Nalpha-sulfonated thyroxine

ID: ALA2074954

PubChem CID: 70691034

Max Phase: Preclinical

Molecular Formula: C15H11I4NO7S

Molecular Weight: 856.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)NS(=O)(=O)O

Standard InChI:  InChI=1S/C15H11I4NO7S/c16-8-4-7(5-9(17)13(8)21)27-14-10(18)1-6(2-11(14)19)3-12(15(22)23)20-28(24,25)26/h1-2,4-5,12,20-21H,3H2,(H,22,23)(H,24,25,26)/t12-/m1/s1

Standard InChI Key:  WDZGBBVWVGSPGU-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  1  0  0  0  0  0999 V2000
    4.5812   -3.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330   -4.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4536   -4.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330   -3.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5812   -4.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905   -2.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1571   -3.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8663   -2.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1501   -4.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4422   -2.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1629   -4.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0054   -4.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4352   -4.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0054   -3.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905   -4.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7146   -4.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1501   -5.3076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181   -2.8369    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.4422   -5.3076    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    5.2847   -2.0133    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    3.8663   -4.4954    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    1.0181   -4.4840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4295   -3.2487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8594   -4.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1440   -2.8362    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9408   -3.0497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5606   -2.2528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5565   -2.1217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3 11  2  0
  4 10  1  0
  5  1  2  0
  6  1  1  0
  7  8  1  0
  8  1  1  0
  9 13  1  0
 10  7  2  0
 11  7  1  0
 12 14  1  0
 13 16  1  0
 14  6  2  0
 15  5  1  0
 16 12  1  0
 17  9  2  0
 18  4  1  0
 19  3  1  0
 20  6  1  0
 21  5  1  0
 22  2  1  0
 13 23  1  1
 24  9  1  0
 12 15  2  0
  2  4  2  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
 25 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074954

   (2R)-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-2-(sulfoamino)propanoic acid

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: 856.94

Molecular Weight (Monoisotopic): 856.6435

AlogP: 3.99

#Rotatable Bonds: 7

Polar Surface Area: 133.16

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -1.96

CX Basic pKa: ┄

CX LogP: 3.59

CX LogD: -0.76

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.24

Np Likeness Score: 0.26

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