Ivermectin B1a

Details

• Internal ID: a079a3c2-fa90-437b-ba0f-c43775a13659
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues > Milbemycins
• IUPAC Name: (1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-[(2S)-butan-2-yl]-21,24-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-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(CCC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5O)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](CC[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]5O)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/C48H74O14/c1-11-25(2)43-28(5)17-18-47(62-43)23-34-20-33(61-47)16-15-27(4)42(26(3)13-12-14-32-24-55-45-40(49)29(6)19-35(46(51)58-34)48(32,45)52)59-39-22-37(54-10)44(31(8)57-39)60-38-21-36(53-9)41(50)30(7)56-38/h12-15,19,25-26,28,30-31,33-45,49-50,52H,11,16-18,20-24H2,1-10H3/b13-12+,27-15+,32-14+/t25-,26-,28-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40+,41-,42-,43+,44-,45+,47+,48+/m0/s1
• InChI Key: AZSNMRSAGSSBNP-XPNPUAGNSA-N
• Popularity: 11,985 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₄O₁₄
• Molecular Weight: 875.10 g/mol
• Exact Mass: 874.50785703 g/mol
• Topological Polar Surface Area (TPSA): 170.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 5.60
• H-Bond Acceptor: 14
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• IVERMECTIN
• Dihydroavermectin B1a
• 70288-86-7
• 22,23-Dihydroavermectin B1a
• 70161-11-4
• 71827-03-7
• Ivermectin Component B1a
• avermectin H2B1a
• C48H74O14
• MK-933
• UNII-91Y2202OUW
• 5-O-demethyl-22,23-dihydroavermectin A1a
• DTXSID8023181
• CHEBI:63941
• 91Y2202OUW
• Soolantra
• (1R,4S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-[(2S)-butan-2-yl]-21,24-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-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
• (2ae,4e,5's,6s,6'r,7s,8e,11r,13r,15s,17ar,20r,20ar,20bs)-6'-[(2s)-Butan-2-Yl]-20,20b-Dihydroxy-5',6,8,19-Tetramethyl-17-Oxo-3',4',5',6,6',10,11,14,15,17,17a,20,20a,20b-Tetradecahydro-2h,7h-Spiro[11,15-Methanofuro[4,3,2-Pq][2,6]benzodioxacyclooctadecine-13,2'-Pyran]-7-Yl 2,6-Dideoxy-4-O-(2,6-Dideoxy-3-O-Methyl-Alpha-L-Arabino-Hexopyranosyl)-3-O-Methyl-Alpha-L-Arabino-Hexopyranoside
• Sklice
• 22,23-Dihydroavermectin B(1)a
• Avermectin A1a, 5-O-demethyl-22,23-dihydro-
• EINECS 276-046-2
• Ivermectin B1a-d2
• BRN 4643153
• 22,23-Dihydro-5-O-demethylavermectin A1a
• Ivermectin [USAN:INN:BAN]
• C48-H74-O14
• NCGC00163233-01
• C48H74O14.C47H72O14
• Ivermectin (IVM)
• IVM
• dihydro avermectin Bla
• Ivermectin component B
• Avermectin A1a, 22,23-dihydro-5-O-demethyl-
• C48-H74-O14.C47-H72-O14
• H2B1a
• Prestwick3_000156
• Ivermectin (MK-0933)
• BSPBio_000292
• SCHEMBL312795
• BPBio1_000322
• CHEMBL263291
• DTXCID303181
• CHEBI:94551
• AZSNMRSAGSSBNP-XPNPUAGNSA-N
• HMS2089M09
• HMS2095O14
• HMS3712O14
• WCA82703
• Tox21_112034
• BDBM50409816
• HB1958
• s1351
• AKOS027470116
• IVERMECTIN COMPONENT B1A [MI]
• AC-6014
• AT36525
• CCG-220156
• NCGC00186639-01
• NCGC00186639-03
• AS-14167
• BI166167
• CAS-71827-03-7
• HY-126937
• AB00513813
• CS-0108408
• 22,23-DIHYDROAVERMECTIN B1A; IVERMECTIN
• AB00513813-02
• AB00513813-03
• AB00513813_04
• Ivermectin, Antibiotic for Culture Media Use Only
• Q-201262
• BRD-K24652731-001-02-7
• BRD-K85554912-001-08-9
• Q27132923
• Ivermectin, British Pharmacopoeia (BP) Reference Standard
• Ivermectin, European Pharmacopoeia (EP) Reference Standard
• Ivermectin, United States Pharmacopeia (USP) Reference Standard
• Ivermectin, Pharmaceutical Secondary Standard; Certified Reference Material
• -oxo-3',4',5',6,6',10,11,14,15,17,17a,20,20a,20b-tetradecahydro-2H,7H-spiro[11,15-methanofuro[4,3,2-pq][2,6]benzodioxacy
• ;(2aE,4E,5'S,6S,6'R,7S,8E,11R,13R,15S,17aR,20R,20aR,20bS)-6'-[(2S)-butan-2-yl]-20,20b-dihydroxy-5',6,8,19-tetramethyl-17
• clooctadecine-13,2'-pyran]-7-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)-3-O-methyl-alpha-L-arabino-hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9676	96.76%
Caco-2	-	0.8729	87.29%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8053	80.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8624	86.24%
OATP1B3 inhibitior	+	0.9333	93.33%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9629	96.29%
P-glycoprotein inhibitior	+	0.7776	77.76%
P-glycoprotein substrate	+	0.9343	93.43%
CYP3A4 substrate	+	0.7463	74.63%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8929	89.29%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.7452	74.52%
CYP inhibitory promiscuity	-	0.6859	68.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5219	52.19%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9112	91.12%
Skin irritation	+	0.5259	52.59%
Skin corrosion	-	0.9409	94.09%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7425	74.25%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.9118	91.18%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8315	83.15%
Acute Oral Toxicity (c)	III	0.4494	44.94%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.8349	83.49%
Thyroid receptor binding	+	0.5258	52.58%
Glucocorticoid receptor binding	+	0.7657	76.57%
Aromatase binding	+	0.6227	62.27%
PPAR gamma	+	0.7844	78.44%
Honey bee toxicity	+	0.8989	89.89%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9747	97.47%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	398.1 nM	Potency	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	3.3 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.11%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.63%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.72%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.12%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.63%	96.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.44%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	92.12%	95.93%
CHEMBL1871	P10275	Androgen Receptor	92.06%	96.43%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.58%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.74%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.07%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.37%	94.45%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.90%	96.47%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.49%	96.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.86%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.59%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.23%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.13%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.08%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.29%	95.89%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	83.44%	98.46%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.09%	95.89%
CHEMBL4208	P20618	Proteasome component C5	82.95%	90.00%
CHEMBL255	P29275	Adenosine A2b receptor	81.10%	98.59%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.82%	97.33%
CHEMBL2581	P07339	Cathepsin D	80.78%	98.95%

Plants that contains it

• Veratrum nigrum
• Veronicastrum sibiricum

Cross-Links

• PubChem: 6321424
• NPASS: NPC183353
• LOTUS: LTS0233194
• wikiData: Q27132923