2-(1-(3-(9-amino-2,3-dihydro-[1,4]dioxino[2,3-g]thieno[2,3-b]quinoline-8-carboxamido)phenyl)ethylideneaminooxy)acetic acid

ID: ALA3261353

PubChem CID: 86763876

Max Phase: Preclinical

Molecular Formula: C24H20N4O6S

Molecular Weight: 492.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=N\OCC(=O)O)c1cccc(NC(=O)c2sc3nc4cc5c(cc4cc3c2N)OCCO5)c1

Standard InChI:  InChI=1S/C24H20N4O6S/c1-12(28-34-11-20(29)30)13-3-2-4-15(7-13)26-23(31)22-21(25)16-8-14-9-18-19(33-6-5-32-18)10-17(14)27-24(16)35-22/h2-4,7-10H,5-6,11,25H2,1H3,(H,26,31)(H,29,30)/b28-12+

Standard InChI Key:  BISUCKVAKOBZCH-KVSWJAHQSA-N

Molfile:  

     RDKit          2D

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    2.4016  -19.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1068  -20.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1034  -20.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8054  -21.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124  -19.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5189  -20.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5129  -20.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2879  -21.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7730  -20.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2976  -19.8672    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5901  -20.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9935  -21.2481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0039  -19.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8107  -21.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2090  -21.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0254  -21.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4400  -21.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0322  -20.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6963  -20.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918  -20.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858  -19.7055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798  -20.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2843  -20.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948  -21.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347  -21.9679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4435  -19.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2607  -19.8504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0376  -19.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6720  -19.1442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4891  -19.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9004  -18.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7176  -18.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4945  -17.7319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 22  2  2  0
 21  1  2  0
  1  4  1  0
  3  2  1  0
  3  4  1  0
  3  6  2  0
  4  5  2  0
  5  8  1  0
  7  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11  7  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
  9 27  1  0
 19 28  1  0
 28 29  2  0
 28 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3261353

   2-[(E)-1-[3-[(15-amino-4,7-dioxa-13-thia-11-azatetracyclo[8.7.0.03,8.012,16]heptadeca-1(17),2,8,10,12(16),14-hexaene-14-carbonyl)amino]phenyl]ethylideneamino]oxyacetic acid

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: 492.51

Molecular Weight (Monoisotopic): 492.1104

AlogP: 3.88

#Rotatable Bonds: 6

Polar Surface Area: 145.36

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.54

CX Basic pKa: 2.87

CX LogP: 2.93

CX LogD: -0.01

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.27

Np Likeness Score: -1.62

References

1. Rechfeld F, Gruber P, Kirchmair J, Boehler M, Hauser N, Hechenberger G, Garczarczyk D, Lapa GB, Preobrazhenskaya MN, Goekjian P, Langer T, Hofmann J..  (2014)  Thienoquinolines as novel disruptors of the PKCε/RACK2 protein-protein interaction.,  57  (8): [PMID:24712764] [10.1021/jm401605c]

Source

Source(1):

• Scientific Literature