(-)-monobromophakellin

ID: ALA506643

PubChem CID: 136117765

Max Phase: Preclinical

Molecular Formula: C11H12BrN5O

Molecular Weight: 310.15

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (-)-Monobromophakellin

Canonical SMILES:  NC1=N[C@]23CCCN2C(=O)c2cc(Br)cn2[C@@H]3N1

Standard InChI:  InChI=1S/C11H12BrN5O/c12-6-4-7-8(18)17-3-1-2-11(17)9(16(7)5-6)14-10(13)15-11/h4-5,9H,1-3H2,(H3,13,14,15)/t9-,11+/m0/s1

Standard InChI Key:  ANCHLEBCUYPRNH-GXSJLCMTSA-N

Molfile:  

     RDKit          2D

 19 22  0  0  0  0  0  0  0  0999 V2000
   15.8475   -0.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4130   -0.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6263    0.1065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1446   -0.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6333   -1.2354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1316    0.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8463   -0.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4580    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1255    1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3042    1.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1316   -1.3830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4166   -0.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8087   -1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1508   -2.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9699   -2.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3153   -0.5735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5665   -1.3862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4130    0.6786    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.5377    1.8783    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
 11  1  1  0
  1  7  1  0
 12  2  1  0
  2  3  1  0
  3  4  1  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
  9 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA506643

   ---

Molecule Features

Natural Product: Yes

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: 310.15

Molecular Weight (Monoisotopic): 309.0225

AlogP: 0.61

#Rotatable Bonds: ┄

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: 7.44

CX LogP: 1.08

CX LogD: 0.76

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.74

Np Likeness Score: 1.20

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