Flustramine A trifluoroacetic acid

ID: ALA4741574

PubChem CID: 162645465

Max Phase: Preclinical

Molecular Formula: C23H30BrF3N2O2

Molecular Weight: 389.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)[C@@]12CCN(C)[C@@H]1N(CC=C(C)C)c1cc(Br)ccc12.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C21H29BrN2.C2HF3O2/c1-7-20(4,5)21-11-13-23(6)19(21)24(12-10-15(2)3)18-14-16(22)8-9-17(18)21;3-2(4,5)1(6)7/h7-10,14,19H,1,11-13H2,2-6H3;(H,6,7)/t19-,21-;/m1./s1

Standard InChI Key:  WNDFBOQDUFXWOU-GNGUGDOWSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    9.6056  -14.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3136  -15.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0216  -14.9185    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3136  -16.1448    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.0157  -15.7319    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6056  -14.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8976  -15.3272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7566  -13.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7555  -14.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4702  -15.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4685  -13.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1837  -13.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1885  -14.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9760  -14.9016    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9682  -13.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4596  -14.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2433  -13.9666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2360  -13.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4480  -12.8919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0408  -15.0672    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.9148  -14.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0411  -14.8113    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5496  -12.8447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9598  -12.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7247  -12.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1328  -12.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5432  -11.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2352  -15.6847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0430  -15.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3022  -16.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1101  -16.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7536  -17.2510    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
 23 25  1  0
 23 26  1  0
 26 27  2  0
 14 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30 32  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: 389.38

Molecular Weight (Monoisotopic): 388.1514

AlogP: 5.35

#Rotatable Bonds: 4

Polar Surface Area: 6.48

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.47

CX LogP: 6.04

CX LogD: 5.99

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.64

Np Likeness Score: 1.95

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