-hydroxybenzoate
• Benzoic acid, 2-hydroxy-, 3-methylbutyl ester
• Salicylic acid, isopentyl ester
• Isopentyl o-hydroxybenzoate
• Isopentyl-2-hydroxyphenyl methanoate
• FEMA No. 2084
• Orchidee
• Sanfoin
• 3-Methylbutyl o-hydroxybenzoate
• NSC 7952
• 34377-38-3
• Isoamylester kyseliny salicylove
• M25E4ZMR0N
• 2-Hydroxybenzoic acid, 3-methylbutyl ester
• NSC-7952
• Benzoic acid, o-hydroxy, 3-methylbutyl ester
• iso-amyl salicylate
• Isoamyl salicylate (natural)
• EINECS 201-730-4
• UNII-M25E4ZMR0N
• BRN 2580465
• Isoamylester kyseliny salicylove [Czech]
• Tressane
• Trefle
• Trefol
• isoamylsalicylate
• AI3-00378
• isopentylsalicylat
• Salicylic Acid Isoamyl Ester
• SCHEMBL113328
• WLN: QR BVO2Y1&1
• (3-methyl-1-butyl) salicylate
• ISOAMYL SALICYLATE [MI]
• AMYL SALICYLATE [MART.]
• CHEMBL2260718
• DTXSID9041655
• ISOAMYL SALICYLATE [FCC]
• ISOAMYL SALICYLATE [FHFI]
• NSC7952
• CHEBI:173601
• ISOPENTYL ALCOHOL, SALICYLATE
• MFCD00020037
• AKOS015856348
• DS-17837
• Isoamyl salicylate, natural, >=98%, FCC
• FT-0651888
• E78224
• A842037
• Q2214309
• W-104039
• Salicylic acid isoamyl ester (contains 2-Methylbutyl salicylate)
• Isoamyl salicylate;3-Methylbutyl o-hydroxybenzoate; 3-Methylbutyl salicylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.9475	94.75%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.9544	95.44%
OATP2B1 inhibitior	-	0.8621	86.21%
OATP1B1 inhibitior	+	0.9514	95.14%
OATP1B3 inhibitior	+	0.9664	96.64%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9386	93.86%
P-glycoprotein inhibitior	-	0.9716	97.16%
P-glycoprotein substrate	-	0.9314	93.14%
CYP3A4 substrate	-	0.5714	57.14%
CYP2C9 substrate	+	0.5875	58.75%
CYP2D6 substrate	-	0.8558	85.58%
CYP3A4 inhibition	-	0.9454	94.54%
CYP2C9 inhibition	-	0.6992	69.92%
CYP2C19 inhibition	-	0.5745	57.45%
CYP2D6 inhibition	-	0.8816	88.16%
CYP1A2 inhibition	+	0.8679	86.79%
CYP2C8 inhibition	-	0.8914	89.14%
CYP inhibitory promiscuity	-	0.9038	90.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7133	71.33%
Carcinogenicity (trinary)	Non-required	0.6325	63.25%
Eye corrosion	-	0.9366	93.66%
Eye irritation	+	0.9897	98.97%
Skin irritation	-	0.6558	65.58%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6631	66.31%
Micronuclear	-	0.9226	92.26%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	+	0.5315	53.15%
Respiratory toxicity	-	0.8778	87.78%
Reproductive toxicity	-	0.7556	75.56%
Mitochondrial toxicity	-	0.9625	96.25%
Nephrotoxicity	-	0.6193	61.93%
Acute Oral Toxicity (c)	III	0.7779	77.79%
Estrogen receptor binding	-	0.6969	69.69%
Androgen receptor binding	-	0.4852	48.52%
Thyroid receptor binding	-	0.5494	54.94%
Glucocorticoid receptor binding	-	0.8221	82.21%
Aromatase binding	-	0.7070	70.70%
PPAR gamma	-	0.5928	59.28%
Honey bee toxicity	-	0.9692	96.92%
Biodegradation	+	0.8500	85.00%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.9686	96.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.60%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.48%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.83%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	89.22%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.94%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.41%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	82.76%	90.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.65%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.44%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.80%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.08%	99.17%

Plants that contains it

• Plumeria rubra
• Vanilla planifolia

Cross-Links

• PubChem: 6874
• LOTUS: LTS0100550
• wikiData: Q2214309