Flustramine C trifluoroacetic acid

ID: ALA4742844

PubChem CID: 162647053

Max Phase: Preclinical

Molecular Formula: C18H20BrF3N2O2

Molecular Weight: 319.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)[C@@]12CCN(C)C1=Nc1cc(Br)ccc12.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C16H19BrN2.C2HF3O2/c1-5-15(2,3)16-8-9-19(4)14(16)18-13-10-11(17)6-7-12(13)16;3-2(4,5)1(6)7/h5-7,10H,1,8-9H2,2-4H3;(H,6,7)/t16-;/m1./s1

Standard InChI Key:  YRJLZZQQJODHCI-PKLMIRHRSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   20.6230  -14.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3307  -14.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0385  -14.4421    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.3307  -15.6680    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.0327  -15.2552    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.6230  -13.6249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9152  -14.8508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9882  -15.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9870  -15.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7007  -16.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6989  -14.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4132  -15.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4180  -15.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2043  -16.1031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1965  -14.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6873  -15.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4698  -15.1695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4626  -14.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6757  -14.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2732  -16.2685    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   19.1403  -15.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7785  -14.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1881  -13.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9548  -14.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3625  -13.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7721  -12.6191    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  2  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
 15 22  1  1
 22 23  1  0
 22 24  1  0
 22 25  1  0
 25 26  2  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: 319.25

Molecular Weight (Monoisotopic): 318.0732

AlogP: 4.28

#Rotatable Bonds: 2

Polar Surface Area: 15.60

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.72

CX LogP: 4.06

CX LogD: 4.05

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.74

Np Likeness Score: 1.42

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