4-oxo-N-((3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)methyl)-3,4,5,6,7,8,9,10-octahydrocycloocta[4,5]thieno[2,3-d]pyrimidine-2-carboxamide

ID: ALA4088060

PubChem CID: 59379730

Max Phase: Preclinical

Molecular Formula: C22H22N4O4S

Molecular Weight: 438.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1COc2ccc(CNC(=O)c3nc4sc5c(c4c(=O)[nH]3)CCCCCC5)cc2N1

Standard InChI:  InChI=1S/C22H22N4O4S/c27-17-11-30-15-8-7-12(9-14(15)24-17)10-23-21(29)19-25-20(28)18-13-5-3-1-2-4-6-16(13)31-22(18)26-19/h7-9H,1-6,10-11H2,(H,23,29)(H,24,27)(H,25,26,28)

Standard InChI Key:  SPBFQBQZZSCDQE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   11.1321   -7.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8412   -8.2714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5503   -7.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5503   -7.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8412   -6.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1321   -7.0456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3234   -8.1175    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4272   -8.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4272   -9.0886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7181   -7.8628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0090   -8.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1809   -6.6370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1809   -5.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8859   -5.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5950   -5.8198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5950   -6.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8859   -7.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2999   -7.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2999   -7.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5950   -8.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8859   -7.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8859   -4.5940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8412   -5.8198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9154   -5.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3983   -6.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2731   -7.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1106   -5.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4499   -5.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3247   -6.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8077   -7.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6123   -7.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
 30  7  1  0
  3  7  1  0
  4 29  1  0
  8  9  2  0
  8 10  1  0
  1  8  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 12 17  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 17 21  2  0
 16 18  2  0
 14 22  2  0
 11 19  1  0
 10 11  1  0
  5 23  2  0
 24 25  1  0
 25 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088060

   3-oxo-N-[(3-oxo-4H-1,4-benzoxazin-6-yl)methyl]-8-thia-4,6-diazatricyclo[7.6.0.02,7]pentadeca-1(9),2(7),5-triene-5-carboxamide

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: 438.51

Molecular Weight (Monoisotopic): 438.1362

AlogP: 2.90

#Rotatable Bonds: 3

Polar Surface Area: 113.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.43

CX Basic pKa: 0.55

CX LogP: 3.08

CX LogD: 2.84

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -1.70

References

1. Mahasenan KV, Bastian M, Gao M, Frost E, Ding D, Zorina-Lichtenwalter K, Jacobs J, Suckow MA, Schroeder VA, Wolter WR, Chang M, Mobashery S..  (2017)  Exploitation of Conformational Dynamics in Imparting Selective Inhibition for Related Matrix Metalloproteinases.,  8  (6): [PMID:28626528] [10.1021/acsmedchemlett.7b00130]

Source

Source(1):

• Scientific Literature