flustramine W; (3R)-6-bromo-3-hydroxy-3-(2-(methylamino)ethyl)-1-(3-methylbut-2-en-yl)indolin-2-one

ID: ALA4752041

PubChem CID: 162652525

Max Phase: Preclinical

Molecular Formula: C16H21BrN2O2

Molecular Weight: 353.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNCC[C@]1(O)C(=O)N(CC=C(C)C)c2cc(Br)ccc21

Standard InChI:  InChI=1S/C16H21BrN2O2/c1-11(2)6-9-19-14-10-12(17)4-5-13(14)16(21,15(19)20)7-8-18-3/h4-6,10,18,21H,7-9H2,1-3H3/t16-/m1/s1

Standard InChI Key:  LEQBIBCLKYBFQN-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   16.8432  -23.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0578  -24.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6368  -24.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8649  -24.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8637  -25.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5718  -26.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5700  -24.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2786  -24.9578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2834  -25.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0678  -26.0308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5478  -25.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1557  -26.1890    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   18.3650  -25.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4267  -24.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0030  -23.7452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7929  -23.9546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3248  -26.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7816  -27.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0386  -28.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4954  -28.8032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8389  -28.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  2  8  1  0
  5 12  1  0
 11 13  2  0
  3 14  1  0
 14 15  1  0
 15 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4752041

   ---

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: 353.26

Molecular Weight (Monoisotopic): 352.0786

AlogP: 2.56

#Rotatable Bonds: 5

Polar Surface Area: 52.57

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.82

CX Basic pKa: 9.49

CX LogP: 2.12

CX LogD: 0.06

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.80

Np Likeness Score: 0.66

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