(+/-)-Gelliusine E

ID: ALA517453

PubChem CID: 10387020

Max Phase: Preclinical

Molecular Formula: C20H21BrN4O

Molecular Weight: 413.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+/-)-Gelliusine E | (+/-)-Gelliusine E|CHEMBL517453

Canonical SMILES:  NCCc1c(C(CN)c2c[nH]c3cc(Br)ccc23)[nH]c2ccc(O)cc12

Standard InChI:  InChI=1S/C20H21BrN4O/c21-11-1-3-13-17(10-24-19(13)7-11)16(9-23)20-14(5-6-22)15-8-12(26)2-4-18(15)25-20/h1-4,7-8,10,16,24-26H,5-6,9,22-23H2

Standard InChI Key:  XDYZPDVYNZANQI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.9402    1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391    0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6539    0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521    1.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3675    1.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723    0.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1598    0.1681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417    0.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1520    1.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667    0.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8834    0.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750    1.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7000    1.5662    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5533   -0.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1696   -1.1719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7053    0.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8802   -0.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6618   -1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2693   -0.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0898    0.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3085    0.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0559   -0.6965    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.4023    2.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2083    2.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4586    3.2537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257    1.6540    0.0000 O   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
  1 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA517453

   (+/-)-Gelliusine E

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: 413.32

Molecular Weight (Monoisotopic): 412.0899

AlogP: 3.71

#Rotatable Bonds: 5

Polar Surface Area: 103.85

Molecular Species: BASE

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.16

CX Basic pKa: 10.20

CX LogP: 1.93

CX LogD: -1.65

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.34

Np Likeness Score: 0.77

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