(4S,5S)-7,9-dibromo-N-[3-[2,6-dibromo-4-[1-hydroxy-2-(methylamino)ethyl]phenoxy]propyl]-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide

Details

• Internal ID: fe717c04-0ca1-4038-b4cc-b574af9746ce
• Taxonomy: Benzenoids > Phenol ethers
• IUPAC Name: (4S,5S)-7,9-dibromo-N-[3-[2,6-dibromo-4-[1-hydroxy-2-(methylamino)ethyl]phenoxy]propyl]-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
• SMILES (Canonical): CNCC(C1=CC(=C(C(=C1)Br)OCCCNC(=O)C2=NOC3(C2O)CC(=C(C(=CO3)Br)OC)Br)Br)O
• SMILES (Isomeric): CNCC(C1=CC(=C(C(=C1)Br)OCCCNC(=O)C2=NO[C@]3([C@H]2O)CC(=C(C(=CO3)Br)OC)Br)Br)O
• InChI: InChI=1S/C22H25Br4N3O7/c1-27-9-16(30)11-6-12(23)19(13(24)7-11)34-5-3-4-28-21(32)17-20(31)22(36-29-17)8-14(25)18(33-2)15(26)10-35-22/h6-7,10,16,20,27,30-31H,3-5,8-9H2,1-2H3,(H,28,32)/t16?,20-,22-/m0/s1
• InChI Key: KHWOJHLZIWAPIG-OIGSQQCRSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₅Br₄N₃O₇
• Molecular Weight: 763.10 g/mol
• Exact Mass: 762.83850 g/mol
• Topological Polar Surface Area (TPSA): 131.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.70
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• RefChem:930140
• (4S,5S)-7,9-dibromo-4-hydroxy-N-(3-(4-(1-hydroxy-2-(methylamino)ethyl)phenoxy)propyl)-8-methoxy-1,11-dioxa-2-azaspiro(4.6)undeca-2,7,9-triene-3-carboxamide
• (4S,5S)-7,9-dibromo-N-(3-(2,6-dibromo-4-(1-hydroxy-2-(methylamino)ethyl)phenoxy)propyl)-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro(4.6)undeca-2,7,9-triene-3-carboxamide
• 1,6-Dioxa-2-azaspiro(4.6)undeca-2,7,9-triene-3-carboxamide, 8,10-dibromo-N-(3-(2,6-dibromo-4-(1-hydroxy-2-(methylamino)ethyl)phenoxy)propyl)-4-hydroxy-9-methoxy-
• 142449-78-3
• CHEMBL517220

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8870	88.70%
Caco-2	-	0.8333	83.33%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.4026	40.26%
OATP2B1 inhibitior	-	0.8586	85.86%
OATP1B1 inhibitior	+	0.8836	88.36%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8555	85.55%
P-glycoprotein inhibitior	+	0.6064	60.64%
P-glycoprotein substrate	+	0.7596	75.96%
CYP3A4 substrate	+	0.7042	70.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7182	71.82%
CYP3A4 inhibition	-	0.7610	76.10%
CYP2C9 inhibition	-	0.7036	70.36%
CYP2C19 inhibition	-	0.6444	64.44%
CYP2D6 inhibition	-	0.8459	84.59%
CYP1A2 inhibition	-	0.7037	70.37%
CYP2C8 inhibition	+	0.6281	62.81%
CYP inhibitory promiscuity	-	0.8507	85.07%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7322	73.22%
Carcinogenicity (trinary)	Non-required	0.5369	53.69%
Eye corrosion	-	0.9791	97.91%
Eye irritation	-	0.9394	93.94%
Skin irritation	-	0.7551	75.51%
Skin corrosion	-	0.9153	91.53%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5054	50.54%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8149	81.49%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.9492	94.92%
Acute Oral Toxicity (c)	III	0.5816	58.16%
Estrogen receptor binding	+	0.7296	72.96%
Androgen receptor binding	+	0.6215	62.15%
Thyroid receptor binding	+	0.5244	52.44%
Glucocorticoid receptor binding	+	0.6847	68.47%
Aromatase binding	+	0.6952	69.52%
PPAR gamma	+	0.6714	67.14%
Honey bee toxicity	-	0.7279	72.79%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.6678	66.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	99.24%	95.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.96%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.27%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.53%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.09%	97.25%
CHEMBL2581	P07339	Cathepsin D	95.52%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	94.53%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.52%	85.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	93.32%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.98%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.27%	91.24%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.21%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.52%	94.00%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	87.97%	95.71%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.34%	100.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	86.13%	94.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	85.92%	92.88%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.17%	90.71%
CHEMBL5028	O14672	ADAM10	85.13%	97.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.90%	98.75%
CHEMBL221	P23219	Cyclooxygenase-1	84.77%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.76%	96.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.59%	97.21%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	82.93%	90.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.92%	95.56%
CHEMBL3891	P07384	Calpain 1	82.66%	93.04%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.08%	94.33%
CHEMBL4040	P28482	MAP kinase ERK2	81.97%	83.82%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.99%	89.67%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 44584721
• LOTUS: LTS0261922
• wikiData: Q105141359