ChemSpider 2D Image | Ivermectin B1a | C48H74O14

Ivermectin B1a

  • Molecular FormulaC48H74O14
  • Average mass875.093 Da
  • Monoisotopic mass874.507874 Da
  • ChemSpider ID16736314

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 20 of 20 defined stereocentres

More details:

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

Ivermectin B1a
Ivermectin [INN] [Wiki] [REDIRECT]
(1'R,2R,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-Butanyl]-21',24'-dihydroxy-12'-{[(2R,4S,5S,6S)-5-{[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-5,11',13',22'-tetramethyl-3,4,5,6-tetrahydro-2'H-spiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]-2'-one
(1'R,2R,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-Butanyl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3,4,5,6-tetrahydrospiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1. ;14,8.020,24]pentacosa[10,14,16,22]tetraen]-12'-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside [ACD/IUPAC Name]
(1'R,2R,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-Butanyl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3,4,5,6-tetrahydrospiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]-12'-yl 2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
(1'R,2R,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-Butanyl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-2'-oxo-3,4,5,6-tetrahydrospiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]-12'-yl-2,6-dideoxy-4-O-(2,6-dideoxy-3-O-methyl-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
(2aE,4E,5'S,6S,6'R,7S,8E,11R,13R,15S,17aR,20R,20aR,20bS)-20,20b-dihydroxy-5',6,8,19-tetramethyl-6'-[(1S)-1-methylpropyl]-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-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
(2aE,4E,5'S,6S,6'R,7S,8E,11R,13R,15S,17aR,20R,20aR,20bS)-6'-(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-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
(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-α-L-arabino-hexopyranosyl)-3-O-methyl-α-L-arabino-hexopyranoside
2,6-Didésoxy-4-O-(2,6-didésoxy-3-O-méthyl-α-L-arabino-hexopyranosyl)-3-O-méthyl-α-L-arabino-hexopyranoside de (1'R,2R,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-butanyl]-21',24'-dihydroxy-5,11',13',22'-tétraméthyl-2'-oxo-3,4,5,6-tétrahydrospiro[pyran-2,6'-[3,7,19]trioxatétracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tétraén]-12'-yle [French]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

91Y2202OUW [DBID]
CHEBI:63941 [DBID]
MK-933 [DBID]
BRN 4643153 [DBID]
UNII:91Y2202OUW [DBID]
UNII-91Y2202OUW [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Toxicity:

      Drug; Avermectin; Metabolite; Lachrymator; Synthetic Compound; Antiparasitic Agent Toxin, Toxin-Target Database T3D4995

    • Chemical Class:

      A macrocyclic lactone that is avermectin B<smallsub>1a</smallsub> in which the double bond present in the spirocyclic ring system has been reduced to a single bond. It is the major component of iverme ctin. ChEBI CHEBI:63941
      A macrocyclic lactone that is avermectin B1a in which the double bond present in the spirocyclic ring system has been reduced to a single bond. It is the major component of ivermectin. ChEBI CHEBI:63941

    • Bio Activity:

      <p>Ivermectin (IVM) is an anthelmintic and positive allosteric modulator of &alpha;7 nicotinic acetylcholine receptors. It also shows activity at purinergic P2X<sub>4</sub>&nbsp;receptors. <p><br />Ivermectin modulates glutamate- and GABA-activated chloride channels and potentiates glycine-gated currents at low concentrations (30 nM). <p><br /><span style=text-decoration: underline;>Use in chemogenetics</span></p> <p>Ivermectin selectively activates the chemogenetic glutamate-gated chloride (GluCl) and glycine-gated chloride (GlyCl) channels which silence neuronal activity.</p> Hello Bio HB1958
      <p>Ivermectin (IVM) is an anthelmintic and positive allosteric modulator of &alpha;7 nicotinic acetylcholine receptors. It also shows activity at purinergic P2X<sub>4</sub>&nbsp;receptors. <p><br />Ivermectin modulates glutamate- and GABA-activated chloride channels and potentiates glycine-gated currents at low concentrations (30 nM).</p> <p>Shows antimicrobial, anticancer and antiviral activities. Recently investigated as part of COVID-19 compound repurposing.</p> <p><br /><span style="text-decoration: underline;">Use in chemogenetics</span></p> <p>Ivermectin selectively activates the chemogenetic glutamate-gated chloride (GluCl) and glycine-gated chloride (GlyCl) channels which silence neuronal activity.</p> Hello Bio HB1958
      Ion channels/Ligand-gated ion channel/Glycine Hello Bio HB1958
      Ion channels/Ligand-gated ion channel/Nicotinic AcH/&alpha;7 Hello Bio HB1958
      Ion channels/Ligand-gated ion channel/Purinergic: P2X/P2X<sub>4</sub> Hello Bio HB1958
      Positive allosteric modulator of ž¤7 neuronal nicotinic acetylcholine receptor Hello Bio HB1958
      Type/Biochemicals & small molecules/Agonists & activators Hello Bio HB1958

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 940.4±65.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.6 mmHg at 25°C
Enthalpy of Vaporization: 155.2±6.0 kJ/mol
Flash Point: 267.3±27.8 °C
Index of Refraction: 1.565
Molar Refractivity: 230.7±0.4 cm3
#H bond acceptors: 14
#H bond donors: 3
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 3
ACD/LogP: 6.61
ACD/LogD (pH 5.5): 6.21
ACD/BCF (pH 5.5): 30848.05
ACD/KOC (pH 5.5): 56881.81
ACD/LogD (pH 7.4): 6.21
ACD/BCF (pH 7.4): 30847.61
ACD/KOC (pH 7.4): 56881.00
Polar Surface Area: 170 Å2
Polarizability: 91.5±0.5 10-24cm3
Surface Tension: 51.9±5.0 dyne/cm
Molar Volume: 708.4±5.0 cm3

Click to predict properties on the Chemicalize site


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