Flustramine V; (R)-6-bromo-3-(2-(methylamino)ethyl)-3-(2-methyl-3-buten-2-yl)indolin-2-one

ID: ALA4740628

PubChem CID: 162644569

Max Phase: Preclinical

Molecular Formula: C16H21BrN2O

Molecular Weight: 337.26

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)[C@@]1(CCNC)C(=O)Nc2cc(Br)ccc21

Standard InChI:  InChI=1S/C16H21BrN2O/c1-5-15(2,3)16(8-9-18-4)12-7-6-11(17)10-13(12)19-14(16)20/h5-7,10,18H,1,8-9H2,2-4H3,(H,19,20)/t16-/m1/s1

Standard InChI Key:  YETBRWDKUMDFIQ-MRXNPFEDSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    5.4479  -24.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6626  -25.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2415  -24.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4696  -25.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4684  -26.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1765  -26.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747  -24.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8833  -25.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8881  -26.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6725  -26.4683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1525  -25.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604  -26.6265    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.9697  -25.7947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0242  -23.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6580  -24.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2333  -23.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8096  -22.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0314  -24.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6077  -24.1827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3976  -24.3921    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
  1 14  1  0
  1 15  1  0
  1 16  1  0
 16 17  2  0
  3 18  1  0
 18 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740628

   ---

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: 337.26

Molecular Weight (Monoisotopic): 336.0837

AlogP: 3.46

#Rotatable Bonds: 5

Polar Surface Area: 41.13

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.00

CX Basic pKa: 10.02

CX LogP: 3.45

CX LogD: 0.91

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.81

Np Likeness Score: 1.46

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