(E)-N-(4,18-Dimethoxy-2-oxa-tricyclo[13.3.1.1(3,7)]icosa-1(19),3,5,7(20),15,17-hexaen-10-yl)-3-(4-fluoro-phenyl)-acrylamide

ID: ALA4522592

PubChem CID: 155543621

Max Phase: Preclinical

Molecular Formula: C30H32FNO4

Molecular Weight: 489.59

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2cc1Oc1cc(ccc1OC)CCC(NC(=O)/C=C/c1ccc(F)cc1)CCCC2

Standard InChI:  InChI=1S/C30H32FNO4/c1-34-26-16-10-22-5-3-4-6-25(32-30(33)18-12-21-7-13-24(31)14-8-21)15-9-23-11-17-27(35-2)29(20-23)36-28(26)19-22/h7-8,10-14,16-20,25H,3-6,9,15H2,1-2H3,(H,32,33)/b18-12+

Standard InChI Key:  GDCNRQJHTXOYQS-LDADJPATSA-N

Molfile:  

 
     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    5.9745  -18.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133  -21.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4347  -19.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0106  -16.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4128  -16.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9557  -20.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9438  -16.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9920  -17.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3739  -19.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7297  -19.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7025  -17.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296  -20.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1516  -18.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9240  -18.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7075  -21.0340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250  -17.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9050  -19.6008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6818  -18.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3971  -18.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5003  -18.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2804  -18.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1832  -16.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7623  -16.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620  -19.5782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2299  -16.7874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6293  -17.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4465  -17.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2116  -18.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8459  -18.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6630  -18.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0593  -18.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8757  -18.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2942  -18.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8905  -17.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0754  -17.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1114  -18.2674    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 24  3  1  0
  6  9  2  0
 17 10  1  0
 15  2  1  0
 11 21  1  0
 16 11  2  0
 21 18  2  0
 22  4  1  0
 23  7  1  0
 14 16  1  0
  5  4  1  0
 18 20  1  0
 18 24  1  0
  7 16  1  0
 12  6  1  0
  1 19  1  0
  8 19  1  0
  9  1  1  0
 13 10  1  0
 20 14  2  0
  1 13  2  0
 12 15  1  0
 20 17  1  0
  8  5  1  0
 10 12  2  0
 22 23  1  0
  5 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 33 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4522592

   ---

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: 489.59

Molecular Weight (Monoisotopic): 489.2315

AlogP: 6.49

#Rotatable Bonds: 5

Polar Surface Area: 56.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.77

CX LogD: 6.77

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.42

Np Likeness Score: 0.29

References

1. Lin H, Bruhn DF, Maddox MM, Singh AP, Lee RE, Sun D..  (2016)  Synthesis and antibacterial evaluation of macrocyclic diarylheptanoid derivatives.,  26  (16): [PMID:27406794] [10.1016/j.bmcl.2016.06.075]

Source

Source(1):

• Scientific Literature