(E)-5-(2-(7-Nitro-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)vinyl)furan-2-carboxylic Acid

ID: ALA4541208

PubChem CID: 155551259

Max Phase: Preclinical

Molecular Formula: C13H7N3O6S

Molecular Weight: 333.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(/C=C/c2nc3c([N+](=O)[O-])csc3c(=O)[nH]2)o1

Standard InChI:  InChI=1S/C13H7N3O6S/c17-12-11-10(7(5-23-11)16(20)21)14-9(15-12)4-2-6-1-3-8(22-6)13(18)19/h1-5H,(H,18,19)(H,14,15,17)/b4-2+

Standard InChI Key:  JNBUPKZSCNZUGC-DUXPYHPUSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.4502  -28.6459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660  -28.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1672  -27.4115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4526  -26.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4526  -26.1784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7401  -28.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408  -27.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571  -27.1549    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.4719  -27.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560  -28.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8726  -28.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5814  -28.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017  -29.2702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2480  -29.8779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9022  -29.4394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2880  -28.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3754  -29.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743  -29.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5849  -28.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0397  -28.3181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3978  -28.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8763  -29.5060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7322  -28.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0
  6  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
  2 11  1  0
 11 12  2  0
 13 14  2  0
 13 15  1  0
 10 13  1  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
M  CHG  2  13   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4541208

   ---

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: 333.28

Molecular Weight (Monoisotopic): 333.0056

AlogP: 2.35

#Rotatable Bonds: 4

Polar Surface Area: 139.33

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.14

CX Basic pKa: ┄

CX LogP: 1.62

CX LogD: -1.84

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.55

Np Likeness Score: -1.01

References

1. Shao X, AbdelKhalek A, Abutaleb NS, Velagapudi UK, Yoganathan S, Seleem MN, Talele TT..  (2019)  Chemical Space Exploration around Thieno[3,2-d]pyrimidin-4(3H)-one Scaffold Led to a Novel Class of Highly Active Clostridium difficile Inhibitors.,  62  (21): [PMID:31584822] [10.1021/acs.jmedchem.9b01198]

Source

Source(1):

• Scientific Literature