(-)-4,5-Diphenylphakellin

ID: ALA476629

PubChem CID: 136117768

Max Phase: Preclinical

Molecular Formula: C23H21N5O

Molecular Weight: 383.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H21N5O/c24-22-25-21-23(26-22)12-7-13-27(23)20(29)18-14-17(15-8-3-1-4-9-15)19(28(18)21)16-10-5-2-6-11-16/h1-6,8-11,14,21H,7,12-13H2,(H3,24,25,26)/t21-,23+/m0/s1

Standard InChI Key:  TVGNBROZCFEFBK-JTHBVZDNSA-N

Molfile:  

     RDKit          2D

 30 35  0  0  0  0  0  0  0  0999 V2000
    8.6201   -8.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1847   -7.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3976   -6.9932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9156   -7.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4046   -8.3359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9038   -6.8280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6189   -7.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2310   -6.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8983   -5.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0766   -6.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9038   -8.4836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1883   -8.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5801   -8.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9224   -9.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7419   -9.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0858   -7.6736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3395   -8.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1847   -6.4208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5259   -5.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7820   -4.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2308   -4.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4236   -4.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1702   -4.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7231   -5.5843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3080   -5.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1336   -5.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5460   -4.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1339   -3.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3051   -3.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8965   -4.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  4  5  2  0
 25 26  2  0
  5 12  1  0
 26 27  1  0
  6  7  1  0
 27 28  2  0
  7  8  2  0
 28 29  1  0
  8  9  1  0
 29 30  2  0
 30 25  1  0
  9 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA476629

   ---

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: 383.45

Molecular Weight (Monoisotopic): 383.1746

AlogP: 3.18

#Rotatable Bonds: 2

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: 7.77

CX LogP: 3.52

CX LogD: 3.00

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.71

Np Likeness Score: 0.73

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