ID: ALA465018

Max Phase: Preclinical

Molecular Formula: C11H13NO4

Molecular Weight: 223.23

Molecule Type: Small molecule

Representations

Synonyms (1): Bendiocarb
Synonyms from Alternative Forms(1):

Canonical SMILES:  CNC(=O)Oc1cccc2c1OC(C)(C)O2

Standard InChI:  InChI=1S/C11H13NO4/c1-11(2)15-8-6-4-5-7(9(8)16-11)14-10(13)12-3/h4-6H,1-3H3,(H,12,13)

Standard InChI Key:  XEGGRYVFLWGFHI-UHFFFAOYSA-N

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

Properties

Molecular Weight: 223.23

Molecular Weight (Monoisotopic): 223.0845

AlogP: 1.91

#Rotatable Bonds: 1

Polar Surface Area: 56.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.57

CX LogD: 1.57

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.79

Np Likeness Score: 0.41

References

1. Alali FQ, Liu XX, McLaughlin JL..  (1999)  Annonaceous acetogenins: recent progress.,  62  (3): [PMID:10096871] [10.1021/np980406d]

2. Vincent F, Nguyen MT, Emerling DE, Kelly MG, Duncton MA..  (2009)  Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.,  19  (23): [PMID:19850474] [10.1016/j.bmcl.2009.09.086]

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Hartsel JA, Wong DM, Mutunga JM, Ma M, Anderson TD, Wysinski A, Islam R, Wong EA, Paulson SL, Li J, Lam PC, Totrov MM, Bloomquist JR, Carlier PR..  (2012)  Re-engineering aryl methylcarbamates to confer high selectivity for inhibition of Anopheles gambiae versus human acetylcholinesterase.,  22  (14): [PMID:22738634] [10.1016/j.bmcl.2012.05.103]

7. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP..  (2013)  Structure-based identification of OATP1B1/3 inhibitors.,  83  (6): [PMID:23571415] [10.1124/mol.112.084152]

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. Verma A, Wong DM, Islam R, Tong F, Ghavami M, Mutunga JM, Slebodnick C, Li J, Viayna E, Lam PC, Totrov MM, Bloomquist JR, Carlier PR..  (2015)  3-Oxoisoxazole-2(3H)-carboxamides and isoxazol-3-yl carbamates: Resistance-breaking acetylcholinesterase inhibitors targeting the malaria mosquito, Anopheles gambiae.,  23  (6): [PMID:25684426] [10.1016/j.bmc.2015.01.026]

11. Knutsson S, Engdahl C, Kumari R, Forsgren N, Lindgren C, Kindahl T, Kitur S, Wachira L, Kamau L, Ekström F, Linusson A..  (2018)  Noncovalent Inhibitors of Mosquito Acetylcholinesterase 1 with Resistance-Breaking Potency.,  61  (23): [PMID:30339371] [10.1021/acs.jmedchem.8b01060]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays