N,N,N-trimethyl-3-bromo-4-methoxytyrosine

ID: ALA3286794

PubChem CID: 90680655

Max Phase: Preclinical

Molecular Formula: C15H19BrF3NO5

Molecular Weight: 317.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CC(C(=O)O)[N+](C)(C)C)cc1Br.O=C([O-])C(F)(F)F

Standard InChI:  InChI=1S/C13H18BrNO3.C2HF3O2/c1-15(2,3)11(13(16)17)8-9-5-6-12(18-4)10(14)7-9;3-2(4,5)1(6)7/h5-7,11H,8H2,1-4H3;(H,6,7)

Standard InChI Key:  SZGBGLOOKCLDNF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 24  0  0  0  0  0  0  0  0999 V2000
   25.5567  -20.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9667  -20.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7395  -20.7832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9637  -21.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5536  -22.2001    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.7809  -21.4951    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.3647  -22.1962    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.7462  -19.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7450  -19.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4531  -20.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1627  -19.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1599  -19.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4513  -18.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4488  -17.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1553  -17.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8661  -18.6983    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   21.4529  -21.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1605  -21.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1603  -22.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8683  -21.1592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5759  -21.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8685  -20.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5706  -20.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4515  -22.7953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8669  -22.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  4  5  1  0
  4  6  1  0
  4  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  0
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 19 24  1  0
 19 25  2  0
M  CHG  2   2  -1  20   1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 317.20

Molecular Weight (Monoisotopic): 316.0543

AlogP: 2.16

#Rotatable Bonds: 5

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.42

CX Basic pKa: ┄

CX LogP: -1.66

CX LogD: -0.89

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.85

Np Likeness Score: 0.81

References

1. Tian LW, Feng Y, Shimizu Y, Pfeifer T, Wellington C, Hooper JN, Quinn RJ..  (2014)  Aplysinellamides A-C, bromotyrosine-derived metabolites from an Australian Aplysinella sp. marine sponge.,  77  (5): [PMID:24758268] [10.1021/np500119e]

Source

Source(1):

• Scientific Literature