Avermectin A2a

Details

• Internal ID: d5a4f8df-7bde-48f4-9d49-007d523226fd
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues > Milbemycins
• IUPAC Name: (1R,4S,4'S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-butan-2-yl-4',24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-21-methoxy-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
• SMILES (Canonical): CCC(C)C1C(C(CC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5OC)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)O)C
• SMILES (Isomeric): CCC(C)[C@@H]1[C@H]([C@H](C[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5OC)C)C(=O)O3)O)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@H]([C@@H](O7)C)O)OC)OC)\C)O)C
• InChI: InChI=1S/C49H76O15/c1-12-25(2)43-29(6)36(50)23-48(64-43)22-34-19-33(63-48)17-16-27(4)42(61-40-21-38(55-10)45(31(8)59-40)62-39-20-37(54-9)41(51)30(7)58-39)26(3)14-13-15-32-24-57-46-44(56-11)28(5)18-35(47(52)60-34)49(32,46)53/h13-16,18,25-26,29-31,33-46,50-51,53H,12,17,19-24H2,1-11H3/b14-13+,27-16+,32-15+/t25?,26-,29-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46+,48-,49+/m0/s1
• InChI Key: JVGWUGTWQIAGHJ-DFAYUBCLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₇₆O₁₅
• Molecular Weight: 905.10 g/mol
• Exact Mass: 904.51842171 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 5.23
• H-Bond Acceptor: 15
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

• 65195-53-1
• SCHEMBL1681224
• CHEBI:29528
• LMPK04000023
• Q27110122
• (1R,4S,4'S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-butan-2-yl-4',24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-21-methoxy-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9888	98.88%
Caco-2	-	0.8713	87.13%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7221	72.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8501	85.01%
OATP1B3 inhibitior	+	0.8882	88.82%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9632	96.32%
P-glycoprotein inhibitior	+	0.7735	77.35%
P-glycoprotein substrate	+	0.9110	91.10%
CYP3A4 substrate	+	0.7442	74.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8929	89.29%
CYP3A4 inhibition	-	0.7270	72.70%
CYP2C9 inhibition	-	0.8874	88.74%
CYP2C19 inhibition	-	0.9075	90.75%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	-	0.8929	89.29%
CYP2C8 inhibition	+	0.7353	73.53%
CYP inhibitory promiscuity	-	0.7765	77.65%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4944	49.44%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9102	91.02%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9399	93.99%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7147	71.47%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.7093	70.93%
skin sensitisation	-	0.8687	86.87%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.8595	85.95%
Acute Oral Toxicity (c)	I	0.4152	41.52%
Estrogen receptor binding	+	0.8644	86.44%
Androgen receptor binding	+	0.8179	81.79%
Thyroid receptor binding	+	0.5469	54.69%
Glucocorticoid receptor binding	+	0.7704	77.04%
Aromatase binding	+	0.5962	59.62%
PPAR gamma	+	0.7880	78.80%
Honey bee toxicity	+	0.8136	81.36%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9467	94.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.58%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.30%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.01%	96.77%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	95.18%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	92.97%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	92.38%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.63%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.06%	91.11%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	90.89%	97.21%
CHEMBL2581	P07339	Cathepsin D	90.59%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	90.42%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.37%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.47%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.61%	89.00%
CHEMBL255	P29275	Adenosine A2b receptor	88.52%	98.59%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.45%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.98%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.52%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.49%	96.47%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.38%	92.62%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.24%	96.38%
CHEMBL4208	P20618	Proteasome component C5	85.11%	90.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.01%	97.28%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.93%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.70%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.12%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.14%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.57%	95.50%
CHEMBL1871	P10275	Androgen Receptor	81.26%	96.43%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.08%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11953987
• LOTUS: LTS0189911
• wikiData: Q27110122