Triiodothyronine sulfate

ID: ALA2074889

Cas Number: 31135-55-4

PubChem CID: 122196

Max Phase: Preclinical

Molecular Formula: C15H12I3NO7S

Molecular Weight: 731.04

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Triiodothyronine sulfate | triiodothyronine sulfate|31135-55-4|Triiodothyronine sulfuric ester|CHEBI:35432|(2S)-2-amino-3-[3,5-diiodo-4-(3-iodo-4-sulfooxyphenoxy)phenyl]propanoic acid|3,5-diiodo-O-[3-iodo-4-(sulfooxy)phenyl]-L-tyrosine|3,3',5-triiodo-L-thyronine sulfate|(2S)-2-AMINO-3-[3,5-DIIODO-4-(3-IODO-4-SULFOOXY-PHENOXY)PHENYL]PROPANOIC ACID|(2S)-2-amino-3-{3,5-diiodo-4-[3-iodo-4-(sulfooxy)phenoxy]phenyl}propanoic acid|3,3',5-Triiodo-L-thyronine 4'-O-Sulfate|L-Tyrosine, 3,5-diiodo-O-(3-iodoShow More⌵

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

Standard InChI:  InChI=1S/C15H12I3NO7S/c16-9-6-8(1-2-13(9)26-27(22,23)24)25-14-10(17)3-7(4-11(14)18)5-12(19)15(20)21/h1-4,6,12H,5,19H2,(H,20,21)(H,22,23,24)/t12-/m0/s1

Standard InChI Key:  XBQYQXVJBNDCGY-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  1  0  0  0  0  0999 V2000
    1.5548   -3.6021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007    1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4972    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4920   -0.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7907   -1.5158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0919   -0.7681    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0940    0.4319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1303   -1.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1321   -0.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1903   -1.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1862   -2.7091    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939   -0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916   -4.9570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 15 18  2  0
 13 19  1  0
 19 20  1  0
 19 21  2  0
 10 21  1  0
  8 22  1  0
 22 23  1  0
 22 24  2  0
  4 24  1  0
  2 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074889

   TRIIODOTHYRONINE SULFATE

Molecule Features

Natural Product: Yes

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: 731.04

Molecular Weight (Monoisotopic): 730.7469

AlogP: 3.43

#Rotatable Bonds: 7

Polar Surface Area: 136.15

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: -2.82

CX Basic pKa: 9.43

CX LogP: 3.39

CX LogD: -0.06

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: 0.57

References

1. Friesema EC, Docter R, Moerings EP, Stieger B, Hagenbuch B, Meier PJ, Krenning EP, Hennemann G, Visser TJ..  (1999)  Identification of thyroid hormone transporters.,  254  (1): [PMID:9918867] [10.1006/bbrc.1998.9974]

2. Drug metabolism data, 

Source

Source(2):

• TP-search Transporter Database
• Curated Drug Metabolism Pathways