methyl 2-[(1R,6S)-1-hydroxy-4-oxo-6-(3-phenylprop-2-enoylamino)cyclohex-2-en-1-yl]acetate

Details

• Internal ID: b5b5be64-a3f9-4910-8966-60e8d9d86775
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Amino acids and derivatives > Gamma amino acids and derivatives
• IUPAC Name: methyl 2-[(1R,6S)-1-hydroxy-4-oxo-6-(3-phenylprop-2-enoylamino)cyclohex-2-en-1-yl]acetate
• InChI: InChI=1S/C18H19NO5/c1-24-17(22)12-18(23)10-9-14(20)11-15(18)19-16(21)8-7-13-5-3-2-4-6-13/h2-10,15,23H,11-12H2,1H3,(H,19,21)/t15-,18-/m0/s1
• InChI Key: WTPJVIGCNHPGKJ-YJBOKZPZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₉NO₅
• Molecular Weight: 329.30 g/mol
• Exact Mass: 329.12632271 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.01
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9105	91.05%
Caco-2	-	0.7648	76.48%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7301	73.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8907	89.07%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.4690	46.90%
P-glycoprotein inhibitior	-	0.7749	77.49%
P-glycoprotein substrate	-	0.6686	66.86%
CYP3A4 substrate	+	0.5985	59.85%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8530	85.30%
CYP3A4 inhibition	-	0.9154	91.54%
CYP2C9 inhibition	-	0.8516	85.16%
CYP2C19 inhibition	-	0.8393	83.93%
CYP2D6 inhibition	-	0.9019	90.19%
CYP1A2 inhibition	-	0.8846	88.46%
CYP2C8 inhibition	+	0.5396	53.96%
CYP inhibitory promiscuity	-	0.8793	87.93%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8022	80.22%
Carcinogenicity (trinary)	Non-required	0.6386	63.86%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.9593	95.93%
Skin irritation	-	0.8209	82.09%
Skin corrosion	-	0.9648	96.48%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7587	75.87%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.7051	70.51%
skin sensitisation	-	0.8928	89.28%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6935	69.35%
Acute Oral Toxicity (c)	III	0.6959	69.59%
Estrogen receptor binding	+	0.6957	69.57%
Androgen receptor binding	+	0.5868	58.68%
Thyroid receptor binding	-	0.6497	64.97%
Glucocorticoid receptor binding	+	0.5579	55.79%
Aromatase binding	-	0.5299	52.99%
PPAR gamma	+	0.5436	54.36%
Honey bee toxicity	-	0.9020	90.20%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9257	92.57%

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	98.83%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.86%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	95.06%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.84%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.59%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.73%	86.33%
CHEMBL2581	P07339	Cathepsin D	90.78%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.31%	96.00%
CHEMBL4208	P20618	Proteasome component C5	88.39%	90.00%
CHEMBL5028	O14672	ADAM10	84.48%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.91%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.28%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.08%	99.23%

Plants that contains it

• Toussaintia orientalis

Cross-Links

• PubChem: 162868220
• LOTUS: LTS0187578
• wikiData: Q105312699