N-bromoacetyl-3,3',5-triiodothyronine

ID: ALA2074819

Cas Number: 76970-94-0

PubChem CID: 122086

Max Phase: Preclinical

Molecular Formula: C17H13BrI3NO5

Molecular Weight: 771.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CBr)N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(=O)O

Standard InChI:  InChI=1S/C17H13BrI3NO5/c18-7-15(24)22-13(17(25)26)5-8-3-11(20)16(12(21)4-8)27-9-1-2-14(23)10(19)6-9/h1-4,6,13,23H,5,7H2,(H,22,24)(H,25,26)/t13-/m0/s1

Standard InChI Key:  AGUVIBCJWRFUTQ-ZDUSSCGKSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    2.5339    8.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194    7.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194    6.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339    6.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484    6.8652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484    7.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    8.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    6.4527    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050    6.4527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050    5.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    5.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050    3.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195    4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195    5.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5339    5.6277    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240    5.6277    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050    3.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3905    1.9152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240    3.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    2.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240    3.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240    1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3240    0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    1.9152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    0.2652    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  3  9  1  0
  9 10  1  0
 10 11  1  0
 10 15  2  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 11 17  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 21 23  2  0
 20 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074819

   L-Tyrosine, N-(bromoacetyl)-O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-

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: 771.91

Molecular Weight (Monoisotopic): 770.7111

AlogP: 4.51

#Rotatable Bonds: 7

Polar Surface Area: 95.86

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.88

CX Basic pKa: ┄

CX LogP: 5.60

CX LogD: 2.05

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: 0.22

References

1. Friesema EC, Ganguly S, Abdalla A, Manning Fox JE, Halestrap AP, Visser TJ..  (2003)  Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter.,  278  (1): [PMID:12871948] [10.1074/jbc.m300909200]

Source

Source(1):

• TP-search Transporter Database