methyl 3-amino-6-benzyl-5,6,7,8-tetrahydrothieno[2,3-b][1,6]naphthyridine-2-carboxylate

ID: ALA4859518

PubChem CID: 1541101

Max Phase: Preclinical

Molecular Formula: C19H19N3O2S

Molecular Weight: 353.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1sc2nc3c(cc2c1N)CN(Cc1ccccc1)CC3

Standard InChI:  InChI=1S/C19H19N3O2S/c1-24-19(23)17-16(20)14-9-13-11-22(10-12-5-3-2-4-6-12)8-7-15(13)21-18(14)25-17/h2-6,9H,7-8,10-11,20H2,1H3

Standard InChI Key:  AADJALJXYKSCIB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   25.8733  -22.6983    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8715  -21.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1653  -22.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1694  -21.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4694  -21.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7609  -21.4672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7568  -22.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4613  -22.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5802  -21.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5849  -22.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3650  -22.5333    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.8423  -21.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3572  -21.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6052  -20.4301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6617  -21.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0745  -22.5669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0662  -21.1515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6701  -23.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0558  -21.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0611  -20.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7738  -19.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7793  -19.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0737  -18.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3610  -19.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3590  -19.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0
  1 10  2  0
  9  2  2  0
  2  4  1  0
  3  4  2  0
  3  8  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 13 14  1  0
 15 16  1  0
 15 17  2  0
 12 15  1  0
 16 18  1  0
  6 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4859518

   Methyl 3-amino-6-benzyl-5H,6H,7H,8H-thieno[2,3-B]1,6-naphthyridine-2-carboxylate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 353.45

Molecular Weight (Monoisotopic): 353.1198

AlogP: 3.22

#Rotatable Bonds: 3

Polar Surface Area: 68.45

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.89

CX LogP: 3.69

CX LogD: 3.68

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -1.70

References

1. Lee S, Lee S, Cil O, Diez-Cecilia E, Anderson MO, Verkman AS..  (2018)  Nanomolar-Potency 1,2,4-Triazoloquinoxaline Inhibitors of the Kidney Urea Transporter UT-A1.,  61  (7.0): [PMID:29589443] [10.1021/acs.jmedchem.8b00343]

Source

Source(1):

• Scientific Literature