Avermectin A1a

Details

• Internal ID: 35bb4fd4-3613-4d7b-aab3-331850170f9b
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (1'R,2R,3S,4'S,6S,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-2-[(2S)-butan-2-yl]-24'-hydroxy-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-3,11',13',22'-tetramethylspiro[2,3-dihydropyran-6,6'-3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene]-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)C
• SMILES (Isomeric): CC[C@H](C)[C@@H]1[C@H](C=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)C
• InChI: InChI=1S/C49H74O14/c1-12-26(2)43-29(5)18-19-48(63-43)24-35-21-34(62-48)17-16-28(4)42(60-40-23-38(54-10)45(32(8)58-40)61-39-22-37(53-9)41(50)31(7)57-39)27(3)14-13-15-33-25-56-46-44(55-11)30(6)20-36(47(51)59-35)49(33,46)52/h13-16,18-20,26-27,29,31-32,34-46,50,52H,12,17,21-25H2,1-11H3/b14-13+,28-16+,33-15+/t26-,27-,29-,31-,32-,34+,35-,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46+,48+,49+/m0/s1
• InChI Key: AFSHKCWTGFDXJR-SQOHEDJBSA-N
• Popularity: 588 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₇₄O₁₄
• Molecular Weight: 887.10 g/mol
• Exact Mass: 886.50785703 g/mol
• Topological Polar Surface Area (TPSA): 159.00 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 6.03
• H-Bond Acceptor: 14
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• Avermectin A1a
• YRI17ZJ0WT
• Antibiotic C 076A1a
• UNII-YRI17ZJ0WT
• Antibiotic C 076A(sub 1a)
• ANTIBIOTIC C-076A1A
• DTXSID8058613
• L-676891
• SCHEMBL1681255
• DTXCID4032299

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9861	98.61%
Caco-2	-	0.8652	86.52%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7504	75.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8547	85.47%
OATP1B3 inhibitior	+	0.8235	82.35%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9795	97.95%
P-glycoprotein inhibitior	+	0.7799	77.99%
P-glycoprotein substrate	+	0.9191	91.91%
CYP3A4 substrate	+	0.7425	74.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8929	89.29%
CYP3A4 inhibition	-	0.7946	79.46%
CYP2C9 inhibition	-	0.8738	87.38%
CYP2C19 inhibition	-	0.8848	88.48%
CYP2D6 inhibition	-	0.9334	93.34%
CYP1A2 inhibition	-	0.8690	86.90%
CYP2C8 inhibition	+	0.7317	73.17%
CYP inhibitory promiscuity	-	0.6462	64.62%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5155	51.55%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9106	91.06%
Skin irritation	-	0.5573	55.73%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7535	75.35%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8673	86.73%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8149	81.49%
Acute Oral Toxicity (c)	I	0.3900	39.00%
Estrogen receptor binding	+	0.8560	85.60%
Androgen receptor binding	+	0.8534	85.34%
Thyroid receptor binding	+	0.5442	54.42%
Glucocorticoid receptor binding	+	0.7649	76.49%
Aromatase binding	+	0.5978	59.78%
PPAR gamma	+	0.7693	76.93%
Honey bee toxicity	+	0.9450	94.50%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9633	96.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.07%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.64%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.23%	96.77%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.87%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.14%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	92.09%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.84%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.38%	96.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.56%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.44%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.39%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.47%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.28%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.89%	95.93%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	88.82%	97.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.50%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.14%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.06%	89.00%
CHEMBL4072	P07858	Cathepsin B	87.83%	93.67%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.75%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.49%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.33%	97.14%
CHEMBL4208	P20618	Proteasome component C5	86.16%	90.00%
CHEMBL255	P29275	Adenosine A2b receptor	85.53%	98.59%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.85%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.62%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.32%	95.89%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	83.89%	92.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.45%	99.23%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.23%	97.28%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.17%	96.90%

Plants that contains it

• Veratrum nigrum
• Veronicastrum sibiricum

Cross-Links

• PubChem: 9832706
• NPASS: NPC85505
• LOTUS: LTS0209073
• wikiData: Q104911546