ID: ALA1312

Max Phase: Preclinical

Molecular Formula: C15H12I3NO4

Molecular Weight: 650.98

Molecule Type: Small molecule

Representations

Synonyms (1): Reverse triiodothyronine
Synonyms from Alternative Forms(1):

Canonical SMILES:  NC(Cc1ccc(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(=O)O

Standard InChI:  InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)

Standard InChI Key:  HZCBWYNLGPIQRK-UHFFFAOYSA-N

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

Properties

Molecular Weight: 650.98

Molecular Weight (Monoisotopic): 650.7901

AlogP: 3.95

#Rotatable Bonds: 5

Polar Surface Area: 92.78

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 0.72

CX Basic pKa: 9.45

CX LogP: 2.80

CX LogD: 2.52

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.43

Np Likeness Score: 0.46

References

1. Rickenbacher U, McKinney JD, Oatley SJ, Blake CC..  (1986)  Structurally specific binding of halogenated biphenyls to thyroxine transport protein.,  29  (5): [PMID:3009810] [10.1021/jm00155a010]

2. McKinney J, Fannin R, Jordan S, Chae K, Rickenbacher U, Pedersen L..  (1987)  Polychlorinated biphenyls and related compound interactions with specific binding sites for thyroxine in rat liver nuclear extracts.,  30  (1): [PMID:3100800] [10.1021/jm00384a014]

3. PubChem BioAssay data set, 

4. 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]

5. Dietrich SW, Bolger MB, Kollman PA, Jorgensen EC..  (1977)  Thyroxine analogues. 23. Quantitative structure-activity correlation studies of in vivo and in vitro thyromimetic activities.,  20  (7): [PMID:195056] [10.1021/jm00217a001]

6. Jurik A, Zdrazil B, Holy M, Stockner T, Sitte HH, Ecker GF..  (2015)  A binding mode hypothesis of tiagabine confirms liothyronine effect on γ-aminobutyric acid transporter 1 (GAT1).,  58  (5): [PMID:25679268] [10.1021/jm5015428]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• TP-search Transporter Database