3,3-dimethyl-8-morpholino-6-(phenethylthio)-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carbonitrile

ID: ALA3401827

PubChem CID: 1289417

Max Phase: Preclinical

Molecular Formula: C23H27N3O2S

Molecular Weight: 409.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Cc2c(C#N)c(SCCc3ccccc3)nc(N3CCOCC3)c2CO1

Standard InChI:  InChI=1S/C23H27N3O2S/c1-23(2)14-18-19(15-24)22(29-13-8-17-6-4-3-5-7-17)25-21(20(18)16-28-23)26-9-11-27-12-10-26/h3-7H,8-14,16H2,1-2H3

Standard InChI Key:  CITLGGQQUFMBKB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6176   -0.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5647   -1.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2876   -2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805   -4.1981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -1.4966    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.1025    1.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8060    0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919    2.9980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5891    3.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853    5.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844    5.9982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127    5.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089    3.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 15  1  0
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 19 20  1  0
 20 21  2  0
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 24 25  1  0
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 26 27  1  0
 27 28  1  0
 28 29  1  0
  1 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3401827

   3,3-Dimethyl-8-morpholin-4-yl-6-(2-phenylethylsulfanyl)-1,4-dihydropyrano[3,4-c]pyridine-5-carbonitrile

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: 409.56

Molecular Weight (Monoisotopic): 409.1824

AlogP: 3.98

#Rotatable Bonds: 5

Polar Surface Area: 58.38

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.50

CX LogP: 4.84

CX LogD: 4.84

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -1.52

References

1. Nguyen ST, Kwasny SM, Ding X, Cardinale SC, McCarthy CT, Kim HS, Nikaido H, Peet NP, Williams JD, Bowlin TL, Opperman TJ..  (2015)  Structure-activity relationships of a novel pyranopyridine series of Gram-negative bacterial efflux pump inhibitors.,  23  (9): [PMID:25818767] [10.1016/j.bmc.2015.03.016]

2. Schillaci D, Spanò V, Parrino B, Carbone A, Montalbano A, Barraja P, Diana P, Cirrincione G, Cascioferro S..  (2017)  Pharmaceutical Approaches to Target Antibiotic Resistance Mechanisms.,  60  (20): [PMID:28594170] [10.1021/acs.jmedchem.7b00215]

3. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

Source

Source(2):

• Scientific Literature
• CO-ADD antimicrobial screening data