Flustramine U; 3-(2-(6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl)ethyl)-3-methyloxazolidin-3-ium chloride

ID: ALA4782317

PubChem CID: 162664544

Max Phase: Preclinical

Molecular Formula: C19H26BrN2O+

Molecular Weight: 378.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)c1[nH]c2cc(Br)ccc2c1CC[N+]1(C)CCOC1

Standard InChI:  InChI=1S/C19H26BrN2O/c1-5-19(2,3)18-16(8-9-22(4)10-11-23-13-22)15-7-6-14(20)12-17(15)21-18/h5-7,12,21H,1,8-11,13H2,2-4H3/q+1

Standard InChI Key:  GYTICIYZHAHKPP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   27.8656   -4.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8645   -5.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5725   -6.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5707   -4.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2794   -4.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2842   -5.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0642   -5.9872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5415   -5.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0564   -4.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1565   -6.1513    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   31.3587   -5.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7715   -6.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7631   -4.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1759   -5.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5833   -4.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3044   -3.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7540   -3.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0020   -2.5013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7764   -2.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7716   -1.4272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9928   -1.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5165   -1.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5786   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  2 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 18 23  1  0
M  CHG  1  18   1
M  END

Alternative Forms

1. Parent:

   

   ALA4782317

   ---

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: 378.33

Molecular Weight (Monoisotopic): 377.1223

AlogP: 4.37

#Rotatable Bonds: 5

Polar Surface Area: 25.02

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.41

CX LogD: 0.41

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.61

Np Likeness Score: 0.96

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