2-{4-[2-(S)-Allyloxycarbonylamino-3-{4-[(2-carboxy-phenyl)-oxalyl-amino]-phenyl}-propionylamino]-butoxy}-6-hydroxy-benz oic acid methyl ester

Details

• Internal ID: ae9189bd-ad9d-4b93-a9ce-48acaabe1c88
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Phenylalanine and derivatives
• IUPAC Name: 2-[4-[(2S)-2-(carboxyamino)-3-[4-(3-hydroxy-2-methoxycarbonylphenoxy)butylamino]-3-oxopropyl]-N-oxaloanilino]benzoic acid
• SMILES (Canonical): COC(=O)C1=C(C=CC=C1OCCCCNC(=O)C(CC2=CC=C(C=C2)N(C3=CC=CC=C3C(=O)O)C(=O)C(=O)O)NC(=O)O)O
• SMILES (Isomeric): COC(=O)C1=C(C=CC=C1OCCCCNC(=O)[C@H](CC2=CC=C(C=C2)N(C3=CC=CC=C3C(=O)O)C(=O)C(=O)O)NC(=O)O)O
• InChI: InChI=1S/C31H31N3O12/c1-45-30(42)25-23(35)9-6-10-24(25)46-16-5-4-15-32-26(36)21(33-31(43)44)17-18-11-13-19(14-12-18)34(27(37)29(40)41)22-8-3-2-7-20(22)28(38)39/h2-3,6-14,21,33,35H,4-5,15-17H2,1H3,(H,32,36)(H,38,39)(H,40,41)(H,43,44)/t21-/m0/s1
• InChI Key: AYMZSPOIUVLDRK-NRFANRHFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₁N₃O₁₂
• Molecular Weight: 637.60 g/mol
• Exact Mass: 637.19077343 g/mol
• Topological Polar Surface Area (TPSA): 229.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 14

Synonyms

• 2-{4-[2-(S)-ALLYLOXYCARBONYLAMINO-3-{4-[(2-CARBOXY-PHENYL)-OXALYL-AMINO]-PHENYL}-PROPIONYLAMINO]-BUTOXY}-6-HYDROXY-BENZ OIC ACID METHYL ESTER

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5103	51.03%
Caco-2	-	0.8897	88.97%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7463	74.63%
OATP2B1 inhibitior	+	0.5768	57.68%
OATP1B1 inhibitior	+	0.8847	88.47%
OATP1B3 inhibitior	+	0.9368	93.68%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9414	94.14%
P-glycoprotein inhibitior	+	0.8107	81.07%
P-glycoprotein substrate	+	0.8522	85.22%
CYP3A4 substrate	+	0.6809	68.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8588	85.88%
CYP3A4 inhibition	-	0.6704	67.04%
CYP2C9 inhibition	-	0.8136	81.36%
CYP2C19 inhibition	-	0.6654	66.54%
CYP2D6 inhibition	-	0.8424	84.24%
CYP1A2 inhibition	-	0.8405	84.05%
CYP2C8 inhibition	+	0.8274	82.74%
CYP inhibitory promiscuity	-	0.8557	85.57%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.6742	67.42%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9263	92.63%
Skin irritation	-	0.7803	78.03%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.6554	65.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5092	50.92%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.5300	53.00%
skin sensitisation	-	0.8978	89.78%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7496	74.96%
Acute Oral Toxicity (c)	III	0.6756	67.56%
Estrogen receptor binding	+	0.7611	76.11%
Androgen receptor binding	+	0.8525	85.25%
Thyroid receptor binding	-	0.4912	49.12%
Glucocorticoid receptor binding	+	0.6250	62.50%
Aromatase binding	+	0.5429	54.29%
PPAR gamma	+	0.7279	72.79%
Honey bee toxicity	-	0.7981	79.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9361	93.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.78%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	99.24%	90.20%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.74%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.55%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	96.02%	95.50%
CHEMBL2535	P11166	Glucose transporter	92.94%	98.75%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.45%	95.17%
CHEMBL3891	P07384	Calpain 1	90.18%	93.04%
CHEMBL3359	P21462	Formyl peptide receptor 1	89.72%	93.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.59%	89.67%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.04%	93.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.21%	96.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.08%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.40%	97.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.33%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	87.31%	94.73%
CHEMBL3492	P49721	Proteasome Macropain subunit	86.96%	90.24%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.22%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.90%	94.00%
CHEMBL4302	P08183	P-glycoprotein 1	84.34%	92.98%
CHEMBL340	P08684	Cytochrome P450 3A4	84.31%	91.19%
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	83.45%	95.52%
CHEMBL5028	O14672	ADAM10	83.07%	97.50%
CHEMBL2321614	Q9NPC2	Potassium channel subfamily K member 9	82.53%	80.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.99%	90.17%
CHEMBL1914	P06276	Butyrylcholinesterase	81.26%	95.00%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.09%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.86%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.77%	97.14%
CHEMBL4072	P07858	Cathepsin B	80.04%	93.67%

Plants that contains it

• Artemisia annua
• Elephantopus mollis
• Euphorbia fischeriana

Cross-Links

• PubChem: 447837
• LOTUS: LTS0150168
• wikiData: Q105100333