(2S)-2-ammonio-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate

Details

• Internal ID: 55f88864-be90-485d-9caa-ca6574a73e8f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Phenylalanine and derivatives
• IUPAC Name: (2S)-2-azaniumyl-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
• InChI: InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1
• InChI Key: XUIIKFGFIJCVMT-LBPRGKRZSA-N
• Popularity: 73 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₁I₄NO₄
• Molecular Weight: 776.87 g/mol
• Exact Mass: 776.6867 g/mol
• Topological Polar Surface Area (TPSA): 97.20 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• (2S)-2-azaniumyl-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
• L-thyroxine zwitterion
• CHEBI:58448
• BDBM408980
• US10377729, T4

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9081	90.81%
Caco-2	-	0.7889	78.89%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6715	67.15%
OATP2B1 inhibitior	+	1.0000	100.00%
OATP1B1 inhibitior	-	0.4281	42.81%
OATP1B3 inhibitior	+	0.9200	92.00%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9072	90.72%
P-glycoprotein inhibitior	-	0.8381	83.81%
P-glycoprotein substrate	-	0.9039	90.39%
CYP3A4 substrate	-	0.5466	54.66%
CYP2C9 substrate	-	0.6390	63.90%
CYP2D6 substrate	-	0.8174	81.74%
CYP3A4 inhibition	-	0.8928	89.28%
CYP2C9 inhibition	+	0.5623	56.23%
CYP2C19 inhibition	-	0.8409	84.09%
CYP2D6 inhibition	-	0.8287	82.87%
CYP1A2 inhibition	+	0.5223	52.23%
CYP2C8 inhibition	+	0.8635	86.35%
CYP inhibitory promiscuity	-	0.6367	63.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6346	63.46%
Carcinogenicity (trinary)	Non-required	0.6339	63.39%
Eye corrosion	-	0.9948	99.48%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.8027	80.27%
Skin corrosion	-	0.9793	97.93%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4598	45.98%
Micronuclear	+	0.7074	70.74%
Hepatotoxicity	+	0.5537	55.37%
skin sensitisation	-	0.7748	77.48%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6355	63.55%
Acute Oral Toxicity (c)	III	0.6489	64.89%
Estrogen receptor binding	+	0.8943	89.43%
Androgen receptor binding	+	0.5307	53.07%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	+	0.8805	88.05%
Aromatase binding	+	0.7656	76.56%
PPAR gamma	+	0.8762	87.62%
Honey bee toxicity	-	0.7678	76.78%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.9795	97.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2047	Q96RI1	Bile acid receptor FXR	7860 nM	IC50	PMID: 23688559
CHEMBL3401	O75469	Pregnane X receptor	11200 nM; 100000 nM	EC50; EC50	PMID: 20966043; PMID: 20966043
CHEMBL1293235	P02545	Prelamin-A/C	707.9 nM	Potency	via CMAUP
CHEMBL2073690	Q6ZQN7	Solute carrier organic anion transporter family member 4C1	8000 nM	IC50	PMID: 14993604
CHEMBL3194	P02766	Transthyretin	10500 nM	IC50	PMID: 19651509
CHEMBL1287617	P22309	UDP-glucuronosyltransferase 1-1	4900 nM; 5600 nM	IC50; IC50	PMID: 21030469; PMID: 21030469

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.29%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.23%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.70%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.72%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.71%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.11%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.39%	96.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.78%	95.89%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.78%	89.34%
CHEMBL4208	P20618	Proteasome component C5	82.69%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.33%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.76%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	80.69%	94.73%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.33%	97.21%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.26%	96.21%

Plants that contains it

• Swertia calycina

Cross-Links

• PubChem: 25201348
• NPASS: NPC197239
• ChEMBL: CHEMBL1624