(E)-N-Adamantan-1-yl-3-(3-bromo-4,5-dihydroxy-phenyl)-acrylamide

ID: ALA3327356

PubChem CID: 118712241

Max Phase: Preclinical

Molecular Formula: C19H22BrNO3

Molecular Weight: 392.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1cc(O)c(O)c(Br)c1)NC12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C19H22BrNO3/c20-15-6-11(7-16(22)18(15)24)1-2-17(23)21-19-8-12-3-13(9-19)5-14(4-12)10-19/h1-2,6-7,12-14,22,24H,3-5,8-10H2,(H,21,23)/b2-1+

Standard InChI Key:  SFMVMPXRLULXGB-OWOJBTEDSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   10.8105   -5.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1692   -4.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0061   -5.3861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4579   -5.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2533   -5.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7101   -5.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0087   -4.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4521   -3.8757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1737   -4.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042   -4.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069   -3.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7058   -4.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4206   -5.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1370   -4.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1341   -3.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4187   -3.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8521   -5.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5660   -4.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2811   -5.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9949   -4.5932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2824   -5.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9909   -5.0101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9923   -3.3585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4187   -2.5251    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  2  4  1  0
  3  5  1  0
  4  6  1  0
  5  6  1  0
  7  8  1  0
  3  7  1  0
  2  9  1  0
  6 10  1  0
 10  8  1  0
  8  9  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 12 22  1  0
 11 23  1  0
 20  6  1  0
 16 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3327356

   ---

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: 392.29

Molecular Weight (Monoisotopic): 391.0783

AlogP: 3.96

#Rotatable Bonds: 3

Polar Surface Area: 69.56

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.16

CX Basic pKa: ┄

CX LogP: 3.81

CX LogD: 3.74

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.54

Np Likeness Score: 0.10

References

1. Chen HZ, Chen YB, Lv YP, Zeng F, Zhang J, Zhou YL, Li HB, Chen LF, Zhou BJ, Gao JR, Xia CN..  (2014)  Synthesis and antitumor activity of feruloyl and caffeoyl derivatives.,  24  (18): [PMID:25160837] [10.1016/j.bmcl.2014.08.024]

Source

Source(1):

• Scientific Literature