(+/-)-Gelliusine F

ID: ALA455857

PubChem CID: 10254385

Max Phase: Preclinical

Molecular Formula: C20H20Br2N4

Molecular Weight: 476.22

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+/-)-Gelliusine F | (+/-)-Gelliusine F|CHEMBL455857

Canonical SMILES:  NCCc1c(C(CN)c2c[nH]c3cc(Br)ccc23)[nH]c2cc(Br)ccc12

Standard InChI:  InChI=1S/C20H20Br2N4/c21-11-2-4-14-17(10-25-18(14)7-11)16(9-24)20-15(5-6-23)13-3-1-12(22)8-19(13)26-20/h1-4,7-8,10,16,25-26H,5-6,9,23-24H2

Standard InChI Key:  OIMJVUYYZQBQMK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   10.7527    1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7516    0.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4664    0.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4646    1.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1800    1.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1848    0.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9723    0.2931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4542    0.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9645    1.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2792    0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6959    0.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6875    1.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5125    1.6912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3658   -0.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9821   -1.0469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5178    0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6927   -0.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4743   -0.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0818   -0.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9023    0.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1210    0.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8684   -0.5715    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   13.2148    2.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0208    2.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2711    3.3787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0368    0.1274    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 12 13  1  0
 11 14  2  0
  3  6  2  0
  1  2  2  0
 14 15  1  0
 15 17  1  0
 16 11  1  0
  5  4  2  0
  6  7  1  0
 16 17  2  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  2  0
 21 16  1  0
  8 10  1  0
 19 22  1  0
  5  6  1  0
  9 23  1  0
 10 11  1  0
 23 24  1  0
 24 25  1  0
 10 12  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA455857

   (+/-)-Gelliusine F

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: 476.22

Molecular Weight (Monoisotopic): 474.0055

AlogP: 4.77

#Rotatable Bonds: 5

Polar Surface Area: 83.62

Molecular Species: BASE

HBA: 2

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.04

CX LogP: 3.84

CX LogD: -0.66

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.34

Np Likeness Score: 0.55

References

1. Bifulco G, Bruno I, Riccio R, Lavayre J, Bourdy G..  (1995)  Further brominated bis- and tris-indole alkaloids from the deep-water New Caledonian marine sponge Orina Sp.,  58  (8): [PMID:7595591] [10.1021/np50122a017]

Source

Source(1):

• Scientific Literature