Fagaramide

Details

• Internal ID: e4e38004-05ed-4f88-8e2b-36b38a7e3399
• Taxonomy: Organoheterocyclic compounds > Benzodioxoles
• IUPAC Name: (E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide
• SMILES (Canonical): CC(C)CNC(=O)C=CC1=CC2=C(C=C1)OCO2
• SMILES (Isomeric): CC(C)CNC(=O)/C=C/C1=CC2=C(C=C1)OCO2
• InChI: InChI=1S/C14H17NO3/c1-10(2)8-15-14(16)6-4-11-3-5-12-13(7-11)18-9-17-12/h3-7,10H,8-9H2,1-2H3,(H,15,16)/b6-4+
• InChI Key: WKWYNAMJWDRHBP-GQCTYLIASA-N
• Popularity: 44 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₇NO₃
• Molecular Weight: 247.29 g/mol
• Exact Mass: 247.12084340 g/mol
• Topological Polar Surface Area (TPSA): 47.60 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.20
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• trans-fagaramide
• 495-86-3
• 60045-88-7
• FOGARAMIDE
• Piperonyl-4-aacrylylisobutylamide
• 2-Propenamide, 3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-
• N-Isobutyl-3,4-methylenedioxycinnamamide
• AI3-30755
• CHEBI:4966
• NSC-94257
• 3-(1,3-Benzodioxo-5-yl)-N-(2-methylpropyl)-2-propenamide
• Cinnamamide, N-isobutyl-3,4-methylenedioxy-
• Cinnamamide, N-isobutyl-3,4- (methylenedioxy)-
• Cinnamamide, N-isobutyl-3,4-(methylenedioxy)-, (E)-
• (E)-3-(1,3-benzodioxol-5-yl)-N-isobutyl-prop-2-enamide
• 2-Propenamide, 3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (2E)-
• C2UHL92KKP
• AC1NQZ1T
• Cinnamamide, N-isobutyl-3,4-(methylenedioxy)-, stereoisomer
• Fagaramid
• NSC 94257
• CHEMBL252709
• SCHEMBL2987846
• SCHEMBL17073972
• Cinnamamide,4-(methylenedioxy)-
• 3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide
• DTXSID001318385
• HMS1750A04
• (E)-3-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)prop-2-enamide
• NSC94257
• AKOS001133721
• N-Isobutyl-3,4-methylenedioxy cinnamide
• Cinnamamide,4-(methylenedioxy)-, stereoisomer
• T5404670
• Q27106593
• Z32386287
• (2E)-3-(1,3-benzodioxol-5-yl)-N-isobutyl-2-propenamide
• 3-(1,3-Benzodioxole-5-yl)-N-(2-methylpropyl)propeneamide
• 2-Propenamide,3-benzodioxol-5-yl)-N-(2-methylpropyl)-, (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	+	0.6657	66.57%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6343	63.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9501	95.01%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6421	64.21%
P-glycoprotein inhibitior	-	0.9346	93.46%
P-glycoprotein substrate	-	0.8465	84.65%
CYP3A4 substrate	-	0.6317	63.17%
CYP2C9 substrate	-	0.8232	82.32%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.6553	65.53%
CYP2C9 inhibition	+	0.5470	54.70%
CYP2C19 inhibition	+	0.5092	50.92%
CYP2D6 inhibition	-	0.5391	53.91%
CYP1A2 inhibition	+	0.7385	73.85%
CYP2C8 inhibition	-	0.9028	90.28%
CYP inhibitory promiscuity	+	0.7904	79.04%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7700	77.00%
Carcinogenicity (trinary)	Non-required	0.5733	57.33%
Eye corrosion	-	0.9815	98.15%
Eye irritation	-	0.8926	89.26%
Skin irritation	-	0.6623	66.23%
Skin corrosion	-	0.8998	89.98%
Ames mutagenesis	-	0.8137	81.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4290	42.90%
Micronuclear	+	0.5881	58.81%
Hepatotoxicity	-	0.5944	59.44%
skin sensitisation	-	0.6582	65.82%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.8313	83.13%
Acute Oral Toxicity (c)	III	0.5707	57.07%
Estrogen receptor binding	-	0.7386	73.86%
Androgen receptor binding	+	0.8769	87.69%
Thyroid receptor binding	+	0.5227	52.27%
Glucocorticoid receptor binding	-	0.8864	88.64%
Aromatase binding	+	0.6194	61.94%
PPAR gamma	-	0.6880	68.80%
Honey bee toxicity	-	0.9473	94.73%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.8336	83.36%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.08%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.04%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.98%	94.80%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.41%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.14%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	92.67%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.43%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.42%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.19%	86.33%
CHEMBL4208	P20618	Proteasome component C5	90.14%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.37%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.07%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.87%	90.71%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.45%	80.96%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.91%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.17%	99.17%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	81.92%	89.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.68%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.47%	92.62%

Plants that contains it

• Artemisia austriaca
• Asarum sagittarioides
• Chrysolaena propinqua
• Daphne blagayana
• Digitalis obscura
• Erythrina variegata
• Kayea elegans
• Magnolia rajaniana
• Onychopetalum amazonicum
• Piper amalago
• Piper guineense
• Piper nigrum
• Piper tuberculatum
• Stevia serrata
• Zanthoxylum armatum
• Zanthoxylum gilletii
• Zanthoxylum heitzii
• Zanthoxylum rubescens
• Zanthoxylum zanthoxyloides

Cross-Links

• PubChem: 5281772
• NPASS: NPC300955
• LOTUS: LTS0066857
• wikiData: Q27106593