(-)-4-Bromo-5-phenylphakellin

ID: ALA476428

PubChem CID: 136117766

Max Phase: Preclinical

Molecular Formula: C17H16BrN5O

Molecular Weight: 386.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC1=N[C@]23CCCN2C(=O)c2cc(Br)c(-c4ccccc4)n2[C@@H]3N1

Standard InChI:  InChI=1S/C17H16BrN5O/c18-11-9-12-14(24)22-8-4-7-17(22)15(20-16(19)21-17)23(12)13(11)10-5-2-1-3-6-10/h1-3,5-6,9,15H,4,7-8H2,(H3,19,20,21)/t15-,17+/m0/s1

Standard InChI Key:  XLKCOBAGHSIJLY-DOTOQJQBSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    0.4877   -8.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477   -7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7348   -6.9265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2168   -7.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7278   -8.2692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2286   -6.7614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4865   -7.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986   -6.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -5.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -5.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2286   -8.4169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -8.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -8.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2099   -9.3186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905   -9.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0466   -7.6069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -8.4201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9477   -6.3541    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6065   -5.3453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504   -4.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -3.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088   -4.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9622   -4.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4093   -5.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -5.1537    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
  5 12  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  6  1  0
 11 12  1  0
 12 13  1  6
 13 14  1  0
 14 15  1  0
 15 11  1  0
  4 16  1  0
  1 17  2  0
  2 18  1  6
  2  6  1  0
 19 20  2  0
 11  1  1  0
 20 21  1  0
  1  7  1  0
 21 22  2  0
 12  2  1  0
 22 23  1  0
  2  3  1  0
 23 24  2  0
 24 19  1  0
 10 19  1  0
  3  4  1  0
  9 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA476428

   ---

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: 386.25

Molecular Weight (Monoisotopic): 385.0538

AlogP: 2.28

#Rotatable Bonds: 1

Polar Surface Area: 75.65

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.52

CX LogP: 2.64

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: 0.97

References

1. Davis RA, Fechner GA, Sykes M, Garavelas A, Pass DM, Carroll AR, Addepalli R, Avery VM, Hooper JN, Quinn RJ..  (2009)  (-)-Dibromophakellin: an alpha2B adrenoceptor agonist isolated from the Australian marine sponge, Acanthella costata.,  17  (6): [PMID:19243956] [10.1016/j.bmc.2009.01.065]

Source

Source(1):

• Scientific Literature