SID85285694

ID: ALA1712445

PubChem CID: 44251503

Max Phase: Preclinical

Molecular Formula: C19H17N3O5

Molecular Weight: 367.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Oc1ccccc1)C(=O)Nc1nnc(-c2ccc3c(c2)OCCO3)o1

Standard InChI:  InChI=1S/C19H17N3O5/c1-12(26-14-5-3-2-4-6-14)17(23)20-19-22-21-18(27-19)13-7-8-15-16(11-13)25-10-9-24-15/h2-8,11-12H,9-10H2,1H3,(H,20,22,23)

Standard InChI Key:  HKTKPNWKGKKNNU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -0.7671    0.4665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7113    1.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7113    2.9370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3519   -1.3849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6808    0.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    1.6225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4523    1.0094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3754   -0.4587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5678    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8534    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9968    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9968    2.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0398    0.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2823    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5678    2.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2823    2.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959   -0.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5314   -1.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4257    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4257    2.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -2.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0465   -1.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079   -2.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2025   -2.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8435   -2.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5381   -3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586   -3.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0
  1 13  1  0
  2 11  1  0
  2 19  1  0
  3 12  1  0
  3 20  1  0
  4 18  1  0
  4 21  1  0
  5 17  2  0
  6  7  1  0
  6 10  2  0
  7 13  2  0
  8 13  1  0
  8 17  1  0
  9 10  1  0
  9 14  2  0
  9 15  1  0
 11 12  2  0
 11 14  1  0
 12 16  1  0
 15 16  2  0
 17 18  1  0
 18 22  1  0
 19 20  1  0
 21 23  2  0
 21 24  1  0
 23 25  1  0
 24 26  2  0
 25 27  2  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1712445

   N-[5-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3,4-oxadiazol-2-yl]-2-phenoxypropanamide

Molecule Features

Natural Product: No

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: 367.36

Molecular Weight (Monoisotopic): 367.1168

AlogP: 2.91

#Rotatable Bonds: 5

Polar Surface Area: 95.71

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.97

CX Basic pKa: ┄

CX LogP: 2.50

CX LogD: 1.99

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: -1.59

References

1. PubChem BioAssay data set, 

2. Chemin, J J, Monteil, A A, Perez-Reyes, E E, Nargeot, J J and Lory, P P.  2001-12-17  Direct inhibition of T-type calcium channels by the endogenous cannabinoid anandamide.  [PMID:11742980]

3. Santi, Celia M CM and 8 more authors.  2002-01-15  Differential inhibition of T-type calcium channels by neuroleptics.  [PMID:11784784]

4. Xiang, Zixiu Z and 24 more authors.  2011-12-21  The Discovery and Characterization of ML218: A Novel, Centrally Active T-Type Calcium Channel Inhibitor with Robust Effects in STN Neurons and in a Rodent Model of Parkinson's Disease.  [PMID:22368764]

5. Giordanetto, Fabrizio F and 15 more authors.  2013-01-01  Discovery of N-[[1-[2-(tert-butylcarbamoylamino)ethyl]-4-(hydroxymethyl)-4-piperidyl]methyl]-3,5-dichloro-benzamide as a selective T-type calcium channel (Cav3.2) inhibitor.  [PMID:23200256]

6. Zhang, Qingwei Q, Xia, Zhiren Z, Joshi, Shailen S, Scott, Victoria E VE and Jarvis, Michael F MF.  2015-06-11  Optimization of ADME Properties for Sulfonamides Leading to the Discovery of a T-Type Calcium Channel Blocker, ABT-639.  [PMID:26101566]

7. Siegrist, Romain R and 13 more authors.  2016-12-08  Structure-Activity Relationship, Drug Metabolism and Pharmacokinetics Properties Optimization, and in Vivo Studies of New Brain Penetrant Triple T-Type Calcium Channel Blockers.  [PMID:27933950]

8. Teleb, Mohamed and 7 more authors.  2017-03-15  Synthesis and biological evaluation of novel N3-substituted dihydropyrimidine derivatives as T-type calcium channel blockers and their efficacy as analgesics in mouse models of inflammatory pain.  [PMID:28233679]

9. Hong, Jin Ri JR, Choi, Young Jin YJ, Keum, Gyochang G and Nam, Ghilsoo G.  2017-09-01  Synthesis and diabetic neuropathic pain-alleviating effects of 2N-(pyrazol-3-yl)methylbenzo[d]isothiazole-1,1-dioxide derivatives.  [PMID:28720324]

10. Nam, Yunchan and 10 more authors.  2020-06-01  Synthesis and cytotoxic effects of 2-thio-3,4-dihydroquinazoline derivatives as novel T-type calcium channel blockers.  [PMID:32327350]

Source

Source(1):

• PubChem BioAssays