3-(17-Ethyl-3,12-dioxo-13-oxa-4,11-diaza-tricyclo[14.2.2.1(6,10)]henicosa-1(19),6,8,10(21),16(20),17-hexaen-2-ylamino)-benzamide

ID: ALA4097785

PubChem CID: 57842563

Max Phase: Preclinical

Molecular Formula: C27H28N4O4

Molecular Weight: 472.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc2ccc1CCOC(=O)Nc1cccc(c1)CNC(=O)C2Nc1cccc(C(N)=O)c1

Standard InChI:  InChI=1S/C27H28N4O4/c1-2-18-14-20-10-9-19(18)11-12-35-27(34)31-22-7-3-5-17(13-22)16-29-26(33)24(20)30-23-8-4-6-21(15-23)25(28)32/h3-10,13-15,24,30H,2,11-12,16H2,1H3,(H2,28,32)(H,29,33)(H,31,34)

Standard InChI Key:  ZUPUKEKKNTYECE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.7341  -11.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4094  -12.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0870  -11.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0871  -10.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7627  -12.1108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4407  -11.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1164  -12.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1399  -11.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8157  -12.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4889  -11.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4877  -10.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8090  -10.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4317   -8.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4351   -9.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1116   -9.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1129  -10.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4389  -10.9403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7642  -10.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7579   -9.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4534   -9.7699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1141  -12.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588  -12.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845  -11.7205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0579  -12.8902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0477   -9.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0427   -8.5575    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  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
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 12 13  2  0
 13 14  1  0
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 15 16  1  0
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 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 21  1  0
 23 22  1  0
 24 23  2  0
 25 24  1  0
 26 25  2  0
  8 26  1  0
 27 26  1  0
 28 27  2  0
 23 28  1  0
 19 29  2  0
  9 30  2  0
  2 31  1  0
 31 32  1  0
 31 33  2  0
 28 34  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097785

   3-[(17-Ethyl-3,12-dioxo-13-oxa-4,11-diazatricyclo[14.2.2.16,10]henicosa-1(18),6(21),7,9,16,19-hexaen-2-yl)amino]benzamide

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: 472.55

Molecular Weight (Monoisotopic): 472.2111

AlogP: 3.92

#Rotatable Bonds: 4

Polar Surface Area: 122.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.53

CX Basic pKa: 0.41

CX LogP: 3.71

CX LogD: 3.71

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.46

Np Likeness Score: 0.28

References

1. Wurtz NR, Parkhurst BL, DeLucca I, Glunz PW, Jiang W, Zhang X, Cheney DL, Bozarth JM, Rendina AR, Wei A, Harper T, Luettgen JM, Wu Y, Wong PC, Seiffert DA, Wexler RR, Priestley ES..  (2017)  Neutral macrocyclic factor VIIa inhibitors.,  27  (12): [PMID:28460818] [10.1016/j.bmcl.2017.04.008]

Source

Source(1):

• Scientific Literature