(2R)-2-amino-4-[4-[(E)-C-[[(3S)-1-[(R)-carboxy-(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl]-N-hydroxycarbonimidoyl]phenoxy]butanoic acid

Details

• Internal ID: 1434a3c1-4435-4a1b-bf2e-f721b9cd3f7a
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Dipeptides
• IUPAC Name: (2R)-2-amino-4-[4-[(E)-C-[[(3S)-1-[(R)-carboxy-(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl]-N-hydroxycarbonimidoyl]phenoxy]butanoic acid
• SMILES (Canonical): C1C(C(=O)N1C(C2=CC(=C(C=C2)O)Cl)C(=O)O)NC(=O)C(=NO)C3=CC=C(C=C3)OCCC(C(=O)O)N
• SMILES (Isomeric): C1[C@@H](C(=O)N1[C@H](C2=CC(=C(C=C2)O)Cl)C(=O)O)NC(=O)/C(=N/O)/C3=CC=C(C=C3)OCC[C@H](C(=O)O)N
• InChI: InChI=1S/C23H23ClN4O9/c24-14-9-12(3-6-17(14)29)19(23(34)35)28-10-16(21(28)31)26-20(30)18(27-36)11-1-4-13(5-2-11)37-8-7-15(25)22(32)33/h1-6,9,15-16,19,29,36H,7-8,10,25H2,(H,26,30)(H,32,33)(H,34,35)/b27-18+/t15-,16+,19-/m1/s1
• InChI Key: UMDAIHWMUXNVSB-IMUCLJOZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₃ClN₄O₉
• Molecular Weight: 534.90 g/mol
• Exact Mass: 534.1153560 g/mol
• Topological Polar Surface Area (TPSA): 212.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.56
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 11

Synonyms

• CID 9577949
• (2R)-2-amino-4-[4-[(E)-C-[[(3S)-1-[(R)-carboxy-(3-chloro-4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl]-N-hydroxycarbonimidoyl]phenoxy]butanoic acid
• 1-Azetidineacetic acid, 3-(((4-(3-amino-3-carboxypropoxy)phenyl)(hydroxyimino)acetyl)amino)-alpha-(3-chloro-4-hydroxyphenyl)-2-oxo-, (3S-(1(S*),3R*(Z(S*))))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6648	66.48%
Caco-2	-	0.8803	88.03%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4851	48.51%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.9097	90.97%
OATP1B3 inhibitior	+	0.9294	92.94%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7817	78.17%
BSEP inhibitior	+	0.8804	88.04%
P-glycoprotein inhibitior	+	0.6496	64.96%
P-glycoprotein substrate	+	0.5844	58.44%
CYP3A4 substrate	+	0.6738	67.38%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8116	81.16%
CYP3A4 inhibition	-	0.7208	72.08%
CYP2C9 inhibition	-	0.7143	71.43%
CYP2C19 inhibition	-	0.5441	54.41%
CYP2D6 inhibition	-	0.8187	81.87%
CYP1A2 inhibition	-	0.6960	69.60%
CYP2C8 inhibition	+	0.6576	65.76%
CYP inhibitory promiscuity	-	0.7688	76.88%
UGT catelyzed	+	0.7362	73.62%
Carcinogenicity (binary)	-	0.6100	61.00%
Carcinogenicity (trinary)	Non-required	0.5490	54.90%
Eye corrosion	-	0.9816	98.16%
Eye irritation	-	0.9501	95.01%
Skin irritation	-	0.7557	75.57%
Skin corrosion	-	0.9224	92.24%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3628	36.28%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.5168	51.68%
skin sensitisation	-	0.8371	83.71%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7752	77.52%
Acute Oral Toxicity (c)	III	0.5106	51.06%
Estrogen receptor binding	+	0.6107	61.07%
Androgen receptor binding	+	0.8385	83.85%
Thyroid receptor binding	+	0.5481	54.81%
Glucocorticoid receptor binding	+	0.6075	60.75%
Aromatase binding	-	0.5667	56.67%
PPAR gamma	+	0.6131	61.31%
Honey bee toxicity	-	0.8483	84.83%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6458	64.58%
Fish aquatic toxicity	+	0.8470	84.70%

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	98.88%	91.11%
CHEMBL4208	P20618	Proteasome component C5	97.70%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	96.55%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.55%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.13%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.89%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	93.80%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.58%	97.09%
CHEMBL236	P41143	Delta opioid receptor	92.57%	99.35%
CHEMBL3437	Q16853	Amine oxidase, copper containing	92.54%	94.00%
CHEMBL2581	P07339	Cathepsin D	91.76%	98.95%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	90.92%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.11%	95.89%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	88.79%	90.24%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.24%	86.33%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.73%	90.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.53%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.71%	94.62%
CHEMBL3729	P22748	Carbonic anhydrase IV	86.46%	99.23%
CHEMBL2243	O00519	Anandamide amidohydrolase	86.41%	97.53%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	85.94%	95.34%
CHEMBL1907	P15144	Aminopeptidase N	85.50%	93.31%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.38%	94.42%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	83.73%	94.97%
CHEMBL261	P00915	Carbonic anhydrase I	83.46%	96.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.12%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	80.58%	91.19%
CHEMBL321	P14780	Matrix metalloproteinase 9	80.18%	92.12%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 9577949
• LOTUS: LTS0139732
• wikiData: Q105275492