Milbemycin A3

Details

• Internal ID: f2992b7a-da8e-4c3a-8f60-26a04c1d2c8f
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues > Milbemycins
• IUPAC Name: (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-5',6',11,13,22-pentamethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
• SMILES (Canonical): CC1CCC2(CC3CC(O2)CC=C(CC(C=CC=C4COC5C4(C(C=C(C5O)C)C(=O)O3)O)C)C)OC1C
• SMILES (Isomeric): C[C@H]1CC[C@]2(C[C@@H]3C[C@H](O2)C/C=C(/C[C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)\C)O[C@@H]1C
• InChI: InChI=1S/C31H44O7/c1-18-7-6-8-23-17-35-28-27(32)21(4)14-26(31(23,28)34)29(33)36-25-15-24(10-9-19(2)13-18)38-30(16-25)12-11-20(3)22(5)37-30/h6-9,14,18,20,22,24-28,32,34H,10-13,15-17H2,1-5H3/b7-6+,19-9+,23-8+/t18-,20-,22+,24+,25-,26-,27+,28+,30-,31+/m0/s1
• InChI Key: ZLBGSRMUSVULIE-GSMJGMFJSA-N
• Popularity: 1,045 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₇
• Molecular Weight: 528.70 g/mol
• Exact Mass: 528.30870374 g/mol
• Topological Polar Surface Area (TPSA): 94.40 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 4.53
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 51596-10-2
• Milbemectin
• Emamectin A3
• Koromite
• Milbeknock
• C76Y8Z9GEX
• (6R,25R)-5-O-Demethyl-28-deoxy-6,28-epoxy-25-methylmilbemycin B
• DTXSID1058391
• CHEBI:39228
• (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-5',6',11,13,22-pentamethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one
• milbemycin alpha1
• (2aE,4E,5'S,6R,6'R,8E,11R,13R,15S,17aR,20R,20aR,20bS)-20,20b-dihydroxy-5',6,6',8,19-pentamethyl-3',4',5',6,6',7,10,11,14,15,17a,20,20a,20b-tetradecahydro-2H,17H-spiro[11,15-methanofuro[4,3,2-pq][2,6]benzodioxacyclooctadecine-13,2'-pyran]-17-one
• (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-5',6',11,13,22-pentamethylspiro(3,7,19-trioxatetracyclo(15.6.1.14,8.020,24)pentacosa-10,14,16,22-tetraene-6,2'-oxane)-2-one
• (2aE,4E,5'S,6R,6'R,8E,11R,13R,15S,17aR,20R,20aR,20bS)-20,20b-dihydroxy-5',6,6',8,19-pentamethyl-3',4',5',6,6',7,10,11,14,15,17a,20,20a,20b-tetradecahydro-2H,17H-spiro(11,15-methanofuro(4,3,2-pq)(2,6)benzodioxacyclooctadecine-13,2'-pyran)-17-one
• RefChem:906257
• 207B6WP2MZ
• DTXCID3032129
• CHEBI:39225
• mixture of milbemycins A3 and A4
• E-187
• 610-705-0
• MILBEMECTIN A3
• Milbemycin
• Milbemycins
• Milbemycin alpha4
• Milbemycin alpha13
• Milbemycin alpha14
• Milbemectin [ISO]
• Mesa
• 51570-36-6
• Matsuguard
• Ultiflora
• C31H44O7
• Milbemycin alpha15
• Antibiotic B 41A3
• Gowan 1725
• UNII-C76Y8Z9GEX
• Milbemectin M.A3
• GWN 1725
• Milbemectin A3 10 microg/mL in Acetonitrile
• MILBEMECTIN [HSDB]
• MILBEMYCIN .ALPHA.1
• MILBEMYCIN A3 [MI]
• orb1694347
• SCHEMBL1685054
• CHEMBL2272396
• (2R,2a'E,2a1'S,4'E,5S,6R,6'R,8'E,11'R,15'S,17a'R,20'R,20a'R)-2a1',20'-Dihydroxy-5,6,6',8',19'-pentamethyl-2a1',3,4,5,6,6',7',10',11',14',15',17a',20',20a'-tetradecahydro-2'H,17'H-spiro[pyran-2,13'-[11,15]methano[1,5]dioxacyclooctadecino[9,8,7-cd]benzofuran]-17'-one
• EX-A6840
• Milbemycin B, 5-O-demethyl-28-deoxy-6-28-epoxy-25-methyl-, (6R,25R)-
• MSK25036-100A
• FM157340
• HY-130423
• CS-0107719
• C18557
• H36798
• MILBEMYCIN OXIME IMPURITY B [EP IMPURITY]
• Milbemectin A3 Solution in Acetonitrile, 100_g/mL
• Q27119774
• Milbemycin B, 5-O-demethyl-28-deoxy-6,28-epoxy-25-methyl-, (6R,25R)-
• (1R,4S,5'S,6R,6'R,8R,10E,13R,14E,16E,20R,21R,24S)-21,24-dihydroxy-5',6',11,13,22-pentamethyl-spiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-tetrahydropyran]-2-one
• [2'R,2a(3)E,4E,5'S,6R,6'R,8E,11R,15S,17aR,20R,20aR,20bS]-20,20b-Dihydroxy-5',6,6',8,19-pentamethyl-6,7,10,11,14,15,17a,20,20a,20b-decahydro-2H,17H-spiro[11,15-methanofuro[4,3,2-pq][2,6]benzodioxacyclooctadecine-13,2'-oxan]-17-one
• 122666-95-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9586	95.86%
Caco-2	-	0.7657	76.57%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8427	84.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8587	85.87%
OATP1B3 inhibitior	+	0.9390	93.90%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6352	63.52%
BSEP inhibitior	+	0.8750	87.50%
P-glycoprotein inhibitior	+	0.7560	75.60%
P-glycoprotein substrate	+	0.8321	83.21%
CYP3A4 substrate	+	0.7196	71.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8808	88.08%
CYP3A4 inhibition	-	0.9299	92.99%
CYP2C9 inhibition	-	0.9412	94.12%
CYP2C19 inhibition	-	0.9542	95.42%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8538	85.38%
CYP2C8 inhibition	+	0.6933	69.33%
CYP inhibitory promiscuity	-	0.9126	91.26%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4624	46.24%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9477	94.77%
Skin irritation	+	0.5962	59.62%
Skin corrosion	-	0.9312	93.12%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4131	41.31%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.7500	75.00%
skin sensitisation	-	0.8995	89.95%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5910	59.10%
Acute Oral Toxicity (c)	III	0.6920	69.20%
Estrogen receptor binding	+	0.7825	78.25%
Androgen receptor binding	+	0.7774	77.74%
Thyroid receptor binding	-	0.5126	51.26%
Glucocorticoid receptor binding	+	0.8237	82.37%
Aromatase binding	+	0.6902	69.02%
PPAR gamma	+	0.6543	65.43%
Honey bee toxicity	+	0.9256	92.56%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9759	97.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.64%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.92%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.62%	96.77%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	91.33%	86.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.91%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.12%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.98%	100.00%
CHEMBL1871	P10275	Androgen Receptor	88.69%	96.43%
CHEMBL1902	P62942	FK506-binding protein 1A	88.43%	97.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.27%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.61%	99.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.47%	97.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.39%	89.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.09%	94.80%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	82.08%	98.46%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.99%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.78%	94.00%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	81.32%	98.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 9828343
• LOTUS: LTS0106201
• wikiData: Q27119774