Lorneamide A

Details

• Internal ID: a205cf52-b6e5-4c88-8d7f-f2051804c44b
• Taxonomy: Phenylpropanoids and polyketides > Cinnamyl alcohols
• IUPAC Name: (E)-4-[2-[(E)-3-hydroxyhex-1-enyl]-4-methylphenyl]but-3-enamide
• SMILES (Canonical): CCCC(C=CC1=C(C=CC(=C1)C)C=CCC(=O)N)O
• SMILES (Isomeric): CCCC(/C=C/C1=C(C=CC(=C1)C)/C=C/CC(=O)N)O
• InChI: InChI=1S/C17H23NO2/c1-3-5-16(19)11-10-15-12-13(2)8-9-14(15)6-4-7-17(18)20/h4,6,8-12,16,19H,3,5,7H2,1-2H3,(H2,18,20)/b6-4+,11-10+
• InChI Key: CNNYMGVUSRNOJM-VIMHMKGSSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₃NO₂
• Molecular Weight: 273.37 g/mol
• Exact Mass: 273.172878976 g/mol
• Topological Polar Surface Area (TPSA): 63.30 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.06
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• (E)-4-(2-((E)-3-hydroxyhex-1-enyl)-4-methylphenyl)but-3-enamide
• (E)-4-[2-[(E)-3-hydroxyhex-1-enyl]-4-methylphenyl]but-3-enamide
• RefChem:154104
• CHEMBL509468

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5756	57.56%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5946	59.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8642	86.42%
OATP1B3 inhibitior	+	0.9487	94.87%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7917	79.17%
P-glycoprotein inhibitior	-	0.8604	86.04%
P-glycoprotein substrate	-	0.7430	74.30%
CYP3A4 substrate	-	0.5459	54.59%
CYP2C9 substrate	-	0.7904	79.04%
CYP2D6 substrate	-	0.8181	81.81%
CYP3A4 inhibition	-	0.5685	56.85%
CYP2C9 inhibition	-	0.6833	68.33%
CYP2C19 inhibition	-	0.6479	64.79%
CYP2D6 inhibition	-	0.7290	72.90%
CYP1A2 inhibition	+	0.5491	54.91%
CYP2C8 inhibition	-	0.7999	79.99%
CYP inhibitory promiscuity	-	0.6727	67.27%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6611	66.11%
Carcinogenicity (trinary)	Non-required	0.6661	66.61%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9927	99.27%
Skin irritation	-	0.8058	80.58%
Skin corrosion	-	0.9547	95.47%
Ames mutagenesis	-	0.7137	71.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7496	74.96%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8202	82.02%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8343	83.43%
Acute Oral Toxicity (c)	III	0.7119	71.19%
Estrogen receptor binding	+	0.5774	57.74%
Androgen receptor binding	-	0.4880	48.80%
Thyroid receptor binding	-	0.5262	52.62%
Glucocorticoid receptor binding	-	0.4672	46.72%
Aromatase binding	+	0.7060	70.60%
PPAR gamma	+	0.6234	62.34%
Honey bee toxicity	-	0.9700	97.00%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5852	58.52%
Fish aquatic toxicity	-	0.5207	52.07%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.81%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.73%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.68%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.91%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	89.86%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.44%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	89.35%	89.63%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.68%	93.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.12%	86.33%
CHEMBL4581	P52732	Kinesin-like protein 1	85.95%	93.18%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.34%	90.71%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.61%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.46%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11778071
• LOTUS: LTS0124730
• wikiData: Q104966139