(S)-7-Chloro-2-[methoxycarbonyl-(4-trifluoromethoxy-phenyl)-aminocarbonyl]-2,5-dihydro-3H-indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylic acid methyl ester

ID: ALA197676

Chembl Id: CHEMBL197676

Cas Number: 174060-41-4

PubChem CID: 107720

Max Phase: Unknown

First Approval: 2011

Molecular Formula: C22H17ClF3N3O7

Molecular Weight: 527.84

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Advion | Avaunt | Indoxacarb (ema epar: veterinary) | Provaunt | Steward | DPX-KN128 | Indoxacarb|173584-44-6|(S)-Indoxacarb|Steward|Insecticide|Provaunt|Advion|Avaunt|Indoxacarb [ISO]|174060-41-4|52H0D26MWR|Indeno(1,2-e)(1,3,4)oxadiazine-4a(3H)-carboxylic acid, 7-chloro-2,5-dihydro-2-(((methoxycarbonyl)(4-(trifluoromethoxy)phenyl)amino)carbonyl)-, methyl ester, (4aS)-|DTXSID1032690|CHEBI:38630|Indoxacarb (JAN)|methyl (4aS)-7-chloro-2-[methoxycarbonyl-[4-(trifluoromethoxy)phenyl]carbamoyl]-3,5-dShow More⌵

Trade Names(1): Activyl

Canonical SMILES:  COC(=O)N(C(=O)N1CO[C@@]2(C(=O)OC)Cc3cc(Cl)ccc3C2=N1)c1ccc(OC(F)(F)F)cc1

Standard InChI:  InChI=1S/C22H17ClF3N3O7/c1-33-18(30)21-10-12-9-13(23)3-8-16(12)17(21)27-28(11-35-21)19(31)29(20(32)34-2)14-4-6-15(7-5-14)36-22(24,25)26/h3-9H,10-11H2,1-2H3/t21-/m0/s1

Standard InChI Key:  VBCVPMMZEGZULK-NRFANRHFSA-N

Alternative Forms

1. Parent:

   

   ALA197676

   INDOXACARB

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 527.84

Molecular Weight (Monoisotopic): 527.0707

AlogP: 4.09

#Rotatable Bonds: 3

Polar Surface Area: 106.97

Molecular Species: NEUTRAL

HBA: 8

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 5.39

CX LogD: 5.39

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.55

Np Likeness Score: 0.01

References

1. Lahm GP, Selby TP, Freudenberger JH, Stevenson TM, Myers BJ, Seburyamo G, Smith BK, Flexner L, Clark CE, Cordova D..  (2005)  Insecticidal anthranilic diamides: a new class of potent ryanodine receptor activators.,  15  (22): [PMID:16165355] [10.1016/j.bmcl.2005.08.034]

2. Brévault T, Oumarou Y, Achaleke J, Vaissayre M, Nibouche S..  (2009)  Initial activity and persistence of insecticides for the control of bollworms (Lepidoptera: Noctuidae) in cotton crops,  28  (5): [10.1016/j.cropro.2008.12.006]

3. Achaleke J, Martin T, Ghogomu RT, Vaissayre M, Brévault T..  (2009)  Esterase-mediated resistance to pyrethroids in field populations of Helicoverpa armigera (Lepidoptera: Noctuidae) from Central Africa.,  65  (10): [PMID:19548293] [10.1002/ps.1807]

4. Duke SO, Cantrell CL, Meepagala KM, Wedge DE, Tabanca N, Schrader KK..  (2010)  Natural toxins for use in pest management.,  2  (8): [PMID:22069667] [10.3390/toxins2081943]

5. Hannig GT, Ziegler M, Marçon PG..  (2009)  Feeding cessation effects of chlorantraniliprole, a new anthranilic diamide insecticide, in comparison with several insecticides in distinct chemical classes and mode-of-action groups.,  65  (9): [PMID:19449341] [10.1002/ps.1781]

6. Zhang Y, Wang JS, Wei DD, Gu YC, Wang XB, Kong LY..  (2013)  Bioactive terpenoids from the fruits of Aphanamixis grandifolia.,  76  (6): [PMID:23772699] [10.1021/np400126q]

7. PubChem BioAssay data set, 

8. European Medicines Agency, 

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• European Medicines Agency