Thieno[3,2-b]pyridine-2-sulfonic acid [1-(1,6-diamino-isoquinolin-7-ylmethyl)-2-oxo-pyrrolidin-3-yl]-amide

ID: ALA85938

PubChem CID: 15546794

Max Phase: Preclinical

Molecular Formula: C21H20N6O3S2

Molecular Weight: 468.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cc2ccnc(N)c2cc1CN1CC[C@H](NS(=O)(=O)c2cc3ncccc3s2)C1=O

Standard InChI:  InChI=1S/C21H20N6O3S2/c22-15-9-12-3-6-25-20(23)14(12)8-13(15)11-27-7-4-16(21(27)28)26-32(29,30)19-10-17-18(31-19)2-1-5-24-17/h1-3,5-6,8-10,16,26H,4,7,11,22H2,(H2,23,25)/t16-/m0/s1

Standard InChI Key:  UORSJJNIHCUTDL-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  1  0  0  0  0  0999 V2000
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    5.7417    0.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292    0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833    0.0708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -1.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833   -1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708   -1.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2542   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  8  1  1
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  4 22  1  0
 32 31  1  0
 17 10  1  0
 23 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA85938

   Thieno[3,2-b]pyridine-2-sulfonic acid [1-(1,6-diamino-isoquinolin-7-ylmethyl)-2-oxo-pyrrolidin-3-yl]-amide

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: 468.56

Molecular Weight (Monoisotopic): 468.1038

AlogP: 2.09

#Rotatable Bonds: 5

Polar Surface Area: 144.30

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.54

CX Basic pKa: 9.34

CX LogP: -0.17

CX LogD: -0.70

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.38

Np Likeness Score: -1.00

References

1. Choi-Sledeski YM, Becker MR, Green DM, Davis R, Ewing WR, Mason HJ, Ly C, Spada A, Liang G, Cheney D, Barton J, Chu V, Brown K, Colussi D, Bentley R, Leadley R, Dunwiddie C, Pauls HW..  (1999)  Aminoisoquinolines: design and synthesis of an orally active benzamidine isostere for the inhibition of factor XA.,  9  (17): [PMID:10498204] [10.1016/s0960-894x(99)00421-7]

2. Pinto DJ, Smallheer JM, Cheney DL, Knabb RM, Wexler RR..  (2010)  Factor Xa inhibitors: next-generation antithrombotic agents.,  53  (17): [PMID:20503967] [10.1021/jm100146h]

Source

Source(1):

• Scientific Literature