Isobutyl cinnamate

Details

• Internal ID: d00317c1-9d80-4146-b7d3-2332301d7169
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acid esters
• IUPAC Name: 2-methylpropyl (E)-3-phenylprop-2-enoate
• SMILES (Canonical): CC(C)COC(=O)C=CC1=CC=CC=C1
• SMILES (Isomeric): CC(C)COC(=O)/C=C/C1=CC=CC=C1
• InChI: InChI=1S/C13H16O2/c1-11(2)10-15-13(14)9-8-12-6-4-3-5-7-12/h3-9,11H,10H2,1-2H3/b9-8+
• InChI Key: IQZUZPKOFSOVET-CMDGGOBGSA-N
• Popularity: 25 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.26 g/mol
• Exact Mass: 204.115029749 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 122-67-8
• Labdanol
• 2-Methylpropyl cinnamate
• CINNAMIC ACID, ISOBUTYL ESTER
• Isobutyl 3-phenylpropenoate
• FEMA No. 2193
• 2-Propenoic acid, 3-phenyl-, 2-methylpropyl ester
• 4NCI0MR7KP
• 2-methylpropyl (E)-3-phenylprop-2-enoate
• NSC-404181
• 2-methylpropyl (2Z)-3-phenylprop-2-enoate
• RefChem:791625
• 204-564-0
• 2-Methylpropyl 3-phenylpropenoate
• Isobutyl 3-phenylacrylate
• MFCD00038289
• 2-methylpropyl (2E)-3-phenylprop-2-enoate
• Isobutyl cinammate
• Isobutyl beta-phenylacrylate
• 2-Methylpropyl beta-phenylacrylate
• 2-Methylpropyl 3-phenyl-2-propenoate
• 31416-74-7
• iso-Butyl cinnamate
• EINECS 204-564-0
• UNII-4NCI0MR7KP
• DTXSID2047646
• NSC 404181
• isobutylcinnamat
• AI3-02384
• E-Isobutylcinnamate
• E-Isobutyl cinnamate
• Isobutyl cinnamate, >=98%
• SCHEMBL868714
• CHEMBL2286136
• DTXCID0027646
• ISOBUTYL CINNAMATE [FCC]
• WLN: 1Y1&1OV1U1R
• ISOBUTYL CINNAMATE [FHFI]
• CHEBI:192920
• HMS1577E01
• Tox21_302557
• AC7839
• isobutyl (E)-3-phenylprop-2-enoate
• NSC404181
• STK204833
• AKOS005415735
• AKOS025310762
• CS-W015404
• Isobutyl cinnamate, >=98%, FCC, FG
• NCGC00256819-01
• BS-14632
• CAS-122-67-8
• Isobutyl (2E)-3-phenyl-2-propenoate #
• LS-14218
• SY015388
• NS00012675
• ST50998845
• Q27260243

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8292	82.92%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7089	70.89%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9321	93.21%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5150	51.50%
P-glycoprotein inhibitior	-	0.9394	93.94%
P-glycoprotein substrate	-	0.9546	95.46%
CYP3A4 substrate	-	0.6571	65.71%
CYP2C9 substrate	-	0.5982	59.82%
CYP2D6 substrate	-	0.8950	89.50%
CYP3A4 inhibition	-	0.9673	96.73%
CYP2C9 inhibition	-	0.8769	87.69%
CYP2C19 inhibition	-	0.8783	87.83%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	+	0.5286	52.86%
CYP2C8 inhibition	-	0.8517	85.17%
CYP inhibitory promiscuity	-	0.6806	68.06%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5584	55.84%
Carcinogenicity (trinary)	Non-required	0.5984	59.84%
Eye corrosion	+	0.5184	51.84%
Eye irritation	+	0.7477	74.77%
Skin irritation	+	0.7206	72.06%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4514	45.14%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.6071	60.71%
skin sensitisation	+	0.9572	95.72%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.6333	63.33%
Mitochondrial toxicity	-	0.9500	95.00%
Nephrotoxicity	-	0.7707	77.07%
Acute Oral Toxicity (c)	III	0.6844	68.44%
Estrogen receptor binding	-	0.8524	85.24%
Androgen receptor binding	+	0.6114	61.14%
Thyroid receptor binding	-	0.7662	76.62%
Glucocorticoid receptor binding	-	0.8424	84.24%
Aromatase binding	+	0.5731	57.31%
PPAR gamma	-	0.9086	90.86%
Honey bee toxicity	-	0.9591	95.91%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5855	58.55%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.63%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.54%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	93.75%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.88%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.74%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.61%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.36%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.38%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	84.04%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.86%	93.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.84%	94.62%
CHEMBL5028	O14672	ADAM10	82.18%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.08%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.05%	95.50%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	80.51%	100.00%

Plants that contains it

• Artemisia salsoloides
• Styrax benzoin

Cross-Links

• PubChem: 778574
• NPASS: NPC303245
• LOTUS: LTS0217570
• wikiData: Q27260243