Dihydroflustramine C trifluoroacetic acid

ID: ALA4758725

PubChem CID: 162657550

Max Phase: Preclinical

Molecular Formula: C17H20BrF3N2O2

Molecular Weight: 307.24

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H19BrN2.C2HF3O2/c1-4-14(2,3)15-7-8-17-13(15)18-12-9-10(16)5-6-11(12)15;3-2(4,5)1(6)7/h4-6,9,13,17-18H,1,7-8H2,2-3H3;(H,6,7)/t13-,15-;/m1./s1

Standard InChI Key:  LSCOMBNYZKCWAD-SWYZXDRTSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   19.4721   -5.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1798   -5.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8875   -5.3364    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.1798   -6.5622    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.8817   -6.1495    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.4721   -4.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7644   -5.7450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6460   -4.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6448   -5.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3586   -5.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3567   -4.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0710   -4.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0758   -5.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8620   -5.5938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8542   -4.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3449   -4.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1274   -4.6602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1202   -3.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3333   -3.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9312   -5.7592    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.9255   -5.5037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.4362   -3.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8458   -2.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6126   -3.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0203   -2.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4299   -2.1100    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
 16 21  1  1
 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: 307.24

Molecular Weight (Monoisotopic): 306.0732

AlogP: 3.64

#Rotatable Bonds: 2

Polar Surface Area: 24.06

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.36

CX LogP: 3.66

CX LogD: 2.65

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.82

Np Likeness Score: 1.68

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