Flustramine E trifluoroacetic acid

ID: ALA4743221

PubChem CID: 162646940

Max Phase: Preclinical

Molecular Formula: C18H22BrF3N2O2

Molecular Weight: 321.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=CC[C@@]12CCN(C)[C@@H]1Nc1cc(Br)ccc12.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C16H21BrN2.C2HF3O2/c1-11(2)6-7-16-8-9-19(3)15(16)18-14-10-12(17)4-5-13(14)16;3-2(4,5)1(6)7/h4-6,10,15,18H,7-9H2,1-3H3;(H,6,7)/t15-,16-;/m0./s1

Standard InChI Key:  AHUDIRNTHPPFRZ-MOGJOVFKSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    9.3167   -6.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0251   -6.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7337   -6.0204    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.0251   -7.2475    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7278   -6.8344    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.3167   -5.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6083   -6.4295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219   -4.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207   -5.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352   -6.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2334   -4.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9485   -4.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9532   -5.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7404   -6.0248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7325   -4.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2238   -5.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0071   -5.0903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -4.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2122   -4.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8063   -6.1904    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.6784   -5.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8051   -5.9346    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3141   -3.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7241   -3.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3095   -2.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7195   -1.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849   -2.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  1  6  2  0
  1  7  1  0
  8  9  2  0
  9 10  1  0
 10 13  2  0
 12 11  2  0
 11  8  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 15 12  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
  9 20  1  0
 17 21  1  0
 16 22  1  1
 15 23  1  1
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 321.26

Molecular Weight (Monoisotopic): 320.0888

AlogP: 4.13

#Rotatable Bonds: 2

Polar Surface Area: 15.27

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.39

CX LogP: 4.08

CX LogD: 4.08

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.82

Np Likeness Score: 2.23

References

1. Di X,Wang S,Oskarsson JT,Rouger C,Tasdemir D,Hardardottir I,Freysdottir J,Wang X,Molinski TF,Omarsdottir S.  (2020)  Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea.,  83  (10): [PMID:33016699] [10.1021/acs.jnatprod.0c00126]

Source

Source(1):

• Scientific Literature